dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b246f45fa6645ec92d12a7f69d24d40 | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C#CCBr>>CC[Si](CC)(CC)OC(C)(C)C#CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.BrCC#CC(C)(C)O[Si](CC)(CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC#CC(C)(C)O[Si](CC)(CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:15][C:16]([CH3:17])([CH3:18])[C:19]1=[CH:20][CH2:21][C@H:22]2[C:23]3=[CH:24][CH:25]=[C:26]4[CH2:27][C@@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][C@H:38]([O:39][Si:40]([CH3:41])([CH3:42])[C:43]([CH3:44])([CH3:45])[CH3:46])[C@:47]4([CH3:48])[C@H:49]3[CH2:50][CH2:51][C@:52]12[C... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C#CCBr | CC[Si](CC)(CC)OC(C)(C)C#CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9ef84a8c80411e848c10c5384ce78141e473ad5db44b97f46285876278d6d001 | 004868630acb495c3cf864467df50d8e3d3bf839809342ad5aeae72f8c34f6c8 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11])-[C:12]>>[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4])-[C:12] | 62 | [{"value": 62.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC#CC(C)(C)O[Si](CC)(CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC#CC(C)(C)... | null | null | null | null | 1α,3β-Bis(tert-Butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (100 mg, 0.175 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-2-pentyne (203 mg, 0.697 mmol), sodium hydride (60% in oil, 42 mg, 1.05 mmol), 15-crown-5 (38 mg, 0.173 mmol) and tetrahydrofuran (3 ml) were reacted using a procedure similar to that... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C#CCBr>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)C#CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2a5237451924062ae26aea06949245a | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br>>CC[Si](CC)(CC)OC(C)(C)C/C=C/OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.Br\C=C\CC(C)(C)O[Si](CC)(CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\C=C\CC(C)(C)O[Si](CC)(CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:15][C:16]([CH3:17])([CH3:18])[C:19]1=[CH:20][CH2:21][C@H:22]2[C:23]3=[CH:24][CH:25]=[C:26]4[CH2:27][C@@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][C@H:38]([O:39][Si:40]([CH3:41])([CH3:42])[C:43]([CH3:44])([CH3:45])[CH3:46])[C@:47]4([CH3:48])[C@H:49]3[CH2:50][CH2:51][C@:52]12[C... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br | CC[Si](CC)(CC)OC(C)(C)C/C=C/OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Acylation | Williamson Ether Synthesis | 3bebab49d1e73ccb378d80c964dd2eb3ac4ae759a028f210c53302497d420909 | 68002c25e6f3b076ffda77fb7b82207a1a988042aa4418cc4cd63986b874c804 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11])-[C:12]>>[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4])-[C:12] | 99 | [{"value": 99.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\\C=C\\CC(C)(C)O[Si](CC)(CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\\C=C\\... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (103 mg, 0.180 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2E)-pentene (211 mg, 0.719 mmol), sodium hydride (60% in oil, 43 mg, 1.08 mmol), 15-crown-5 (40 mg, 0.182 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedur... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)C/C=C/OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3e80b1865d34207a9241eaeb472ffcb | CCC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C\Br>>CCC(C)(O/C=C\CC(C)(C)O[Si](CC)(CC)CC)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(CC)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.Br\C=C/CC(C)(C)O[Si](CC)(CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(CC)O\C=C/CC(C)(C)O[Si](CC)(CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[C:20]1=[CH:21][CH2:22][C@H:23]2[C:24]3=[CH:25][CH:26]=[C:27]4[CH2:28][C@@H:29]([O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:38][C@H:39]([O:40][Si:41]([CH3:42])([CH3:43])[C:44]([CH3:45])([CH3:46])[CH3:47])[C@:48]4([CH3:49])[C@H:50]3[CH2:51][CH2:52][C@:53]1... | CCC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C\Br | CCC(C)(O/C=C\CC(C)(C)O[Si](CC)(CC)CC)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Acylation | Williamson Ether Synthesis | 3bebab49d1e73ccb378d80c964dd2eb3ac4ae759a028f210c53302497d420909 | 68002c25e6f3b076ffda77fb7b82207a1a988042aa4418cc4cd63986b874c804 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br/[CH;D2;+0:1]=[C:2]\[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8](-[C:9])(-[C;D1;H3:10])-[OH;D1;+0:11])-[C:12]>>[C:5]-[C:6]=[C:7](-[C:8](-[C:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]/[CH;D2;+0:1]=[C:2]\[C:3]-[C:4])-[C:12] | 100 | [{"value": 100.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(CC)O\\C=C/CC(C)(C)O[Si](CC)(CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(CC)O\\C=C... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-ethylpregna-5,7,16-triene (103 mg, 0.180 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2Z)-pentene (211 mg, 0.719 mol), sodium hydride (60% in oil, 43 mg, 1.08 mmol), 15-crown-5 (40 mg, 0.182 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CCC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C\Br>O1CCCC1>CCC(C)(O/C=C\CC(C)(C)O[Si](CC)(CC)CC)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4bbe192ac8e24825a0f792208891f093 | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(C#CCBr)(CC)O[Si](CC)(CC)CC>>CCC(C#CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)(CC)O[Si](CC)(CC)CC | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.BrCC#CC(CC)(O[Si](CC)(CC)CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC#CC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:7][C:8]([CH3:9])([CH3:10])[C:11]1=[CH:12][CH2:13][C@H:14]2[C:15]3=[CH:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:40])[C@H:41]3[CH2:42][CH2:43][C@:44]12[CH3:... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(C#CCBr)(CC)O[Si](CC)(CC)CC | CCC(C#CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)(CC)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9ef84a8c80411e848c10c5384ce78141e473ad5db44b97f46285876278d6d001 | 004868630acb495c3cf864467df50d8e3d3bf839809342ad5aeae72f8c34f6c8 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11])-[C:12]>>[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4])-[C:12] | 37.7 | [{"value": 37.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC#CC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC#CC(CC)... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (100 mg, 0.17 mmol), 1-bromo-4-ethyl-4-triethylsilyloxy-2-hexyne (150 mg, 0.47 mmol), sodium hydride (60% in oil, 41 mg, 1.02 mmol), 15-crown-5 (37 mg, 0.17 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure simila... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(C#CCBr)(CC)O[Si](CC)(CC)CC>O1CCCC1>CCC(C#CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)(CC)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c180d7eb82f148dfb0d5d778d315e9db | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(C/C=C\Br)O[Si](CC)(CC)CC>>CCC(CC)(C/C=C\OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.Br\C=C/CC(CC)(O[Si](CC)(CC)CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\C=C/CC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:9][C:10]([CH3:11])([CH3:12])[C:13]1=[CH:14][CH2:15][C@H:16]2[C:17]3=[CH:18][CH:19]=[C:20]4[CH2:21][C@@H:22]([O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][C@H:32]([O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[C@:41]4([CH3:42])[C@H:43]3[CH2:44][CH2:45][C@:46]12[CH... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(C/C=C\Br)O[Si](CC)(CC)CC | CCC(CC)(C/C=C\OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Acylation | Williamson Ether Synthesis | 3bebab49d1e73ccb378d80c964dd2eb3ac4ae759a028f210c53302497d420909 | 68002c25e6f3b076ffda77fb7b82207a1a988042aa4418cc4cd63986b874c804 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br/[CH;D2;+0:1]=[C:2]\[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11])-[C:12]>>[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]/[CH;D2;+0:1]=[C:2]\[C:3]-[C:4])-[C:12] | 72 | [{"value": 72.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\\C=C/CC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\\C=C/... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (100 mg, 0.175 mmol), 1-bromo-4-ethyl-4-triethylsilyloxy-(2Z)-hexene (224 mg, 0.697 mmol), sodium hydride (60% in oil, 42 mg, 1.05 mmol), 15-crown-5 (38 mg, 0.173 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(C/C=C\Br)O[Si](CC)(CC)CC>O1CCCC1>CCC(CC)(C/C=C\OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c425bee2d9844a92859ff71873587bbf | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(C/C=C/Br)O[Si](CC)(CC)CC>>CCC(CC)(C/C=C/OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.Br\C=C\CC(CC)(O[Si](CC)(CC)CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\C=C\CC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:9][C:10]([CH3:11])([CH3:12])[C:13]1=[CH:14][CH2:15][C@H:16]2[C:17]3=[CH:18][CH:19]=[C:20]4[CH2:21][C@@H:22]([O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][C@H:32]([O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[C@:41]4([CH3:42])[C@H:43]3[CH2:44][CH2:45][C@:46]12[CH... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(C/C=C/Br)O[Si](CC)(CC)CC | CCC(CC)(C/C=C/OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Acylation | Williamson Ether Synthesis | 3bebab49d1e73ccb378d80c964dd2eb3ac4ae759a028f210c53302497d420909 | 68002c25e6f3b076ffda77fb7b82207a1a988042aa4418cc4cd63986b874c804 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11])-[C:12]>>[C:5]-[C:6]=[C:7](-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4])-[C:12] | 62 | [{"value": 62.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\\C=C\\CC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O\\C=C... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (400 mg, 0.698 mmol), 1-bromo-4-ethyl-4-triethylsilyloxy-(2E)-hexene (0.897 g, 2.79 mmol), sodium hydride (60% in oil, 0.168 g, 4.188 mmol), 15-crown-5 (0.14 ml, 0.698 mmol) and tetrahydrofuran (12 ml) were subjected to reaction using a proc... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(C/C=C/Br)O[Si](CC)(CC)CC>O1CCCC1>CCC(CC)(C/C=C/OC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-abf3dd53ffae4780b6342c0773508a49 | CC(C)(O)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O | CC(C)(C)[Si](C)(C)[O:20][C@@H:19]1[CH2:18][C:17]2=[CH:16][CH:15]=[C:14]3[C@@H:13]4[CH2:12][CH:11]=[C:10]([C:7]([O:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])([CH3:8])[CH3:9])[C@@:29]4([CH3:30])[CH2:28][CH2:27][C@@H:26]3[C@@:24]2([CH3:25])[C@@H:22]([O:23][Si](C)(C)C(C)(C)C)[CH2:21]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][O:6... | CC(C)(O)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 79 | [{"value": 79.0, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(2-hydroxy-2-methylpropoxy)-20-methylpregna-5,7,16-triene (35.6 mg, 0.0552 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (0.35 ml) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heatin... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | O1CCCC1 | null | null | CC(C)(O)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CC(C)(O)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-119241f1e30f4606852a9293fbdb4883 | CCC(O)(CC)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)C(COC(C)(C1=CC[C@H]2C3=CC=C4C[C@H](C[C@@H]([C@]4(C)[C@H]3CC[C@]12C)O)O)C)(CC)O | CC(C)(C)[Si](C)(C)[O:22][C@@H:21]1[CH2:20][C:19]2=[CH:18][CH:17]=[C:16]3[C@@H:15]4[CH2:14][CH:13]=[C:12]([C:9]([O:8][CH2:7][C:3]([CH2:2][CH3:1])([OH:4])[CH2:5][CH3:6])([CH3:10])[CH3:11])[C@@:31]4([CH3:32])[CH2:30][CH2:29][C@@H:28]3[C@@:26]2([CH3:27])[C@@H:24]([O:25][Si](C)(C)C(C)(C)C)[CH2:23]1>>[CH3:1][CH2:2][C:3]([OH:... | CCC(O)(CC)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC(O)(CC)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 94 | [{"value": 94.0, "product": "C(C)C(COC(C)(C1=CC[C@H]2C3=CC=C4C[C@H](C[C@@H]([C@]4(C)[C@H]3CC[C@]12C)O)O)C)(CC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "C(C)C(COC(C)(C1=CC[C@H]2C3=CC=C4C[C@H](C[C@@H]([C@]4(C)[C@H]3CC[C@]12C)O)O)C)(CC)O", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(2-ethyl-2-hydroxybutoxy)-20-methylpregna-5,7,16-triene (32.0 mg, 0.0475 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (0.3 ml, 0.3 mmol) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | O1CCCC1 | null | null | CCC(O)(CC)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CCC(O)(CC)COC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-805121a5f5d34460872e41c108db4b33 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC1(C)OC1CBr>>CC1(C)OC1COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.[H-].[Na+].BrCC1C(C)(C)O1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC1C(C)(C)O1)O[Si](C)(C)C(C)(C)C | [OH:7][CH2:8][C:9]1=[CH:10][CH2:11][C@H:12]2[C:13]3=[CH:14][CH:15]=[C:16]4[CH2:17][C@@H:18]([O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][C@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@:37]4([CH3:38])[C@H:39]3[CH2:40][CH2:41][C@:42]12[CH3:43].Br[CH2:6][CH:5... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC1(C)OC1CBr | CC1(C)OC1COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1=C(COCC2CO2)C2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[C:5]-[C:6]=[C:7](-[C:8]-[OH;D1;+0:9])-[C:10]>>[C:5]-[C:6]=[C:7](-[C:8]-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1)-[C:10] | 81.1 | [{"value": 81.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC1C(C)(C)O1)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC1C(C)(C... | null | null | null | null | A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (51.6 mg, 0.0947 mmol), sodium hydride (95%, 21.1 mg, 0.879 mmol) and 1-bromo-2,3-epoxy-3-methylbutane (91.2 mg, 0.553 mmol) in tetrahydrofuran (1 ml) was stirred at room temperature for 20 min. and refluxed under heating for 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CO1.C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1.C(C)(=O)OCC | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC1(C)OC1CBr>O1CCCC1.C(C)(=O)OCC>CC1(C)OC1COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7fd4f7d8e38425ba62bc91da9c29ed4 | CC1(C)OC1COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC([BH-](C(CC)C)C(CC)C)C.[Li+].[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC1C(C)(C)O1)O[Si](C)(C)C(C)(C)C.CCC([BH-](C(CC)C)C(CC)C)C.[Li+].[OH-].[Na+].OO>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O[Si](C)(C)C(C)(C)C | [CH3:1][C:2]1([CH3:3])[O:4][CH:5]1[CH2:6][O:7][CH2:8][C:9]1=[CH:10][CH2:11][C@H:12]2[C:13]3=[CH:14][CH:15]=[C:16]4[CH2:17][C@@H:18]([O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][C@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@:37]4([CH3:38])[C@H:39]3[CH2:40]... | CC1(C)OC1COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.C(C)(=O)OCC | Reduction | OtherReaction | fb68e1f7e7aa0012b71755c2e659c5ca3af240790d29315ee068c102a1263dc2 | ac77f1c31bbb4f9df2f7d9b876f6243f6ca37479f36d1e779ab0e1e90922def4 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | [#8:1]-[C:2]-[CH;D3;+0:3]1-[O;H0;D2;+0:4]-[C:5]-1(-[C;D1;H3:6])-[C;D1;H3:7]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[OH;D1;+0:4] | 87 | [{"value": 87.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)... | null | null | 1 | HOUR | At room temperature, a solution of 1.0M L-SELECTRIDE in tetrahydrofuran (0.25 ml, 0.25 mmol) was added to a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(2,3-epoxy-3-methylbutoxymethyl)androsta-5,7,16-triene (48.3 mg, 0.0768 mmol) in tetrahydrofuran (2 ml) and stirred at the same temperature for 1 hour. To the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | C1CO1 | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | O1CCCC1.C(C)(=O)OCC | null | 1 | CC1(C)OC1COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1.C(C)(=O)OCC>CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d8d9b3d9d69d439b898cc3da5dad74d8 | CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O | CC(C)(C)[Si](C)(C)[O:19][C@@H:18]1[CH2:17][C:16]2=[CH:15][CH:14]=[C:13]3[C@@H:12]4[CH2:11][CH:10]=[C:9]([CH2:8][O:7][CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[C@@:28]4([CH3:29])[CH2:27][CH2:26][C@@H:25]3[C@@:23]2([CH3:24])[C@@H:21]([O:22][Si](C)(C)C(C)(C)C)[CH2:20]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][O:7][C... | CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 82 | [{"value": 82.0, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutoxymethyl)androsta-5,7,16-triene (40.0 mg, 0.0634 mmol) and a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (0.4 ml, 0.4 mmol) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heating for 1 hour), worke... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | null | null | null | CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fcbac95b81c24dac8b57a9b0f6fda1a1 | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC1(C)OC1CBr>>CC(C)(O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC([BH-](C(CC)C)C(CC)C)C.[Li+].O1CCCC1.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.[H-].[Na+].BrCC1C(C)(C)O1.[OH-].[Na+].OO>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:7][C:8]([CH3:9])([CH3:10])[C:11]1=[CH:12][CH2:13][C@H:14]2[C:15]3=[CH:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:40])[C@H:41]3[CH2:42][CH2:43][C@:44]12[CH3:... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC1(C)OC1CBr | CC(C)(O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 582d7d0e2791030ab802c70e7bf642b8dfc7e3c25a708cf942edeab4e0e6f0ef | 826d1333eb2b345d0c50f458d857543fab5b748885fcae047c31a1171432bf9d | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[O;H0;D2;+0:3]-[C:4]-1(-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8]=[C:9](-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[OH;D1;+0:13])-[C:14]>>[C:7]-[C:8]=[C:9](-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[OH;D1;+0:3])-[C:14] | 93.2 | [{"value": 93.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(C)(C)O)[C@]4(CC[C@@H]3[... | null | null | 12 | HOUR | A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (67.7 mg, 0.118 mmol), sodium hydride (60% in oil, 40.0 mg, 1.00 mmol) and 1-bromo-2,3-epoxy-3-methylbutane (100 mg, 0.606 mmol) in tetrahydrofuran (1 ml) was refluxed under heating for 1.5 hours. To the thus obtained reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Tertiary alcohol | Ether.Tertiary alcohol | C1CO1 | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Br- | O1CCCC1.C(C)(=O)OCC | null | 12 | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC1(C)OC1CBr>O1CCCC1.C(C)(=O)OCC>CC(C)(O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-535b11fdc0c14b828a6d5ca418dab416 | C=CC(=O)N(C)C.CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>>CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Cl-].[NH4+].CN(C(C=C)=O)C.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.[H-].[Na+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]=[CH2:7].[OH:8][CH2:9][C:10]1=[CH:11][CH2:12][C@H:13]2[C:14]3=[CH:15][CH:16]=[C:17]4[CH2:18][C@@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][C@H:29]([O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[C@:38]4([CH3:39])[C@H:40... | C=CC(=O)N(C)C.CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | oxa-Michael addition | f7c7da7c78eb65b9b2c8f63d0f16c4d5887e45e01ac1a9ea608f777c535e8cd7 | d7c87de309863ac8797e1e336d1d5992291f9ca863376e68ebcf1e8fd5f0e442 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | [C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[C:8]-[C:9]=[C:10](-[C:11]-[OH;D1;+0:12])-[C:13]>>[C:8]-[C:9]=[C:10](-[C:11]-[O;H0;D2;+0:12]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[C:4](=[O;D1;H0:5])-[#7:2](-[C;D1;H3:1])-[C;D1;H3:3])-[C:13] | 93.2 | [{"value": 92.