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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0972b428a21c41088cff53aef93eb87c | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN(C)C(=O)OC(C)(C)C)cc1>>CNCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | C(C)(C)(C)OC(=O)N(C)CC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.FC(C(=O)O)(F)F>>FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNC)=O)C2=C(C=CC=C2)OC)C=C1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[CH2:26][CH2:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[O:34][CH3:35])[cH:36][cH:37]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:... | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN(C)C(=O)OC(C)(C)C)cc1 | CNCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]>>[C;D1;H3:2]-[NH;D2;+0:1]-[C:3]-[c:4] | 98.9 | [{"value": 98.9, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-(N-tert-Butoxycarbonyl-N-methylamino)methyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (144 mg, 0.239 mmol) was dissolved in methylene chloride (4 ml) to which was subsequently added dropwise trifluoroacetic acid (0.4 ml) while cooling in an ice bath. After 2 hours of stirring at the same... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(CN(C)C(=O)OC(C)(C)C)cc1>C(Cl)Cl>CNCc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccccc2OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13297e7c81bb418aa27b32cfac5bc697 | CC(C)(C)N=C=O.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(=O)NC(C)(C)C)cc1 | NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)(C)(C)N=C=O>>C(C)(C)(C)NC(NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)=O | [C:34](=[O:35])=[N:36][C:37]([CH3:38])([CH3:39])[CH3:40].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1)[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([NH2:33])[cH:41][cH:42]1>>[CH3:1][O... | CC(C)(C)N=C=O.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1 | COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(=O)NC(C)(C)C)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 77.6 | [{"value": 77.6, "product": "C(C)(C)(C)NC(NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "C(C)(C)(C)NC(NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (77.7 mg, 0.164 mmol) and tertbutyl isocyanate (0.022 ml, 0.196 mmol), the procedure of inventive Example 144 was repeated to obtain 72.9 mg (77.6%) of the title compound in a colorless oily form.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(N)cc1>>COc1ccccc1N(CCN1CCC(C(=O)c2ccc(F)cc2)CC1)C(=O)c1ccc(NC(=O)NC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1cf1796f970a4f61aff232d412aa105f | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.N#C[O-]>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(N)=O)cc2)c1 | [OH-].[Na+].[O-]C#N.[K+].NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C([O-])(O)=O.[Na+]>>N(C(=O)N)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([NH2:32])[cH:36][cH:37]2)[cH:38]1.[C:33](#[N:34])[O-:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]... | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.N#C[O-] | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(N)=O)cc2)c1 | null | null | C(C)(=O)O.O | Acylation | OtherReaction | f8798d1193af6f9b314ac8855e814716b90ff3758bcfa29778cc632fcaa83b7a | 5efe06db19c806d9e9798893351dc14c0cc48f1e8f8c857f54c6171e86c96a1b | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[O-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 48.4 | [{"value": 48.4, "product": "N(C(=O)N)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "N(C(=O)N)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (237.2 mg, 0.50 mmol) was dissolved in acetic acid-water (1:2, 1.8 ml) to which was subsequently added dropwise an aqueous solution (0.5 ml) of potassium cyanate (81.1 mg, 0.90 mmol) After 3 hours of stirring at room temperature, the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | C(C)(=O)O.O | null | null | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.N#C[O-]>C(C)(=O)O.O>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(N)=O)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-325ebeb3b83e42ed8fa3b3afdd734121 | CI.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1>>CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(OC)cc2)cc1 | [Cl-].[NH4+].[H-].[Na+].C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CI>>CCC(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | I[CH3:1].[CH3:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[c:30]2[cH:31][cH:32][c:33]([O:34][CH3:35])[cH:36][cH:37]2)[cH:38][cH:39]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5... | CI.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1 | CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(OC)cc2)cc1 | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_primary | 0e09d968095a587418cca2841b1e4f096e8103de8fbb60e833faf1fb3df36a41 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | I-[CH3;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | 80.4 | [{"value": 80.4, "product": "CCC(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.3, "product": "CCC(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) was dissolved in THF (3.0 ml) to which were subsequently added 60% sodium hydride {28.0 mg, 0.70 mmol) and methyl iodide (0.060 ml, 1.00 mmol) at room temperature, followed by 2 hours of stirring. The reaction so... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HI | C1CCOC1 | null | 2 | CI.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1>C1CCOC1>CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(OC)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-af152361a976447c83199ce000045ab8 | COC1CCC(OC)O1.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1>>COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(-n3cccc3)cc2)cc1 | NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.COC1OC(CC1)OC>>N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CO[CH:32]1O[CH:35](OC)[CH2:34][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][CH2:24]2)[C:25](=[O:26])[c:27]2[cH:28][cH:29][c:30]([NH2:31])[cH:36][cH:37]2)[cH:38][cH:39]1>>[CH3:1][O:2][c:3]1[cH:4]... | COC1CCC(OC)O1.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1 | COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(-n3cccc3)cc2)cc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0e9d22b0723ec2930c6f0b28cb06c2d86835df697b962917265b2a52889a76e9 | 37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccc(-n3cccc3)cc2)c2ccccc2)CC1 | C-O-[CH;D3;+0:1]1-O-[CH;D3;+0:2](-O-C)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[NH2;D1;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[n;H0;D3;+0:5]1:[cH;D2;+0:1]:[cH;D2;+0:4]:[cH;D2;+0:3]:[cH;D2;+0:2]:1):[c:9]:[c:10] | 82.6 | [{"value": 82.0, "product": "N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (237.0 mg, 0.50 mmol) was dissolved in acetic acid (5.0 ml), and the solution was mixed with 2,5-dimethoxytetrahydrofuran (0.065 ml, 0.50 mmol) and heated for 1 hour under reflux. After cooling, acetic acid was distilled off under a reduced... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine | null | C1CCOC1 | c1cc[nH]c1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1cc[nH]c1 | HO- | C(C)(=O)O | null | null | COC1CCC(OC)O1.COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)cc1>C(C)(=O)O>COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(-n3cccc3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a87ab204e6184d2c93e710080ffacda1 | COC1CCC(OC)O1.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(-n3cccc3)cc2)c1 | NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.COC1OC(CC1)OC>>N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | CO[CH:33]1O[CH:36](OC)[CH2:35][CH2:34]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([NH2:32])[cH:37][cH:38]2)[cH:39]1>>[CH3:1][O:2][c:3]1[cH:4]... | COC1CCC(OC)O1.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(-n3cccc3)cc2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0e9d22b0723ec2930c6f0b28cb06c2d86835df697b962917265b2a52889a76e9 | 37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccc(-n3cccc3)cc2)c2ccccc2)CC1 | C-O-[CH;D3;+0:1]1-O-[CH;D3;+0:2](-O-C)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[NH2;D1;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[n;H0;D3;+0:5]1:[cH;D2;+0:1]:[cH;D2;+0:4]:[cH;D2;+0:3]:[cH;D2;+0:2]:1):[c:9]:[c:10] | 78 | [{"value": 78.0, "product": "N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.1 mg, 0.50 mmol) and 2,5-dimethoxytetrahydrofuran (0.066 ml, 0.50 mmol), the procedure of Inventive Example 149 was repeated to obtain 205.0 mg (78.0%) of the title compound in a light brown amorphous form.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine | null | C1CCOC1 | c1cc[nH]c1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1cc[nH]c1 | HO- | null | null | null | COC1CCC(OC)O1.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(-n3cccc3)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-afe5cbc25fd340cf8536ac9ee64ce538 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1>>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(O)c2)cc1 | B(Br)(Br)Br.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C([O-])(O)=O.[Na+]>>C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)O)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | C[O:34][c:33]1[cH:32][cH:31][cH:30][c:29]([N:11]([C:9]([c:8]2[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:37][cH:36]2)=[O:10])[CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:35]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]... | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1 | CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(O)c2)cc1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 76.7 | [{"value": 76.7, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)O)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)O)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (50.0 mg, 0.10 mmol) was dissolved in methylene chloride (3.0 ml) to which was subsequently added a methylene chloride solution (1 ml) of boron tribromide (0.018 ml, 0.19 mmol) at 0° C. After 12 hours of stirring at 0° C. to room temp... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 12 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)c1>C(Cl)Cl>CC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccc(O)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-210fb1b1e78248f89d667958215bdb36 | O=C(Nc1cccnc1)c1ccc([N+](=O)[O-])cc1.O=C(c1ccccc1)C1CCN(CCCl)CC1>>O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2cccnc2)CC1 | [I-].[Na+].[N+](=O)([O-])C1=CC=C(C(=O)NC=2C=NC=CC2)C=C1.[H-].[Na+].[Cl-].[Na+].ClCCN1CCC(CC1)C(C1=CC=CC=C1)=O>>[N+](=O)([O-])C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1 | [NH:15]([C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][n:31][cH:32]1.Cl[CH2:14][CH2:13][N:12]1[CH2:11][CH2:10][CH:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:34][CH2:33]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH:9]1[CH2:10][CH... | O=C(Nc1cccnc1)c1ccc([N+](=O)[O-])cc1.O=C(c1ccccc1)C1CCN(CCCl)CC1 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2cccnc2)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[O;D1;H0:4]=[C:5](-[c:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:5](=[O;D1;H0:4])-[c:6])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | 24 | [{"value": 24.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | In an atmosphere of argon, 4-nitro-N-(3-pyridyl)benzamide (973 mg, 4.00 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (176 mg, 60%, 4.40 mmol) at room temperature, stirred for 1 hour at 60° C., and added dropwise 1-(2-chloroethyl)-4-benzoylpiperidine (1.38 g, 5.49 mmol) and a catalyt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HCl | CN(C)C=O | 60 | 1 | O=C(Nc1cccnc1)c1ccc([N+](=O)[O-])cc1.O=C(c1ccccc1)C1CCN(CCCl)CC1>CN(C)C=O>O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2cccnc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83156c93ebe44f9b836d2b41d4fbb6ea | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)C(F)(F)F>>O=C(c1ccc(F)cc1)C1CCN(CCN(C(=O)c2ccc(NC(=O)C(F)(F)F)cc2)c2cccnc2)CC1 | C([O-])(O)=O.[Na+].N1=CC=CC=C1.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.FC(C(=O)O)(F)F>>FC(C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)(F)F | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([NH2:23])[cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][n:36][cH:37]2)[CH2:38][CH2:39]1.O[C:24](=[O:25])[C:26]([F:27])([F:28])[F:29]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]... | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)C(F)(F)F | O=C(c1ccc(F)cc1)C1CCN(CCN(C(=O)c2ccc(NC(=O)C(F)(F)F)cc2)c2cccnc2)CC1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 81.2 | [{"value": 81.2, "product": "FC(C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "FC(C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 3 | HOUR | 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (229.3 mg, 0.51 mmol) was dissolved in methylene chloride (2.0 ml) to which were subsequently added pyridine (0.05 ml, 0.62 mmol) and anhydrous trifluoroacetic acid (0.09 ml, 0.64 mmol) at 0° C. After 3 hours of stirring at 0° C. to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HO- | C(Cl)Cl | null | 3 | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)C(F)(F)F>C(Cl)Cl>O=C(c1ccc(F)cc1)C1CCN(CCN(C(=O)c2ccc(NC(=O)C(F)(F)F)cc2)c2cccnc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-579f2de7dc1447cc98ef05252e3642bd | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(Cl)c1ccccc1>>O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1)c1ccccc1 | C([O-])(O)=O.