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(... | null | null | 30 | MINUTE | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-hydroxymethylandrosta-5,7,16-triene (951 mg, 1.75 mmol) in tetrahydrofuran (17.5 ml), was added sodium hydride (60% in oil, 105 mg, 2.62 mmol), followed by stirring under nitrogen stream at room temperature for 30 min. After adding N,N-dimethylacrylamide (540 mg... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Vinyl | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | O1CCCC1 | null | 0.5 | C=CC(=O)N(C)C.CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>O1CCCC1>CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa466e4402f844efbbd164d3cf1c23bb | CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Cl-].[NH4+].Cl[Ce](Cl)Cl.O1CCCC1.C(C)[Mg]Br.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C.O1CCCC1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(CC)(O)CC)O[Si](C)(C)C(C)(C)C | CN([C:3](=[O:4])[CH2:7][CH2:8][O:9][CH2:10][C:11]1=[CH:12][CH2:13][C@H:14]2[C:15]3=[CH:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:40])[C@H:41]3[CH2:42][CH2:43][... | CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC(O)(CC)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | null | Functional Group Interconversion | OtherReaction | 4e89bd3b6f1dae16ca265385a8e13d357db2ec6b1542aa318708859fb61ad9eb | 4d5323d9e013bb3a490067f70b6ce5c7da5f30c3fdbeb30b2d6862dc3cd4bb84 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-N(-[CH3;D1;+0:1])-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D4;+0:2](-[OH;D1;+0:3])(-[C:6]-[C;D1;H3:7])-[C:8]-[CH3;D1;+0:1] | 56 | [{"value": 56.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(CC)(O)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Tetrahydrofuran (11 ml) was mixed with anhydrous cerous (III) chloride (2.33 g, 9.46 mmol), stirred under nitrogen stream at room temperature for 30 min., cooled with ice, mixed with ethylmagnesium bromide (0.96 mol/l, 9.0 ml, 8.6 mmol) and stirred for 30 min. The reaction solution was mixed with a solution of 1α,3β-bi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Tertiary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | null | null | 0.5 | CN(C)C(=O)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-57fc10183ae24c289d5d5e52fdec0be2 | C=CC(=O)N(C)C.CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CN(C)C(=O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.CN(C(C=C)=O)C.[H-].[Na+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(=O)N(C)C)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]=[CH2:7].[OH:8][C:9]([CH3:10])([CH3:11])[C:12]1=[CH:13][CH2:14][C@H:15]2[C:16]3=[CH:17][CH:18]=[C:19]4[CH2:20][C@@H:21]([O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][C@H:31]([O:32][Si:33]([CH3:34])([CH3:35])[C:36]([CH3:37])([CH3:38])[CH3:39])[C@:40]... | C=CC(=O)N(C)C.CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CN(C)C(=O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | oxa-Michael addition | 714eaa0e6de1d85d58a88133b4d5e95857344ec278e90cde0496674a55b79739 | ea8641c928da9fe5f2bca5bb859dbb223e9e99eefdf70a15450fd2e768112e0a | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | [C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[C:8]-[C:9]=[C:10](-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[OH;D1;+0:14])-[C:15]>>[C:8]-[C:9]=[C:10](-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[O;H0;D2;+0:14]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[C:4](=[O;D1;H0:5])-[#7:2](-[C;D1;H3:1])-[C;D1;H3:3])-[C:15... | 47.1 | [{"value": 47.1, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(=O)N(C)C)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.1, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(=O)N(C)C)[C@]4(CC[C@@... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (200 mg, 0.36 mmol), N,N-dimethylacrylamide (107 mg, 1.08 mmol), sodium hydride (60% in oil, 23 mg, 0.56 mmol) and tetrahydrofuran (4 ml) were subjected to reaction using a procedure similar to that of Example 25(1) (17 hours at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Vinyl | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | O1CCCC1 | null | null | C=CC(=O)N(C)C.CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CN(C)C(=O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f76a56a7c1944a91b3e37927785e3331 | CN(C)C(=O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(=O)N(C)C)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.Cl[Ce](Cl)Cl.C(C)[Mg]Br.O1CCCC1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | N([C:3](=[O:4])[CH2:7][CH2:8][O:9][C:10]([CH3:11])([CH3:12])[C:13]1=[CH:14][CH2:15][C@H:16]2[C:17]3=[CH:18][CH:19]=[C:20]4[CH2:21][C@@H:22]([O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][C@H:32]([O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[C@:41]4([CH3:42])[C@H:43]3... | CN(C)C(=O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | null | Miscellaneous | OtherReaction | 73a53c3699641f342e1262e87a7f18e7e1a58b3ae6a2bb965100bc5ca5aa8072 | 874533d67f572a036e87d660456c519859ccdb0867854a53cf4201fd273afc22 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-N(-[CH3;D1;+0:5])-[CH3;D1;+0:6]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[OH;D1;+0:4])(-[C:7]-[C;D1;H3:8])-[CH2;D2;+0:5]-[CH3;D1;+0:6] | 51.7 | [{"value": 51.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(N,N-dimethylaminocarbonylethoxy)-20-methylpregna-5,7,16-triene (133 mg, 0.20 mmol), anhydrous cerous (III) chloride (2.17 g, 8.8 mmol), ethylmagnesium bromide (8.3 ml, 8.0 mmol) and tetrahydrofuran (10 ml) were subjected to reaction using a procedure similar to that of Example ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Tertiary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | null | null | null | CN(C)C(=O)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f1ca6185ce24e27b5c2376a8ade2ba8 | CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O | CC(C)(C)[Si](C)(C)[O:23][C@@H:22]1[CH2:21][C:20]2=[CH:19][CH:18]=[C:17]3[C@@H:16]4[CH2:15][CH:14]=[C:13]([C:10]([O:9][CH2:8][CH2:7][C:3]([CH2:2][CH3:1])([OH:4])[CH2:5][CH3:6])([CH3:11])[CH3:12])[C@@:32]4([CH3:33])[CH2:31][CH2:30][C@@H:29]3[C@@:27]2([CH3:28])[C@@H:25]([O:26][Si](C)(C)C(C)(C)C)[CH2:24]1>>[CH3:1][CH2:2][C... | CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 100 | [{"value": 100.0, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCC(CC)(O)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O", "details": "CALCULATEDPERCENTYIELD", "i... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(3-ethyl-3-hydroxypentyloxy)-20-methylpregna-5,7,16-triene (85 mg, 0.12 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (1.2 ml) and tetrahydrofuran (4.6 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (3 hours), worked up and... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | O1CCCC1 | null | null | CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CCC(O)(CC)CCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8eca95401ac24e66a48eeaee52e9b4de | CC(C)(C)OC(=O)CBr.CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>>CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.[H-].[Na+].C1COCCOCCOCCOCCO1.BrCC(=O)OC(C)(C)C>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:9][CH2:10][C:11]1=[CH:12][CH2:13][C@H:14]2[C:15]3=[CH:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:4... | CC(C)(C)OC(=O)CBr.CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4541d644834c1bca555c4310180b1edadd2271c26488a32c314314a2e4f9c76f | 1858e49e1dc71f5ec31a1f9e719a3d52cdbfbbd98e3e0f8a48e0f56789173453 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[C:10]=[C:11](-[C:12]-[OH;D1;+0:13])-[C:14]>>[C:9]-[C:10]=[C:11](-[C:12]-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[C:14] | 78.1 | [{"value": 78.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(=O)... | null | null | null | null | A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (1.0 g, 1.84 mmol), sodium hydride (60% in oil, 220 mg, 5.50 mmol), 15-crown-5 (400 mg, 1.82 mmol) and t-butyl bromoacetate (0.55 ml, 3.69 mmol) in tetrahydrofuran (20 ml) was refluxed under heating for 1 hour and 15 min. The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Ester.Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1.C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)CBr.CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>O1CCCC1.C(C)(=O)OCC>CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09f817b1421040bf81adda1049ebfd49 | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | O.[Cl-].[NH4+].[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C.C[Mg]Br.O1CCCC1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(C)(C)O)O[Si](C)(C)C(C)(C)C | CC(C)([CH3:3])[O:4][C:2](=O)[CH2:5][O:6][CH2:7][C:8]1=[CH:9][CH2:10][C@H:11]2[C:12]3=[CH:13][CH:14]=[C:15]4[CH2:16][C@@H:17]([O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][C@H:27]([O:28][Si:29]([CH3:30])([CH3:31])[C:32]([CH3:33])([CH3:34])[CH3:35])[C@:36]4([CH3:37])[C@H:38]3[CH2:39][CH2:40... | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 0b851953c6b990603b6c2ce705013e806d0e3ec15190715f96b2920bbd66bf77 | b84ab3aa125fecf72904a057d293902a2500c7c549137a262c925c1887e56d13 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-[CH3;D1;+0:1])-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=O)-[C:4]-[#8:5]>>[#8:5]-[C:4]-[C;H0;D4;+0:3](-[C;D1;H3:6])(-[CH3;D1;+0:1])-[OH;D1;+0:2] | 70.2 | [{"value": 70.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(C)(C)O)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.2, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(C)(C)O)O[... | null | null | 30 | MINUTE | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(tert-butoxycarbonylmethoxymethyl)androsta-5,7,16-triene (175 mg, 0.266 mmol) in tetrahydrofuran (4 ml), was added dropwise a 0.93M methylmagnesium bromide/tetrahydrofuran solution (3 ml, 2.79 mmol) at external temperature of −30° C., followed by stirring at the... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Tertiary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HO- | O1CCCC1 | null | 0.5 | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CC(C)(O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6c03d50094e243f4919677055cf73518 | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C.C(C)[Mg]Br.O1CCCC1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(CC)(O)CC)O[Si](C)(C)C(C)(C)C | CC(C)(C)O[C:3](=[O:4])[CH2:7][O:8][CH2:9][C:10]1=[CH:11][CH2:12][C@H:13]2[C:14]3=[CH:15][CH:16]=[C:17]4[CH2:18][C@@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][C@H:29]([O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[C@:38]4([CH3:39])[C@H:40]3[CH2:41][CH2:42][C@... | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 0b851953c6b990603b6c2ce705013e806d0e3ec15190715f96b2920bbd66bf77 | b84ab3aa125fecf72904a057d293902a2500c7c549137a262c925c1887e56d13 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C;H0;D4;+0:1](-[OH;D1;+0:2])(-[C:5]-[C;D1;H3:6])-[C:7]-[C;D1;H3:8] | 81.3 | [{"value": 81.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(CC)(O)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(CC)(O)C... | null | null | null | null | A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(tert-butoxycarbonylmethoxymethyl)androsta-5,7,16-triene (175 mg, 0.266 mmol) in tetrahydrofuran (4 ml) was subjected to reaction with a 0.96M ethylmagnesium bromide/tetrahydrofuran solution (3 ml, 2.88 mmol) using a procedure similar to that of Example 27(2) (exte... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Tertiary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | O1CCCC1 | null | null | CC(C)(C)OC(=O)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a773ccc2032d4a18904f46db6e89d973 | CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC(CC)(O)CC)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)C(COCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O)O)(CC)O | CC(C)(C)[Si](C)(C)[O:20][C@@H:19]1[CH2:18][C:17]2=[CH:16][CH:15]=[C:14]3[C@@H:13]4[CH2:12][CH:11]=[C:10]([CH2:9][O:8][CH2:7][C:3]([CH2:2][CH3:1])([OH:4])[CH2:5][CH3:6])[C@@:29]4([CH3:30])[CH2:28][CH2:27][C@@H:26]3[C@@:24]2([CH3:25])[C@@H:22]([O:23][Si](C)(C)C(C)(C)C)[CH2:21]1>>[CH3:1][CH2:2][C:3]([OH:4])([CH2:5][CH3:6]... | CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 72 | [{"value": 72.0, "product": "C(C)C(COCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O)O)(CC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "C(C)C(COCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O)O)(CC)O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-{2-ethyl-2-hydroxybutoxymethyl}androsta-5,7,16-triene (139 mg, 0.216 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (1.3 ml, 1.3 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (4 hours), worked u... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | O1CCCC1 | null | null | CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CCC(O)(CC)COCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e66355c7f5344561854354458ec36a7e | CC(C)(O)C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)C/C=C\OCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC#CC(C)(C)O)O.N1=CC=CC2=CC=CC=C12>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO\C=C/CC(C)(C)O)O | [CH3:1][C:2]([CH3:3])([OH:4])[C:5]#[C:6][CH2:7][O:8][CH2:9][C:10]1=[CH:11][CH2:12][C@H:13]2[C:14]3=[CH:15][CH:16]=[C:17]4[CH2:18][C@@H:19]([OH:20])[CH2:21][C@H:22]([OH:23])[C@:24]4([CH3:25])[C@H:26]3[CH2:27][CH2:28][C@:29]12[CH3:30]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5]/[CH:6]=[CH:7]\[O:8][CH2:9][C:10]1=[CH:11][CH2:12]... | CC(C)(O)C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)C/C=C\OCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | [Pd] | CO | Miscellaneous | OtherReaction | 2cb46d90d4ce375341220560e877f5d7e4c63abc1c248ae9e08e17759b4c1c9a | ab900cf836def760791838ce6e44f66c180fd21fe805999101fd878f395b1783 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | [C:1]=[C:2]-[C:3]-[#8:4]-[CH2;D2;+0:5]-[C;H0;D2;+0:6]#[C;H0;D2;+0:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;D1;H1:11]>>[C:1]=[C:2]-[C:3]-[#8:4]/[CH;D2;+0:5]=[CH;D2;+0:6]\[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;D1;H1:11] | 78 | [{"value": 78.0, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO\\C=C/CC(C)(C)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO\\C=C/CC(C)(C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | 1α,3β-Dihydroxy-17-(4-hydroxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene (78 mg, 0.189 mmol), quinoline (12.3 mg, 0.0952 mmol), 5% palladium/barium sulfate (16 mg) and methanol (5 ml) were stirred at room temperature for 2 hours under a hydrogen atmosphere. The reaction mixture was filtered, evaporated for rem... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Alkyne | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | [Pd].CO | null | null | CC(C)(O)C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C>[Pd].CO>CC(C)(O)C/C=C\OCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9953d635993c4e47977430099ff37e58 | CCC(O)(C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)CC>>CCC(O)(CC)C/C=C\OCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | C(C)C(C#CCOCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O)O)(CC)O.N1=CC=CC2=CC=CC=C12>>C(C)C(C\C=C/OCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O)O)(CC)O | [CH3:1][CH2:2][C:3]([OH:4])([CH2:5][CH3:6])[C:7]#[C:8][CH2:9][O:10][CH2:11][C:12]1=[CH:13][CH2:14][C@H:15]2[C:16]3=[CH:17][CH:18]=[C:19]4[CH2:20][C@@H:21]([OH:22])[CH2:23][C@H:24]([OH:25])[C@:26]4([CH3:27])[C@H:28]3[CH2:29][CH2:30][C@:31]12[CH3:32]>>[CH3:1][CH2:2][C:3]([OH:4])([CH2:5][CH3:6])[CH2:7]/[CH:8]=[CH:9]\[O:10... | CCC(O)(C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)CC | CCC(O)(CC)C/C=C\OCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | [Pd] | CO | Miscellaneous | OtherReaction | 2cb46d90d4ce375341220560e877f5d7e4c63abc1c248ae9e08e17759b4c1c9a | ab900cf836def760791838ce6e44f66c180fd21fe805999101fd878f395b1783 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | [C:1]=[C:2]-[C:3]-[#8:4]-[CH2;D2;+0:5]-[C;H0;D2;+0:6]#[C;H0;D2;+0:7]-[C:8](-[C:9])(-[C:10])-[O;D1;H1:11]>>[C:1]=[C:2]-[C:3]-[#8:4]/[CH;D2;+0:5]=[CH;D2;+0:6]\[CH2;D2;+0:7]-[C:8](-[C:9])(-[C:10])-[O;D1;H1:11] | null | [] | null | null | null | null | The fraction (0.3 g) containing 17-(4-ethyl-4-hydroxy-2-hexynyloxymethyl)-1α,3β-dihydroxyandrosta-5,7,16-triene obtained in Example 11 (2), 5% palladium/barium sulfate (0.3 g), quinoline (0.03 ml, 0.2538 mmol) and methanol (6.8 ml) were subjected to reaction using a procedure similar to that of Example 29(1) (4 hours) ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Alkyne | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | null | [Pd].CO | null | null | CCC(O)(C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)CC>[Pd].CO>CCC(O)(CC)C/C=C\OCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d6a628d7eb941198bff4b0c0a9ab257 | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>>CCC(CC)(CCCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.BrCCCC(CC)(O[Si](CC)(CC)CC)CC.CO.[OH-].[K+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C(C)(C)C | CC(=O)[S:9][CH2:10][C:11]1=[CH:12][CH2:13][C@H:14]2[C:15]3=[CH:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:40])[C@H:41]3[CH2:42][CH2:43][C@:44]12[CH3:45].Br[CH2:... | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(CCCBr)O[Si](CC)(CC)CC | CCC(CC)(CCCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | ac55b1813a50f413501bd3cd7115530e7b82e267a203d71b1e207485ab027747 | 2e4a9869295789d93ad40520a43348bbebd282f62196fc6899c2f5df92cb929d | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C(=O)-[S;H0;D2;+0:4]-[C:5]-[C:6](=[C:7]-[C:8])-[C:9]>>[C:8]-[C:7]=[C:6](-[C:5]-[S;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9] | 91.3 | [{"value": 91.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]... | null | null | 5 | MINUTE | To a solution of 17-acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (274 mg, 0.454 mmol) and 1-bromo-4-ethyl-4-(triethylsilyloxy)hexane (294 mg, 0.909 mmol) in tetrahydrofuran (2 ml), was added a 1M potassium hydroxide methanol solution (3 ml) under a nitrogen atmosphere, followed by stirri... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbo-thioester | Monosulfide | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | 0.083333 | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>O1CCCC1>CCC(CC)(CCCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6735f5f88fa44dda823410e416ee3fd | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)CCCCBr>>CC[Si](CC)(CC)OC(C)(C)CCCCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.BrCCCCC(C)(C)O[Si](CC)(CC)CC.CO.[OH-].[K+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCCCC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C | CC(=O)[S:16][CH2:17][C:18]1=[CH:19][CH2:20][C@H:21]2[C:22]3=[CH:23][CH:24]=[C:25]4[CH2:26][C@@H:27]([O:28][Si:29]([CH3:30])([CH3:31])[C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][C@H:37]([O:38][Si:39]([CH3:40])([CH3:41])[C:42]([CH3:43])([CH3:44])[CH3:45])[C@:46]4([CH3:47])[C@H:48]3[CH2:49][CH2:50][C@:51]12[CH3:52].Br[CH2... | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)CCCCBr | CC[Si](CC)(CC)OC(C)(C)CCCCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | ac55b1813a50f413501bd3cd7115530e7b82e267a203d71b1e207485ab027747 | 2e4a9869295789d93ad40520a43348bbebd282f62196fc6899c2f5df92cb929d | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C(=O)-[S;H0;D2;+0:4]-[C:5]-[C:6](=[C:7]-[C:8])-[C:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[C:5]-[C:6](=[C:7]-[C:8])-[C:9] | 93.4 | [{"value": 93.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCCCC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]1... | null | null | null | null | 17-Acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (262 mg, 0.434 mmol), 1-bromo-5-triethylsilyloxy-5-methylhexane (266 mg, 0.860 mmol), a 1M potassium hydroxide methanol solution (3 ml) and tetrahydrofuran (2 ml) were subjected to reaction using a procedure similar to that of Example 31(1)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbo-thioester | Monosulfide | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)CCCCBr>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)CCCCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3aa0f12e1abf4c07b006015c14a90f4e | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br>>CC[Si](CC)(CC)OC(C)(C)C/C=C/SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.Br\C=C\CC(C)(C)O[Si](CC)(CC)CC.CO.[OH-].[K+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CS\C=C\CC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C | CC(=O)[S:15][CH2:16][C:17]1=[CH:18][CH2:19][C@H:20]2[C:21]3=[CH:22][CH:23]=[C:24]4[CH2:25][C@@H:26]([O:27][Si:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][C@H:36]([O:37][Si:38]([CH3:39])([CH3:40])[C:41]([CH3:42])([CH3:43])[CH3:44])[C@:45]4([CH3:46])[C@H:47]3[CH2:48][CH2:49][C@:50]12[CH3:51].Br/[CH... | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br | CC[Si](CC)(CC)OC(C)(C)C/C=C/SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 414ef9d7284b3a3a3ca4f3037df8885fc317c70df763f998bdece1a30f85b3fd | 950082924a0524bfc0063f92485d7f4b587dbc9668e1d8f834d8cda3a56bc402 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4].C-C(=O)-[S;H0;D2;+0:5]-[C:6]-[C:7](=[C:8]-[C:9])-[C:10]>>[C:9]-[C:8]=[C:7](-[C:6]-[S;H0;D2;+0:5]/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4])-[C:10] | 90 | [{"value": 90.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CS\\C=C\\CC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C... | null | null | null | null | 17-Acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (304 mg, 0.504 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2E)-pentene (296 mg, 1.01 mmol), a 1M potassium hydroxide methanol solution (3 ml) and tetrahydrofuran (2 ml) were subjected to reaction using a procedure similar to that of Example... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Monosulfide | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)C/C=C/SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b40612350df64afcb83face9bc2e6092 | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC(C)(O)CCBr>>CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.BrCCC(C)(C)O.CO.[OH-].[K+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O[Si](C)(C)C(C)(C)C | CC(=O)[S:7][CH2:8][C:9]1=[CH:10][CH2:11][C@H:12]2[C:13]3=[CH:14][CH:15]=[C:16]4[CH2:17][C@@H:18]([O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][C@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@:37]4([CH3:38])[C@H:39]3[CH2:40][CH2:41][C@:42]12[CH3:43].Br[CH2:6]... | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC(C)(O)CCBr | CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | ac55b1813a50f413501bd3cd7115530e7b82e267a203d71b1e207485ab027747 | 2e4a9869295789d93ad40520a43348bbebd282f62196fc6899c2f5df92cb929d | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C(=O)-[S;H0;D2;+0:4]-[C:5]-[C:6](=[C:7]-[C:8])-[C:9]>>[C:8]-[C:7]=[C:6](-[C:5]-[S;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9] | 93 | [{"value": 93.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)... | null | null | null | null | 17-Acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (67.7 mg, 0.112 mmol), 1-bromo-3-hydroxy-3-methylbutane (93.5 mg, 0.560 mmol), 1M potassium hydroxide methanol solution (1 ml) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure similar to that of Example 31(1) (at room... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbo-thioester | Monosulfide | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC(C)(O)CCBr>O1CCCC1>CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ee07af8e70c4954abdedabfc16b7f64 | CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O | CC(C)(C)[Si](C)(C)[O:19][C@@H:18]1[CH2:17][C:16]2=[CH:15][CH:14]=[C:13]3[C@@H:12]4[CH2:11][CH:10]=[C:9]([CH2:8][S:7][CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[C@@:28]4([CH3:29])[CH2:27][CH2:26][C@@H:25]3[C@@:23]2([CH3:24])[C@@H:21]([O:22][Si](C)(C)C(C)(C)C)[CH2:20]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][S:7][C... | CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 95.5 | [{"value": 95.0, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-triene (63.5 mg, 0.0981 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (1 ml) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heating for... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Other | O1CCCC1 | null | null | CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1>CC(C)(O)CCSCC1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf7db74464e144219f9c73c4d6f70138 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>>C=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3[C@@]12C)O[Si](C)(C)C(C)(C)C.O1CCCC1.O1CCCC1.CC(C)([O-])C.[K+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@@]12C)=C)O[Si](C)(C)C(C)(C)C | [CH2:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH:8]=[C:9]4[CH2:10][C@@H:11]([O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][C@H:21]([O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[C@:30]4([CH3:31])[C@H:32]3[CH2:33][CH2:34][C@:35]12[CH3:36]>>[CH2:1]=[C:2]1[CH2:3][CH2:4]... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | C=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O.CCCCCC.CC(=O)C.CO | Miscellaneous | OtherReaction | 7c25aa6c39004c295ea8e39669430c4214ce17cd1d210263e8fa8499e631cdcc | 4741489b7ce48b1006256d06e81c9d9d68657901282cd304500858c7d1cda546 | C=C1CC[C@@H]2C1CC[C@@H]1C3CCCCC3=CC[C@@H]21 | [C:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-1>>[C:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[C;H0;D3;+0:7]-1=[C;D1;H2:8] | null | [] | 60 | CELSIUS | 2 | HOUR | A mixture of tetrahydrofuran (70 ml), methyltriphenylphosphonium bromide (50 g) and potassium t-butoxide (13.9 g) were stirred at 60° C. for 2 hours, while under suspension. To this suspension, was added 1α,3β-bis(tert-butyldimethylsilyloxy)androst-5-ene (18.7 g) and tetrahydrofuran (60 ml), followed by reaction for 2 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Vinyl | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | Other | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.CCCCCC.CC(=O)C.CO | 60 | 2 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.CCCCCC.CC(=O)C.CO>C=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72031b92e7964eb6b128206455f66ab4 | C=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.OO>>CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@@]12C)=C)O[Si](C)(C)C(C)(C)C.C12CCCC(CCC1)B2.[OH-].[Na+].OO>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][C:11]2=[CH:12][CH2:13][C@H:14]3[C@@H:15]4[CH2:16][CH2:17][C:18](=[CH2:19])[C@@:21]4([CH3:22])[CH2:23][CH2:24][C@@H:25]3[C@@:26]2([CH3:27])[C@@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37]1.O[OH:20]>>[CH3:1]... | C=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.OO | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 14323edfe0584e2510a42abdde4fbf731fb650ba7151b53acb5cab26e269514a | 4ceb30033bcfd57c382fe05e353b68e7f657859dbacaaa785451a244b2657476 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | O-[OH;D1;+0:1].[C:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8]-1=[CH2;D1;+0:9]>>[C:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[C:6]-[C:7]-[C@@H;D3;+0:8]-1-[CH2;D2;+0:9]-[OH;D1;+0:1] | null | [] | null | null | 4 | HOUR | To 1α,3β-bis(tert-butyldimethylsilyloxy)-17-methyleneandrost-5-ene (30.3 g), was added 9-borabicyclo[3,3,1]nonane (0.5M solution in tetrahydrofuran, 228 ml) and reacted by stirring at room temperature for 4 hours. Under cooling with ice, a 3M sodium hydroxide solution (150 ml) and then a 30% hydrogen peroxide solution ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Vinyl | Primary alcohol | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | Other | CO | null | 4 | C=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.OO>CO>CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b555da856334d37b2959f11092ad220 | C=CC(=O)N(C)C.CC(C)(C)[Si](C)(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>>CN(C)C(=O)CCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1CC(CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.CN(C(C=C)=O)C.[H-].[Na+].C1COCCOCCOCCOCCO1.[Cl-].[NH4+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH:6]=[CH2:7].[OH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C@@H:14]3[CH2:15][CH:16]=[C:17]4[CH2:18][CH:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][C@H:29]([O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[C@:38]4([CH3:39])[C@H... | C=CC(=O)N(C)C.CC(C)(C)[Si](C)(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | CN(C)C(=O)CCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | oxa-Michael addition | f7c7da7c78eb65b9b2c8f63d0f16c4d5887e45e01ac1a9ea608f777c535e8cd7 | d7c87de309863ac8797e1e336d1d5992291f9ca863376e68ebcf1e8fd5f0e442 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | [C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[C:4](=[O;D1;H0:5])-[#7:2](-[C;D1;H3:1])-[C;D1;H3:3] | 60.8 | [{"value": 60.8, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1α,3-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene (18.4 g), was added N,N-dimethylacrylamide (9.95 g), sodium hydride (60% in oil, 2.0 g), 15-crown-5 (2.2 g) and tetrahydrofuran (73.5 ml), followed by reaction at 0° C. for 8 hours. After stopping the reaction by adding a saturated aqueous ammoniu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Vinyl | Ether | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | null | O1CCCC1 | null | null | C=CC(=O)N(C)C.CC(C)(C)[Si](C)(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>O1CCCC1>CN(C)C(=O)CCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-679f47ec92954ed5999bb1baa4b6b5fd | CC(C)(C#N)N=NC(C)(C)C#N.CCCCCC.CN(C)C(=O)CCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.O=C1CCC(=O)N1Br>>CN(C)C(=O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.O=C1N=NC(=O)N1c1ccccc1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C.CCCCCC>>C1(=CC=CC=C1)N1C(N=NC1=O)=O.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)... | CC(C)(C#N)[N:47]=[N:48]C(C)(C)C#N.[CH3:52][CH2:57][CH2:56][CH2:55][CH2:54][CH3:53].[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][O:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C@@H:14]3[CH2:15][CH:16]=[C:17]4[CH2:18][C@@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][C@H:29]([O:30][... | CC(C)(C#N)N=NC(C)(C)C#N.CCCCCC.CN(C)C(=O)CCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.O=C1CCC(=O)N1Br | CN(C)C(=O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.O=C1N=NC(=O)N1c1ccccc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 83057f1ad2c8f1f7a09b95693a904e8d2b903f3ff7c23fef5e808847f97a5652 | bc22e3b1b2c63e1c9de6e4cce4e1e3342dd819aa8074d8f4b543ef014f34b736 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1.O=C1N=NC(=O)N1c1ccccc1 | Br-[N;H0;D3;+0:1]1-[C;H0;D3;+0:2](=[O;D1;H0:3])-C-C-[C;H0;D3;+0:4]-1=[O;D1;H0:5].C-C(-C)(-C#N)-[N;H0;D2;+0:6]=[N;H0;D2;+0:7]-C(-C)(-C)-C#N.[CH3;D1;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH3;D1;+0:13].[C:14]-[C:15](-[C:16])-[C@@H;D3;+0:17]1-[CH2;D2;+0:18]-[C:19]=[C:20](-[C:21])-[C:22]-[C:23]-1... | 140.2 | [{"value": 140.2, "product": "C1(=CC=CC=C1)N1C(N=NC1=O)=O.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(N,N-dimethylaminocarbonylethoxymethyl)androst-5-ene (15 g), were added N-bromosuccinimide (5.36 g), 2,2′-azobis isobutyronitrile (1.06 g), hexane (120 ml) and tetrahydrofuran (30 ml), followed by reflux under heating for 15 min. After cooling to room temperature, the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Diazene.Nitrile.Nitrile.Tertiary amide.Tertiary amide | Diazene.Substituted dicarboximide.Conjugated diene | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1.C1CC[NH]C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1.C1N=NC[NH]1.c1ccccc1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1.C1N=NC[NH]1.c1ccccc1 | HBr | O1CCCC1 | null | null | CC(C)(C#N)N=NC(C)(C)C#N.CCCCCC.CN(C)C(=O)CCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.O=C1CCC(=O)N1Br>O1CCCC1>CN(C)C(=O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.O=C1N=NC(=O)N1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5385123b715d4c92b06b49dff910a28e | CN(C)C(=O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | C1(=CC=CC=C1)N1C(N=NC1=O)=O.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C.O1CCCC1.CC(C)([O-])C.[K+]>>C1(=CC=CC=C1)N1C(N=NC1=O)=O.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C | CN(C)C(=O)CC[O:20][CH2:19][C@H:18]1[CH2:17][CH2:16][C@H:15]2[C:14]3=[CH:13][CH:12]=[C:11]4[CH2:10][C@@H:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:37][C@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@:26]4([CH3:27])[C@H:25]3[CH2:24][CH2:23][C@@:21]21[CH3:22]>>[CH3:... | CN(C)C(=O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | null | null | [Cl-].[Na+].O | Reduction | Cleavage of alkoxy ethers to alcohols | 60ac9a93d999cff681f127f66d1aed73076ddbd2f72a568d7688aea508340e75 | ed5b96494aea9c4ef78dc6eafcbfb0f1e3b4b57ea3d84f02d5723a8aad400f9f | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | C-N(-C)-C(=O)-C-C-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 80.1 | [{"value": 80.1, "product": "C1(=CC=CC=C1)N1C(N=NC1=O)=O.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(N,N-dimethylaminocarbonylethoxymethyl)androsta-5,7-diene 4-phenyl-1,2,4-triazoline-3,5-dione adduct (9 g), were added tetrahydrofuran (90 ml) and then potassium t-butoxide (10.5 g), followed by reaction at room temperature for 10 min. After stopping the reaction by adding s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide | Primary alcohol | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | HO- | [Cl-].[Na+].O | null | null | CN(C)C(=O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>[Cl-].[Na+].O>CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4ff8f2783c34484a23ef81f6b6b95cc | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>>C[C@]12CC[C@H]3C(=CC=C4C[C@@H](O)C[C@H](O)[C@@]43C)[C@@H]1CC[C@@H]2CO | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O | CC(C)(C)[Si](C)(C)[O:12][C@@H:11]1[CH2:10][C:9]2=[CH:8][CH:7]=[C:6]3[C@H:5]([CH2:4][CH2:3][C@@:2]4([CH3:1])[C@H:18]3[CH2:19][CH2:20][C@@H:21]4[CH2:22][OH:23])[C@@:16]2([CH3:17])[C@@H:14]([O:15][Si](C)(C)C(C)(C)C)[CH2:13]1>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C:6](=[CH:7][CH:8]=[C:9]4[CH2:10][C@@H:11]([OH:12])[CH2:13]... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | C[C@]12CC[C@H]3C(=CC=C4C[C@@H](O)C[C@H](O)[C@@]43C)[C@@H]1CC[C@@H]2CO | null | null | C(C)(=O)OCC | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 96.2 | [{"value": 96.2, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androsta-5,7-diene (1.0 g), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (11 ml), followed by reflux for 6 hours. After adding ethyl acetate, the reaction mixture was washed with saturated brine, a saturated aqueous sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@H]3CCC[C@H]3C2=C1 | Other | C(C)(=O)OCC | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1>C(C)(=O)OCC>C[C@]12CC[C@H]3C(=CC=C4C[C@@H](O)C[C@H](O)[C@@]43C)[C@@H]1CC[C@@H]2CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-851c9b370e384106b3146c8a63abe960 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>>CCC(CC)(CCCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | BrCCCC(CC)(O[Si](CC)(CC)CC)CC.[H-].[K+].C1COCCOCCOCCOCCOCCO1.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.[Cl-].[NH4+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C... | [OH:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]2[C@@H:15]3[CH2:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:40])[C@H:41]3[CH2:42][CH2:43][C@:44]12[CH3:45].Br[CH2:... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CCC(CC)(CCCBr)O[Si](CC)(CC)CC | CCC(CC)(CCCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 99.6 | [{"value": 99.6, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene (11.0 g) was dissolved in tetrahydrofuran. Under cooling with ice, potassium hydride (30% in oil, 200.3 g) and 18-crown-6 (2.64 g) were added to the solution, which was then stirred for 5 min. 1-Bromo-4-ethyl-4-(triethylsilyloxy)hexane (25.91 g) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | HBr | O1CCCC1 | null | 0.083333 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>O1CCCC1>CCC(CC)(CCCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d995151a34f5417984c86604a34de416 | CCC(CC)(CCCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC>>CCC(CC)(CCCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | C1(=CC=CC=C1)N1C(N=NC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C(C)(C)C.BrN1C(CCC1=O)=O>>C1(=CC=CC=C1)N1C(N=NC1=O)=O.[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@... | [CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([CH2:6][CH2:7][CH2:8][O:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]2[C@@H:15]3[CH2:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH... | CCC(CC)(CCCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | CCC(CC)(CCCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | CCCCCC | Oxidation | OtherReaction | 59e599993b7b3b967c8da247b1e66f54ad495c7a1835473b960fabbca47978b2 | 0b9fdf82b0e2b620f0b6676b9714eb5a5219404b4adc877f914530378ab5be4a | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | [C:1]-[C:2](-[C:3])-[C@@H;D3;+0:4]1-[CH2;D2;+0:5]-[C:6]=[C:7](-[C:8])-[C:9]-[C:10]-1-[C:11]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[C:6]=[C:7](-[C:8])-[C:9]-[C:10]-1-[C:11] | null | [] | null | null | null | null | To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androst-5-ene (1.0 g), were added hexane (15 ml), N-bromosuccinimide (336.4 mg) and then 2,2′-azobis isobutyronitrile (77.6 mg), followed by reaction under reflux for 30 min. After cooling with ice, the mixture was filtered to remo... | 10.6084/m9.figshare.5104873.v1 | null | null | Conjugated diene | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | null | CCCCCC | null | null | CCC(CC)(CCCOC[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC>CCCCCC>CCC(CC)(CCCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9a7ef79a04e4412a1b1f87986ec6afe | CC(C)(O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O | CC(C)(C)[Si](C)(C)[O:19][C@@H:18]1[CH2:17][C:16]2=[CH:15][CH:14]=[C:13]3[C@@H:12]4[CH2:11][CH2:10][C@H:9]([CH2:8][O:7][CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[C@@:28]4([CH3:29])[CH2:27][CH2:26][C@@H:25]3[C@@:23]2([CH3:24])[C@@H:21]([O:22][Si](C)(C)C(C)(C)C)[CH2:20]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][O:7]... | CC(C)(O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | C(C)(=O)OCC | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 91.7 | [{"value": 91.7, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COCCC(C)(C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(3-hydroxy-3-methylbutoxymethyl)androsta-5,7-diene (700 mg), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (20 ml), followed by reaction for 6 hours. After adding ethyl acetate, the reaction mixture was washed with saturated brine, a saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | Other | C(C)(=O)OCC | null | null | CC(C)(O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>C(C)(=O)OCC>CC(C)(O)CCOC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b7011ffb0c84fa6b7126d0ffa4f7f41 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CS(=O)(=O)Cl>>CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](COS(C)(=O)=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.C(C)N(CC)CC.CS(=O)(=O)Cl>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COS(=O)(=O)C)O[Si](C)(C)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][C:11]2=[CH:12][CH:13]=[C:14]3[C@@H:15]4[CH2:16][CH2:17][C@H:18]([CH2:19][OH:20])[C@@:25]4([CH3:26])[CH2:27][CH2:28][C@@H:29]3[C@@:30]2([CH3:31])[C@@H:32]([O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[CH2:41]1.Cl[S:21]([C... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CS(=O)(=O)Cl | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](COS(C)(=O)=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 | null | null | O1CCCC1.CCCCCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 91 | [{"value": 91.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COS(=O)(=O)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)COS(=... | 0 | CELSIUS | 1 | HOUR | A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androsta-5,7-diene (150 mg, 0.274 mmol) and triethylamine (0.153 ml, 1.10 mmol) in tetrahydrofuran (2.3 ml) was cooled to 0° C., followed by the addition of methanesulfonyl chloride (63 μl, 0.814 mmol) and stirring at 0° C. for 1 hour. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | HCl | O1CCCC1.CCCCCC | 0 | 1 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](CO)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CS(=O)(=O)Cl>O1CCCC1.CCCCCC>CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@@H]4CC[C@H](COS(C)(=O)=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bde3da8b39744ff283da6cf2d0b42318 | CC(=O)SC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC(C)(O)CCBr>>CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSC(C)=O)O[Si](C)(C)C(C)(C)C.BrCCC(C)(O)C.CO.[OH-].[K+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O[Si](C)(C)C(C)(C)C | CC(=O)[S:7][CH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]2[C:13]3=[CH:14][CH:15]=[C:16]4[CH2:17][C@@H:18]([O:19][Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][C@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@:37]4([CH3:38])[C@H:39]3[CH2:40][CH2:41][C@:42]12[CH3:43].Br[CH2:... | CC(=O)SC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC(C)(O)CCBr | CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | ac55b1813a50f413501bd3cd7115530e7b82e267a203d71b1e207485ab027747 | 2e4a9869295789d93ad40520a43348bbebd282f62196fc6899c2f5df92cb929d | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C(=O)-[S;H0;D2;+0:4]-[C:5]-[C:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[C:5]-[C:6] | 90.5 | [{"value": 90.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC... | null | null | 1 | HOUR | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(acetylthiomethyl)androsta-5,7-diene (135 mg, 0.223 mmol) and 4-bromo-2-methylbutan-2-ol (186 mg, 1.12 mmol) in tetrahydrofuran (1.5 ml), was added a 1M potassium hydroxide methanol solution (1.5 ml), followed by stirring at room temperature for 1 hour. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbo-thioester | Monosulfide | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | HBr | O1CCCC1 | null | 1 | CC(=O)SC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CC(C)(O)CCBr>O1CCCC1>CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a56bf1980954911b5d4f2db94f288e4 | CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>>CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O[Si](C)(C)C(C)(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O | CC(C)(C)[Si](C)(C)[O:19][C@@H:18]1[CH2:17][C:16]2=[CH:15][CH:14]=[C:13]3[C@@H:12]4[CH2:11][CH2:10][C@H:9]([CH2:8][S:7][CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[C@@:28]4([CH3:29])[CH2:27][CH2:26][C@@H:25]3[C@@:23]2([CH3:24])[C@@H:21]([O:22][Si](C)(C)C(C)(C)C)[CH2:20]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][S:7]... | CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.C(C)(=O)OCC | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3C2=C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](=[C:5])-[C:6]-[C:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:9]-1>>[C:5]=[C:4]1-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-[C:7](-[OH;D1;+0:8])-[C:6]-1 | 84 | [{"value": 84.0, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@@]12C)CSCCC(C)(C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7-diene (130 mg, 0.215 mmol) in tetrahydrofuran (1 ml), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (2.15 ml, 2.15 mmol), followed by reflux under heating for 5 hours. The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3C2=C1 | Other | O1CCCC1.C(C)(=O)OCC | null | null | CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C>O1CCCC1.C(C)(=O)OCC>CC(C)(O)CCSC[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-917ca00bfa7848439af464b8b18dd5bb | CNN.COc1ccc(OC)c(C(=O)O)c1.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>COc1ccc(OC)c(C(=S)N(C)N)c1 | C1CCC(CC1)N=C=NC2CCCCC2.COC1=C(C(=O)O)C=C(C=C1)OC.CNN.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>CN(N)C(C1=C(C=CC(=C1)OC)OC)=S | [NH:12]([CH3:13])[NH2:14].O=[C:10](O)[c:9]1[c:6]([O:7][CH3:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:11])S2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([C:10](=[S:11])[N:12]([CH3:13])[NH2:14])[cH:15]1 | CNN.COc1ccc(OC)c(C(=O)O)c1.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | COc1ccc(OC)c(C(=S)N(C)N)c1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 47d7c2005d1e7811627afd45f1badff9791a2fb612e24bc6785162cdb2f64974 | bfbc8035f907b8a9898ad994e28561387663bddd432650d77e24e3cb196c5bc2 | c1ccccc1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[N;D1;H2:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[N;D1;H2:8])-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[c:3](:[c:4]):[c:5] | 116.8 | [{"value": 82.0, "product": "CN(N)C(C1=C(C=CC(=C1)OC)OC)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 116.8, "product": "CN(N)C(C1=C(C=CC(=C1)OC)OC)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | DCC (4.5 g, 21.8 mmol) was added in one portion to a solution of 2,5-dimethoxybenzoic acid (3.6 g, 20 mol), methylhydrazine (1.2 ml, 23 mmol) and DMAP (30 mg, cat.) in CH2Cl2(60 ml) cooled in an ice bath. The reaction mixture was stirred overnight at room temperature. The slurry was cooled at −20° C. for 1 h and filter... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ether.Ether.Monosulfide.Monosulfide | Hydrazine.Thioamide | c1ccccc1.P1SPS1.c1ccccc1 | null | c1ccccc1 | Other | CN(C)C=1C=CN=CC1.C(Cl)Cl.C(C)(=O)OCC | null | 8 | CNN.COc1ccc(OC)c(C(=O)O)c1.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>CN(C)C=1C=CN=CC1.C(Cl)Cl.C(C)(=O)OCC>COc1ccc(OC)c(C(=S)N(C)N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16183485148f4b48b77ba0ac5d33f916 | NN>>c1ccnnc1 | NN.N[C@@H](CCC(N)=O)C(=O)O>>N1=NC=CC=C1.N[C@@H](CCC(N)=O)C(=O)O | [NH2:14][NH2:15]>>[cH:11]1[cH:12][cH:13][n:14][n:15][cH:16]1 | NN | c1ccnnc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3cc0159d461fee0fd6cc80b5d78917c7ffe2a593cffe4d961936985f7fad1d5f | ee3fba3c00b79a80c27ae38af6a02a8b0939483a226bcd6fe6c12c9f7aba8e28 | c1ccnnc1 | [NH2;D1;+0:1]-[NH2;D1;+0:2]>>[c:3]1:[c:4]:[c:5]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[c:6]:1 | 5 | [{"value": 5.0, "product": "N1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | FIG. 2 depicts a schematic diagram 200 depicting the treatment of hydrazine waste to glutamine or a derivative thereof, in accordance with a preferred embodiment of the present invention. The hydrogenization of pyridazine using 5% Pd/C can provide glutamine in a 45% yield. Although this pyridazine is not easily biodegr... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine | null | null | c1ccnnc1 | c1ccnnc1 | Other | null | null | null | NN>>c1ccnnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-74e87f9a12ac48378338e6e65b39ebfc | CCC(C)=O.CCCC=O.CCCCC(C=O)CC>>CCCC(=O)CCC.CCCC=CC(C)=O.CCCCCC(=O)CC.CCCCCC(C)=O | C(C)C(C=O)CCCC.C(CCC)=O.C(C)C(=O)C>>C(CCCC)C(=O)C.C(CCC)=CC(C)=O.C(CC)C(=O)CCC.CCC(CCCCC)=O | [CH3:21][C:22](=[O:23])[CH2:24][CH3:25].[CH3:9][CH2:10][CH2:11][CH:12]=[O:16].[CH:1]([CH:4]([CH2:6][CH3:7])[CH2:30][CH2:29][CH2:28][CH3:17])=[O:5]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[CH2:6][CH2:7][CH3:8].[CH3:9][CH2:10][CH2:11][CH:12]=[CH:13][C:14]([CH3:15])=[O:16].[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23]... | CCC(C)=O.CCCC=O.CCCCC(C=O)CC | CCCC(=O)CCC.CCCC=CC(C)=O.CCCCCC(=O)CC.CCCCCC(C)=O | null | null | C(C(C)C)C(=O)C | C-C Coupling | OtherReaction | c863ff4502a4872a6e4a37d5c6a5043afe51243a70baf7fc6f67034ac154a1ef | ae04af4f751dea9f079b0e8a3c2680e7045a9ae69ebb7a0d2e3b92543677c2db | null | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[CH2;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[CH3;D1;+0:7])-[CH;D2;+0:8]=[O;H0;D1;+0:9].[C:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13].[C:14]-[C:15]-[CH;D2;+0:16]=[O;H0;D1;+0:17]>>[C;D1;H3:18]-[CH2;D2;+0:7]-[C:6]-[C;H0;D3;+0:5](=[O;H0;D1;+0:9])-[C:19]-[C:20]-[CH3;D1;+0:8].[C;D1;H3:21]-[C:22]-[CH2;D2... | null | [] | null | null | null | null | U.S. Pat. No. 2,088,018 describes the preparation of secondary alcohols by simple aldol condensation of aldehydes, namely 2-ethylhexaldehyde and butyraldehyde, onto ketones, namely methyl ethyl ketone, methyl amyl ketone, methyl isobutyl ketone, butylideneacetone, dipropyl ketone and methylheptanone, and the subsequent... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ketone | Ketone.Ketone.Ketone.Ketone | null | null | null | Other | C(C(C)C)C(=O)C | null | null | CCC(C)=O.CCCC=O.CCCCC(C=O)CC>C(C(C)C)C(=O)C>CCCC(=O)CCC.CCCC=CC(C)=O.CCCCCC(=O)CC.CCCCCC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-385a60180831478591c2e7f190c4b233 | C=COCCCCCCOC=C.OCCCCCCO>>C=COCCCCCCO | C([O-])([O-])=O.[Na+].[Na+].C(CCCCCO)O.C(C)(=O)OC=C.C(=C)OCCCCCCOC=C>>C(=C)OCCCCCCO | C=COCCCCCCO[CH:2]=[CH2:1].[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10]>>[CH2:1]=[CH:2][O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10] | C=COCCCCCCOC=C.OCCCCCCO | C=COCCCCCCO | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 84ff68ba5901d637da9c9d96551f0a1d17ca7657a982fa1072af8fd2b0b32d3b | 509a7a4b565cd49ff866c9f0586bc0ffa851a5f12533282130d9eeb123692a41 | null | C=C-O-C-C-C-C-C-C-O-[CH;D2;+0:1]=[C;D1;H2:2].[C:3]-[C:4]-[OH;D1;+0:5]>>[C:3]-[C:4]-[O;H0;D2;+0:5]-[CH;D2;+0:1]=[C;D1;H2:2] | null | [] | 100 | CELSIUS | 6 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,6-hexanediol (118 mg, 1 mmol) and vinyl acetate (344 mg, 4 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 6 hours. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Vinyl.Vinyl | Ether | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 6 | C=COCCCCCCOC=C.OCCCCCCO>C1(=CC=CC=C1)C>C=COCCCCCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c6dfb5bc8847406e9ee7580fa7097c57 | C=COC12CC3CC(C1)CC(OC=C)(C3)C2.OC12CC3CC(C1)CC(O)(C3)C2>>C=COC12CC3CC(CC(O)(C3)C1)C2 | C([O-])([O-])=O.[Na+].[Na+].C12(CC3(CC(CC(C1)C3)C2)O)O.C(C)(=O)OC=C.C(=C)OC12CC3(CC(CC(C1)C3)C2)OC=C>>C(=C)OC12CC3(CC(CC(C1)C3)C2)O | C=COC12CC3CC(C1)CC(O[CH:2]=[CH2:1])(C3)C2.[OH:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][C:10]([OH:11])([CH2:12]3)[CH2:13]1)[CH2:14]2>>[CH2:1]=[CH:2][O:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][C:10]([OH:11])([CH2:12]3)[CH2:13]1)[CH2:14]2 | C=COC12CC3CC(C1)CC(OC=C)(C3)C2.OC12CC3CC(C1)CC(O)(C3)C2 | C=COC12CC3CC(CC(O)(C3)C1)C2 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 5411ddf257e28c4fcac9f3bbf029b667684799b45386358bb0a46d43aed6f2f0 | 3d4b98bfc4b1b8d1e4c33891a182aafedfecac35089df3e0715a245c9efed478 | C1C2CC3CC1CC(C2)C3 | C=C-O-C12-C-C3-C-C(-C-1)-C-C(-O-[CH;D2;+0:1]=[C;D1;H2:2])(-C-3)-C-2.[C:3]-[C:4](-[OH;D1;+0:5])(-[C:6])-[C:7]>>[C:3]-[C:4](-[O;H0;D2;+0:5]-[CH;D2;+0:1]=[C;D1;H2:2])(-[C:6])-[C:7] | null | [] | 100 | CELSIUS | 5 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,3-adamantanediol (1 mmol) and vinyl acetate (6 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 5 hours. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary alcohol.Vinyl.Vinyl | Ether | C1C2CC3CC1CC(C2)C3 | null | C1C2CC3CC1CC(C2)C3 | HO- | C1(=CC=CC=C1)C | 100 | 5 | C=COC12CC3CC(C1)CC(OC=C)(C3)C2.OC12CC3CC(C1)CC(O)(C3)C2>C1(=CC=CC=C1)C>C=COC12CC3CC(CC(O)(C3)C1)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-504342d31d0a441d9ce7df3f5695b57d | C=COC12CC3CC(O)(C1)CC(OC=C)(C3)C2.OC12CC3CC(O)(C1)CC(O)(C3)C2>>C=COC12CC3CC(O)(CC(O)(C3)C1)C2 | C([O-])([O-])=O.[Na+].[Na+].C12(CC3(CC(CC(C1)C3)(C2)O)O)O.C(C)(=O)OC=C.C(=C)OC12CC3(CC(CC(C1)(C3)OC=C)C2)O.C(=C)OC12CC3(CC(CC(C1)C3)(C2)OC=C)OC=C>>C(=C)OC12CC3(CC(CC(C1)C3)(C2)O)O | C=COC12CC3CC(O)(C1)CC(O[CH:2]=[CH2:1])(C3)C2.[OH:3][C:4]12[CH2:5][CH:6]3[CH2:7][C:8]([OH:9])([CH2:10][C:11]([OH:12])([CH2:13]3)[CH2:14]1)[CH2:15]2>>[CH2:1]=[CH:2][O:3][C:4]12[CH2:5][CH:6]3[CH2:7][C:8]([OH:9])([CH2:10][C:11]([OH:12])([CH2:13]3)[CH2:14]1)[CH2:15]2 | C=COC12CC3CC(O)(C1)CC(OC=C)(C3)C2.OC12CC3CC(O)(C1)CC(O)(C3)C2 | C=COC12CC3CC(O)(CC(O)(C3)C1)C2 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 5e2557d8390ce5e5031ff4061978a5df7a5894ecb5b1c87aa0ac5f6af1da458c | a7f89e1882cdb2909dd701fc44e8118d7023049a5b1500a5a5aabb84f2aa72bc | C1C2CC3CC1CC(C2)C3 | C=C-O-C12-C-C3-C-C(-O)(-C-1)-C-C(-O-[CH;D2;+0:1]=[C;D1;H2:2])(-C-3)-C-2.[C:3]-[C:4](-[OH;D1;+0:5])(-[C:6])-[C:7]>>[C:3]-[C:4](-[O;H0;D2;+0:5]-[CH;D2;+0:1]=[C;D1;H2:2])(-[C:6])-[C:7] | null | [] | 100 | CELSIUS | 5 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,3,5-adamantanetriol (1 mmol) and vinyl acetate (9 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 5 hours. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary alcohol.Tertiary alcohol.Vinyl.Vinyl | Ether | C1C2CC3CC1CC(C2)C3 | null | C1C2CC3CC1CC(C2)C3 | HO- | C1(=CC=CC=C1)C | 100 | 5 | C=COC12CC3CC(O)(C1)CC(OC=C)(C3)C2.OC12CC3CC(O)(C1)CC(O)(C3)C2>C1(=CC=CC=C1)C>C=COC12CC3CC(O)(CC(O)(C3)C1)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b42039f3bdaf413c95f8ecda28d765ed | C=C(C)OCCCCCCCC.CCCCCCCCO>>CCCCCCCCOC(C)=O | C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)O.C(C)(=O)OC(=C)C.C(CCCCCCC)OC(C)(C)OCCCCCCCC.C(=C)(C)OCCCCCCCC>>C(C)(=O)OCCCCCCCC | CCCCCCCC[O:12][C:10](C)=[CH2:11].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=C(C)OCCCCCCCC.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 12ba798a7bffce408863524d31eb3a42a39322f073effb080907c6d58029487b | 6e85e98260bc6172724d060165d0fcfc69391dedb179e5c21597d647017827cb | null | C-C-C-C-C-C-C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](-C)=[CH2;D1;+0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:1] | null | [] | 100 | CELSIUS | 15 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and sodium carbonate (0.03 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and isopropenyl acetate (5 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 15 hours. The reaction mixture was analy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Vinyl | Ester | null | null | null | Other | C1(=CC=CC=C1)C | 100 | 15 | C=C(C)OCCCCCCCC.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb0ae9e5c0614e48b91c03afdb979d47 | C=C(C)OCCCCCCCC.CCCCCCCCO>>CCCCCCCCOC(C)=O | C(=C)(C)OCCCCCCCC.C(CCCCCCC)OC(C)(C)OCCCCCCCC.F[B-](F)(F)F.C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)O.C(C)(=O)OC(=C)C>>C(C)(=O)OCCCCCCCC | CCCCCCCC[O:12][C:10](C)=[CH2:11].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=C(C)OCCCCCCCC.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 12ba798a7bffce408863524d31eb3a42a39322f073effb080907c6d58029487b | 6e85e98260bc6172724d060165d0fcfc69391dedb179e5c21597d647017827cb | null | C-C-C-C-C-C-C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](-C)=[CH2;D1;+0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:1] | null | [] | 100 | CELSIUS | 15 | HOUR | To a mixture of bis(1,5-cyclooctadiene)iridium tetrafluoroborate [Ir(cod)2]+BF4− (0.01 mmol) and sodium carbonate (0.03 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and isopropenyl acetate (5 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 15 hours. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Vinyl | Ester | null | null | null | Other | C1(=CC=CC=C1)C | 100 | 15 | C=C(C)OCCCCCCCC.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac5dce3512a44a70a5b765db9973a4c7 | CCCCCCCCO.CCCCCCCCOC(C)=O>>CCCCCCCCOC(C)OC(C)=O | C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)O.C(C)(=O)OC=C.C(C)(=O)OCCCCCCCC.C(=C)OCCCCCCCC>>C(C)(=O)OC(C)OCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].CCCCCC[CH2:11][CH2:10][O:12][C:13]([CH3:14])=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH:10]([CH3:11])[O:12][C:13]([CH3:14])=[O:15] | CCCCCCCCO.CCCCCCCCOC(C)=O | CCCCCCCCOC(C)OC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 979b8325f6c86bd7f54883d4339d8941e9012bd27a51cce50286476d3a7986f1 | 9dc366785c78d3f697d5ebd42f23b786ef7a373defee7e9fd1a94b3dd2d792cb | null | C-C-C-C-C-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH;D3;+0:2](-[CH3;D1;+0:1])-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6] | null | [] | 100 | CELSIUS | 2 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and sodium carbonate (0.1 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (5 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mixture was analyzed by g... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester.Ether | null | null | null | Other | C1(=CC=CC=C1)C | 100 | 2 | CCCCCCCCO.CCCCCCCCOC(C)=O>C1(=CC=CC=C1)C>CCCCCCCCOC(C)OC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-780852031da347f0a2c25019e1f5cc01 | C=COC(C)=O.CCCCCCCCO>>CCCCCCCCOC(C)=O | C(O)([O-])=O.[Na+].C(CCCCCCC)O.C(C)(=O)OC=C.C(=C)OCCCCCCCC>>C(C)(=O)OCCCCCCCC | C=C[O:9][C:10]([CH3:11])=[O:12].O[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=COC(C)=O.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Transesterification | 1f62a48d697c8d05270b2586da78dd3983b9960afc30c6a9d1ec3949e81d4234 | 89037c7729098ddd0eec149343f13d88dc823f0d1194aa0a012d1107ef8d2f4e | null | C=C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4] | null | [] | 100 | CELSIUS | 2 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and sodium hydrogencarbonate (1.2 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (2 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mixture was analy... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Vinyl | Ester | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 2 | C=COC(C)=O.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13e0412b39c54058b57aa132f24b8794 | C=COC(C)=O.CCCCCCCCO>>CCCCCCCCOC(C)=O | C(=C)OCCCCCCCC.F[B-](F)(F)F.C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)O.C(C)(=O)OC=C>>C(C)(=O)OCCCCCCCC | C=C[O:9][C:10]([CH3:11])=[O:12].O[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=COC(C)=O.