[Na+].N1=CC=CC=C1.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[CH2:26][CH2:27]2)[c:28]2[cH:29][cH:30][cH:31][n:32][cH:33]2)[cH:34][cH:35]1.Cl[C:2](=[O:1])[c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1>>[O:1]=[C:2]([NH:3][... | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(Cl)c1ccccc1 | O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 71.3 | [{"value": 70.6, "product": "C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | 14 | HOUR | 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (225.3 mg, 0.50 mmol) was dissolved in methylene chloride (2.0 ml) to which were subsequently added pyridine (0.05 ml, 0.62 mmol) and benzoyl chloride (0.09 ml, 0.77 mmol). After 14 hours of stirring at room temperature, the reaction solution was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | 14 | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(Cl)c1ccccc1>C(Cl)Cl>O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df4b0db0bdde491cb5906e69e4e16de2 | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1.O=C(Cl)c1ccccc1>>O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1)c1ccccc1 | NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1.C(C1=CC=CC=C1)(=O)Cl.N1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[CH2:25][CH2:26]2)[c:27]2[cH:28][cH:29][cH:30][n:31][cH:32]2)[cH:33][cH:34]1.Cl[C:2](=[O:1])[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1>>[O:1]=[C:2]([NH:3][c:4]1[c... | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1.O=C(Cl)c1ccccc1 | O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1)c1ccccc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 85.9 | [{"value": 85.9, "product": "C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Using 4-amino-N-[2-(4-benzoylpiperidino)ethyl]-N-(3-pyridyl)benzamide (210.7 mg, 0.49 mmol), benzoyl chloride (0.07 ml, 0.60 mmol) and pyridine (0.05 ml, 0.62 mmol), the procedure of Inventive Example 165 was repeated to obtain 224.3 mg (85.9%) of the title compound in a colorless powder form.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1 | HCl | null | null | null | Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1.O=C(Cl)c1ccccc1>>O=C(Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccccc3)CC2)c2cccnc2)cc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e047a94edb4343a0b2070338fbae9a7f | Cl>>Cl | FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1.Cl.CCOCC>>Cl.FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1 | [ClH:38]>>[ClH:38] | Cl | Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 99.8 | [{"value": 99.8, "product": "Cl.FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-(N-hydroxyimino)-N-(2-methoxyphenyl)benzenesulfonamide (65 mg, 0.12 mmol) was dissolved in methylene chloride (2 ml) to which was subsequently added saturated hydrogen chloride/ether solution (1 ml). After 5 minutes of stirring, the solvent was removed by evaporation, and th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)Cl | null | 0.083333 | Cl>C(Cl)Cl>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e34cf84fd5b941c6b9c20c5106e6df70 | O=C(O)C(=O)O>>O=C(O)C(=O)O | FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1.C(C(=O)O)(=O)O>>C(C(=O)O)(=O)O.FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1 | [O:37]=[C:38]([OH:39])[C:40](=[O:41])[OH:42]>>[O:37]=[C:38]([OH:39])[C:40](=[O:41])[OH:42] | O=C(O)C(=O)O | O=C(O)C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 79.2 | [{"value": 79.2, "product": "C(C(=O)O)(=O)O.FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "C(C(=O)O)(=O)O.FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 5 | MINUTE | N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-3-methoxy-N-(2-methoxyphenyl)benzamide (107 mg, 0.218 mmol) was dissolved in methanol (10 ml) to which was subsequently added oxalic acid (19.7 mg, 0.218 mmol). After 5 minutes of stirring at room temperature, methanol was removed by evaporation, and the resulting residue was ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | 0.083333 | O=C(O)C(=O)O>CO>O=C(O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6520b67c10374e1083985864bd8780e4 | O=C(O)C(=O)O>>O=C(O)C(=O)O.O=C(O)C(=O)O | N[C@H](C(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C.C(C(=O)O)(=O)O>>C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.N[C@H](C(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C | [O:42]=[C:43]([OH:50])[C:51](=[O:52])[OH:53]>>[O:42]=[C:43]([OH:44])[C:45](=[O:46])[OH:47].[O:48]=[C:49]([OH:50])[C:51](=[O:52])[OH:53] | O=C(O)C(=O)O | O=C(O)C(=O)O.O=C(O)C(=O)O | null | null | CO | Miscellaneous | OtherReaction | d52db42154f846296f410f93ad678e29ddc4afd10ba8f991fe2f0397ee45638b | fe8a5e2dc0843e8c5be2b5940263c4d09e942bd97e1a4358b629c45d65454049 | null | [O;D1;H0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;D1;H1:6]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[O;D1;H1:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[O;D1;H0:11]=[C:12](-[OH;D1;+0:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;D1;H1:6] | 85.1 | [{"value": 85.1, "product": "C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.N[C@H](C(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.N[C@H](C(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C... | null | null | 5 | MINUTE | 4-[(S)-2-Aminopropionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (84.7 mg, 0.155 mmol) was dissolved in methanol (5 ml) and mixed with oxalic acid (28 mg, 0.311 mmol). After 5 minutes of stirring at room temperature, methanol was removed by evaporation, and the resulting amorp... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid | null | null | null | Other | CO | null | 0.083333 | O=C(O)C(=O)O>CO>O=C(O)C(=O)O.O=C(O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-302c0855e821470884d0b4e53dc0fedc | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | C(\C=C\C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1>>C(\C=C\C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | [O:39]=[C:40]([OH:41])/[CH:42]=[CH:43]/[C:44](=[O:45])[OH:46]>>[O:39]=[C:40]([OH:41])/[CH:42]=[CH:43]/[C:44](=[O:45])[OH:46] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 80 | [{"value": 80.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "C(\\C=C\\C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "... | null | null | null | null | 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (282.4 mg, 0.55 mmol) was dissolved in methanol (1.5 ml) and mixed with a methanol solution (3.0 ml) of fumaric acid (63.8 mg, 0.55 mmol) at 0° C. Thereafter, the thus precipitated crystals were collected by filtration and washed with... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8098aa2891d4fcea8abf7e7fa4e55c8 | O=C(O)C(O)C(O)C(=O)O>>O=C(O)C(O)C(O)C(=O)O | C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C(O)C(O)C(=O)O)(=O)O>>C(C(O)C(O)C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | [O:39]=[C:40]([OH:41])[CH:42]([OH:43])[CH:44]([OH:45])[C:46](=[O:47])[OH:48]>>[O:39]=[C:40]([OH:41])[CH:42]([OH:43])[CH:44]([OH:45])[C:46](=[O:47])[OH:48] | O=C(O)C(O)C(O)C(=O)O | O=C(O)C(O)C(O)C(=O)O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 75.3 | [{"value": 75.3, "product": "C(C(O)C(O)C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "C(C(O)C(O)C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details":... | null | null | null | null | Using 4-acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) and tartaric acid (35.0 mg, 0.30 mmol), the procedure of Inventive Example 211 was repeated to obtain 143.0 mg (75.3%) of the title compound in a colorless powder form.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | O=C(O)C(O)C(O)C(=O)O>>O=C(O)C(O)C(O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5a1347378234e5ea5c192cce8e4d5a5 | O=C(O)/C=C\C(=O)O>>O=C(O)/C=C\C(=O)O | C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1 | [O:39]=[C:40]([OH:41])/[CH:42]=[CH:43]\[C:44](=[O:45])[OH:46]>>[O:39]=[C:40]([OH:41])/[CH:42]=[CH:43]\[C:44](=[O:45])[OH:46] | O=C(O)/C=C\C(=O)O | O=C(O)/C=C\C(=O)O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 86.3 | [{"value": 82.0, "product": "C(\\C=C/C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "C(\\C=C/C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1", "details": "CA... | null | null | null | null | Using 4-acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) and maleic acid (45.0 mg, 0.30 mmol), the procedure of Inventive Example 211 was repeated to obtain 164.0 mg (82.0%) of the title compound in a colorless powder form.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | O=C(O)/C=C\C(=O)O>>O=C(O)/C=C\C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5dbd58a197604caab9440bf88042ff6e | O=C(O)/C=C\C(=O)O>>O=C(O)/C=C\C(=O)O | C(\C=C/C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1>>C(\C=C/C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1 | [O:33]=[C:34]([OH:35])/[CH:36]=[CH:37]\[C:38](=[O:39])[OH:40]>>[O:33]=[C:34]([OH:35])/[CH:36]=[CH:37]\[C:38](=[O:39])[OH:40] | O=C(O)/C=C\C(=O)O | O=C(O)/C=C\C(=O)O | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 65 | [{"value": 65.0, "product": "C(\\C=C/C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.9, "product": "C(\\C=C/C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | 4-Amino-N-[2-(4-benzoylpiperidino)ethyl]-N-(3-pyridyl)benzamide (3.00 g, 7.00 mmol) was dissolved in ethanol (10.0 ml) to which was subsequently added a ethanol solution (20.0 ml) of maleic acid (812.0 mg, 7.00 mmol) at room temperature, and then stirred. After the solvent was removed by evaporation, the thus precipita... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | O=C(O)/C=C\C(=O)O>C(C)O>O=C(O)/C=C\C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a962f676bde548c9a208b5b8ceb746c5 | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.O=C(O)/C=C/C(=O)O>>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.O=C(O)/C=C/C(=O)O | C(\C=C\C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1>>C(\C=C\C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C2=CC(=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:26](=[O:27])[c:28]2[cH:34][cH:65][c:66]([NH2:67])[cH:68][cH:69]2)[cH:35]1.[CH:29](\[C:61](=[O:37])[OH:73])=[CH:75]/[C:76](=[O:77])[OH:78]>>... | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.O=C(O)/C=C/C(=O)O | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.O=C(O)/C=C/C(=O)O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d99497f14d4f4bc92f42b4b0346079b94e44e7f2193cc22aed8edda8f26f9827 | 7d7ef14e29161ac6606a818938036c070d59cc351f9ef3544d96d28ae95e8fcd | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2ccccc2)CC1 | [C:1]-[#7:2](-[c:3])-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9](-[N;D1;H2:10]):[c:11]:[cH;D2;+0:12]:1.[O;D1;H0:13]=[C:14](-[O;D1;H1:15])/[CH;D2;+0:16]=[CH;D2;+0:17]/[C;H0;D3;+0:18](=[O;H0;D1;+0:19])-[OH;D1;+0:20]>>[C:1]-[#7:2](-[c:3])-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]1:[cH;D2;+0:17]:[c:21]:[c:... | 90.1 | [{"value": 90.0, "product": "C(\\C=C\\C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C2=CC(=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "C(\\C=C\\C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C2=CC(=CC=C2)O... | null | null | null | null | 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (475.0 mg, 1.00 mmol) was dissolved in methanol (4.0 ml) and mixed with a methanol solution (3.0 ml) of fumaric acid (58.0 mg, 0.50 mmol) at 0° C. Thereafter, the thus precipitated crystals were collected by filtration and recrystallized fr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aromatic halide.Carboxylic acid.Ketone.Ether.Tertiary amide.Primary amine.Tertiary amine | c1ccccc1 | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | CO | null | null | COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.O=C(O)/C=C/C(=O)O>CO>COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.COc1cccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(N)cc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1d509de57fab4ad7907e706bebccd055 | O=C(O)/C=C/C(=O)O.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1>>O=C(O)/C=C/C(=O)O.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 | C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1 | [O:1]=[C:16]([OH:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[OH:8].[cH:2]1[c:27]([C:25]([CH:24]2[CH2:23][CH2:22][N:21]([CH2:55][CH2:54][N:53]([C:51]([c:50]3[cH:49][cH:13][c:12]([NH:11][CH:10]=[O:9])[cH:78][cH:77]3)=[O:52])[c:71]3[cH:72][cH:73][cH:74][n:75][cH:76]3)[CH2:35][CH2:34]2)=[O:26])[cH:33][cH:32][c:30]([F:31])[cH:29]1>>[O:... | O=C(O)/C=C/C(=O)O.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 | O=C(O)/C=C/C(=O)O.