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Transesterification | 1f62a48d697c8d05270b2586da78dd3983b9960afc30c6a9d1ec3949e81d4234 | 89037c7729098ddd0eec149343f13d88dc823f0d1194aa0a012d1107ef8d2f4e | null | C=C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4] | null | [] | 100 | CELSIUS | 2 | HOUR | To a mixture of bis(1,5-cyclooctadiene)iridium tetrafluoroborate [Ir(cod)2]+BF4− (0.01 mmol) and sodium carbonate (0.6 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (2 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mixture was analyzed... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Vinyl | Ester | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 2 | C=COC(C)=O.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa8ea40883fd4d5a90129da3c6e88bf3 | C=COC(C)=O.CCCCCCCCO>>CCCCCCCCOC(C)=O | C(CCCCCCC)O.C(C)(=O)OC=C.C(=C)OCCCCCCCC>>C(C)(=O)OCCCCCCCC | C=C[O:9][C:10]([CH3:11])=[O:12].O[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=COC(C)=O.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Transesterification | 1f62a48d697c8d05270b2586da78dd3983b9960afc30c6a9d1ec3949e81d4234 | 89037c7729098ddd0eec149343f13d88dc823f0d1194aa0a012d1107ef8d2f4e | null | C=C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4] | null | [] | 100 | CELSIUS | 2 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and 4MgCO3-Mg(OH)2-5H2O (0.6 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (2 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mixture was analyzed b... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Vinyl | Ester | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 2 | C=COC(C)=O.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0d8f2c0bcb84cc8bc7bda50ca92ca8c | C=COC(C)=O.CCCCCCCCO>>CCCCCCCCOC(C)=O | C(C)N(CC)CC.C(CCCCCCC)O.C(C)(=O)OC=C.C(=C)OCCCCCCCC>>C(C)(=O)OCCCCCCCC | C=C[O:9][C:10]([CH3:11])=[O:12].O[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=COC(C)=O.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Transesterification | 1f62a48d697c8d05270b2586da78dd3983b9960afc30c6a9d1ec3949e81d4234 | 89037c7729098ddd0eec149343f13d88dc823f0d1194aa0a012d1107ef8d2f4e | null | C=C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4] | null | [] | 100 | CELSIUS | 2 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and triethylamine (0.6 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (2 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mixture was analyzed by gas ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Vinyl | Ester | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 2 | C=COC(C)=O.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9348e9232724437a8b3011be6c2796dc | C=COC(C)=O.CCCCCCCCO>>CCCCCCCCOC(C)=O | C(=C)OCCCCCCCC.F[B-](F)(F)F.C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)O.C(C)(=O)OC=C>>C(C)(=O)OCCCCCCCC | C=C[O:9][C:10]([CH3:11])=[O:12].O[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | C=COC(C)=O.CCCCCCCCO | CCCCCCCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Transesterification | 1f62a48d697c8d05270b2586da78dd3983b9960afc30c6a9d1ec3949e81d4234 | 89037c7729098ddd0eec149343f13d88dc823f0d1194aa0a012d1107ef8d2f4e | null | C=C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4] | null | [] | 100 | CELSIUS | 2 | HOUR | To a mixture of (1,5-cyclooctadiene)(acetonitrile)iridium tetrafluoroborate [Ir(cod) (CH3CN)]+BF4− (0.01 mmol) and sodium carbonate (0.6 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (2 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Vinyl | Ester | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 2 | C=COC(C)=O.CCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23d6d4ffa44348848a0b664c32a65c64 | C=COC(C)=O.C=COCCOCCOCCOC=C>>C=COCCOCCOCCOC(C)=O | C(C)(=O)[O-].[Na+].C(COCCOCCO)O.C(C)(=O)OC=C.C(=C)OCCOCCOCCO.C(=C)OCCOCCOCCOC=C>>C(C)(=O)OCCOCCOCCOC=C | C=C[O:12][C:13]([CH3:14])=[O:15].C=CO[CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH:2]=[CH2:1]>>[CH2:1]=[CH:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]([CH3:14])=[O:15] | C=COC(C)=O.C=COCCOCCOCCOC=C | C=COCCOCCOCCOC(C)=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 702a5c0357c1cd0d935ea1bb3ff21417ad2b347673544c22573bc5f20dde36f1 | 76a119fe11a2760904d23496e6a03c8ef2943f7f0eca5c1e59b734558929b11b | null | C=C-O-[CH2;D2;+0:1]-[C:2]-[#8:3].C=C-[O;H0;D2;+0:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7] | null | [] | 100 | CELSIUS | 6 | HOUR | To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and sodium acetate (1.2 mmol) in toluene (2.0 ml),triethylene glycol (1 mmol) and vinyl acetate (4 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 6 hours. The reaction mixture was analyzed by gas... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Vinyl.Vinyl | Ester | null | null | null | HO- | C1(=CC=CC=C1)C | 100 | 6 | C=COC(C)=O.C=COCCOCCOCCOC=C>C1(=CC=CC=C1)C>C=COCCOCCOCCOC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9fd399b1e47447c491fc9dd0e5816314 | Brc1ccccn1.Cc1cc(C)c(CC#N)c(C)c1>>Cc1cc(C)c(C(C#N)c2ccccn2)c(C)c1 | [NH4+].[Cl-].CC1=C(C(=CC(=C1)C)C)CC#N.BrC1=NC=CC=C1.CC(C)([O-])C.[K+]>>N1=C(C=CC=C1)C(C#N)C1=C(C=C(C=C1C)C)C | Br[c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][C:8]#[N:9])[c:16]([CH3:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH:7]([C:8]#[N:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[c:16]([CH3:17])[cH:18]1 | Brc1ccccn1.Cc1cc(C)c(CC#N)c(C)c1 | Cc1cc(C)c(C(C#N)c2ccccn2)c(C)c1 | null | null | CS(=O)C | C-C Coupling | Hurtley reaction | 8f95a6a4dbf65d683dbaed1144079febc7be23de24a7c40bb0b3588067e89135 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(Cc2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 4 | HOUR | Add dropwise over a 1-hour period a mixed solution of 2-(2,4,6-trimethylphenyl)ethanenitrile (20 g; 0.126 mol) and 2-bromopyridine (35 g; 0.22 mol) in DMSO (25 mL) to a solution of potassium t-butoxide (35 g; 0.31 mol) dissolved in DMSO (125 mL). After the addition, stir the mixture for 4 h at ambient temperature and s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | CS(=O)C | null | 4 | Brc1ccccn1.Cc1cc(C)c(CC#N)c(C)c1>CS(=O)C>Cc1cc(C)c(C(C#N)c2ccccn2)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-950f94b2156b4e3ba6cbaf232186d86d | CCOC(=O)CBr.Cc1cc(C)c(C(C#N)c2ccccn2)c(C)c1>>CCOC(=O)c1c(N)c(-c2c(C)cc(C)cc2C)c2ccccn12 | CC(C)([O-])C.[K+].BrCC(=O)OCC.N1=C(C=CC=C1)C(C#N)C1=C(C=C(C=C1C)C)C.C([O-])([O-])=O.[K+].[K+]>>NC=1C(=C2C=CC=CN2C1C(=O)OCC)C1=C(C=C(C=C1C)C)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[C:7](#[N:8])[CH:9]([c:10]1[c:11]([CH3:12])[cH:13][c:14]([CH3:15])[cH:16][c:17]1[CH3:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH2:8])[c:9](-[c:10]2[c:11]([CH3:12])[cH:13][c:14]([CH3:15])[cH:16][c:17]2[CH3:18])[c:19]2[cH:20][cH... | CCOC(=O)CBr.Cc1cc(C)c(C(C#N)c2ccccn2)c(C)c1 | CCOC(=O)c1c(N)c(-c2c(C)cc(C)cc2C)c2ccccn12 | null | null | CS(=O)C.[NH4+].[Cl-] | Aromatic Heterocycle Formation | OtherReaction | 02387becbb0a0174e67eb86acd80dfe071e3507fb464bb83cb9adde301540e54 | dbe50c1f4efdf7f701346d96862c76be1bb037ffd95658422881cd1a6cf8422f | c1ccc(-c2ccn3ccccc23)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[CH;D3;+0:10](-[C;H0;D2;+0:11]#[N;H0;D1;+0:12])-[c:13](:[c:14]):[n;H0;D2;+0:15]:[c:16]:[c:17]):[c:18](-[C;D1;H3:19]):[c:20]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:11](-[NH2;D1;+0:12]):[c;H0;D3;+0:10](-[c;H... | null | [] | 0 | CELSIUS | 1 | DAY | Slowly add dropwise ethyl bromoacetate (23 mL; 0.21 mol) over a 3-hour period to a mixture of 2-(2-pyridinyl)-2-(2,4,6-trimethylphenyl)-ethanenitrile (22.3 g; 0.094 mol) and potassium carbonate (78 g; 0.57 mol) suspended in DMSO (100 mL). Stir the mixture for 1 day, pour into an aqueous NH4Cl solution (ca. 1 L), and ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Nitrile | Ester.Primary amine | c1ccncc1 | c1ccn2cccc2c1 | c1ccccc1.c1ccn2cccc2c1 | HBr | CS(=O)C.[NH4+].[Cl-] | 0 | 24 | CCOC(=O)CBr.Cc1cc(C)c(C(C#N)c2ccccn2)c(C)c1>CS(=O)C.[NH4+].[Cl-]>CCOC(=O)c1c(N)c(-c2c(C)cc(C)cc2C)c2ccccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-44429aaa5f9c4912afa90daad3429515 | CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2.CCOC(=O)c1c(N)c(-c2c(C)cc(C)cc2C)c2ccccn12>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(O)c23)c(C)c1 | NC=1C(=C2C=CC=CN2C1C(=O)OCC)C1=C(C=C(C=C1C)C)C.CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C.COC(C)(C)OC.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(=CC=CC=C1)C>>CC=1C=C(C2=C(C=C3C(=CC=CN23)C2=C(C=C(C=C2C)C)C)N1)O | CC1([CH3:17])C2CC(=O)C1(CS(=O)(=O)O)[CH2:12][CH2:13]2.CCO[C:19]([c:18]1[n:11]2[cH:10][cH:9][cH:8][cH:14][c:21]2[c:7](-[c:6]2[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:24][c:22]2[CH3:23])[c:16]1[NH2:15])=[O:20]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH:13][c:14]2[n:15][c:16]([CH3:17]... | CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2.CCOC(=O)c1c(N)c(-c2c(C)cc(C)cc2C)c2ccccn12 | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(O)c23)c(C)c1 | null | null | null | C-C Coupling | OtherReaction | adee181db23e8f608a48d2c5ef58b9961d9c9d17bb6a2928e4d7bedb66dd5be0 | 5d1c49fd3b82c2013b6db54c337ac490521c2e95f871f3869fc30e0aec8dd54e | c1ccc(-c2cccn3c2cc2ncccc23)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:4](-[NH2;D1;+0:5]):[c;H0;D3;+0:6](-[c:7](:[c:8]):[c:9]):[c;H0;D3;+0:10]2:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:[c:14]:[n;H0;D3;+0:15]:1:2.C-C1(-[CH3;D1;+0:16])-C2-C-C(=O)-C-1(-C-S(-O)(=O)=O)-[CH2;D2;+0:17]-[CH2;D2;+0:18]-2>>[CH3;D1;+0:16]-[c;H0;D3;+0:4]1:[c... | null | [] | null | null | null | null | To a solution of 2-ethyl 2-amino-1-(2,4,6-trimethylphenyl)indolizine-3-carboxylate (19.2 g; 59.6 mmol) in 2,2-dimethoxypropane (100 mL), add dl-camphorsulfonic acid (0.2 g). Stir the mixture at reflux for 30 min and then distill slowly to remove ca. 60 mL of volatiles over a 30-minute period. Cool the solution to ambie... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine.Sulfonic acid | Aromatic alcohol | C1CC2CCC1C2.c1ccn2cccc2c1 | c1ccn2c(c1)cc1ncccc12 | c1ccccc1.c1ccn2c(c1)cc1ncccc12 | HO- | null | null | null | CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2.CCOC(=O)c1c(N)c(-c2c(C)cc(C)cc2C)c2ccccn12>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(O)c23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-448b30c85c3f44b9b5daf07c67a8ae6c | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(O)c23)c(C)c1.O=P(Cl)(Cl)Cl>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(Cl)c23)c(C)c1 | CC=1C=C(C2=C(C=C3C(=CC=CN23)C2=C(C=C(C=C2C)C)C)N1)O.OC1=CC(=NC=2C(=C3C=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C.P(=O)(Cl)(Cl)Cl>>ClC1=CC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C | O[c:19]1[cH:18][c:16]([CH3:17])[n:15][c:14]2[cH:13][c:12]3[c:7](-[c:6]4[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:24][c:22]4[CH3:23])[cH:8][cH:9][cH:10][n:11]3[c:21]21.O=P(Cl)(Cl)[Cl:20]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH:13][c:14]2[n:15][c:16]([CH3:17])[cH:18][c:19]([Cl:20])... | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(O)c23)c(C)c1.O=P(Cl)(Cl)Cl | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(Cl)c23)c(C)c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 11a2af47b57335970e56251de17e6ee61937240e53ea068e5b5ae61ecd817d06 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cccn3c2cc2ncccc23)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10](:[c:11]):[c:12]:2:1>>[C;D1;H3:5]-[c:4]1:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10](:[c:11]):[c:12]:2:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:3]:1 | null | [] | null | null | null | null | Heat at 100° C. for 1 h a solution of 4-hydroxy-2-methyl-10-(2,4,6-trimethylphenyl)pyridino-[2,3-b]indolizine 2-methyl-9-(2,4,6-trimethylphenyl)pyrido[2,3-b]-indolizin-4-ol (10.1 g; 32 mmol) in phosphorus oxychloride (60 mL), cool to ambient temperature, and concentrate in vacuo. Partition the residue into ice water an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccn2c(c1)cc1ncccc12 | c1ccn2c(c1)cc1ncccc12 | c1ccccc1.c1ccn2c(c1)cc1ncccc12 | HCl | null | null | null | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(O)c23)c(C)c1.O=P(Cl)(Cl)Cl>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(Cl)c23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2b444a23c00341c5a009ee678e673ced | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(Cl)c23)c(C)c1.NCCN>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(NCCN)c23)c(C)c1 | ClC1=CC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C.C(CN)N>>NCCNC1=CC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C | Cl[c:19]1[cH:18][c:16]([CH3:17])[n:15][c:14]2[cH:13][c:12]3[c:7](-[c:6]4[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:27][c:25]4[CH3:26])[cH:8][cH:9][cH:10][n:11]3[c:24]21.[NH2:20][CH2:21][CH2:22][NH2:23]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH:13][c:14]2[n:15][c:16]([CH3:17])[cH:18]... | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(Cl)c23)c(C)c1.NCCN | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(NCCN)c23)c(C)c1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | f25174d3f1cf7e2df5fcfaa6b1cf490b9776a217f28eb2d399728d8149e2491f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cccn3c2cc2ncccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9](:[c:10]):[c:11]:2:1.[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9](:[c:10]):[c:11]:2:1 | null | [] | null | null | null | null | Heat a solution of 4-chloro-2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]-indolizine (0.35 g, 1.04 mmol), and ethylene diamine (0.32 g, 1.04 mmol) in dry NMP (3 mL) at 100° C. for 5 h. Pour the cooled mixture onto water (30 mL) and extract twice with EtOAc (30 mL). Wash the combined extract with brine (30 mL), dry,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccn2c(c1)cc1ncccc12 | c1ccn2c(c1)cc1ncccc12 | c1ccccc1.c1ccn2c(c1)cc1ncccc12 | HCl | CN1CCCC1=O | null | null | Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(Cl)c23)c(C)c1.NCCN>CN1CCCC1=O>Cc1cc(C)c(-c2cccn3c2cc2nc(C)cc(NCCN)c23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d79be6d72524b4e94ffad33aa9b2707 | CCOc1ccc(CC(=O)NCCNc2cc(C)nc3cc4c(-c5c(C)cc(C)cc5C)cccn4c23)cc1OC>>CCOc1ccc(CCNCCNc2cc(C)nc3cc4c(-c5c(C)cc(C)cc5C)cccn4c23)cc1OC | N(C)(C)CC.C(C)OC1=C(C=C(C=C1)CC(=O)NCCNC1=CC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C)OC.[AlH3]>>C(C)OC1=C(C=C(C=C1)CCNCCNC1=CC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C)OC | O=[C:9]([CH2:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:38]([O:39][CH3:40])[cH:37]1)[NH:10][CH2:11][CH2:12][NH:13][c:14]1[cH:15][c:16]([CH3:17])[n:18][c:19]2[cH:20][c:21]3[c:22](-[c:23]4[c:24]([CH3:25])[cH:26][c:27]([CH3:28])[cH:29][c:30]4[CH3:31])[cH:32][cH:33][cH:34][n:35]3[c:36]12>>[CH3:1][CH2:2][O:3][c:4]1[cH... | CCOc1ccc(CC(=O)NCCNc2cc(C)nc3cc4c(-c5c(C)cc(C)cc5C)cccn4c23)cc1OC | CCOc1ccc(CCNCCNc2cc(C)nc3cc4c(-c5c(C)cc(C)cc5C)cccn4c23)cc1OC | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CCNCCNc2ccnc3cc4c(-c5ccccc5)cccn4c23)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[c:5] | null | [] | null | null | 15 | MINUTE | Treat a solution of 2-(4-ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-9-(2,4,6-trimethyl-phenyl)-pyridino[2,3-b]indolizin-4-ylamino]-ethyl}-acetamide (0.08 g, 0.145 mmol) in THF (5 mL) with AlH3.NMe2Et (3 mL, 1.45 mmol) and heat to reflux for 14 h. Cool the resulting mixture to ambient temperature, quench with Na2CO3.10H2O ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccccc1.c1ccn2c(c1)cc1ncccc12 | Other | C1CCOC1 | null | 0.25 | CCOc1ccc(CC(=O)NCCNc2cc(C)nc3cc4c(-c5c(C)cc(C)cc5C)cccn4c23)cc1OC>C1CCOC1>CCOc1ccc(CCNCCNc2cc(C)nc3cc4c(-c5c(C)cc(C)cc5C)cccn4c23)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4395eea2939440faae29dd616f8797af | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(O)c23)c(C)c1.O=P(Cl)(Cl)Cl>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(Cl)c23)c(C)c1 | CC=1N=C(C2=C(C=C3C(=CC=CN23)C2=C(C=C(C=C2C)C)C)N1)O.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C | O[c:19]1[n:18][c:16]([CH3:17])[n:15][c:14]2[cH:13][c:12]3[c:7](-[c:6]4[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:24][c:22]4[CH3:23])[cH:8][cH:9][cH:10][n:11]3[c:21]21.O=P(Cl)(Cl)[Cl:20]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH:13][c:14]2[n:15][c:16]([CH3:17])[n:18][c:19]([Cl:20])[c... | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(O)c23)c(C)c1.O=P(Cl)(Cl)Cl | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(Cl)c23)c(C)c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 011132c403ee0a5007ec254ed22d995bfd8c53aaea0928f360354c85698fcdc2 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cccn3c2cc2ncncc23)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9](:[c:10]):[c:11]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9](:[c:10]):[c:11]:2:1 | null | [] | null | null | null | null | Heat at 100° C. for 2 h a solution of 2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indolizin-4-ol (120 mg) in phosphorus oxychloride (2 mL), cool to ambient temperature, and concentrate in vacuo. Partition the residue into ice water and CH2Cl2. Extract the aqueous phase twice with CH2Cl2 and wash the combined org... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccn2c(c1)cc1ncncc12 | c1ccn2c(c1)cc1ncncc12 | c1ccccc1.c1ccn2c(c1)cc1ncncc12 | HCl | null | null | null | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(O)c23)c(C)c1.O=P(Cl)(Cl)Cl>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(Cl)c23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9b776e6a19444b638cd2ea1c6264dace | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(Cl)c23)c(C)c1.NCCN>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCN)c23)c(C)c1 | ClC1=NC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C.C(CN)N.CCOC(=O)C>>NCCNC1=NC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C | Cl[c:19]1[n:18][c:16]([CH3:17])[n:15][c:14]2[cH:13][c:12]3[c:7](-[c:6]4[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:27][c:25]4[CH3:26])[cH:8][cH:9][cH:10][n:11]3[c:24]21.[NH2:20][CH2:21][CH2:22][NH2:23]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH:13][c:14]2[n:15][c:16]([CH3:17])[n:18][c... | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(Cl)c23)c(C)c1.NCCN | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCN)c23)c(C)c1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 62f88a9d5fc18db0c9f152c03e9572f705ab74d8c34a818f2de56fdd152c9027 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cccn3c2cc2ncncc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](:[c:9]):[c:10]:2:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](:[c:9]):[c:10]:2:1 | null | [] | null | null | null | null | Heat a solution of 4-chloro-2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indolizine (0.3 g, 0.89 mmol), and ethylene diamine (0.6 mL, 8.93 mmol) in dry NMP (3 mL) at 100° C. for 14 h. Pour the cooled mixture onto water (30 mL) and extracte twice with EtOAc (30 mL). Wash the combined extracts with brine (30 mL), d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccn2c(c1)cc1ncncc12 | c1ccn2c(c1)cc1ncncc12 | c1ccccc1.c1ccn2c(c1)cc1ncncc12 | HCl | CN1CCCC1=O | null | null | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(Cl)c23)c(C)c1.NCCN>CN1CCCC1=O>Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCN)c23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b280c7e4cd58488ab2913354e1aa71a7 | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCN)c23)c(C)c1.O=C1CCCC1>>Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCNC4CCCC4)c23)c(C)c1 | NCCNC1=NC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C.C1(CCCC1)=O.