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e0dd5bcaad88b046af8e17e6365574936f8c260d3d40d3e396f8a17ad590e6b4 | b3be6655e88bf7057db2af69af8f15e012e15c8526e235ce83853278f54d5884 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | [#7;a:1]:[c:2]:[c:3]-[#7:4](-[C:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10](-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16](-[F;D1;H0:17]):[cH;D2;+0:18]:[cH;D2;+0:19]:2)-[C:20]-[C:21]-1)-[C:22](=[O;D1;H0:23])-[c:24]1:[c:25]:[cH;D2;+0:26]:[c;H0;D3;+0:27](-[#7:28]-[C:29]=[O;D1;H0:30]):[cH;D2;+0:31]:[... | 52.1 | [{"value": 52.1, "product": "C(\\C=C\\C(=O)O)(=O)O.C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.1, "product": "C(\\C=C\\C(=O)O)(=O)O.C(=O)NC1=CC=C(C(=O)N(C=2C=NC... | null | null | null | null | Using 4-formylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (208.8 mg, 0.44 mmol) and fumaric acid (25.8 mg, 0.22 mmol), the procedure of Inventive Example 271 was repeated to obtain 122.2 mg (52.1%) of the title compound in a colorless powder form.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Tertiary amine | Aromatic halide.Carboxylic acid.Ketone.Ketone.Secondary amide.Tertiary amide.Tertiary amine.Tertiary amine | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | O=C(O)/C=C/C(=O)O.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1>>O=C(O)/C=C/C(=O)O.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7ace0fd1bbf443febb2d3c42fd67234e | CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | C(CCCC)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(CCCC)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(CCCC)(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:39][cH:49][c:50]([C:51](=[O:52])[N:53]([CH2:54][CH2:15][N:14]2[CH2:18][CH2:19][CH:20]([C:21](=[O:22])[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[CH2:30][CH2:31]2)[c:71]2[cH:72][cH:73][cH:74][n:75][cH:76]2)[cH:77][cH:78]1.[CH:9](=[CH:11]/[C:12](=[O:13])[OH... | CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 77a6e278dd1899fb2b2794161dc642076da2e1e94a9c21a82946154653e6ba6d | 8f534bc4e0c26fc38c60205abe754e433ff59df7fb20cdb9be5e34183702ecfd | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | [#7;a:1]:[c:2]:[c:3]-[#7:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:7]1-[CH2;D2;+0:8]-[C:9]-[C:10](-[C:11]=[O;D1;H0:12])-[C:13]-[CH2;D2;+0:14]-1)-[C:15](=[O;D1;H0:16])-[c:17]1:[c:18]:[cH;D2;+0:19]:[c;H0;D3;+0:20](-[#7:21]-[C:22](-[C:23])=[O;D1;H0:24]):[cH;D2;+0:25]:[cH;D2;+0:26]:1.[O;D1;H0:27]=[C;H0;D3;+0:28](-[OH;D1;... | 84 | [{"value": 84.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C(CCCC)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(CCCC)(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C(CCCC)(=O)NC1=C... | null | null | null | null | Using 4-valerylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]-ethyl}-N-(3-pyridyl)benzamide (139.4 mg, 0.26 mmol) and fumaric acid (15.4 mg, 0.13 mmol), the procedure of inventive Example 271 was repeated to obtain 128.5 mg (84.0%) of the title compound in a light brown amorphous powder form.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Tertiary amine | Aromatic halide.Carboxylic acid.Carboxylic acid.Ketone.Secondary amide.Tertiary amide.Tertiary amine.Tertiary amine | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CCCCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0202fb642d54f90b89cb29bdb39c9eb | CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | CNC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.CNC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CNC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1 | [CH3:1][NH:2][c:3]1[cH:4][cH:5][c:40]([C:41](=[O:42])[N:43]([CH2:44][CH2:45][N:46]2[CH2:26][CH2:25][CH:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:14][CH2:47]2)[c:61]2[cH:62][cH:63][cH:64][n:65][cH:66]2)[cH:67][cH:68]1.[CH:6](\[C:7](=[O:8])[OH:71])=[CH:73]/[C:74](=[O:75])[OH:76]>>[CH3:1][... | CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1ea08c88515e18492fc92ff8d1ebda2338cf66e7185546e193e7efa43313715a | 136cf14da7a3e2c40cd9243eaea88d757bbca88fc839111ff5e0267ced2fe70f | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | [#7;a:1]:[c:2]:[c:3]-[#7:4](-[C:5]-[C:6]-[N;H0;D3;+0:7]1-[CH2;D2;+0:8]-[C:9]-[C:10](-[C:11](=[O;D1;H0:12])-[c:13])-[CH2;D2;+0:14]-[CH2;D2;+0:15]-1)-[C:16](=[O;D1;H0:17])-[c;H0;D3;+0:18]1:[c:19]:[cH;D2;+0:20]:[c;H0;D3;+0:21](-[#7:22]-[C;D1;H3:23]):[c:24]:[cH;D2;+0:25]:1.[O;D1;H0:26]=[C:27](-[O;D1;H1:28])/[CH;D2;+0:29]=[... | 79.2 | [{"value": 79.2, "product": "C(\\C=C\\C(=O)O)(=O)O.CNC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CNC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "C(\\C=C\\C(=O)O)(=O)O.CNC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC... | null | null | null | null | Using 4-methylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (209.5 mg, 0.45 mmol) and fumaric acid (26.7 mg, 0.23 mmol), the procedure of Inventive Example 271 was repeated to obtain 184.9 mg (79.2%) of the title compound in a light brown powder form.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Aromatic halide.Carboxylic acid.Ketone.Tertiary amide.Secondary amine.Tertiary amine.Tertiary amine | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CNc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77277727d2c54daf907c8832e8787aea | CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | CS(=O)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.CS(=O)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CS(=O)(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1 | [CH3:1][S:2](=[O:3])([NH:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[c:30]2[cH:31][cH:32][cH:33][n:34][cH:35]2)[cH:36][cH:37]1)=[O:48].[CH:38](=[CH:46]/[C:47](=[O:57])[OH:77])\[C:80](=... | CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0cc1932952fb7ddce4943e7c0fc955dc2cef39e8498759d96225f32b90a1a247 | a1d0154ed7de4e2cdea2e4f9329a9a5cbd5fa165b1d2696743349d8850c6f002 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | [C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[#7:5]-[c:6].[O;D1;H0:7]=[C;H0;D3;+0:8](-[O;D1;H1:9])/[CH;D2;+0:10]=[CH;D2;+0:11]/[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[OH;D1;+0:14]>>[#7:15]-[#16:16](-[CH3;D1;+0:10])(=[O;D1;H0:17])=[O;D1;H0:18].[C:19]-[#7:20](-[c:21])-[C;H0;D3;+0:12](=[O;H0;D1;+0:4])-[c;H0;D3;+0:... | 43.3 | [{"value": 43.3, "product": "C(\\C=C\\C(=O)O)(=O)O.CS(=O)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CS(=O)(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.3, "product": "C(\\C=C\\C(=O)O)(=O)O.CS(=O)(=O)NC1=CC=C... | null | null | null | null | Using 4-methanesulfonylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (216.8 mg, 0.41 mmol) and fumaric acid (24.3 mg, 0.21 mmol), the procedure of Inventive Example 271 was repeated to obtain 103.4 mg (43.3%) of the title compound in a light brown powder form.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid.Carboxylic acid | Sulfonamide.Sulfonamide.Aromatic halide.Carboxylic acid.Carboxylic acid.Ketone.Tertiary amide.Tertiary amine | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CS(=O)(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-034be36ecab9479fa366c758723e800c | CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | C(C)OC(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(C)OC(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)OC(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1 | [C:4](=[O:5])([NH:6][c:7]1[cH:38][cH:47][c:48]([C:49](=[O:50])[N:51]([CH2:52][CH2:53][N:54]2[CH2:30][CH2:29][CH:19]([C:20](=[O:21])[c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[CH2:18][CH2:55]2)[c:69]2[cH:70][cH:71][cH:72][n:73][cH:74]2)[cH:75][cH:76]1)[O:41][CH2:40][CH3:39].[CH:1](=[CH:10]/[C:11]([OH:3])=[O:12])... | CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d8074e10f13e8c947e4401144c88430dacf96ad4b076ac58e69be8208df1e890 | ce6ebc241c0180bc5b7e4aa5c52e1db4bf6065e3c24c593e4e764aae52ad3fd1 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | [#7;a:1]:[c:2]:[c:3]-[#7:4](-[C:5]-[C:6]-[N;H0;D3;+0:7]1-[CH2;D2;+0:8]-[C:9]-[C:10](-[C:11](=[O;D1;H0:12])-[c:13])-[CH2;D2;+0:14]-[CH2;D2;+0:15]-1)-[C:16](=[O;D1;H0:17])-[c:18]1:[c:19]:[cH;D2;+0:20]:[c;H0;D3;+0:21](-[#7:22]-[C;H0;D3;+0:23](=[O;D1;H0:24])-[O;H0;D2;+0:25]-[C:26]-[C;D1;H3:27]):[cH;D2;+0:28]:[cH;D2;+0:29]:... | 75 | [{"value": 75.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C(C)OC(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)OC(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C(C)OC(=O)NC1=CC=C... | null | null | null | null | Using 4-ethoxycarbonylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (121.9 mg, 0.24 mmol) and fumaric acid (14.0 mg, 0.12 mmol), the procedure of Inventive Example 271 was repeated to obtain 103.8 mg (75.0%) of the title compound in a light yellow amorphous powder form.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Carboxylic acid.Ether.Tertiary amine | Aromatic halide.Carbamic ester.Carbamic ester.Carboxylic acid.Carboxylic acid.Ketone.Ether.Ether.Tertiary amide.Tertiary amine.Tertiary amine | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.CCOC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13e89f18360245ff8b311352b34982c9 | NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | N(C(=O)N)C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.N(C(=O)N)C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.N(C(=O)N)C1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1 | [NH2:1][C:2](=[O:3])[NH:4][c:5]1[cH:42][cH:43][c:44]([C:45](=[O:46])[N:47]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[c:20]3[cH:6][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]2)[c:65]2[cH:66][cH:67][cH:68][n:69][cH:70]2)[cH:71][cH:72]1.[C:9](=[O:10])([OH:75])/[CH:76]=[CH:77]/[C:78](=[O:79])[... | NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 56fb88dc2a8ec61671fa24ae794a358eda9ef9d167b2c536313e037c1a77c0a9 | 325c796fb6a1dde76d7100a8e360c70bcf9a979d17e7bce1f300a284d4404e43 | O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1.O=C(c1ccccc1)C1CCN(CCN(C(=O)c2ccccc2)c2cccnc2)CC1 | [#7:1]-[C:2]-[CH2;D2;+0:3]-[N;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[#7:11]-[C:12](-[N;D1;H2:13])=[O;D1;H0:14]):[cH;D2;+0:15]:[c:16]:1)-[c:17](:[c:18]):[c:19]:[#7;a:20]:[c:21].[C:22]-[C:23](=[O;D1;H0:24])-[c;H0;D3;+0:25]1:[c:26]:[c:27]:[c:28](-[F;D1;H0:29]):[cH;D2;+0:30]:[cH;D2;+0:... | 56.5 | [{"value": 56.3, "product": "C(\\C=C\\C(=O)O)(=O)O.N(C(=O)N)C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.N(C(=O)N)C1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.5, "product": "C(\\C=C\\C(=O)O)(=O)O.N(C(=O)N)C1=CC=C(C(=O)... | null | null | null | null | Using 4-ureido-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (174.1 mg, 0.36 mmol) and fumaric acid (20.8 mg, 0.18 mmol), the procedure of Inventive Example 271 was repeated to obtain 111.3 mg (56.3%) of the title compound in a colorless powder form.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Tertiary amide | Aromatic halide.Carboxylic acid.Ketone.Ketone.Urea.Tertiary amide.Tertiary amide.Tertiary amine | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | null | null | null | NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O>>NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.NC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2cccnc2)cc1.O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-306a34f7cedd44f8814563b5b59e069e | ClCC1CO1>>O | C(Cl)C1CO1.CN(C)C=1C=CC(=CC1)C(=C2C=CC(=[N+](C)C)C=C2)C=3C=CC(=CC3)N(C)C.[Cl-].CCCCOCCOCCOCCO.ClCCCCCCCC.C(Cl)C1CO1>>CCCCOCCOCCOCCO.O | ClCC1C[O:15]1>>[OH2:15] | ClCC1CO1 | O | null | [Br-].C(C)[N+](CC)(CC)CC | C(C)(=O)O.C1(=CC=CC=C1)C.O | Deprotection | OtherReaction | a619f2e0552ef75ef9030e73f4b1ba8ca084840857fdafad4b59fd097c293d2d | 0c91e0607effca920df6a9d3a12c737d83516506f3670708be3ed1e59dc9b90b | null | Cl-C-C1-C-[O;H0;D2;+0:1]-1>>[OH2;D0;+0:1] | null | [] | 55 | CELSIUS | null | null | To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)150 -OH (surfactant) and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)50 -... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | null | C1CO1 | null | null | HCl | [Br-].C(C)[N+](CC)(CC)CC.C(C)(=O)O.C1(=CC=CC=C1)C.O | 55 | null | ClCC1CO1>[Br-].C(C)[N+](CC)(CC)CC.C(C)(=O)O.C1(=CC=CC=C1)C.O>O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa1345f1ddf34fbca738e90d0801abc6 | C1CO1.CC(=O)O.CC(=O)O.CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)C)cc2)cc1.ClCC1CO1.ClCC1CO1>>CCCCOCCOCCOCCO.O | OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.C(Cl)C1CO1.C1CO1.C(Cl)C1CO1.C(C)(=O)O.C(C)(=O)O.CN(C)C=1C=CC(=CC1)C(=C2C=CC(=[N+](C)C)C=C2)C=3C=CC(=CC3)N(C)C.[Cl-]>>CCCCOCCOCCOCCO.O | [CH2:2]1[CH2:3][O:11]1.C[C:6](=O)[OH:5].CC(=O)[OH:15].CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)[CH3:1])cc2)cc1.Cl[CH2:10][CH:9]1[CH2:7][O:8]1.Cl[CH2:12][CH:13]1[CH2:4][O:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14].[OH2:15] | C1CO1.CC(=O)O.CC(=O)O.CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)C)cc2)cc1.ClCC1CO1.ClCC1CO1 | CCCCOCCOCCOCCO.O | null | [Br-].C(C)[N+](CC)(CC)CC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | e5ce9d35bb099894796d2d2252d3dbc197d128e21deb0a1c8abbe13527bff6a4 | c8581f7c1d3afdaf3f59e3a015db52ccf6715724aa72f51cf92bb224b8af1304 | null | C-C(=O)-[OH;D1;+0:1].C-N(-C)-c1:c:c:c(-C(=C2-C=C-C(=[N+](-C)-C)-C=C-2)-c2:c:c:c(-N(-C)-[CH3;D1;+0:2]):c:c:2):c:c:1.C-[C;H0;D3;+0:3](=O)-[OH;D1;+0:4].Cl-[CH2;D2;+0:5]-[CH;D3;+0:6]1-[#8:7]-[CH2;D2;+0:8]-1.Cl-[CH2;D2;+0:9]-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[O;H0;D2;+0:12]-1.[CH2;D2;+0:13]1-[CH2;D2;+0:14]-[O;H0;D2;+0:15]-1>>[C... | null | [] | 60 | CELSIUS | 8 | HOUR | To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of DNP-(EO)6 -OH and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of bis-phenol A ethoxylated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid.Carboxylic acid.Ether.Ether.Ether.Tertiary amine.Tertiary amine | Ether.Ether.Ether.Primary alcohol | C1CO1.c1ccccc1.C1=CCC=CC1.c1ccccc1.C1CO1.C1CO1 | null | null | HCl | [Br-].C(C)[N+](CC)(CC)CC.C1(=CC=CC=C1)C | 60 | 8 | C1CO1.CC(=O)O.CC(=O)O.CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)C)cc2)cc1.ClCC1CO1.ClCC1CO1>[Br-].C(C)[N+](CC)(CC)CC.C1(=CC=CC=C1)C>CCCCOCCOCCOCCO.O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e7b93282e05f4addbe5f6faab80d2b9a | ClC(Cl)(Cl)CC(Cl)(Cl)Cl.FC(F)(F)CC(F)(F)F>>FC(F)(F)CC(F)(F)Cl | C(F)(F)(F)CC(F)(F)F.C(Cl)(Cl)(Cl)CC(Cl)(Cl)Cl.[OH-].[K+]>>C(F)(F)(F)CC(F)(F)Cl | ClC(Cl)(Cl)CC(Cl)(Cl)[Cl:9].F[C:6]([CH2:5][C:2]([F:1])([F:3])[F:4])([F:7])[F:8]>>[F:1][C:2]([F:3])([F:4])[CH2:5][C:6]([F:7])([F:8])[Cl:9] | ClC(Cl)(Cl)CC(Cl)(Cl)Cl.FC(F)(F)CC(F)(F)F | FC(F)(F)CC(F)(F)Cl | null | Cl[Ti](Cl)(Cl)Cl | null | Functional Group Interconversion | OtherReaction | 5c1cc0a421428092036357338c2a9e28d4ea48f9a9bb3b8a410f65d0db5b5151 | e96241dee8c87f77fef64eedceb32664ca29c817802fd0a7f1f1f0888f1617b4 | null | Cl-C(-Cl)(-Cl)-C-C(-Cl)(-Cl)-[Cl;H0;D1;+0:1].F-[C;H0;D4;+0:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[Cl;H0;D1;+0:1]-[C;H0;D4;+0:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | null | [] | -10 | CELSIUS | null | null | A 600 mL, magnetically stirred, model autoclave fitted with a condenser (maintained at -10° C.), was evacuated, cooled to about -40° C., and charged with 0.6.9 g (0.036 mol) TiCl4 followed by 64 g (0.255 mol) CCl3CH2CCl3, and 102.5 g (5 mol) HF. The temperature was increased to 120° C. and maintained at that temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trichloro group.Trichloro group | Tertiary halide.Tertiary halide.Tertiary halide | null | null | null | HF | Cl[Ti](Cl)(Cl)Cl | -10 | null | ClC(Cl)(Cl)CC(Cl)(Cl)Cl.FC(F)(F)CC(F)(F)F>Cl[Ti](Cl)(Cl)Cl>FC(F)(F)CC(F)(F)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-784b63b848274e07b64f901c8865b018 | CC(C)(C)[Si](C)(C)Cl.O=C1C=CC(O)C1>>CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | OC1C=CC(C1)=O.C(C)N(CC)CC.[Si](C)(C)(C(C)(C)C)Cl>>O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)Cl.O=C1C=CC(O)C1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | null | CN(C1=CC=NC=C1)C | O1CCCC1 | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | O=C1C=CCC1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[C:10]=[C:11]-[C:12](-[OH;D1;+0:13])-[C:14]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:13]-[C:12]1-[C:11]=[C:10]-[C:9](=[O;D1;H0:8])-[C:14]-1 | 83.2 | [{"value": 83.2, "product": "O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | A solution of 4-hydroxy-2-cyclopentenone (191 g, 1.95 mol, prepared in example 1) and triethylamine (430 mL, 3.09 mol) in anhydrous tetrahydrofuran (1L) is treated with 4-dimethylaminopyridine (4.90 g, 40.0 mmol). The solution is cooled to 0° C. and treated portionwise, over 10 minutes, with tert-butyldimethylsilyl chl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | C1=CCCC1 | HCl | CN(C1=CC=NC=C1)C.O1CCCC1 | 0 | 8 | CC(C)(C)[Si](C)(C)Cl.O=C1C=CC(O)C1>CN(C1=CC=NC=C1)C.O1CCCC1>CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6ecf5a0a0dd4c20a3f46740fd5078c7 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | COC(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O.[I-].[Li+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | CCCCCCC | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 74 | [{"value": 74.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.9, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 5 | MINUTE | A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (50.2 g, 236 mmol) in anhydrous toluene (1L) under an atmosphere of argon is treated with lithium iodide (160 g, 1.20 mol). The mixture is cooled to -20° C. and treated with lithium aluminum hydride (9.0 g, 237 mmol) in one portion. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | CCCCCCC | -20 | 0.083333 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>CCCCCCC>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-555b3522584c4bcfba8254bfe842b079 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | COC(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O.[I-].[Li+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 68 | [{"value": 68.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 5 | MINUTE | A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (175 g, 824 mmol) in anhydrous toluene (1.5L) under an atmosphere of argon is treated with lithium iodide (240 g, 1.79 mol). The mixture is cooled to -20° C. and treated with lithium aluminum hydride (13.5 g, 356 mmol) in one portion. The re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | C1(=CC=CC=C1)C | -20 | 0.083333 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>C1(=CC=CC=C1)C>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ce9d725cf794ddb8c67a20faaad2014 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O.[I-].[Li+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C(C)OCC | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 80 | [{"value": 80.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 90 | MINUTE | A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (1.01 g, 4.76 mmol) in anhydrous ethyl ether (20 mL) under an atmosphere of argon is treated with lithium iodide (3.20 g, 23.9 mmol). The mixture is cooled to -78° C. and treated with lithium aluminum hydride (184 mg, 4.85 mmol) in one porti... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | C(C)OCC | -78 | 1.5 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>C(C)OCC>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72213fef623a4ce0b58fb21b87067c20 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | COC(C)(C)C.O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O.[Br-].[Li+].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 69.2 | [{"value": 69.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 2 | HOUR | A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (501 mg, 2.36 mmol) in anhydrous toluene (10 mL) under an atmosphere of argon is treated with lithium bromide (1.06 g, 12.2 mmol). The mixture is cooled to -20° C. with an ice/salt bath and treated with lithium aluminum hydride (92.0 mg, 2.4... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | C1(=CC=CC=C1)C | -20 | 2 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>C1(=CC=CC=C1)C>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-763abd07f6784692a9ffa1edeb4f4481 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O.[OH-].[Na+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | [Cl-].[Cl-].[Zn+2] | null | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 64.4 | [{"value": 64.4, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 2 | HOUR | A stirred solution of ZnCl2 (19 mL, 19 mmol, 1M in ether) is treated with 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) under an atmosphere of argon. The solution is cooled to -20° C. and treated dropwise with lithium aluminum hydride (9.0 mL, 9.0 mmol, 1M in ether) at such a rate as to keep the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | [Cl-].[Cl-].[Zn+2] | -20 | 2 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>[Cl-].[Cl-].[Zn+2]>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4213d05daadd4cc1a427b80287607a1d | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | COC(C)(C)C.O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O.[Mg+2].[Br-].[Br-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH:10]=[CH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 64.4 | [{"value": 64.4, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -25 | CELSIUS | 2 | HOUR | A stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) in anhydrous toluene (15 mL) under an atmosphere of argon is treated with MgBr2 (3.5 g, 19.0 mol). The mixture is cooled to -25° C. and treated with lithium aluminum hydride (178 mg, 4.69 mmol) in one portion, followed by addition of a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | C1(=CC=CC=C1)C | -25 | 2 | CC(C)(C)[Si](C)(C)OC1C=CC(=O)C1>C1(=CC=CC=C1)C>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-023d1f3b80054964a96469c5b88a1cdd | C1=COCCC1.O=C1C=CC(O)C1>>O=C1C=CC(OC2CCCCO2)C1 | OC1C=CC(C1)=O.O1CCCC=C1.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>O1C(CCCC1)OC1C=CC(C1)=O | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]([OH:6])[CH2:13]1>>[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[CH2:13]1 | C1=COCCC1.O=C1C=CC(O)C1 | O=C1C=CC(OC2CCCCO2)C1 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | oxa-Michael addition | 7dbeed209463058f59d43728a589e5f7e9550a2179664f08902eb30ad7ba383b | 2683964549e7d2a3e8c7989efc3c7275468eaa2a5d254179937977d9931444d1 | O=C1C=CC(OC2CCCCO2)C1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[O;D1;H0:7]=[C:8]1-[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]=[C:13]-1>>[O;D1;H0:7]=[C:8]1-[C:9]-[C:10](-[O;H0;D2;+0:11]-[CH;D3;+0:6]2-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-2)-[C:12]=[C:13]-1 | 76 | [{"value": 76.0, "product": "O1C(CCCC1)OC1C=CC(C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 4-hydroxy-2-cyclopentenone (1.41 g, 14.4 mmol) in tetrahydrofuran (24 mL) is treated with 3,4-dihydro-2H-pyran (2 mL) and pyridinium p-toluenesulfonate (500 mg, PPTS). The reaction is stirred at room temperature for 18 hours. The reaction mixture is then diluted with ethyl acetate (25 mL) and washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1=CCCC1.C1CCOCC1 | null | C(C)(=O)OCC.O1CCCC1 | null | 18 | C1=COCCC1.O=C1C=CC(O)C1>C(C)(=O)OCC.O1CCCC1>O=C1C=CC(OC2CCCCO2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fcb0d5dcdda04901928d4fd9c09849c7 | O=C1C=CC(OC2CCCCO2)C1>>O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | [OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[I-].[Li+].O1C(CCCC1)OC1C=CC(C1)=O>>O1C(CCCC1)O[C@H]1C=C[C@H](C1)O | [O:1]=[C:2]1[CH:3]=[CH:4][CH:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[CH2:13]1>>[OH:1][C@@H:2]1[CH:3]=[CH:4][C@H:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[CH2:13]1 | O=C1C=CC(OC2CCCCO2)C1 | O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | null | null | C1(=CC=CC=C1)C.COC(C)(C)C | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=C[C@H](OC2CCCCO2)CC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1>>[OH;D1;+0:1]-[C@H;D3;+0:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 73.5 | [{"value": 73.0, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A slurry of lithium aluminum hydride (222 mg, 5.8 mmol), lithium iodide (3.2 g, 24 mmol), tert-butyl methyl ether (6 mL) and toluene (16 mL) is cooled to -15° C. A solution of 4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enone (2.179 g, 11.97 mmol, prepared in example 5) in tert-butyl methyl ether (2 mL) and toluene (2 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1.C1CCOCC1 | null | C1(=CC=CC=C1)C.COC(C)(C)C | null | 0.5 | O=C1C=CC(OC2CCCCO2)C1>C1(=CC=CC=C1)C.COC(C)(C)C>O[C@@H]1C=C[C@H](OC2CCCCO2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46441d6502ac4bf9a6e8aa14f7c747f1 | CC(C)(C)OC(=N)C(Cl)(Cl)Cl.O=C1C=CC(O)C1>>CC(C)(C)OC1C=CC(=O)C1 | C([O-])(O)=O.[Na+].ClC(C(OC(C)(C)C)=N)(Cl)Cl.B(F)(F)F.CCOCC.OC1C=CC(C1)=O>>C(C)(C)(C)OC1C=CC(C1)=O | N=C(O[C:2]([CH3:1])([CH3:3])[CH3:4])C(Cl)(Cl)Cl.[OH:5][CH:6]1[CH:7]=[CH:8][C:9](=[O:10])[CH2:11]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH:6]1[CH:7]=[CH:8][C:9](=[O:10])[CH2:11]1 | CC(C)(C)OC(=N)C(Cl)(Cl)Cl.O=C1C=CC(O)C1 | CC(C)(C)OC1C=CC(=O)C1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | e1602c7639e9590c57e1f519302834b854314fa06b50f2e00792e7923548c28a | 9939e71487b269001d097fe9b7393354dcb141bf54208fca597f111e50af4454 | O=C1C=CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]=[C:11]-1>>[C;D1;H3:2]-[C;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:9]-[C:8]1-[C:7]-[C:6](=[O;D1;H0:5])-[C:11]=[C:10]-1 | 40 | [{"value": 40.0, "product": "C(C)(C)(C)OC1C=CC(C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.7, "product": "C(C)(C)(C)OC1C=CC(C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 6.5 | CELSIUS | 2 | HOUR | A solution of 4-hydroxy-2-cyclopentenone (1.15 g, 11.7 mmol) in methylene chloride is cooled to 3° C. and treated sequentially with tert-butyl trichloroacetimidate (4.2 mL, 23.7 mmol) and boron trifluoride diethyl etherate (0.15 mL). The reaction mixture is stirred at 3-10° C. for 2 hours and then allowed to warm to ro... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol | Ether | null | null | C1=CCCC1 | HCl | C(Cl)Cl | 6.5 | 2 | CC(C)(C)OC(=N)C(Cl)(Cl)Cl.O=C1C=CC(O)C1>C(Cl)Cl>CC(C)(C)OC1C=CC(=O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e0e346db372f42efa4e13b85899186f1 | CC(C)(C)OC1C=CC(=O)C1>>CC(C)(C)O[C@H]1C=C[C@@H](O)C1 | [OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[I-].