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C1(CCCC1)NCCNC1=NC(=NC=2C=C3C(=CC=CN3C21)C2=C(C=C(C=C2C)C)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH:13][c:14]2[n:15][c:16]([CH3:17])[n:18][c:19]([NH:20][CH2:21][CH2:22][NH2:23])[c:29]32)[c:30]([CH3:31])[cH:32]1.O=[C:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11]3[c:12]2[cH... | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCN)c23)c(C)c1.O=C1CCCC1 | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCNC4CCCC4)c23)c(C)c1 | null | null | ClC(C)Cl.C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b85679fed5f5625b57908374666b40667904d1ae7fb913f5564f84f7e4e3c6f0 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(-c2cccn3c2cc2ncnc(NCCNC4CCCC4)c23)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1 | null | [] | null | null | 14 | HOUR | Treat a solution of (2-aminoethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indolizin-4-yl]amine (0.07 g, 0.19 mmol), cyclopentanone (0.02 mL, 0.19 mmol) and acetic acid (0.01 mL, 0.19 mmol) in dry dichloroethane (3 mL) with sodium triacetoxyborohydride (0.06 g, 0.27 mmol) and stir at ambient temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCC1 | C1CCCC1 | c1ccccc1.c1ccn2c(c1)cc1ncncc12.C1CCCC1 | Other | ClC(C)Cl.C(Cl)Cl | null | 14 | Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCN)c23)c(C)c1.O=C1CCCC1>ClC(C)Cl.C(Cl)Cl>Cc1cc(C)c(-c2cccn3c2cc2nc(C)nc(NCCNC4CCCC4)c23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f807ff24e2804cd888c618644e5b2c6f | CCOc1ccc(CC(=O)NCCN)cc1OC>>CCOc1ccc(CCNCCN)cc1OC | N(C)(C)CC.NCCNC(CC1=CC(=C(C=C1)OCC)OC)=O.[AlH3]>>C(C)OC1=C(C=C(CCNCCN)C=C1)OC | O=[C:9]([CH2:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:15]([O:16][CH3:17])[cH:14]1)[NH:10][CH2:11][CH2:12][NH2:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][NH2:13])[cH:14][c:15]1[O:16][CH3:17] | CCOc1ccc(CC(=O)NCCN)cc1OC | CCOc1ccc(CCNCCN)cc1OC | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccccc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[c:5] | null | [] | null | null | 15 | MINUTE | Treat a solution of N-(2-amino-ethyl)-2-(4-ethoxy-3-methoxy-phenyl)acetamide (0.7 g, 2.77 mmol) in THF (10 mL) with AlH3.NMe2Et (55 mL, 27.74 mmol) and heat to reflux for 14 h. Cool the resulting mixture to ambient temperature, quench with Na2CO3.10H2O (0.5 g) and stir at ambient temperature for 15 min. Filter the solu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1 | Other | C1CCOC1 | null | 0.25 | CCOc1ccc(CC(=O)NCCN)cc1OC>C1CCOC1>CCOc1ccc(CCNCCN)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e7d3d12db8c48dab2f087c8ed44a567 | COc1cc(C)c(-c2cn(C)c3c(Cl)nc(C)nc23)c(C)c1.COc1ccc(CC(=O)NCCN)cc1>>COc1ccc(CC(=O)NCCNc2nc(C)nc3c(-c4c(C)cc(OC)cc4C)cn(C)c23)cc1 | ClC=1C2=C(N=C(N1)C)C(=CN2C)C2=C(C=C(C=C2C)OC)C.NCCNC(CC1=CC=C(C=C1)OC)=O.O>>COC1=CC=C(C=C1)CC(=O)NCCNC1=NC(=NC2=C1N(C=C2C2=C(C=C(C=C2C)OC)C)C)C | Cl[c:14]1[n:15][c:16]([CH3:17])[n:18][c:19]2[c:20](-[c:21]3[c:22]([CH3:23])[cH:24][c:25]([O:26][CH3:27])[cH:28][c:29]3[CH3:30])[cH:31][n:32]([CH3:33])[c:34]12.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][NH2:13])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])... | COc1cc(C)c(-c2cn(C)c3c(Cl)nc(C)nc23)c(C)c1.COc1ccc(CC(=O)NCCN)cc1 | COc1ccc(CC(=O)NCCNc2nc(C)nc3c(-c4c(C)cc(OC)cc4C)cn(C)c23)cc1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Cc1ccccc1)NCCNc1ncnc2c(-c3ccccc3)c[nH]c12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]:2:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]:2:1 | null | [] | null | null | null | null | Heat a solution of 4-chloro-7-(4-methoxy-2,6-dimethyl-phenyl)-2,5-dimethyl-5H-pyrrolo[3,2-d]pyrimidine (120 mg, 0.38 mmol) and N-(2-amino-ethyl)-2-(4-methoxyphenyl)-acetamide (125 mg) in NMP (2 mL) for 14 h at 130° C. Pour into water (5 mL) and extract with EtOAc (2×10 mL). Dry the combined organic extracts over Na2SO4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]ccc2n1 | HCl | CN1CCCC1=O | null | null | COc1cc(C)c(-c2cn(C)c3c(Cl)nc(C)nc23)c(C)c1.COc1ccc(CC(=O)NCCN)cc1>CN1CCCC1=O>COc1ccc(CC(=O)NCCNc2nc(C)nc3c(-c4c(C)cc(OC)cc4C)cn(C)c23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d153384e7cbd4e5eaba1412a6dbe40b4 | Cc1cc(Cl)c([N+](=O)[O-])c(O)n1.NCc1ccccc1>>Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(O)n1 | ClC1=C(C(=NC(=C1)C)O)[N+](=O)[O-].C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC1=C(C(=NC(=C1)C)O)[N+](=O)[O-] | Cl[c:4]1[cH:3][c:2]([CH3:1])[n:19][c:17]([OH:18])[c:13]1[N+:14](=[O:15])[O-:16].[NH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([N+:14](=[O:15])[O-:16])[c:17]([OH:18])[n:19]1 | Cc1cc(Cl)c([N+](=O)[O-])c(O)n1.NCc1ccccc1 | Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(O)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](-[O;D1;H1:7]):[c:8]:1-[#7;+:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;+:9]-[c:8]1:[c:6](-[O;D1;H1:7]):[#7;a:5]:[c:3](-[C;D1;H3:4]):[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:10]-[C:11]-[c:12] | null | [] | null | null | null | null | Stir a solution of 4-chloro-6-methyl-3-nitro-pyridin-2-ol (10.0 g, 53.0 mmol) and benzyl amine (17.3 g, 159 mmol) in EtOH (30 mL) at ambient temperature for 12 h, then concentrate in vacuo. Pour the resulting residue into water, acidify to pH 3 with 1N HCl and filter. Wash the precipitate several times with water to ob... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CCO | null | null | Cc1cc(Cl)c([N+](=O)[O-])c(O)n1.NCc1ccccc1>CCO>Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(O)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ba0681111f0441e59ee860871cbd6cb3 | Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(O)n1.O=P(Cl)(Cl)Cl>>Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(Cl)n1 | C(C1=CC=CC=C1)NC1=C(C(=NC(=C1)C)O)[N+](=O)[O-].P(=O)(Cl)(Cl)Cl>>C(C1=CC=CC=C1)NC1=C(C(=NC(=C1)C)Cl)[N+](=O)[O-] | O[c:17]1[c:13]([N+:14](=[O:15])[O-:16])[c:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:3][c:2]([CH3:1])[n:19]1.O=P(Cl)(Cl)[Cl:18]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([N+:14](=[O:15])[O-:16])[c:17]([Cl:18])[n:19]1 | Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(O)n1.O=P(Cl)(Cl)Cl | Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(Cl)n1 | null | [Cl-].C[N+](C)(C)C | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | ab85b19a1f19bdb0596b983dc6471067aedf5e7b894e737e6d16cd077bd81b42 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(CNc2ccncc2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[#7;+:6]):[c:7]>>[#7;+:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[#7;a:3]:[c:4] | null | [] | null | null | null | null | Heat a solution of 4-benzylamino-6-methyl-3-nitro-pyridin-2-ol (13.70 g, 52.8 mmol) and tetramethylammonium chloride (6.0 g, 52.8 mmol) to reflux in phosphorus oxychloride (15 mL) for 5 h. After cooling, remove the excess phosphorus oxychloride in vacuo. Triturate the residue in ice-water (400 mL) to obtain the title c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | [Cl-].C[N+](C)(C)C | null | null | Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(O)n1.O=P(Cl)(Cl)Cl>[Cl-].C[N+](C)(C)C>Cc1cc(NCc2ccccc2)c([N+](=O)[O-])c(Cl)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93a0e0392bfb41d1a4ce35af9bec7f30 | CC1=C([N+](=O)[O-])C(C)(NCc2ccccc2)CC(C)(C)C1Nc1ccccn1>>CC1=C(N)C(C)(NCc2ccccc2)CC(C)(C)C1Nc1ccccn1 | CC1(CC(C(=C(C1NC1=NC=CC=C1)C)[N+](=O)[O-])(C)NCC1=CC=CC=C1)C>>NC1=C(C(C(CC1(C)NCC1=CC=CC=C1)(C)C)NC1=NC=CC=C1)C | O=[N+:4]([O-])[C:3]1=[C:2]([CH3:1])[CH:19]([NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[C:16]([CH3:17])([CH3:18])[CH2:15][C:5]1([CH3:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][C:2]1=[C:3]([NH2:4])[C:5]([CH3:6])([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C:16]([CH3:17... | CC1=C([N+](=O)[O-])C(C)(NCc2ccccc2)CC(C)(C)C1Nc1ccccn1 | CC1=C(N)C(C)(NCc2ccccc2)CC(C)(C)C1Nc1ccccn1 | null | [Fe] | C(C)(=O)O.CO | Reduction | Reduction of nitro groups to amines | af6c5b301491be261a262616a03eb9b7e8465cf4d54efa20d6e4ba026dae1843 | 932aeb69032745ef767518b2869fbe1b80680a98af29f5f41fa577be193d71ee | C1=CC(Nc2ccccn2)CCC1NCc1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2](=[C:3](-[C;D1;H3:4])-[C:5])-[C:6]>>[C:5]-[C:3](-[C;D1;H3:4])=[C:2](-[NH2;D1;+0:1])-[C:6] | null | [] | 70 | CELSIUS | null | null | Add iron powder (7.0 g) to a solution of 6-methyl-3-nitro-4-[benzylamino](2-pyridyl)(2,4,6-trimethylphenyl)amine (8.75 g, 23.2 mmol) in acetic acid (14 mL) and MeOH (70 mL). Heat the resulting mixture at 70° C. for 1 h, cool to ambient temperature, and filter through a pad of celite. Evaporate the filtrate to dryness u... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Enamine | null | null | C1=CCCCC1.c1ccccc1.c1ccncc1 | Other | [Fe].C(C)(=O)O.CO | 70 | null | CC1=C([N+](=O)[O-])C(C)(NCc2ccccc2)CC(C)(C)C1Nc1ccccn1>[Fe].C(C)(=O)O.CO>CC1=C(N)C(C)(NCc2ccccc2)CC(C)(C)C1Nc1ccccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed258c7e10b54f8bb28c48f09d702f3d | Cc1cc(C)c(-n2c(C)nc3c(NCc4ccccc4)cc(C)nc32)c(C)c1>>Cc1cc(C)c(-n2cnc3c(N)cc(C)nc32)c(C)c1 | CC=1N(C2=NC(=CC(=C2N1)NCC1=CC=CC=C1)C)C1=C(C=C(C=C1C)C)C>>CC1=CC(=C2C(=N1)N(C=N2)C2=C(C=C(C=C2C)C)C)N | C[c:8]1[n:7](-[c:6]2[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:20][c:18]2[CH3:19])[c:17]2[c:10]([n:9]1)[c:11]([NH:12]Cc1ccccc1)[cH:13][c:14]([CH3:15])[n:16]2>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]([NH2:12])[cH:13][c:14]([CH3:15])[n:16][c:17]23)[c:18]([CH3:19])[cH:20]1 | Cc1cc(C)c(-n2c(C)nc3c(NCc4ccccc4)cc(C)nc32)c(C)c1 | Cc1cc(C)c(-n2cnc3c(N)cc(C)nc32)c(C)c1 | null | [OH-].[Pd+2].[OH-] | C(C)(=O)O | Deprotection | OtherReaction | a8cfbee1f0bfb6466a347fd6c1b5d43b8b332ef3673c8f86756b7c7c72e838f8 | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(-n2cnc3cccnc32)cc1 | C-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4](-[NH;D2;+0:5]-C-c3:c:c:c:c:c:3):[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[#7;a:10]:1-[c:11]>>[NH2;D1;+0:5]-[c:4]1:[c:6]:[c:7]:[#7;a:8]:[c:9]2:[#7;a:10](-[c:11]):[cH;D2;+0:1]:[#7;a:2]:[c:3]:1:2 | null | [] | null | null | 20 | HOUR | Add palladium hydroxide (0.05 g) to a solution of [2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]benzylamine (0.15 g, 0.42 mmol) in acetic acid (10 mL). Hydrogenate the mixture at a pressure of 50 psi for 20 hr. Filter the reaction mixture through celite, evaporate to dryness under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1.c1ccc2nc[nH]c2n1 | c1ccc2nc[nH]c2n1 | c1ccccc1.c1ccc2nc[nH]c2n1 | Other | [OH-].[Pd+2].[OH-].C(C)(=O)O | null | 20 | Cc1cc(C)c(-n2c(C)nc3c(NCc4ccccc4)cc(C)nc32)c(C)c1>[OH-].[Pd+2].[OH-].C(C)(=O)O>Cc1cc(C)c(-n2cnc3c(N)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-742e002137e348309f2ac695e2683299 | Cc1cc(C)c(-n2cnc3c(N)cc(C)nc32)c(C)c1.O=C(Cl)CCl>>Cc1cc(C)c(-n2cnc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 | C([O-])([O-])=O.[K+].[K+].CC1=CC(=C2C(=N1)N(C=N2)C2=C(C=C(C=C2C)C)C)N.C(C)(C)N(C(C)C)CC.ClCC(=O)Cl>>CC1=CC(=C2C(=N1)N(C=N2)C2=C(C=C(C=C2C)C)C)NC(CCl)=O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]([NH2:12])[cH:17][c:18]([CH3:19])[n:20][c:21]23)[c:22]([CH3:23])[cH:24]1.Cl[C:13](=[O:14])[CH2:15][Cl:16]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][C:13](=[O:14])[CH2:15][Cl:16])[cH:17][c:18]([CH3:19])[n:20][c:21... | Cc1cc(C)c(-n2cnc3c(N)cc(C)nc32)c(C)c1.O=C(Cl)CCl | Cc1cc(C)c(-n2cnc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 | null | null | ClCCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-n2cnc3cccnc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1:2>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1:2 | null | [] | null | null | null | null | Treat a solution of 5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-ylamine (0.05 g, 1.9 mmol), and N,N-diisopropylethylamine, (0.04 mL, 0.21 mmol) in 1,2-dichloroethane (5 mL) with chloroacetyl chloride (0.017 mL, 0.21 mmol). Heat the solution to reflux for 3 h, cool to ambient temperature, and pour into a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2nc[nH]c2n1 | HCl | ClCCCl | null | null | Cc1cc(C)c(-n2cnc3c(N)cc(C)nc32)c(C)c1.O=C(Cl)CCl>ClCCCl>Cc1cc(C)c(-n2cnc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce05fb09294841c38a6645dcd2a972b8 | Cc1cc(C)c(-n2cnc3c(NC(=O)CCl)cc(C)nc32)c(C)c1>>Cc1cc(C)c(-n2cnc3c(NCCCl)cc(C)nc32)c(C)c1 | CC1=CC(=C2C(=N1)N(C=N2)C2=C(C=C(C=C2C)C)C)NC(CCl)=O>>ClCCNC1=C2C(=NC(=C1)C)N(C=N2)C2=C(C=C(C=C2C)C)C | O=[C:13]([NH:12][c:11]1[c:10]2[n:9][cH:8][n:7](-[c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:23][c:21]3[CH3:22])[c:20]2[n:19][c:17]([CH3:18])[cH:16]1)[CH2:14][Cl:15]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][CH2:14][Cl:15])[cH:16][c:17]([CH3:18])[n:19][c:20]23)[c:21]([CH3:22... | Cc1cc(C)c(-n2cnc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 | Cc1cc(C)c(-n2cnc3c(NCCCl)cc(C)nc32)c(C)c1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(-n2cnc3cccnc32)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3]:[c:4]:[#7;a:5])-[C:6]-[Cl;D1;H0:7]>>[#7;a:5]:[c:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-[C:6]-[Cl;D1;H0:7] | null | [] | null | null | null | null | Treat a solution of N-[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide (0.04 g, 0.10 mmol) in THF (5 mL) with borane-methyl sulfide complex (0.03 mL, 0.30 mmol). Heat the mixture to reflux for 8 h and quench at ambient temperature with a large excess of MeOH, followed by 6 N HCl (2 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccc2nc[nH]c2n1 | Other | C1CCOC1 | null | null | Cc1cc(C)c(-n2cnc3c(NC(=O)CCl)cc(C)nc32)c(C)c1>C1CCOC1>Cc1cc(C)c(-n2cnc3c(NCCCl)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e1c295b6c13a4b0693de6ccd9488b432 | CCOc1ccc(CCN)cc1OC.Cc1cc(C)c(-n2cnc3c(NCCCl)cc(C)nc32)c(C)c1>>CCOc1ccc(CCNCCNc2cc(C)nc3c2ncn3-c2c(C)cc(C)cc2C)cc1OC | ClCCNC1=C2C(=NC(=C1)C)N(C=N2)C2=C(C=C(C=C2C)C)C.C(C)OC1=C(C=C(CCN)C=C1)OC>>C(C)OC1=C(C=C(C=C1)CCNCCNC1=C2C(=NC(=C1)C)N(C=N2)C2=C(C=C(C=C2C)C)C)OC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][NH2:10])[cH:33][c:34]1[O:35][CH3:36].Cl[CH2:11][CH2:12][NH:13][c:14]1[cH:15][c:16]([CH3:17])[n:18][c:19]2[c:20]1[n:21][cH:22][n:23]2-[c:24]1[c:25]([CH3:26])[cH:27][c:28]([CH3:29])[cH:30][c:31]1[CH3:32]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][N... | CCOc1ccc(CCN)cc1OC.Cc1cc(C)c(-n2cnc3c(NCCCl)cc(C)nc32)c(C)c1 | CCOc1ccc(CCNCCNc2cc(C)nc3c2ncn3-c2c(C)cc(C)cc2C)cc1OC | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCNCCNc2ccnc3c2ncn3-c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | null | null | null | null | Heat a solution of (2-chloroethyl)[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-amine (0.030 g, 0.09 mmol) and 4-ethoxy-3-methoxy phenethylamine (0.10 g, 0.55 mmol) in dry NMP (2 mL) at 110° C. for 16 h. Pour the cooled mixture onto water (20 mL) and extract twice with EtOAc (20 mL). Wash the combine... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2n1.c1ccccc1 | HCl | CN1CCCC1=O | null | null | CCOc1ccc(CCN)cc1OC.Cc1cc(C)c(-n2cnc3c(NCCCl)cc(C)nc32)c(C)c1>CN1CCCC1=O>CCOc1ccc(CCNCCNc2cc(C)nc3c2ncn3-c2c(C)cc(C)cc2C)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9c5398839e8430bb7f6e5356ef0486f | Cc1cc(C)c(-n2c(C)nc3c(NCc4ccccc4)cc(C)nc32)c(C)c1>>Cc1cc(C)c(-n2c(C)nc3c(N)cc(C)nc32)c(C)c1 | CC=1N(C2=NC(=CC(=C2N1)NCC1=CC=CC=C1)C)C1=C(C=C(C=C1C)C)C>>CC=1N(C2=NC(=CC(=C2N1)N)C)C1=C(C=C(C=C1C)C)C | c1ccc(C[NH:13][c:12]2[c:11]3[n:10][c:8]([CH3:9])[n:7](-[c:6]4[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:21][c:19]4[CH3:20])[c:18]3[n:17][c:15]([CH3:16])[cH:14]2)cc1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[c:8]([CH3:9])[n:10][c:11]3[c:12]([NH2:13])[cH:14][c:15]([CH3:16])[n:17][c:18]23)[c:19]([CH3:20])[cH:21]1 | Cc1cc(C)c(-n2c(C)nc3c(NCc4ccccc4)cc(C)nc32)c(C)c1 | Cc1cc(C)c(-n2c(C)nc3c(N)cc(C)nc32)c(C)c1 | null | [OH-].[Pd+2].[OH-] | C(C)(=O)O | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(-n2cnc3cccnc32)cc1 | C(-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1:2)-c1:c:c:c:c:c:1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1:2 | null | [] | null | null | 20 | HOUR | Add palladium hydroxide (2.0 g) to a solution of [2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]benzylamine (1.50 g, 4.05 mmol) in acetic acid (10 mL). Hydrogenate the mixture at a pressure of 40 psi for 20 hr. Filter the reaction mixture through celite, evaporate to dryness under reduced pressure,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2nc[nH]c2n1 | Other | [OH-].[Pd+2].[OH-].C(C)(=O)O | null | 20 | Cc1cc(C)c(-n2c(C)nc3c(NCc4ccccc4)cc(C)nc32)c(C)c1>[OH-].[Pd+2].[OH-].C(C)(=O)O>Cc1cc(C)c(-n2c(C)nc3c(N)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bd9ebd31ce7044ed8c20fc1c6accae44 | Cc1cc(C)c(-n2c(C)nc3c(N)cc(C)nc32)c(C)c1.O=C(Cl)CCl>>Cc1cc(C)c(-n2c(C)nc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 | C([O-])([O-])=O.[K+].[K+].CC=1N(C2=NC(=CC(=C2N1)N)C)C1=C(C=C(C=C1C)C)C.C(C)(C)N(C(C)C)CC.ClCC(=O)Cl>>CC=1N(C2=NC(=CC(=C2N1)NC(CCl)=O)C)C1=C(C=C(C=C1C)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[c:8]([CH3:9])[n:10][c:11]3[c:12]([NH2:13])[cH:18][c:19]([CH3:20])[n:21][c:22]23)[c:23]([CH3:24])[cH:25]1.Cl[C:14](=[O:15])[CH2:16][Cl:17]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[c:8]([CH3:9])[n:10][c:11]3[c:12]([NH:13][C:14](=[O:15])[CH2:16][Cl:17])[cH:18][c:19]([C... | Cc1cc(C)c(-n2c(C)nc3c(N)cc(C)nc32)c(C)c1.O=C(Cl)CCl | Cc1cc(C)c(-n2c(C)nc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 | null | null | ClCCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-n2cnc3cccnc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1:2>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1:2 | null | [] | null | null | null | null | Treat a solution of 2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridine-7-ylamine (0.8 g, 2.85 mmol), and N,N-diisopropylethylamine, (0.54 mL, 3.13 mmol) in 1,2-dichloroethane (10 mL) with chloroacetyl chloride (0.25 mL, 3.13 mmol). Heat the solution to reflux for 5 h, cool to ambient temperature, and pour i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2nc[nH]c2n1 | HCl | ClCCCl | null | null | Cc1cc(C)c(-n2c(C)nc3c(N)cc(C)nc32)c(C)c1.O=C(Cl)CCl>ClCCCl>Cc1cc(C)c(-n2c(C)nc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc91cab80c8644bc95cc5487d3e22d00 | Cc1cc(C)c(-n2c(C)nc3c(NC(=O)CCl)cc(C)nc32)c(C)c1>>Cc1cc(C)c(-n2c(C)nc3c(NCCCl)cc(C)nc32)c(C)c1 | CC=1N(C2=NC(=CC(=C2N1)NC(CCl)=O)C)C1=C(C=C(C=C1C)C)C>>CC=1N(C2=NC(=CC(=C2N1)NCCCl)C)C1=C(C=C(C=C1C)C)C | O=[C:14]([NH:13][c:12]1[c:11]2[n:10][c:8]([CH3:9])[n:7](-[c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:24][c:22]3[CH3:23])[c:21]2[n:20][c:18]([CH3:19])[cH:17]1)[CH2:15][Cl:16]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[c:8]([CH3:9])[n:10][c:11]3[c:12]([NH:13][CH2:14][CH2:15][Cl:16])[cH:17][c:18]([CH3:19])[n:20][c:21... | Cc1cc(C)c(-n2c(C)nc3c(NC(=O)CCl)cc(C)nc32)c(C)c1 | Cc1cc(C)c(-n2c(C)nc3c(NCCCl)cc(C)nc32)c(C)c1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(-n2cnc3cccnc32)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3]:[c:4]:[#7;a:5])-[C:6]-[Cl;D1;H0:7]>>[#7;a:5]:[c:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-[C:6]-[Cl;D1;H0:7] | null | [] | null | null | null | null | Treat a solution of N-[2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide (0.91 g, 2.55 mmol) in THF (5 mL) with borane-methyl sulfide complex (0.8 mL, 7.65 mmol). Heat the mixture to reflux for 18 h and quench at ambient temperature with a large excess of MeOH, followed by 6N HCl (5 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccc2nc[nH]c2n1 | Other | C1CCOC1 | null | null | Cc1cc(C)c(-n2c(C)nc3c(NC(=O)CCl)cc(C)nc32)c(C)c1>C1CCOC1>Cc1cc(C)c(-n2c(C)nc3c(NCCCl)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-51435ab0d0544cf9ae8e09c96b30e6c1 | Cc1cc(C)c(-n2c(C)nc3c(NCCCl)cc(C)nc32)c(C)c1.NC1CCCCC1>>Cc1cc(C)c(-n2c(C)nc3c(NCCNC4CCCCC4)cc(C)nc32)c(C)c1 | CC=1N(C2=NC(=CC(=C2N1)NCCCl)C)C1=C(C=C(C=C1C)C)C.C1(CCCCC1)N>>CC=1N(C2=NC(=CC(=C2N1)NCCNC1CCCCC1)C)C1=C(C=C(C=C1C)C)C | Cl[CH2:15][CH2:14][NH:13][c:12]1[c:11]2[n:10][c:8]([CH3:9])[n:7](-[c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:30][c:28]3[CH3:29])[c:27]2[n:26][c:24]([CH3:25])[cH:23]1.