[Li+].C(C)(C)(C)OC1C=CC(C1)=O>>C(C)(C)(C)O[C@H]1C=C[C@H](C1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH:6]1[CH:7]=[CH:8][C:9](=[O:10])[CH2:11]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C@H:6]1[CH:7]=[CH:8][C@@H:9]([OH:10])[CH2:11]1 | CC(C)(C)OC1C=CC(=O)C1 | CC(C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C1(=CC=CC=C1)C.COC(C)(C)C | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1>>[OH;D1;+0:1]-[C@H;D3;+0:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 42 | [{"value": 42.0, "product": "C(C)(C)(C)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.0, "product": "C(C)(C)(C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A slurry of lithium aluminum hydride (55 mg, 1.44 mmol), lithium iodide (1.65 g, 5.76 mmol), tert-butyl methyl ether (2 mL) and toluene (3 mL) is cooled to -15° C. The slurry is treated dropwise with 4-tert-butoxy-cyclopent-2-enone(430 mg, 2.79 mmol, dissolved in 1 mL of toluene) over 5 minutes. The reaction mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | C1(=CC=CC=C1)C.COC(C)(C)C | null | 2 | CC(C)(C)OC1C=CC(=O)C1>C1(=CC=CC=C1)C.COC(C)(C)C>CC(C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4080122b276c4fa69f2e3e82eeb5a920 | C=COC(C)=O.CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>>CC(=O)OC1C=CC(O[Si](C)(C)C(C)(C)C)C1 | C(Cl)(Cl)Cl.[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O.C(Cl)(Cl)Cl.C(C)N(CC)CC.C(C)(=O)OC=C.[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O>>[Si](C)(C)(C(C)(C)C)OC1C=CC(C1)OC(C)=O | [CH3:1][C:2](=[O:3])[O:4][CH:5]=[CH2:6].O[C@@H]1C=[CH:7][C@H:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH:6]=[CH:7][CH:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1 | C=COC(C)=O.CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | CC(=O)OC1C=CC(O[Si](C)(C)C(C)(C)C)C1 | null | null | COC(C)(C)C | C-C Coupling | Transesterification | 92af04861d06eaca931c3f45788ceb88c1b9d7e6fcee8f51a3677fb2464fa656 | 09fd45f837e2e59063089c7c3532ccf9271bc2124817e628316fb7f09c7d1378 | C1=CCCC1 | null | 51.1 | [{"value": 51.0, "product": "[Si](C)(C)(C(C)(C)C)OC1C=CC(C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.1, "product": "[Si](C)(C)(C(C)(C)C)OC1C=CC(C1)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | Cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (10.0 g, 46.6 mmol, prepared in example 3a) is dissolved in tert-butyl methyl ether (60 mL, anhydrous). To the solution is added triethylamine (4.5 mL, 32.3 mmol), pancreatin (30 g, available from Sigma Chemical Company), and vinyl acetate (22 mL, 239 mmol). The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Vinyl | Ester | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | HO- | COC(C)(C)C | null | 7 | C=COC(C)=O.CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>COC(C)(C)C>CC(=O)OC1C=CC(O[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23a5242235f843fa9d331c47debf3305 | C=COC(C)=O.O[C@@H]1C=C[C@H](OC2CCCCO2)C1>>CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | C(Cl)(Cl)Cl.O1C(CCCC1)O[C@H]1C=C[C@H](C1)O.C(Cl)(Cl)Cl.C(C)N(CC)CC.C(C)(=O)OC=C.O1C(CCCC1)O[C@H]1C=C[C@H](C1)O>>O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O | C=CO[C:2]([CH3:1])=[O:3].[OH:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15]2)[CH2:16]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15]2)[CH2:16]1 | C=COC(C)=O.O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | null | null | COC(C)(C)C | Acylation | Transesterification | 892ec5198c524815f90afb1f95f6ea3087d4dce6703007366f357ec486f2b695 | 67dea10bb93a5d805949b0584770f4ae4a5967d92b967e6003c59314fe37aee1 | C1=C[C@H](OC2CCCCO2)CC1 | C=C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1 | 45 | [{"value": 45.0, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.9, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | Cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (1.091 g, 5.92 mmol, prepared in example 6) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.59 mL, 4.2 mmol), pancreatin (3.2 g, available from Sigma Chemical Company), and vinyl acetate (2.7 mL, 29 mmol). The react... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Vinyl | Ester | null | null | C1=CCCC1.C1CCOCC1 | HO- | COC(C)(C)C | null | 7 | C=COC(C)=O.O[C@@H]1C=C[C@H](OC2CCCCO2)C1>COC(C)(C)C>CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b7d46a26dfbe492a852ae078a89b028a | CC(=O)OC1C=CC(O[Si](C)(C)C(C)(C)C)C1>>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | [Si](C)(C)(C(C)(C)C)OC1C=CC(C1)OC(C)=O.O.[OH-].[Li+].O>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O | CC(=O)[O:13][CH:12]1[CH:11]=[CH:10][CH:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1 | CC(=O)OC1C=CC(O[Si](C)(C)C(C)(C)C)C1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C1CCOC1.CO.O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | C1=CCCC1 | C-C(=O)-[O;H0;D2;+0:1]-[CH;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[C@@H;D3;+0:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 92 | [{"value": 92.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Dissolve (-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester (2.3 mmol, prepared in example 10) in THF/methanol/water (2.7/0.9/0.9 mL). Add lithium hydroxide monohydrate (2.5 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with water (10 mL) and extract wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1=CCCC1 | HO- | C1CCOC1.CO.O | null | 3 | CC(=O)OC1C=CC(O[Si](C)(C)C(C)(C)C)C1>C1CCOC1.CO.O>CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73c1b39d43c34bba9c7f0a1fb0614d7e | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1>>O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | O.[OH-].[Li+].O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O.COC(C)(C)C.O>>O1C(CCCC1)O[C@H]1C=C[C@H](C1)O | CC(=O)[O:1][C@@H:2]1[CH:3]=[CH:4][C@H:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[CH2:13]1>>[OH:1][C@@H:2]1[CH:3]=[CH:4][C@H:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[CH2:13]1 | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | null | null | C(Cl)(Cl)Cl.C1CCOC1.CO.O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | C1=C[C@H](OC2CCCCO2)CC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1>>[OH;D1;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 93 | [{"value": 93.0, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (106 mg, 0.47 mmol, prepared in example 11) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.57 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with tert-butyl meth... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1=CCCC1.C1CCOCC1 | HO- | C(Cl)(Cl)Cl.C1CCOC1.CO.O | null | 3 | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1>C(Cl)(Cl)Cl.C1CCOC1.CO.O>O[C@@H]1C=C[C@H](OC2CCCCO2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ac771ea14f8470d9583f912bd68a7b3 | C=COC(C)=O.CC(C)(C)O[C@H]1C=C[C@@H](O)C1>>CC(=O)O[C@@H]1C=C[C@H](OC(C)(C)C)C1 | C(C)N(CC)CC.C(C)(=O)OC=C.C(Cl)(Cl)Cl.C(C)(C)(C)O[C@H]1C=C[C@H](C1)O>>C(C)(C)(C)O[C@H]1C=C[C@H](C1)OC(C)=O | C=CO[C:2]([CH3:1])=[O:3].[OH:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14]1 | C=COC(C)=O.CC(C)(C)O[C@H]1C=C[C@@H](O)C1 | CC(=O)O[C@@H]1C=C[C@H](OC(C)(C)C)C1 | null | null | COC(C)(C)C | Acylation | Transesterification | 892ec5198c524815f90afb1f95f6ea3087d4dce6703007366f357ec486f2b695 | 67dea10bb93a5d805949b0584770f4ae4a5967d92b967e6003c59314fe37aee1 | C1=CCCC1 | C=C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1 | 50 | [{"value": 50.0, "product": "C(C)(C)(C)O[C@H]1C=C[C@H](C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | Cis-4-tert-butyloxy-cyclopent-2-enol (485 mg, 3.1 mmol, prepared in example 9) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.7 eq), pancreatin (3 wt eq, available from Sigma Chemical Company), and vinyl acetate (5 eq). The reaction is allowed to stir for 17 hours... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Vinyl | Ester | null | null | C1=CCCC1 | HO- | COC(C)(C)C | null | 17 | C=COC(C)=O.CC(C)(C)O[C@H]1C=C[C@@H](O)C1>COC(C)(C)C>CC(=O)O[C@@H]1C=C[C@H](OC(C)(C)C)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-722e940fd7a54e458d6fcaedb1602d00 | CC(=O)O[C@@H]1C=C[C@H](OC(C)(C)C)C1>>CC(C)(C)O[C@H]1C=C[C@@H](O)C1 | O.[OH-].[Li+].C(Cl)(Cl)Cl.C(C)(C)(C)O[C@H]1C=C[C@H](C1)OC(C)=O.O>>C(C)(C)(C)O[C@H]1C=C[C@H](C1)O | CC(=O)[O:10][C@@H:9]1[CH:8]=[CH:7][C@H:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:11]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C@H:6]1[CH:7]=[CH:8][C@@H:9]([OH:10])[CH2:11]1 | CC(=O)O[C@@H]1C=C[C@H](OC(C)(C)C)C1 | CC(C)(C)O[C@H]1C=C[C@@H](O)C1 | null | null | C1CCOC1.CO.O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | C1=CCCC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1>>[OH;D1;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 101 | [{"value": 101.0, "product": "C(C)(C)(C)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Dissolve (-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester (90 mg, 0.45 mmol, prepared in example 14) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (23.7 mg) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1=CCCC1 | HO- | C1CCOC1.CO.O | null | 2 | CC(=O)O[C@@H]1C=C[C@H](OC(C)(C)C)C1>C1CCOC1.CO.O>CC(C)(C)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-443e36063c0a47edae71957a9c2af350 | C=COC(C)=O.CCN(CC)CC.O[C@@H]1C=C[C@H](OCc2ccccc2)C1>>CC(=O)O[C@@H]1C=C[C@H](OCc2ccccc2)C1.O[C@@H]1C=C[C@H](OCc2ccccc2)C1 | C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O.C(C)N(CC)CC.C(C)(=O)OC=C.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl>>C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O.C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)OC(C)=O | [CH3:1][C:2](=[O:3])[O:18][CH:19]=[CH2:20].N([CH2:29][CH3:28])([CH2:30][CH3:25])[CH2:31][CH3:24].[C@@H:5]1([OH:23])[CH:6]=[CH:7][C@H:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2... | C=COC(C)=O.CCN(CC)CC.O[C@@H]1C=C[C@H](OCc2ccccc2)C1 | CC(=O)O[C@@H]1C=C[C@H](OCc2ccccc2)C1.O[C@@H]1C=C[C@H](OCc2ccccc2)C1 | null | null | COC(C)(C)C | Aromatic Heterocycle Formation | OtherReaction | 8803c3c25f969d3fead08ac604515af42718a94f1cbf68fec7e7b35748f12230 | 7dd832249f1f72966346dc7ec4ca1592cb736718d1c1e34c640377989877afdc | C1=C[C@H](OCc2ccccc2)CC1.C1=C[C@H](OCc2ccccc2)CC1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH;D2;+0:5]=[CH2;D1;+0:6].[CH3;D1;+0:7]-[CH2;D2;+0:8]-N(-[CH2;D2;+0:9]-[CH3;D1;+0:10])-[CH2;D2;+0:11]-[CH3;D1;+0:12].[OH;D1;+0:13]-[C@H;D3;+0:14]1-[C:15]-[C:16]-[C:17]=[C:18]-1>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[#8:19]-[C@H;D3;+0:14]1-[C:15]-[C:16]-[C:17]... | 70 | [{"value": 29.0, "product": "C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | Cis-4-benzyloxy-cyclopent-2-enol (500 mg, prepared in example 16) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.7 eq), pancreatin (3 wt eq, available from Sigma Chemical Company), and vinyl acetate (5 eq). The reaction is allowed to stir for 7 hours at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Tertiary amine.Vinyl | Ester.Ether.Secondary alcohol | C1=CCCC1 | C1=CCCC1.C1=CCCC1.c1ccccc1 | C1=CCCC1.c1ccccc1.C1=CCCC1.c1ccccc1 | null | COC(C)(C)C | null | 7 | C=COC(C)=O.CCN(CC)CC.O[C@@H]1C=C[C@H](OCc2ccccc2)C1>COC(C)(C)C>CC(=O)O[C@@H]1C=C[C@H](OCc2ccccc2)C1.O[C@@H]1C=C[C@H](OCc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91b9cd4f6514451c9af570b41fa98ef5 | CC(=O)O[C@@H]1C=C[C@H](OCc2ccccc2)C1>>O[C@@H]1C=C[C@H](OCc2ccccc2)C1 | O.[OH-].[Li+].C(Cl)(Cl)Cl.C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)OC(C)=O.O>>C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O | CC(=O)[O:1][C@@H:2]1[CH:3]=[CH:4][C@H:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1>>[OH:1][C@@H:2]1[CH:3]=[CH:4][C@H:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1 | CC(=O)O[C@@H]1C=C[C@H](OCc2ccccc2)C1 | O[C@@H]1C=C[C@H](OCc2ccccc2)C1 | null | null | C1CCOC1.CO.O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | C1=C[C@H](OCc2ccccc2)CC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1>>[OH;D1;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 92.8 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Dissolve (-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester (158 mg, 0.68 mmol, prepared in example 17) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.75 mmol) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1=CCCC1.c1ccccc1 | HO- | C1CCOC1.CO.O | null | 2 | CC(=O)O[C@@H]1C=C[C@H](OCc2ccccc2)C1>C1CCOC1.CO.O>O[C@@H]1C=C[C@H](OCc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cd21d400e0ca42969b8c9e946aa2ff9e | CC(=O)OC(C)=O.CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>>CC(=O)O[C@@H]1C=C[C@H](O[Si](C)(C)C(C)(C)C)C1 | C(C)(=O)OC(C)=O.C(C)(=O)OCC.CCCCCC.[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O.C(C)OCC>>[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)OC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1 | CC(=O)OC(C)=O.CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | CC(=O)O[C@@H]1C=C[C@H](O[Si](C)(C)C(C)(C)C)C1 | null | null | N1=CC=CC=C1 | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | C1=CCCC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1 | 98 | [{"value": 98.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (1 g, 4.67 mmol, prepared in example 10) in pyridine (20 mL) and treat with acetic anhydride (2 mL). Stir the reaction overnight. Dilute the reaction with diethyl ether (100 mL), wash with 3M hydrochloric acid (3×100 mL), saturated sodium bicarbonate (100 mL... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | C1=CCCC1 | HO- | N1=CC=CC=C1 | null | null | CC(=O)OC(C)=O.CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>N1=CC=CC=C1>CC(=O)O[C@@H]1C=C[C@H](O[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-00533d2621284180b8d6e372c9496cb7 | CC(=O)OC(C)=O.O[C@@H]1C=C[C@H](OC2CCCCO2)C1>>CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | C(C)(=O)OCC.C(C)(=O)OC(C)=O.CN(C)C1=NC=CC=C1.O1C(CCCC1)O[C@H]1C=C[C@H](C1)O>>O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15]2)[CH2:16]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH:6]=[CH:7][C@H:8]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15]2)[CH2:16]1 | CC(=O)OC(C)=O.O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | null | null | N1=CC=CC=C1 | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | C1=C[C@H](OC2CCCCO2)CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]1-[C:6]-[C:7]-[C:8]=[C:9]-1 | 81 | [{"value": 81.0, "product": "O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve (-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (292 mg, 1.59 mmol, prepared in example 11) in pyridine (2.8 mL) and treat with acetic anhydride (0.39 mL) and dimethylaminopyridine (16 mg). Stir the reaction overnight. Concentrate the reaction under vacuum, dissolve the residue with ethyl acetate (10 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | C1=CCCC1.C1CCOCC1 | HO- | N1=CC=CC=C1 | null | null | CC(=O)OC(C)=O.O[C@@H]1C=C[C@H](OC2CCCCO2)C1>N1=CC=CC=C1>CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b9e268c96f04af98cb23843c3e81f50 | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1>>CC(=O)O[C@H]1C=C[C@@H](O)C1 | C([O-])(O)=O.C1(=CC=C(C=C1)S(=O)(=O)O)C.O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O.C([O-])([O-])=O>>C(C)(=O)O[C@H]1C=C[C@H](C1)O | C1CCC([O:9][C@H:8]2[CH:7]=[CH:6][C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:10]2)OC1>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH:6]=[CH:7][C@@H:8]([OH:9])[CH2:10]1 | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1 | CC(=O)O[C@H]1C=C[C@@H](O)C1 | null | null | C(Cl)(Cl)Cl.C(C)O | Reduction | OtherReaction | 0b83bf1290e2ee90e436d69e159e123816ec005a202c40da90352984400ae7f0 | 628b56b3f4fed40b9cc8e2f7565bcae98d5e36a3f75394461dabd987fb619482 | C1=CCCC1 | C1-C-C-C(-[O;H0;D2;+0:1]-[C:2]2-[C:3]-[C:4]-[C:5]=[C:6]-2)-O-C-1>>[OH;D1;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 75 | [{"value": 75.0, "product": "C(C)(=O)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "C(C)(=O)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (192 mg, 0.85 mmol, prepared in example 11) in ethanol (1.5 mL) and treat with p-toluenesulfonic acid (11.7 mg). Stir the reaction at room temperature for 2 hours. Add carbonate or bicarbonate to neutralize the reaction mixture and concent... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Secondary alcohol | C1CCOCC1 | null | C1=CCCC1 | HO- | C(Cl)(Cl)Cl.C(C)O | null | null | CC(=O)O[C@@H]1C=C[C@H](OC2CCCCO2)C1>C(Cl)(Cl)Cl.C(C)O>CC(=O)O[C@H]1C=C[C@@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f043af33bf7d4a64ba8d85518371337b | CC(=O)O[C@H]1C=C[C@@H](O)C1>>CC(=O)O[C@@H]1CC[C@H](O)C1 | C(C)(=O)O[C@H]1C=C[C@H](C1)O.C(C)N(CC)CC>>C(C)(=O)O[C@H]1C[C@H](CC1)O | [CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH:6]=[CH:7][C@@H:8]([OH:9])[CH2:10]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH2:6][CH2:7][C@H:8]([OH:9])[CH2:10]1 | CC(=O)O[C@H]1C=C[C@@H](O)C1 | CC(=O)O[C@@H]1CC[C@H](O)C1 | null | [Ni] | C(C)O | Reduction | Hydrogenation (double to single) | fd2b5380b956a588192941128a1966dad6a191947eb2dd12a24d8008fa2ed0c2 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCC1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]1-[C:6]-[C:7](-[O;D1;H1:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-1>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]1-[C:6]-[C:7](-[O;D1;H1:8])-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1 | 87.3 | [{"value": 87.0, "product": "C(C)(=O)O[C@H]1C[C@H](CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "C(C)(=O)O[C@H]1C[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Dissolve (-)-cis-4-acetoxy-cyclopent-2-enol (11.0 g, 77.4 mmol, prepared in example 19) in ethanol (50 mL) and treat with Raney nickel (1.1 g, previously washed with water (2×50 mL) and ethanol (2×50 mL), Ra--Ni). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. After 20 minutes, filter... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | [Ni].C(C)O | null | 0.333333 | CC(=O)O[C@H]1C=C[C@@H](O)C1>[Ni].C(C)O>CC(=O)O[C@@H]1CC[C@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8055ba3e80dd4839935a05e583536aad | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>>CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O.[BH4-].[Na+]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 | null | [Ni] | C(C)O | Reduction | Hydrogenation (double to single) | fd2b5380b956a588192941128a1966dad6a191947eb2dd12a24d8008fa2ed0c2 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCC1 | [#8:1]-[C:2]1-[C:3]-[C:4](-[O;D1;H1:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1>>[#8:1]-[C:2]1-[C:3]-[C:4](-[O;D1;H1:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1 | 87.3 | [{"value": 87.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5.25 | HOUR | Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (28.85 g, 135 mmol, prepared in example 10) in ethanol (75 mL) and treated with Raney nickel (1.85 g, 32 mmol, previously washed with water (2×50 mL) and ethanol (2×50 mL)). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. Af... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | [Ni].C(C)O | 0 | 5.25 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>[Ni].C(C)O>CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61afa5168bfe4df280f2c9386fbd28fe | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1.CS(=O)(=O)Cl>>CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](OS(C)(=O)=O)C1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O.CS(=O)(=O)Cl.C(C)N(CC)CC>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)OS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:18]1.Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([O:13][S:14]([CH3:15])(=[O:16])=[O:17])[CH2:18]1 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1.CS(=O)(=O)Cl | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](OS(C)(=O)=O)C1 | null | null | COC(C)(C)C | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCCC1 | 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:8]>>[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])-[C:8] | 97 | [{"value": 97.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)OS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)OS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 2 | HOUR | Dissolve (-)-cis-3-tert-butyldimethylsilyloxy-cyclopentanol (9.20 g, 42.5 mmol) in anhydrous tert-butyl methyl ether (50 mL) and cool to -5° C. Treat the solution with methanesulfonyl chloride (3.6 g, 46.5 mmol, mesyl chloride), followed by triethylamine (7.2 mL, 51.7 mmol), at such a rate as to keep the temperature be... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CCCC1 | HCl | COC(C)(C)C | -5 | 2 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1.CS(=O)(=O)Cl>COC(C)(C)C>CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](OS(C)(=O)=O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc292523a26943b1a8ab4fada76c991b | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1C=CC(O)C1>>O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl.N12CCCCCC2=NCCC1.OC1C=CC(C1)=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC1C=CC(C1)=O | Cl[C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]([OH:6])[CH2:26]1>>[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]([O:6][C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1C=CC(O)C1 | O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 5ab68839e2c0c36dcda93f3c0a707140e3d24e3e006f5c14702a7b8884a9a81e | 26c50c761bd192b9bbaacc80ceb1f72503dc7c2f688b52834534ac0a03b55cce | O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[O;D1;H0:11]=[C:12]1-[C:13]-[C:14](-[OH;D1;+0:15])-[C:16]=[C:17]-1>>[O;D1;H0:11]=[C:12]1-[C:13]-[C:14](-[O;H0;D2;+0:15]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10])-[C:16]=[C:17]-1 | 37 | [{"value": 36.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC1C=CC(C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC1C=CC(C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A solution of trityl chloride (3.44 g, 12.3 mmol) in methylene chloride (20 mL) is treated sequentially with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.2 mL, 14.7 mmol, DBU) and 4-hydroxy-2-cyclopentenone (1.01 g, 10.0 mmol, in 5 mL of methylene chloride, prepared in example 1). The reaction is stirred for 3 days at room te... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Secondary alcohol | Ether | null | null | C1=CCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 72 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1C=CC(O)C1>C(Cl)Cl>O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-802e8dff62b74fa49096ebf9f90abcb7 | O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1>>O[C@@H]1C=C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC1C=CC(C1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[I-].[Li+].COC(C)(C)C>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O | [O:1]=[C:2]1[CH:3]=[CH:4][CH:5]([O:6][C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1>>[OH:1][C@@H:2]1[CH:3]=[CH:4][C@H:5]([O:6][C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[... | O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | O[C@@H]1C=C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)CC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1>>[OH;D1;+0:1]-[C@H;D3;+0:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1 | 95 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 1 | HOUR | A slurry of 4-trityloxy-2-cyclopentenone (1.03 g, 3.03 mmol, prepared in example 27) in toluene (8 mL) is cooled to -20° C. and treated sequentially with lithium aluminum hydride (76 mg, 2.0 mL), lithium iodide (1.06 g, 7.9 mmol) and dropwise with tert-butyl methyl ether (2 mL, over 5 minutes). The reaction is stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | -20 | 1 | O=C1C=CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1>C1(=CC=CC=C1)C>O[C@@H]1C=C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3b90e77842a74c70b595bd258a689f2e | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>>CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O.[H][H]>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([OH:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:14]1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 | null | null | CO | Reduction | Hydrogenation (double to single) | fd2b5380b956a588192941128a1966dad6a191947eb2dd12a24d8008fa2ed0c2 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCC1 | [#8:1]-[C:2]1-[C:3]-[C:4](-[O;D1;H1:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1>>[#8:1]-[C:2]1-[C:3]-[C:4](-[O;D1;H1:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1 | 92 | [{"value": 92.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18.5 | HOUR | Combine (+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (2.50 g, 11.6 mmol, prepared in example 3) and Ni2B (8.5 mL of a 0.14M slurry in methanol, 10 mol %) in methanol (14 mL). Stir the slurry under an atmosphere of hydrogen for 18.5 hours. Then replace the hydrogen atmosphere with nitrogen, filter through diat... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | CO | null | 18.5 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1>CO>CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b1dad0bf641048d099cfa0228402d3a6 | C=COC(C)=O.CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1>>CC(=O)O[C@@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)C1 | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O.C(C)N(CC)CC.C(C)(=O)OC=C>>C(C)(=O)O[C@H]1C[C@H](CC1)O[Si](C)(C)C(C)(C)C | C=CO[C:2]([CH3:1])=[O:3].[OH:4][C@H:5]1[CH2:6][CH2:7][C@@H:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH2:6][CH2:7][C@H:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17]1 | C=COC(C)=O.CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1 | CC(=O)O[C@@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)C1 | null | null | COC(C)(C)C | Acylation | Transesterification | 892ec5198c524815f90afb1f95f6ea3087d4dce6703007366f357ec486f2b695 | 67dea10bb93a5d805949b0584770f4ae4a5967d92b967e6003c59314fe37aee1 | C1CCCC1 | C=C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7] | 49 | [{"value": 49.0, "product": "C(C)(=O)O[C@H]1C[C@H](CC1)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Combine (+/-)-cis-3-tert-butyldimethylsilyloxycyclopentanol (2.119 g, 9.8 mmol, prepared in example 29), pancreatin (6.2 g, 3 weight equivalents), triethylamine (0.9 mL, 6.5 mmol) and vinyl acetate (4.3 mL) in tert-butyl methyl ether (12 mL) and stir for 27 hours at room temperature. Then filter the reaction through di... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Vinyl | Ester | null | null | C1CCCC1 | HO- | COC(C)(C)C | null | null | C=COC(C)=O.CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](O)C1>COC(C)(C)C>CC(=O)O[C@@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d03242f3367b42868367bf19135dae30 | COc1cc(C=O)cc(Br)c1O>>COc1cc(C=O)cc(C#N)c1O | C(C)(=O)OCC.BrC=1C=C(C=O)C=C(C1O)OC.CC(=O)N(C)C>>C(=O)C=1C=C(C#N)C(=C(C1)OC)O | Br[c:9]1[cH:8][c:5]([CH:6]=[O:7])[cH:4][c:3]([O:2][CH3:1])[c:12]1[OH:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([C:10]#[N:11])[c:12]1[OH:13] | COc1cc(C=O)cc(Br)c1O | COc1cc(C=O)cc(C#N)c1O | null | null | CO | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[O;D1;H1:7]):[c:8]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[O;D1;H1:7]):[c:8] | null | [] | null | null | null | null | A mixture of 23.1 g of 3-bromo-4-hydroxy-5-methoxy benzaldehyde, 9.3 g of cuprous cyanide and 140 ml of dimethyl acetamide (DMA) was refluxed for 2 hours with stirring. After cooling, the mixture was poured over ice and extract&d with an ethyl acetate--methanol mixture (90-10). The organic phase was washed and dried an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CO | null | null | COc1cc(C=O)cc(Br)c1O>CO>COc1cc(C=O)cc(C#N)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ff9fcd9cfe74e8dbd93a16959bf292e | COc1cc(C=O)cc(C#N)c1O>>N#Cc1cc(C=O)cc(O)c1O | C(=O)C=1C=C(C#N)C(=C(C1)OC)O.B(Br)(Br)Br>>C(=O)C=1C=C(C#N)C(=C(C1)O)O | C[O:10][c:9]1[cH:8][c:5]([CH:6]=[O:7])[cH:4][c:3]([C:2]#[N:1])[c:11]1[OH:12]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([OH:10])[c:11]1[OH:12] | COc1cc(C=O)cc(C#N)c1O | N#Cc1cc(C=O)cc(O)c1O | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72.4 | [{"value": 72.4, "product": "C(=O)C=1C=C(C#N)C(=C(C1)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 18 g of the product of Step A and 400 ml of dichloromethane were mixed together under nitrogen and the mixture was cooled to 0° C. 150 ml of a molar solution of boron tribromide in dichloromethane were added and the mixture stood for one night at ambient temperature. It was concentrated, cooled again to 0° C. and 250 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl | 0 | null | COc1cc(C=O)cc(C#N)c1O>ClCCl>N#Cc1cc(C=O)cc(O)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-49d72313e0d6412c95d675c45339c241 | COc1cc(C=O)cc(Cl)c1O>>O=Cc1cc(O)c(O)c(Cl)c1 | ClC=1C(=C(C=C(C=O)C1)OC)O.B(Br)(Br)Br>>ClC=1C=C(C=O)C=C(C1O)O | C[O:6][c:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:11][c:9]([Cl:10])[c:7]1[OH:8]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([Cl:10])[cH:11]1 | COc1cc(C=O)cc(Cl)c1O | O=Cc1cc(O)c(O)c(Cl)c1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 77.3 | [{"value": 77.3, "product": "ClC=1C=C(C=O)C=C(C1O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 37.2 g of commercial 5-chloro vanillin and 800 ml of dichloromethane were mixed together under nitrogen and cooled to 0° C. 300 ml of a molar solution of boron tribromide in dichloromethane are added and the mixture stood for one night at ambient temperature. It was concentrated, cooled again to 0° C. and acidified. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl | 0 | null | COc1cc(C=O)cc(Cl)c1O>ClCCl>O=Cc1cc(O)c(O)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9efe6333e98c4733b21ed3413c8658d8 | COc1cc(C=O)cc([N+](=O)[O-])c1O>>O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C(=C(C=C(C=O)C1)OC)O.B(Br)(Br)Br>>[N+](=O)([O-])C=1C=C(C=O)C=C(C1O)O | C[O:6][c:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:13][c:9]([N+:10](=[O:11])[O-:12])[c:7]1[OH:8]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | COc1cc(C=O)cc([N+](=O)[O-])c1O | O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 55.4 | [{"value": 55.4, "product": "[N+](=O)([O-])C=1C=C(C=O)C=C(C1O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | DAY | 35 g of 5-nitro vanillin (commercial) and 1200 ml of dichloromethane were mixed together under nitrogen and the mixture was cooled to 0° C. 533 ml of a molar solution of boron tribromide in dichloromethane were added and the mixture stood for 2 days at abmient temperature and then was concentrated. The residue was take... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl | 0 | 48 | COc1cc(C=O)cc([N+](=O)[O-])c1O>ClCCl>O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23ad7b54403248708606eeee9fbf6470 | COc1cc(C=O)cc(I)c1O>>O=Cc1cc(O)c(O)c(I)c1 | IC=1C(=C(C=C(C=O)C1)OC)O.B(Br)(Br)Br>>IC=1C=C(C=O)C=C(C1O)O | C[O:6][c:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:11][c:9]([I:10])[c:7]1[OH:8]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([I:10])[cH:11]1 | COc1cc(C=O)cc(I)c1O | O=Cc1cc(O)c(O)c(I)c1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 66.2 | [{"value": 66.2, "product": "IC=1C=C(C=O)C=C(C1O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 16 | HOUR | 37.2 g of 5-iodo vanillin (commercial) and 360 ml of dichloromethane were mixed together under nitrogen and the mixture was cooled to 0° C. 135 ml of a molar solution of boron tribromide in dichloromethane were added and the mixture stood for 16 hours at ambient temperature and was then concentrated, cooled to 0° C. an... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl | 0 | 16 | COc1cc(C=O)cc(I)c1O>ClCCl>O=Cc1cc(O)c(O)c(I)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cad495ca4824beabdad8a4e8de68a2c | O=CC(=O)O.Oc1cccc(F)c1O>>O=C(O)C(O)c1ccc(F)c(O)c1O | Cl.FC1=C(C(O)=CC=C1)O.C(C=O)(=O)O.[OH-].[Na+]>>FC1=C(C(=C(C=C1)C(C(=O)O)O)O)O | [O:1]=[C:2]([OH:3])[CH:4]=[O:5].[cH:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([OH:12])[c:13]1[OH:14]>>[O:1]=[C:2]([OH:3])[CH:4]([OH:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([OH:12])[c:13]1[OH:14] | O=CC(=O)O.Oc1cccc(F)c1O | O=C(O)C(O)c1ccc(F)c(O)c1O | null | null | O | C-C Coupling | OtherReaction | 236dc10d6be2d7527fb96a5b91492b698c2d2e32974acf29ee0457d6cf74bb4a | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5].[O;D1;H1:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[O;D1;H1:6]):[c:8] | 59 | [{"value": 59.0, "product": "FC1=C(C(=C(C=C1)C(C(=O)O)O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 51.2 g of 3-fluorocatechol and 36.8 g of glyoxylic acid were dissolved at 20° C. in 160 ml of water and 34.8 g of sodium hydroxide in solution in 400 ml of water were added to this solution cooled to 0° C. The mixture was heated for 4 hours at 46° C., then cooled to 0° C. and the pH was brought to 4.6 by the addition o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | 0 | null | O=CC(=O)O.Oc1cccc(F)c1O>O>O=C(O)C(O)c1ccc(F)c(O)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-30ada60bc0e74527b46c8f5abdf6a8c0 | COCCOCOc1ccc(C=O)c(Cl)c1OCOCCOC.[OH-]>>COCCOCOc1ccc(C(O)C(=O)O)c(Cl)c1OCOCCOC | [Cl-].[Li+].[OH-].[K+].ClC1=C(C=O)C=CC(=C1OCOCCOC)OCOCCOC.C(Br)(Br)Br.O1CCOCC1.C(Br)(Br)Br>>ClC1=C(C=CC(=C1OCOCCOC)OCOCCOC)C(C(=O)O)O | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([CH:12]=[O:13])[c:17]([Cl:18])[c:19]1[O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26].[OH-:16]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([OH:13])[C:14](=[O:15])[OH:16])[c:17]([Cl:18])[c:19]1[O:20][CH2:21][O:22][CH... | COCCOCOc1ccc(C=O)c(Cl)c1OCOCCOC.[OH-] | COCCOCOc1ccc(C(O)C(=O)O)c(Cl)c1OCOCCOC | null | null | O | Acylation | OtherReaction | e4754e3793ba0362af7cd262e2f320471fced6da69cfa59aaf69349f987b0106 | 7b79ddb9582ae558ef0424125dcd16c236a764b78e4d8d3057436676b03c02cd | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;D1;H0:7]=[C:8](-[OH;D1;+0:6])-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 24 | HOUR | 2.42 g of lithium chloride and 7.02 g of potassium hydroxide were dissolved in 30 ml of water at 0° C. and a solution of 10 g of 2-chloro-3,4-bis-[(2-methoxy-ethoxy)-methoxy] benzaldehyde (synthesized in Preparation 1), 2.8 ml of bromoform and 38 ml of dioxane were added to this mixture. The mixture was stirred for 24 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid.Secondary alcohol | null | null | c1ccccc1 | null | O | 0 | 24 | COCCOCOc1ccc(C=O)c(Cl)c1OCOCCOC.[OH-]>O>COCCOCOc1ccc(C(O)C(=O)O)c(Cl)c1OCOCCOC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5043e9c099ff4fda98d9234332a5cc3e | COCCOCOc1cc(C(O)C(=O)O)cc(F)c1OCOCCOC.[N-]=[N+]=C(c1ccccc1)c1ccccc1>>COCCOCOc1cc(C(O)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC | O.C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1.FC=1C=C(C=C(C1OCOCCOC)OCOCCOC)C(C(=O)O)O>>FC=1C=C(C=C(C1OCOCCOC)OCOCCOC)C(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)O | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][c:10]([CH:11]([OH:12])[C:13](=[O:14])[OH:15])[cH:29][c:30]([F:31])[c:32]1[O:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39].[N-]=[N+]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH... | COCCOCOc1cc(C(O)C(=O)O)cc(F)c1OCOCCOC.[N-]=[N+]=C(c1ccccc1)c1ccccc1 | COCCOCOc1cc(C(O)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC | null | null | ClCCl.CCOCC | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 8531b6eb3abfd6846ce0cb8d79abac610072134e0cc0be40cc269196cd4eea5b | d6eab3abd961fdb019332f17e55277b8a7c7f7a1f79c71be7a6248f0a0e6a15e | O=C(Cc1ccccc1)OC(c1ccccc1)c1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[N-]=[N+]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH;D3;+0:5](-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11] | null | [] | null | null | 16 | HOUR | 5.3 g of the acid of Step A were dissolved in 66 ml of dichloromethane and then 46 ml of a solution of diphenyl diazomethane at 6.5 g in ether were added at 15° C. The mixture was stirred for 16 hours at ambient temperature and then water was added, followed by decanting and acidifying with acetic acid. Washing with a ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCl.CCOCC | null | 16 | COCCOCOc1cc(C(O)C(=O)O)cc(F)c1OCOCCOC.[N-]=[N+]=C(c1ccccc1)c1ccccc1>ClCCl.CCOCC>COCCOCOc1cc(C(O)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a483aea8a4b498cbaefafb7e4383a84 | COCCOCOc1cc(C(ON)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC.O=C(O)C(=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>COCCOCOc1cc(C(ON=C(C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC | O(N)C(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=C(C(=C1)OCOCCOC)OCOCCOC)F.O=C(C(=O)O)C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>FC=1C=C(C=C(C1OCOCCOC)OCOCCOC)C(C(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O)ON=C(C(=O)O)C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][c:10]([CH:11]([O:12][NH2:13])[C:43](=[O:44])[O:45][CH:46]([c:47]2[cH:48][cH:49][cH:50][cH:51][cH:52]2)[c:53]2[cH:54][cH:55][cH:56][cH:57][cH:58]2)[cH:59][c:60]([F:61])[c:62]1[O:63][CH2:64][O:65][CH2:66][CH2:67][O:68][CH3:69].O=[C:14]([C:15](=[O:16])[OH:17])[c:18]1... | COCCOCOc1cc(C(ON)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC.O=C(O)C(=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | COCCOCOc1cc(C(ON=C(C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | O=C(OC(c1ccccc1)c1ccccc1)C(ON=Cc1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:5]1:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:1.[#8:10]-[C:11](=[O;D1;H0:12])-[C:13]-[#8:14]-[NH2;D1;+0:15]>>[#8:10]-[C:11](=[O;D1;H0:12])-[C:13]-[#8:14]-[N;H0;D2;+0:15]=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:5]1:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:1 | 56 | [{"value": 56.0, "product": "FC=1C=C(C=C(C1OCOCCOC)OCOCCOC)C(C(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O)ON=C(C(=O)O)C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.640 g of the product of Step D and and 0.474 g of oxo-[2-[(triphenylmethyl)-amino]-thiazol-4-yl]-acetic acid (Belgian Patent Application No. 864,828) were stirred for 4 and a half hours under nitrogen and at ambient temperature in the presence of 20 ml of methanol. Then, the solvent was eliminated, and the residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CO | null | null | COCCOCOc1cc(C(ON)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC.O=C(O)C(=O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>CO>COCCOCOc1cc(C(ON=C(C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)C(=O)OC(c2ccccc2)c2ccccc2)cc(F)c1OCOCCOC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a2d6a5f5e06e41cb9bec46be781f750a | BrC(Br)Br.COCCOCOc1c(C#N)ccc(C=O)c1OCOCCOC.[OH-]>>COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC | Cl.C(#N)C1=C(C(=C(C=O)C=C1)OCOCCOC)OCOCCOC.O1CCOCC1.C(Br)(Br)Br.[Br-].[Li+].[OH-].[K+]>>C(#N)C1=C(C(=C(C=C1)C(C(=O)O)Br)OCOCCOC)OCOCCOC | Br[CH:17](Br)[Br:16].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]([CH:15]=[O:18])[c:20]1[O:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27].[OH-:19]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]([CH:15]([Br:16])[C:17](=[O:18])[OH:1... | BrC(Br)Br.COCCOCOc1c(C#N)ccc(C=O)c1OCOCCOC.[OH-] | COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC | null | null | O.C(C)(=O)OCC | Acylation | OtherReaction | 365e7b5786ba406db9acc92273a73ca3606e1fc9beae7164dff36307d584b0e8 | 94f09b5eead91e2869e1eda1f358c9ebd11ae8f3e4a576f716d34b3e7202c271 | c1ccccc1 | Br-[CH;D3;+0:1](-Br)-[Br;H0;D1;+0:2].