[NH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[n:7]2[c:8]([CH3:9])[n:10][c:11]3[c:12]([NH:13][CH2:14... | Cc1cc(C)c(-n2c(C)nc3c(NCCCl)cc(C)nc32)c(C)c1.NC1CCCCC1 | Cc1cc(C)c(-n2c(C)nc3c(NCCNC4CCCCC4)cc(C)nc32)c(C)c1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(-n2cnc3c(NCCNC4CCCCC4)ccnc32)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5](-[C:4])-[C:7] | null | [] | null | null | null | null | Heat a solution of [2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine (0.04 g, 0.12 mmol), and cyclohexyl amine (0.13 mL g, 1.16 mmol) in dry NMP (2 mL) at 80° C. for 20 h. Pour the cooled mixture onto water (20 mL) and extract twice with ethyl acetate (20 mL). Wash the combined ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.C1CCCCC1.c1ccc2nc[nH]c2n1 | HCl | CN1CCCC1=O | null | null | Cc1cc(C)c(-n2c(C)nc3c(NCCCl)cc(C)nc32)c(C)c1.NC1CCCCC1>CN1CCCC1=O>Cc1cc(C)c(-n2c(C)nc3c(NCCNC4CCCCC4)cc(C)nc32)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d65f2cf901554667a889a13c32f7fb06 | COc1ccc(CNc2cc(C)nc3c2nc(C)n3-c2ccc(Cl)cc2Cl)cc1>>Cc1cc(N)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2NCC2=CC=C(C=C2)OC)C)C.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F.S(O)(O)(=O)=O>>ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2N)C)C | COc1ccc(C[NH:5][c:4]2[cH:3][c:2]([CH3:1])[n:20][c:19]3[c:6]2[n:7][c:8]([CH3:9])[n:10]3-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])cc1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[c:19]2[n:20]1 | COc1ccc(CNc2cc(C)nc3c2nc(C)n3-c2ccc(Cl)cc2Cl)cc1 | Cc1cc(N)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | null | null | C(=O)(O)[O-].[Na+] | Reduction | OtherReaction | bd6cc2ddd30b209c36eb43f9e2d163a4da40f8a48bda8b578aa13caf5d4fe5dd | 79272555d5bd71219cf9e8b42c4ac12a30bbf383c58cfbccf49a5a990e3653c1 | c1ccc(-n2cnc3cccnc32)cc1 | C-O-c1:c:c:c(-C-[NH;D2;+0:1]-[c:2]2:[c:3]:[c:4]:[#7;a:5]:[c:6]3:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:3:2):c:c:1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1 | null | [] | null | null | null | null | Stir a solution of [3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-yl](4-methoxybenzyl)amine (4.23 g, 10 mmol), anisole (3.2 mL, 29.6 mmol), trifluoroacetic acid (80 mL), and concentrated sulfuric acid (2 mL) at ambient temperature for 14 h. Add the resulting mixture dropwise to ice-water and dilute with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2[nH]cnc2n1.c1ccccc1 | HO- | C(=O)(O)[O-].[Na+] | null | null | COc1ccc(CNc2cc(C)nc3c2nc(C)n3-c2ccc(Cl)cc2Cl)cc1>C(=O)(O)[O-].[Na+]>Cc1cc(N)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdfd86257a8f43f7bfd2fa8ca41ff73e | Cc1cc(N)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1.O=C(Cl)CCl>>Cc1cc(NC(=O)CCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | C([O-])([O-])=O.[K+].[K+].ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2N)C)C.C(C)(C)N(C(C)C)CC.ClCC(=O)Cl>>ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2NC(CCl)=O)C)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:10]2[n:11][c:12]([CH3:13])[n:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[c:23]2[n:24]1.Cl[C:6](=[O:7])[CH2:8][Cl:9]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[CH2:8][Cl:9])[c:10]2[n:11][c:12]([CH3:13])[n:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[C... | Cc1cc(N)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1.O=C(Cl)CCl | Cc1cc(NC(=O)CCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | null | null | ClCCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-n2cnc3cccnc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:1>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:1 | null | [] | null | null | null | null | Treat a solution of 3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-ylamine (0.2 g, 0.65 mmol), and N,N-diisopropylethylamine, (0.12 mL, 0.72 mmol) in 1,2-dichloroethane (10 mL) with chloroacetyl chloride (0.06 mL, 30.72 mmol). Heat the solution to reflux for 2 h, cool to ambient temperature, and pour into... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2n1.c1ccccc1 | HCl | ClCCCl | null | null | Cc1cc(N)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1.O=C(Cl)CCl>ClCCCl>Cc1cc(NC(=O)CCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b4d01944ca74127aa34c6e0d30c2413 | Cc1cc(NC(=O)CCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1>>Cc1cc(NCCCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2NC(CCl)=O)C)C>>ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2NCCCl)C)C | O=[C:6]([NH:5][c:4]1[cH:3][c:2]([CH3:1])[n:23][c:22]2[c:9]1[n:10][c:11]([CH3:12])[n:13]2-[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]1[Cl:21])[CH2:7][Cl:8]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][Cl:8])[c:9]2[n:10][c:11]([CH3:12])[n:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[Cl:21])[c:22]2[n:23... | Cc1cc(NC(=O)CCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | Cc1cc(NCCCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(-n2cnc3cccnc32)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3]:[c:4]:[#7;a:5])-[C:6]-[Cl;D1;H0:7]>>[#7;a:5]:[c:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-[C:6]-[Cl;D1;H0:7] | null | [] | null | null | null | null | Treat a solution of N-[3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide (1.0 g, 2.6 mmol) in THF (5 mL) with borane-methyl sulfide complex (0.8 mL, 7.8 mmol). Heat the mixture to reflux for 3 h and quench at ambient temperature with a large excess of MeOH followed by 5 N HCl (2 mL). Re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccc2[nH]cnc2n1.c1ccccc1 | Other | C1CCOC1 | null | null | Cc1cc(NC(=O)CCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1>C1CCOC1>Cc1cc(NCCCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f94f7901d2048a4838a642508af10ca | Cc1cc(NCCCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1.NC1CCCC1>>Cc1cc(NCCNC2CCCC2)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2NCCCl)C)C.C1(CCCC1)N>>ClC1=C(C=CC(=C1)Cl)N1C(=NC=2C1=NC(=CC2NCCNC2CCCC2)C)C | Cl[CH2:7][CH2:6][NH:5][c:4]1[cH:3][c:2]([CH3:1])[n:28][c:27]2[c:14]1[n:15][c:16]([CH3:17])[n:18]2-[c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][c:25]1[Cl:26].[NH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]2[n:15][c:16]([CH... | Cc1cc(NCCCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1.NC1CCCC1 | Cc1cc(NCCNC2CCCC2)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(-n2cnc3c(NCCNC4CCCC4)ccnc32)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5](-[C:4])-[C:7] | null | [] | null | null | null | null | Heat a solution of [3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine (0.08 g, 0.22 mmol), and cyclopentyl amine (0.2 mL g, 0.22 mmol) in dry NMP (3 mL) at 80° C. for 20 h. Pour the cooled mixture onto water (30 mL) and extract twice with EtOAc (50 mL). Wash the combined extracts with... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | C1CCCC1.c1ccc2[nH]cnc2n1.c1ccccc1 | HCl | CN1CCCC1=O | null | null | Cc1cc(NCCCl)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1.NC1CCCC1>CN1CCCC1=O>Cc1cc(NCCNC2CCCC2)c2nc(C)n(-c3ccc(Cl)cc3Cl)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-863e557edd7e499d827a0df1bcec0c60 | CC(=O)c1c(Cl)cccc1Cl.CCOC(=O)C(=O)OCC>>CCOC(=O)C(=O)CC(=O)c1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)C(C)=O.C(C(=O)OCC)(=O)OCC.[H-].[Na+]>>ClC1=C(C(=CC=C1)Cl)C(CC(C(=O)OCC)=O)=O | [CH3:8][C:9](=[O:10])[c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18].CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18] | CC(=O)c1c(Cl)cccc1Cl.CCOC(=O)C(=O)OCC | CCOC(=O)C(=O)CC(=O)c1c(Cl)cccc1Cl | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 75e47111412c372865b4b8c2556a24f38f2daf372ab5522938a6e976b4732185 | 907e247f98c28f5bcc369b20fadcc26c24574c2b68d4b59762f1e8515d373c02 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10] | null | [] | null | null | null | null | To a solution of 2′,6′-dichloroacetophenone (12.5 g, 66 mmol) and diethyl oxalate (14.6 g, 100 mmol) in 450 mL of anhydrous toluene, cautiously add sodium hydride (60% dispersion in mineral oil, 2.8 g, 70 mmol). Cautiously heat the reaction mixture to reflux under N2 for 1 h, cool to ambient temperature and pour onto i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone.Ketone | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)c1c(Cl)cccc1Cl.CCOC(=O)C(=O)OCC>C1(=CC=CC=C1)C>CCOC(=O)C(=O)CC(=O)c1c(Cl)cccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f1f42acdc234f729f366de830183706 | CCOC(=O)C(=O)CC(=O)c1c(Cl)cccc1Cl.O=N[O-]>>CCOC(=O)C(=O)C(=NO)C(=O)c1c(Cl)cccc1Cl | Cl.N(=O)[O-].[Na+].ClC1=C(C(=CC=C1)Cl)C(CC(C(=O)OCC)=O)=O>>ClC1=C(C(=CC=C1)Cl)C(C(C(C(=O)OCC)=O)=NO)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:11](=[O:12])[c:13]1[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]1[Cl:20].O=[N:9][O-:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[C:8](=[N:9][OH:10])[C:11](=[O:12])[c:13]1[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]1[Cl:20] | CCOC(=O)C(=O)CC(=O)c1c(Cl)cccc1Cl.O=N[O-] | CCOC(=O)C(=O)C(=NO)C(=O)c1c(Cl)cccc1Cl | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 9638fdacd8d405b0a44d1ce6aba3da753854cff65501b5a57f0aafc95fc4c4f0 | d3bd726ddd957b1a2366e6bbf86ce90af8c1a91be2fc86e65360edda049ba84b | c1ccccc1 | O=[N;H0;D2;+0:1]-[O-;H0;D1:2].[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[N;H0;D2;+0:1]-[OH;D1;+0:2])-[C:10](=[O;D1;H0:11])-[c:12] | null | [] | null | null | null | null | Slowly bubble N2O3 gas (generated by the dropwise addition of concentrated HCl into an aqueous solution of sodium nitrite) into a stirred solution of ethyl 4-(2,6-dichlorophenyl)-2,4-dioxobutanoate (14.4 g, 50 mmol) in EtOH (300 mL) until the reaction is complete (as determined by TLC). Remove the EtOH by evaporation u... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Nitroso | Ketone.Ketone.Oxime | null | null | c1ccccc1 | HO- | CCO | null | null | CCOC(=O)C(=O)CC(=O)c1c(Cl)cccc1Cl.O=N[O-]>CCO>CCOC(=O)C(=O)C(=NO)C(=O)c1c(Cl)cccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee8a7298a6884a1f828e5aabb66ebe39 | CCOC(=O)C(=O)C(=NO)C(=O)c1c(Cl)cccc1Cl.CNN>>CCOC(=O)c1nn(C)c(-c2c(Cl)cccc2Cl)c1N | CNN.ClC1=C(C(=CC=C1)Cl)C(C(C(C(=O)OCC)=O)=NO)=O.Cl>>NC=1C(=NN(C1C1=C(C=CC=C1Cl)Cl)C)C(=O)OCC | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:19]([C:10](=O)[c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18])=[N:20]O.[NH2:7][NH:8][CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][n:8]([CH3:9])[c:10](-[c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19]1[NH2:20] | CCOC(=O)C(=O)C(=NO)C(=O)c1c(Cl)cccc1Cl.CNN | CCOC(=O)c1nn(C)c(-c2c(Cl)cccc2Cl)c1N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | e4c6ec0e05e1c203106a5b5aa997e8a1ccd7f76a640bd7c557c3b58ce08a8ce3 | 5d820015a1c4befea2445c7bdac96cc1fe907ff48e6873810c167772c5bb36e5 | c1ccc(-c2ccn[nH]2)cc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5](-[Cl;D1;H0:6]):[c:7]):[c:8](-[Cl;D1;H0:9]):[c:10])-[C;H0;D3;+0:11](=O)-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15].[C;D1;H3:16]-[NH;D2;+0:17]-[NH2;D1;+0:18]>>[C:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:11]1:[n;H0;D2;+0:18]:[n;H0;D3;+0:17](-[C;D1;H3... | null | [] | null | null | 8 | HOUR | To a solution of ethyl 4-(2,6-dichlorophenyl)-3-(hydroxyimino)-2,4-dioxobutanoate (14 g, 44 mmol) in MeOH (400 mL) at 0° C., add dropwise-concentrated HCl (10 mL) followed by methyl hydrazine (2.02 g, 44 mmol). Stir the reaction mixture at ambient temperature for 8 h and concentrate in vacuo. Partition the residue betw... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone.Ester.Oxime | Ester.Primary amine | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | CO | null | 8 | CCOC(=O)C(=O)C(=NO)C(=O)c1c(Cl)cccc1Cl.CNN>CO>CCOC(=O)c1nn(C)c(-c2c(Cl)cccc2Cl)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-54c31ae7d8f345268fd8807691204861 | Cc1nc(Cl)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1.NCCN>>Cc1nc(NCCN)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1 | ClC1=C(C(=CC=C1)Cl)C=1N(N=C2C1N=C(N=C2Cl)C)C.C(CN)N>>NCCNC1=NC(=NC=2C1=NN(C2C2=C(C=CC=C2Cl)Cl)C)C | Cl[c:4]1[n:3][c:2]([CH3:1])[n:23][c:22]2[c:9]1[n:10][n:11]([CH3:12])[c:13]2-[c:14]1[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]1[Cl:21].[NH2:5][CH2:6][CH2:7][NH2:8]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][CH2:6][CH2:7][NH2:8])[c:9]2[n:10][n:11]([CH3:12])[c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:22]2[n:... | Cc1nc(Cl)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1.NCCN | Cc1nc(NCCN)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 90788f58b1dab3f5c9d9dae91bbc2ea7662e25e823d106feb56d7b4d01eeed0b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2[nH]nc3cncnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7](-[C;D1;H3:8]):[#7;a:9]:[c:10]:2:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7](-[C;D1;H3:8]):[#7;a:9]:[c:10]:2:1 | null | [] | null | null | null | null | To a stirred solution of 3-(2,6-dichlorophenyl)-7-chloro-2,5-dimethylpyrazolo[4,3-d]pyrimidine (652 mg, 2.0 mmol) in acetonitrile (50 mL) at 50° C., add ethylene diamine (2.4 g, 40 mmol) in one portion. Maintain the reaction at 50° C. for 2 h, cool to ambient temperature and remove the volatiles by evaporation. Partiti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ncc2n1 | c1ncc2[nH]ncc2n1 | c1ncc2[nH]ncc2n1.c1ccccc1 | HCl | C(C)#N | null | null | Cc1nc(Cl)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1.NCCN>C(C)#N>Cc1nc(NCCN)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b888f0018af40c7a2290f4c72bf12da | CCOc1ccc(CC(=O)O)cc1OC.Cc1nc(NCCN)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1>>CCOc1ccc(C(Nc2nc(C)nc3c(-c4c(Cl)cccc4Cl)n(C)nc23)C(N)=O)cc1OC | NCCNC1=NC(=NC=2C1=NN(C2C2=C(C=CC=C2Cl)Cl)C)C.CN1CCOCC1.C(C)OC1=C(C=C(C=C1)CC(=O)O)OC.O=C1OCCN1P(=O)(N1C(OCC1)=O)Cl>>ClC1=C(C(=CC=C1)Cl)C=1N(N=C2C(=NC(=NC21)C)NC(C(=O)N)C2=CC(=C(C=C2)OCC)OC)C | O[C:29]([CH2:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32]1)=[O:31].C(C[NH2:30])[NH:9][c:10]1[n:11][c:12]([CH3:13])[n:14][c:15]2[c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[n:25]([CH3:26])[n:27][c:28]12>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([NH:9][c:10]2[... | CCOc1ccc(CC(=O)O)cc1OC.Cc1nc(NCCN)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1 | CCOc1ccc(C(Nc2nc(C)nc3c(-c4c(Cl)cccc4Cl)n(C)nc23)C(N)=O)cc1OC | null | null | CN(C(C)=O)C.CCOC(=O)C | Acylation | OtherReaction | 7fd04dea0988f7e8650366ae1e798c3a521907e16b31c0690d4a8ad7bb63ddcf | 96ca7822a3bd0940a911422d3c93a7753d1a74d2e8ab35b13ac09ac85eb42ae5 | c1ccc(CNc2ncnc3c(-c4ccccc4)[nH]nc23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-C-C-[NH;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[c:14]:[#7;a:15]:[#7;a:16]:[c:17]:1:2>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[NH;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]2:[c:14]:[#7;a:15]:[#7;a:16]:[c:1... | null | [] | null | null | 14 | HOUR | To a stirred solution of (2-aminoethyl)[3-(2,6-dichlorophenyl)-2,5-dimethylpyrazolo[3,4-e]pyrimidin-7-yl]amine (175 mg, 0.5 mmol) in N,N-dimethylacetamide (5 mL), add 4-methylmorpholine (101 mg, 1.0 mmol), 2-(4-ethoxy-3-methoxyphenyl)acetic acid (115 mg, 0.55 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (331 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine | Primary amide.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ncc2n[nH]cc2n1 | HO- | CN(C(C)=O)C.CCOC(=O)C | null | 14 | CCOc1ccc(CC(=O)O)cc1OC.Cc1nc(NCCN)c2nn(C)c(-c3c(Cl)cccc3Cl)c2n1>CN(C(C)=O)C.CCOC(=O)C>CCOc1ccc(C(Nc2nc(C)nc3c(-c4c(Cl)cccc4Cl)n(C)nc23)C(N)=O)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8e838d24581408dac1aacea7fd8421f | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)n1>>Cc1nc(Cl)c(N)c(Cl)n1 | ClC1=NC(=NC(=C1[N+](=O)[O-])Cl)C>>ClC1=NC(=NC(=C1N)Cl)C | O=[N+:7]([O-])[c:6]1[c:4]([Cl:5])[n:3][c:2]([CH3:1])[n:10][c:8]1[Cl:9]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([Cl:9])[n:10]1 | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)n1 | Cc1nc(Cl)c(N)c(Cl)n1 | null | [Fe] | C(C)(=O)O.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cncnc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[Cl;D1;H0:9]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:2]:1-[NH2;D1;+0:1] | null | [] | 65 | CELSIUS | null | null | Add iron powder (6.0 g) to a solution of 4,6 dichloro-2-methyl-5-nitro-pyrimidine (6.50 g, 31 mmol) in acetic acid (11 mL) and MeOH (50 mL). Heat the resulting mixture at 65° C. for 1 h. After cooling, to ambient temperature, filter the mixture through a pad of celite, and evaporate the filtrate to dryness under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cncnc1 | Other | [Fe].C(C)(=O)O.CO | 65 | null | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)n1>[Fe].C(C)(=O)O.CO>Cc1nc(Cl)c(N)c(Cl)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee748f942cea4117896b641bc673b6a5 | Cc1cc(C)c(-c2cccc3c(Br)cc(C)nc23)c(C)c1.NCCN>>Cc1cc(C)c(-c2cccc3c(NCCN)cc(C)nc23)c(C)c1 | BrC1=CC(=NC2=C(C=CC=C12)C1=C(C=C(C=C1C)C)C)C.C(CN)N>>NCCNC1=CC(=NC2=C(C=CC=C12)C1=C(C=C(C=C1C)C)C)C | Br[c:12]1[c:11]2[cH:10][cH:9][cH:8][c:7](-[c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:24][c:22]3[CH3:23])[c:21]2[n:20][c:18]([CH3:19])[cH:17]1.[NH2:13][CH2:14][CH2:15][NH2:16]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]([NH:13][CH2:14][CH2:15][NH2:16])[cH:17][c:18]([CH3:19])[n:20][c:... | Cc1cc(C)c(-c2cccc3c(Br)cc(C)nc23)c(C)c1.NCCN | Cc1cc(C)c(-c2cccc3c(NCCN)cc(C)nc23)c(C)c1 | null | null | C(CO)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cccc3cccnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | 4 | HOUR | In a sealed tube, heat 4-bromo-2-methyl-8-(2,4,6-trimethyl-phenyl)-quinoline (100 mg, 0.29 mmol) at 140° C. in a mixture of ethylene glycol (1 mL) and ethylene diamine (0.3 mL). After 4 h, cool the reaction mixture and partition between saturated aqueous NaHCO3 and chloroform. Dry the combined organic extracts on Na2SO... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr | C(CO)O | null | 4 | Cc1cc(C)c(-c2cccc3c(Br)cc(C)nc23)c(C)c1.NCCN>C(CO)O>Cc1cc(C)c(-c2cccc3c(NCCN)cc(C)nc23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f213b349498040b1b9d7ad3b03a50bd3 | CNCCNc1cc(C)nc(Oc2c(C)cc(C)cc2C)c1C.COc1ccc(CC(=O)O)cc1OC>>COc1ccc(CC(=O)NCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC | CC=1C(=NC(=CC1NCCNC)C)OC1=C(C=C(C=C1C)C)C.COC=1C=C(C=CC1OC)CC(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O>>COC=1C=C(C=CC1OC)CC(=O)NCCNC1=C(C(=NC(=C1)C)OC1=C(C=C(C=C1C)C)C)C | C[NH:10][CH2:11][CH2:12][NH:13][c:14]1[cH:15][c:16]([CH3:17])[n:18][c:19]([O:20][c:21]2[c:22]([CH3:23])[cH:24][c:25]([CH3:26])[cH:27][c:28]2[CH3:29])[c:30]1[CH3:31].O[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32]1)=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[NH:10][C... | CNCCNc1cc(C)nc(Oc2c(C)cc(C)cc2C)c1C.COc1ccc(CC(=O)O)cc1OC | COc1ccc(CC(=O)NCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC | null | null | CN(C)C=O.CCOC(=O)C | Acylation | OtherReaction | 5a5ff76e01d051a03a2c77088c884912413ce09f49ca50e186c0fb9c62ad0bd2 | 9b702924f2df230008ea1edd297d6a4305f6e78d7804dff7e838c4286e010bf9 | O=C(Cc1ccccc1)NCCNc1ccnc(Oc2ccccc2)c1 | C-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[c:7]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[c:7] | null | [] | null | null | null | null | Stir a solution of [3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)-4-pyridyl][2-(methylamino)ethyl]amine (68 mg, 0.23 mmol), 3,4-dimethoxyphenylacetic acid (59 mg, 0.3 mmol), EDC (59 mg, 0.3 mmol) and HOBT (41 mg, 0.3 mmol) in DMF (1.0 mL) for 12 h. Dilute the reaction mixture with EtOAc (10 mL) and wash with saturated aq Na... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | CN(C)C=O.CCOC(=O)C | null | null | CNCCNc1cc(C)nc(Oc2c(C)cc(C)cc2C)c1C.COc1ccc(CC(=O)O)cc1OC>CN(C)C=O.CCOC(=O)C>COc1ccc(CC(=O)NCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f046879ca3246f4b57f746bea94b86f | COc1ccc(CC(=O)NCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC>>COc1ccc(CCNCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC | COC=1C=C(C=CC1OC)CC(=O)NCCNC1=C(C(=NC(=C1)C)OC1=C(C=C(C=C1C)C)C)C>>COC=1C=C(C=CC1OC)CCNCCNC1=C(C(=NC(=C1)C)OC1=C(C=C(C=C1C)C)C)C | O=[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31]1)[NH:9][CH2:10][CH2:11][NH:12][c:13]1[cH:14][c:15]([CH3:16])[n:17][c:18]([O:19][c:20]2[c:21]([CH3:22])[cH:23][c:24]([CH3:25])[cH:26][c:27]2[CH3:28])[c:29]1[CH3:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][CH2:10][CH2:11][... | COc1ccc(CC(=O)NCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC | COc1ccc(CCNCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC | null | null | C(Cl)(Cl)Cl.CO.C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CCNCCNc2ccnc(Oc3ccccc3)c2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[c:5] | null | [] | null | null | null | null | Add BH3 in THF (1 M solution, 0.3 mmol, 0.3 mL) to a solution of the crude 2-(3,4-dimethoxyphenyl)-N-(2-{[3,6-dimethyl-2-(2,4,6-trimethylphenoxy)(4-pyridyl)]amino}ethyl) acetamide in THF (2.0 mL) at ambient temperature. Heat the reaction mixture under reflux for 15 h, dilute with a solution of 10% aq HCV/MeOH (1:1, 2 m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | C(Cl)(Cl)Cl.CO.C1CCOC1 | null | null | COc1ccc(CC(=O)NCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC>C(Cl)(Cl)Cl.CO.C1CCOC1>COc1ccc(CCNCCNc2cc(C)nc(Oc3c(C)cc(C)cc3C)c2C)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1703578e8f0548f3b5fb59ecb4a819e6 | CCOc1ccc(CCN)cc1OC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.Cc1cc(C)c(Nc2cc(NCCN)nc(C)n2)c(C)c1>>CCOc1ccc(CC(=O)NCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | NCCNC1=NC(=NC(=C1)NC1=C(C=C(C=C1C)C)C)C.C(C)OC1=C(C=C(CCN)C=C1)OC.C(C)(C)N(C(C)C)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>C(C)OC1=C(C=C(C=C1)CC(=O)NCCNC1=NC(=NC(=C1)NC1=C(C=C(C=C1C)C)C)C)OC | N[CH2:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32]1.CN(C)[P+](N(C)C)(N(C)C)[O:10]n1nnc2ccccc21.[NH2:11][CH2:12][CH2:13][NH:14][c:15]1[cH:16][c:17]([NH:18][c:19]2[c:20]([CH3:21])[cH:22][c:23]([CH3:24])[cH:25][c:26]2[CH3:27])[n:28][c:29]([CH3:30])[n:31]1>>[CH3:1][CH2:2][O:3][c:4]1[cH... | CCOc1ccc(CCN)cc1OC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.Cc1cc(C)c(Nc2cc(NCCN)nc(C)n2)c(C)c1 | CCOc1ccc(CC(=O)NCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | null | null | C(Cl)Cl | Acylation | OtherReaction | cfa0c8edd50211f798565f1f3ee293d20dceaf8bf7f85f12f401d7e690fe524c | bf4cc782380223a2c801d48a0a69f6e4dea018cf7baecf2e6477eb9dab060c74 | O=C(Cc1ccccc1)NCCNc1cc(Nc2ccccc2)ncn1 | C-N(-C)-[P+](-[O;H0;D2;+0:1]-n1:n:n:c2:c:c:c:c:c:2:1)(-N(-C)-C)-N(-C)-C.N-[CH2;D2;+0:2]-[C:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[C:3]-[c:4] | null | [] | null | null | 14 | HOUR | To a solution of (2-aminoethyl){2-methyl-6-[(2,4,6-trimethylphenyl)amino]pyrimidin-4-yl}amine (0.36 g, 1.26 mmol), 4-ethoxy-3-methoxyphenethylamine (0.26 g, 1.26 mmol)) and N,N diisopropylethyl amine (0.24 ml, 1.38 mmol in CH2Cl2 (5 mL), add benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.61 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | Secondary amide | c1ccc2[nH]nnc2c1 | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | C(Cl)Cl | null | 14 | CCOc1ccc(CCN)cc1OC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.Cc1cc(C)c(Nc2cc(NCCN)nc(C)n2)c(C)c1>C(Cl)Cl>CCOc1ccc(CC(=O)NCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2635e5060ee4ca2a9981737d112e6cd | CCOc1ccc(CC(=O)NCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC>>CCOc1ccc(CCNCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | N(C)(C)CC.C(C)OC1=C(C=C(C=C1)CC(=O)NCCNC1=NC(=NC(=C1)NC1=C(C=C(C=C1C)C)C)C)OC.[AlH3]>>C(C)OC1=C(C=C(C=C1)CCNCCNC1=NC(=NC(=C1)NC1=C(C=C(C=C1C)C)C)C)OC | O=[C:9]([CH2:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31]1)[NH:10][CH2:11][CH2:12][NH:13][c:14]1[cH:15][c:16]([NH:17][c:18]2[c:19]([CH3:20])[cH:21][c:22]([CH3:23])[cH:24][c:25]2[CH3:26])[n:27][c:28]([CH3:29])[n:30]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][NH:10][CH2:11]... | CCOc1ccc(CC(=O)NCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | CCOc1ccc(CCNCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CCNCCNc2cc(Nc3ccccc3)ncn2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[c:5] | null | [] | null | null | 15 | MINUTE | Heat a solution of 2-(4-ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-4-ylamino]ethyl}-acetamide (0.324 g, 0.68 mmol) in THF (10 mL) with AlH3.NMe2Et (14 mL, 6.78 mmol) to reflux for 14 h. Cool the resulting mixture to ambient temperature, quench with Na2CO3.10H2O (1.0 g) and stir at... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | C1CCOC1 | null | 0.25 | CCOc1ccc(CC(=O)NCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC>C1CCOC1>CCOc1ccc(CCNCCNc2cc(Nc3c(C)cc(C)cc3C)nc(C)n2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb6b609ad68141eda11b3cb0a92c7fe2 | C1CNCCN1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCOS(=O)(=O)c2ccc(C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCNCC2)cc1 | CC1=CC=C(C=C1)S(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.N1CCNCC1.[OH-].[Na+]>>COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCNCC1 | [NH:33]1[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]1.Cc1ccc(S(=O)(=O)O[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:40][cH:39]3)([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]32)cc1>>[... | C1CNCCN1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCOS(=O)(=O)c2ccc(C)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCNCC2)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 3012dc60c14310d621abae8cd9ce102b1b72363f5aa91786df5d66245515072b | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | c1ccc(C2COc3ccccc3C2CCCCCCCCCN2CCNCC2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]):c:c:1.[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 81 | [{"value": 81.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 9-{7-(Methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman-4-yl}nonyl 4-methylbenzenesulfonate (540 mg, 0.843 mmol) and piperazine (2.2 g, 25.5 mmol) were dissolved in dioxane and then the mixture was refluxed for 2 hours. The mixture was cooled down to room temperature, basified to pH 13 using 5N-NaOH, and the... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | C1C[NH]CCN1 | c1ccccc1.c1ccc2c(c1)CCCO2.C1C[NH]CCN1 | TsOH.HO- | O1CCOCC1 | null | null | C1CNCCN1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCOS(=O)(=O)c2ccc(C)cc2)cc1>O1CCOCC1>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b65e146e05a14a1a8dfc125bbb52583a | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCNCC2)cc1.Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCN(CCCC(F)(F)C(F)(F)F)CC2)cc1 | COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCNCC1.C(=O)([O-])[O-].[K+].[K+].FC(CCCOS(=O)(=O)C1=CC=C(C=C1)C)(C(F)(F)F)F>>COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCN(CC1)CCCC(C(F)(F)F)(F)F | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][NH:36][CH2:47][CH2:48]2)[cH:49][cH:50]1.Cc1ccc(S(=O)(=O)O[CH2:37][C... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCNCC2)cc1.Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCN(CCCC(F)(F)C(F)(F)F)CC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 9d271698b0c48162ad18ec9c479844bc505434e9294038bc9af6d1140123fb4f | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | c1ccc(C2COc3ccccc3C2CCCCCCCCCN2CCNCC2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]):c:c:1.[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 48.6 | [{"value": 48.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCN(CC1)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCN(CC1)CCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | 7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-(9-piperazinylnonyl)-3-methylchroman (380 mg, 0.685 mmol), K2CO3 (190 mg, 1.375 mmol) and 4,4,5,5,5-pentafluoropentyl-4-methylbenzenesulfonate (460 mg, 1.384 mmol) were refluxed under acetone for 15 hours. After the mixture was cooled down to room temperature, water was a... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccc2c(c1)CCCO2.C1C[NH]CC[NH]1 | TsOH.HO- | O | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCNCC2)cc1.Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1>O>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCN(CCCC(F)(F)C(F)(F)F)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-502f9fd81a9f4c6b8b752215ee2a5228 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCN(CCCC(F)(F)C(F)(F)F)CC2)cc1>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCCN1CCN(CCCC(F)(F)C(F)(F)F)CC1 | COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCN1CCN(CC1)CCCC(C(F)(F)F)(F)F>>OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCN1CCN(CC1)CCCC(C(F)(F)F)(F)F | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][N:32]([CH2:33][CH2:34][CH2:35][C:36]([F:37])([F:38])[C:39]([F:40])([F:41])[F:42])[CH2:43][CH2:44]2)[cH:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCN(CCCC(F)(F)C(F)(F)F)CC2)cc1 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCCN1CCN(CCCC(F)(F)C(F)(F)F)CC1 | null | null | Cl.CO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2CCCCCCCCCN2CCNCC2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 88 | [{"value": 88.0, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCN1CCN(CC1)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | 7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}-3-methylchroman (210 mg, 0.294 mmol) was dissolved in 2N-HCl solution in methanol, and the mixture was stirred at 50° C. for 1 hour. The mixture was cooled down to room temperature, adjusted to pH=9 using aqueous NaHCO... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.C1C[NH]CC[NH]1 | HO- | Cl.CO | 50 | 1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN2CCN(CCCC(F)(F)C(F)(F)F)CC2)cc1>Cl.CO>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCCN1CCN(CCCC(F)(F)C(F)(F)F)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-590bd6cc73ae45b885ec4d481e80acdd | Cc1cc(C(C)(C)C)cc(C(C)(C)C)c1.O=C1CCC(=O)N1Br>>CC(C)(C)c1cc(CBr)cc(C(C)(C)C)c1 | C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)C.BrN1C(CCC1=O)=O>>C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CBr | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH3:8])[cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16]1.O=C1CCC(=O)N1[Br:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH2:8][Br:9])[cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16]1 | Cc1cc(C(C)(C)C)cc(C(C)(C)C)c1.O=C1CCC(=O)N1Br | CC(C)(C)c1cc(CBr)cc(C(C)(C)C)c1 | null | CC(C)(C#N)N=NC(C)(C)C#N | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 61.2 | [{"value": 61.0, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 3,5-Bis(t-butyl)-1-methylbenzene (200 mg, 0.98 mmol) was dissolved in carbon tetrachloride (4 ml), and then N-bromosuccinimide (192 mg, 1.08 mmol) and AIBN (α,α′-azabisisobutyronitrile) (2 mg) were added thereto. The mixture was heated under reflux and stirred for 5 hours. The filtrate obtained from the filtration of t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | CC(C)(C#N)N=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl | null | 5 | Cc1cc(C(C)(C)C)cc(C(C)(C)C)c1.O=C1CCC(=O)N1Br>CC(C)(C#N)N=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>CC(C)(C)c1cc(CBr)cc(C(C)(C)C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c4bcea7fa9f4f4fbae5be5b7622ef17 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)c1cc(CBr)cc(C(C)(C)C)c1>>CC(C)(C)OC(=O)N1CCN(Cc2cc(C(C)(C)C)cc(C(C)(C)C)c2)CC1 | C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CBr.N1(CCNCC1)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:27][CH2:28]1.Br[CH2:12][c:13]1[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][c:... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)c1cc(CBr)cc(C(C)(C)C)c1 | CC(C)(C)OC(=O)N1CCN(Cc2cc(C(C)(C)C)cc(C(C)(C)C)c2)CC1 | null | null | CC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:5]-[C:6]-[C:7]-1):[c:4] | 56.1 | [{"value": 56.0, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.1, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3,5-Bis(t-butyl)-1-(bromomethyl)benzene (170 mg, 0.60 mmol), t-butyl piperazine carboxylate (102 mg, 0.55 mmol) and potassium carbonate (151 mg, 1.10 mmol) were dissolved in a solvent mixture of acetone (2 ml) and DMF (0.2 ml), and the mixture was stirred overnight while heated under reflux. The reaction mixture was ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(=O)C.CN(C)C=O | null | 8 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)c1cc(CBr)cc(C(C)(C)C)c1>CC(=O)C.CN(C)C=O>CC(C)(C)OC(=O)N1CCN(Cc2cc(C(C)(C)C)cc(C(C)(C)C)c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b404b72e8764ac39f42611c05e23403 | CC(C)(C)c1cc(CN2CCNCC2)cc(C(C)(C)C)c1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCl)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCN3CCN(Cc4cc(C(C)(C)C)cc(C(C)(C)C)c4)CC3)cc2)cc1 | CCCCCC.ClCCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [NH:31]1[CH2:32][CH2:33][N:34]([CH2:35][c:36]2[cH:37][c:38]([C:39]([CH3:40])([CH3:41])[CH3:42])[cH:43][c:44]([C:45]([CH3:46])([CH3:47])[CH3:48])[cH:49]2)[CH2:50][CH2:51]1.Cl[CH2:30][CH2:29][O:28][c:27]1[cH:26][cH:25][c:24]([CH:23]2[C:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:55][cH:54]3)([CH3:10])[CH2:11]... | CC(C)(C)c1cc(CN2CCNCC2)cc(C(C)(C)C)c1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCl)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCN3CCN(Cc4cc(C(C)(C)C)cc(C(C)(C)C)c4)CC3)cc2)cc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CC(=O)C.CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCN(CCOc3ccc(C4c5ccccc5OCC4c4ccccc4)cc3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 51 | [{"value": 51.0, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC"... | null | null | null | null | (3RS,4SR)-4-[4-(2-Chloroethoxy)phenyl]-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman (210 mg, 0.42 mmol) and {(3,5-bis(t-butyl)phenyl]methyl}piperazine (243 mg, 0.84 mmol) were dissolved in a solvent mixture of acetone (4 ml) and DMF (0.4 ml). To the mixture potassium carbonate (116 mg, 0.84 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CC(=O)C.CN(C)C=O.C(C)(=O)OCC | null | null | CC(C)(C)c1cc(CN2CCNCC2)cc(C(C)(C)C)c1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCl)cc2)cc1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CC(=O)C.CN(C)C=O.C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCN3CCN(Cc4cc(C(C)(C)C)cc(C(C)(C)C)c4)CC3)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9084cee2c4444cc081748c35eeb32eb2 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCN3CCN(Cc4cc(C(C)(C)C)cc(C(C)(C)C)c4)CC3)cc2)cc1>>CC(C)(C)c1cc(CN2CCN(CCOc3ccc(C4c5ccc(O)cc5OCC4(C)c4ccc(O)cc4)cc3)CC2)cc(C(C)(C)C)c1 | C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.Cl.C([O-])(O)=O.[Na+]>>C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O | COC[O:25][c:24]1[cH:23][cH:22][c:21]2[c:27]([cH:26]1)[O:28][CH2:29][C:30]([CH3:31])([c:32]1[cH:33][cH:34][c:35]([O:36]COC)[cH:37][cH:38]1)[CH:20]2[c:19]1[cH:18][cH:17][c:16]([O:15][CH2:14][CH2:13][N:12]2[CH2:11][CH2:10][N:9]([CH2:8][c:7]3[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:49][c:44]([C:45]([CH3:46])([CH3:47]... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCN3CCN(Cc4cc(C(C)(C)C)cc(C(C)(C)C)c4)CC3)cc2)cc1 | CC(C)(C)c1cc(CN2CCN(CCOc3ccc(C4c5ccc(O)cc5OCC4(C)c4ccc(O)cc4)cc3)CC2)cc(C(C)(C)C)c1 | null | null | ClCCl.CO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(CN2CCN(CCOc3ccc(C4c5ccccc5OCC4c4ccccc4)cc3)CC2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 54 | [{"value": 54.0, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.9, "product": "C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)CN1CCN(CC1)CCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O", "details":... | null | null | 2 | HOUR | (3RS,4SR)-4-{4-{2-{4-{[3,5-Bis(t-butyl)phenyl]methyl}piperazinyl}ethoxy}phenyl}-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman (150 mg, 0.21 mmol) was dissolved in methanol (1.5 ml), 6N-HCl (2 ml) was added portionwise thereto, and the mixture was stirred at 50–60° C. for 2 hours. The reaction solution... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HO- | ClCCl.CO | null | 2 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCN3CCN(Cc4cc(C(C)(C)C)cc(C(C)(C)C)c4)CC3)cc2)cc1>ClCCl.CO>CC(C)(C)c1cc(CN2CCN(CCOc3ccc(C4c5ccc(O)cc5OCC4(C)c4ccc(O)cc4)cc3)CC2)cc(C(C)(C)C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-088a750a1a0243b2a737763c3b29f920 | COc1ccc(C2(C)COc3cc(OC)ccc3C2CCCCCO)cc1.Cc1ccc(S(=O)(=O)Cl)cc1>>COc1ccc(C2(C)COc3cc(OC)ccc3C2CCCCCOS(=O)(=O)c2ccc(C)cc2)cc1 | OCCCCCC1C(COC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.O>>COC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCOS(=O)(=O)C1=CC=C(C=C1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][O:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[cH:36][cH:37]1.Cl[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([CH3:33])[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3... | COc1ccc(C2(C)COc3cc(OC)ccc3C2CCCCCO)cc1.Cc1ccc(S(=O)(=O)Cl)cc1 | COc1ccc(C2(C)COc3cc(OC)ccc3C2CCCCCOS(=O)(=O)c2ccc(C)cc2)cc1 | null | null | N1=CC=CC=C1.ClCCl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCCCCC1c2ccccc2OCC1c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 53 | [{"value": 53.0, "product": "COC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCOS(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "COC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCOS(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | (3RS,4RS)-4-(5-Hydroxypentyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylchroman (430 mg, 1.2 mmol) was dissolved in a solvent mixture of pyridine (12 ml) and dichloromethane (4 ml), which was then cooled down to 0° C. p-Toluenesulfonylchloride (460 mg, 2.3 mmol) was added dropwise thereto, and the mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HCl | N1=CC=CC=C1.ClCCl | null | 3 | COc1ccc(C2(C)COc3cc(OC)ccc3C2CCCCCO)cc1.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1.ClCCl>COc1ccc(C2(C)COc3cc(OC)ccc3C2CCCCCOS(=O)(=O)c2ccc(C)cc2)cc1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.