[O;H0;D1;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[OH-;D0:8]>>[Br;H0;D1;+0:2]-[CH;D3;+0:4](-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[OH;D1;+0:8])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 72 | HOUR | 440 microliters of bromoform were added at -5° C. to a mixture of 4.26 mg of lithium bromide, 598 mg of potassium hydroxide and 5 ml of water and then, a solution of 825 mg of a 4-cyano-2,3-bis-[(2-methoxy-ethoxy)-methoxy]-benzaldehyde (preparation given hereafter) in 5 ml of dioxane was added dropwise. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Aldehyde | Secondary halide.Carboxylic acid | null | null | c1ccccc1 | HBr | O.C(C)(=O)OCC | null | 72 | BrC(Br)Br.COCCOCOc1c(C#N)ccc(C=O)c1OCOCCOC.[OH-]>O.C(C)(=O)OCC>COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9e556f57e168442bbbc24bcb8ff4afba | COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC.[N-]=[N+]=C(c1ccccc1)c1ccccc1>>COCCOCOc1c(C#N)ccc(C(Br)C(=O)OC(c2ccccc2)c2ccccc2)c1OCOCCOC | C(#N)C1=C(C(=C(C=C1)C(C(=O)O)Br)OCOCCOC)OCOCCOC.C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1>>C(#N)C1=C(C(=C(C=C1)C(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)Br)OCOCCOC)OCOCCOC | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]([CH:15]([Br:16])[C:17](=[O:18])[OH:19])[c:33]1[O:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40].[N-]=[N+]=[C:20]([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH3:1][O:2][CH2:3][CH2:4][... | COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC.[N-]=[N+]=C(c1ccccc1)c1ccccc1 | COCCOCOc1c(C#N)ccc(C(Br)C(=O)OC(c2ccccc2)c2ccccc2)c1OCOCCOC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 8531b6eb3abfd6846ce0cb8d79abac610072134e0cc0be40cc269196cd4eea5b | d6eab3abd961fdb019332f17e55277b8a7c7f7a1f79c71be7a6248f0a0e6a15e | O=C(Cc1ccccc1)OC(c1ccccc1)c1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[N-]=[N+]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH;D3;+0:5](-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The product of Step A was dissolved in 10 ml of methylene chloride and 470 mg of diphenyl diazomethane were added. Evaporation was carried out followed by chromatography on silica (eluant: cyclohexane - ethyl acetate (2-1)) to obtain 450 mg of the desired, product.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | null | COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC.[N-]=[N+]=C(c1ccccc1)c1ccccc1>C(Cl)Cl>COCCOCOc1c(C#N)ccc(C(Br)C(=O)OC(c2ccccc2)c2ccccc2)c1OCOCCOC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81159db6893c43669dd5945fbf20ea55 | COc1ccc(F)c(F)c1.OO>>COc1ccc(F)c(F)c1O | COB(OC)OC.Cl.OO.FC=1C=C(C=CC1F)OC.[Li+].CCC[CH2-]>>FC1=C(C(=CC=C1F)OC)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[cH:10]1.O[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[OH:11] | COc1ccc(F)c(F)c1.OO | COc1ccc(F)c(F)c1O | null | null | CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | ae2c40671d5fdb818f0b6d803c1d8cceca080b6105aceeca1808a097ec52d441 | a2fdf414569b219d462bc05c91ebf31e5426b96645f5c78cb091f50cc92fc345 | c1ccccc1 | O-[OH;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[F;D1;H0:7]):[c:8]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[OH;D1;+0:1]):[c:6](-[F;D1;H0:7]):[c:8] | null | [] | null | null | null | null | Using the procedure of Example 39, 125 g of 3,4-difluoroanisole (commercial) and 500 ml of a 1.6M solution of N-butyllithium in hexane were reacted at -72° C., and then 92.4 ml of trimethylborate, 500 ml of hydrochloric acid and 120 g of intermediate compound were reacted and the product was reacted with 440 ml of 30% ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | CCCCCC | null | null | COc1ccc(F)c(F)c1.OO>CCCCCC>COc1ccc(F)c(F)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a2ecc42a142468888fdaba3359f6ee1 | COCCOCOc1cc(C=CC(=O)[O-])c(Cl)c(Cl)c1OCOCCOC>>C=Cc1cc(OCOCCOC)c(OCOCCOC)c(Cl)c1Cl | ClC1=C(C=CC(=O)[O-])C=C(C(=C1Cl)OCOCCOC)OCOCCOC.[H-].C(C(C)C)[Al+]CC(C)C>>ClC1=C(C=C)C=C(C(=C1Cl)OCOCCOC)OCOCCOC | O=C([O-])[CH:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])[c:13]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[c:21]([Cl:22])[c:23]1[Cl:24]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])[c:13]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[c:21](... | COCCOCOc1cc(C=CC(=O)[O-])c(Cl)c(Cl)c1OCOCCOC | C=Cc1cc(OCOCCOC)c(OCOCCOC)c(Cl)c1Cl | null | null | null | Reduction | OtherReaction | 02b7eac01118bfd51c4a58b62814356740b902aea3dbc3f759c729b8b0806524 | 49d4bca12f98a39ef3d7cf431ba8a8e145ac0803658b55b3a56347c5526e322e | c1ccccc1 | O=C(-[O-])-[CH;D2;+0:1]=[C:2]-[c:3]>>[CH2;D1;+0:1]=[C:2]-[c:3] | 99.6 | [{"value": 99.6, "product": "ClC1=C(C=C)C=C(C(=C1Cl)OCOCCOC)OCOCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Stage C of Example 40, 20 g of ester of Step B and 88 ml of diisobutylaluminium hydride were reacted to obtain 17.9 g of the expected product melting at 60° C.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | null | Vinyl | null | null | c1ccccc1 | Other | null | null | null | COCCOCOc1cc(C=CC(=O)[O-])c(Cl)c(Cl)c1OCOCCOC>>C=Cc1cc(OCOCCOC)c(OCOCCOC)c(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ce42197cace4f5dad3160cf94f08e0c | C=Cc1cc(OCOCCOC)c(OCOCCOC)c(Cl)c1Cl.O=C(OO)c1cccc(Cl)c1>>C=CC12C=C(OCOCCOC)C(OCOCCOC)=C(Cl)C1(Cl)O2 | ClC1=C(C=C)C=C(C(=C1Cl)OCOCCOC)OCOCCOC.ClC1=CC(=CC=C1)C(=O)OO>>ClC12C(C=C)(C=C(C(=C1Cl)OCOCCOC)OCOCCOC)O2 | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])[c:13]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[c:21]([Cl:22])[c:23]1[Cl:24].O=C(O[OH:25])c1cccc(Cl)c1>>[CH2:1]=[CH:2][C:3]12[CH:4]=[C:5]([O:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])[C:13]([O:14][CH2:15][O:16][CH2:17][CH2:18][O... | C=Cc1cc(OCOCCOC)c(OCOCCOC)c(Cl)c1Cl.O=C(OO)c1cccc(Cl)c1 | C=CC12C=C(OCOCCOC)C(OCOCCOC)=C(Cl)C1(Cl)O2 | null | null | C1CCCCC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 72b2f8ff6740abd6644cb0a780d40368540147b13a2e0e8432a1a20e777dd1fd | a81bf860526a3cc8482c48e2baecd9d5497fdceb000730fed6b6c4f895adc8c2 | C1=CC2OC2C=C1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[#8:3]-[c;H0;D3;+0:4]1:[c;H0;D3;+0:5](-[Cl;D1;H0:6]):[c;H0;D3;+0:7](-[Cl;D1;H0:8]):[c;H0;D3;+0:9](-[C:10]=[C;D1;H2:11]):[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[#8:14]-[C:15]>>[C:2]-[#8:3]-[C;H0;D3;+0:4]1=[C;H0;D3;+0:5](-[Cl;D1;H0:6])-[C;H0;D4;+0:7]2(-[Cl;D1;H0:8])-[O;H0;D2;+0:1]-... | 99.6 | [{"value": 99.6, "product": "ClC12C(C=C)(C=C(C(=C1Cl)OCOCCOC)OCOCCOC)O2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Stage D of Example 40, 13.2 g of thee allylic alcohol of Step C and 10.3 g of m-chloro perbenzoic acid were reacted to obtain 13.7 g of the expected product with a Rf=0.25 (AcOEt-cyclohexane 6-4).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Peroxide | Tertiary halide.Alkenyl halide.Ether.Ether.Ether | c1ccccc1.c1ccccc1 | C1=CC2OC2C=C1 | C1=CC2OC2C=C1 | HCl | C1CCCCC1.C(C)(=O)OCC | null | null | C=Cc1cc(OCOCCOC)c(OCOCCOC)c(Cl)c1Cl.O=C(OO)c1cccc(Cl)c1>C1CCCCC1.C(C)(=O)OCC>C=CC12C=C(OCOCCOC)C(OCOCCOC)=C(Cl)C1(Cl)O2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6e731b1d7e854c2a8e627b73580568d3 | CCCCCCCCBr.CCOC(=O)OCC>>CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC | Cl.BrCCCCCCCC.[Mg].C(OCC)(OCC)=O>>C(CCCCCCC)C(O)(CCCCCCCC)CCCCCCCC | Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O([CH2:2][CH3:1])[C:9](O[CH2:3][CH3:6])=[O:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:10])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26] | CCCCCCCCBr.CCOC(=O)OCC | CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC | null | null | C(C)OCC | C-C Coupling | OtherReaction | 8706ba12a6e3eac34bcc4e6f93267fb45dbd62c681eb88a043e053be354fdd53 | 66c8a44d5e8977ee5c977d626a3446a6c88153f3dc208477947005725264b4ae | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[CH2;D2;+0:5]-O-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-[CH2;D2;+0:8]-[CH3;D1;+0:9]>>[C:10]-[C:11]-[C;H0;D4;+0:6](-[OH;D1;+0:7])(-[C:12]-[C:13]-[CH2;D2;+0:9]-[C:14]-[C:15]-[CH2;D2;+0:8]-[CH2;D2;+0:5]-[C;D1;H3:4])-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 30 | CELSIUS | 1 | HOUR | This compound may be prepared in the following manner. Three moles of 1-bromooctane are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester | Tertiary alcohol | null | null | null | Br- | C(C)OCC | 30 | 1 | CCCCCCCCBr.CCOC(=O)OCC>C(C)OCC>CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0a83914dba048c6a657be3218f2bd5a | CCCCCCCCC(Cl)(CCCCCCCC)CCCCCCCC.CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC>>CCCCCCCCC(C)(CCCCCCCC)CCCCCCCC | C(CCCCCCC)C(CCCCCCCC)(CCCCCCCC)Cl.C(CCCCCCC)C(O)(CCCCCCCC)CCCCCCCC.[Cl-].[Ca+2].[Cl-].C[Al](C)C.Cl>>C(CCCCCCC)C(C)(CCCCCCCC)CCCCCCCC | CCCCCCCCC(Cl)(CCCCCCCC)CCCCCCC[CH3:10].O[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([CH3:10])([CH2:11][CH2:... | CCCCCCCCC(Cl)(CCCCCCCC)CCCCCCCC.CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC | CCCCCCCCC(C)(CCCCCCCC)CCCCCCCC | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 272b9cd949524b0f15cc42e5bff323005c8996c8af1fcaa2d39cd5f393a7d26f | bd96ef07d60c9b141f8e4bcb3de7c88b60e9a3e72642350d7d8f0d1588ccd78f | null | C-C-C-C-C-C-C-C-C(-Cl)(-C-C-C-C-C-C-C-C)-C-C-C-C-C-C-C-[CH3;D1;+0:1].O-[C;H0;D4;+0:2](-[C:3]-[C:4])(-[C:5]-[C:6])-[C:7]-[C:8]>>[C:4]-[C:3]-[C;H0;D4;+0:2](-[CH3;D1;+0:1])(-[C:5]-[C:6])-[C:7]-[C:8] | null | [] | 0 | CELSIUS | null | null | This compound may be prepared in the following manner. Three moles of 1-bromooctane are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary alcohol | null | null | null | null | HCl | C(Cl)Cl | 0 | null | CCCCCCCCC(Cl)(CCCCCCCC)CCCCCCCC.CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC>C(Cl)Cl>CCCCCCCCC(C)(CCCCCCCC)CCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5831ca84c85c45188e821732a2150987 | CCCCCCCCCCBr.CCOC(=O)OCC>>CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC | Cl.BrCCCCCCCCCC.[Mg].C(OCC)(OCC)=O>>C(CCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCC | Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O([CH2:2][CH3:1])[C:11](O[CH2:14][CH3:15])=[O:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:12])([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][C... | CCCCCCCCCCBr.CCOC(=O)OCC | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC | null | null | C(C)OCC | C-C Coupling | OtherReaction | 8706ba12a6e3eac34bcc4e6f93267fb45dbd62c681eb88a043e053be354fdd53 | 66c8a44d5e8977ee5c977d626a3446a6c88153f3dc208477947005725264b4ae | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[CH2;D2;+0:5]-O-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-[CH2;D2;+0:8]-[CH3;D1;+0:9]>>[C:10]-[C:11]-[CH2;D2;+0:5]-[C;D1;H3:4].[C:12]-[C:13]-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[C:14]-[C;H0;D4;+0:6](-[OH;D1;+0:7])(-[C:15]-[C:16])-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 30 | CELSIUS | 1 | HOUR | Three moles of 1-bromodecane was slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether was slowly added to the mixture. After stirring for one hour at 30° C., the mixture was slowly poured into 1.8 liters ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester | Tertiary alcohol | null | null | null | Br- | C(C)OCC | 30 | 1 | CCCCCCCCCCBr.CCOC(=O)OCC>C(C)OCC>CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-43db573a1030471e9bdddb88415b043e | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC.Cl>>CCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC | Cl.C(CCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCC.[Cl-].[Ca+2].[Cl-]>>C(CCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCC)Cl | O[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[ClH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2... | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC.Cl | CCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC | null | null | C(Cl)Cl | Miscellaneous | Alcohol to chloride_HCl | 06eab52f623b8fb0d86400eecae376db031ba5e5becb07a748e186ad18f204bc | 34c38d962daad1da1e92c0e4cf09f41371ed52dbd062ebc36fca2e0c616df50b | null | O-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[C:6]-[C:7].[ClH;D0;+0:8]>>[C:5]-[C:4]-[C;H0;D4;+0:1](-[Cl;H0;D1;+0:8])(-[C:2]-[C:3])-[C:6]-[C:7] | 90 | [{"value": 90.0, "product": "C(CCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | One mole of tri-n-decylcarbinol was added to a mixture of 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas was slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magn... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Tertiary halide | null | null | null | HO- | C(Cl)Cl | null | null | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC.Cl>C(Cl)Cl>CCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5601d68778243e1afd472a048d0d106 | CCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC>>CCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCC | C(CCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCC)Cl.C[Al](C)C>>C(CCCCCCCCC)C(C)(CCCCCCCCCC)CCCCCCCCCC | Cl[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:1... | CCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC | CCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | d06dc960ad45ba0387d757dfc480fdfd624a6cb7f28b4f8a95745d58a488baf5 | 404c724ad3ca06f39bc871693871aba7ab416f4e80555c466ba262b8bc4d8d51 | null | Cl-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:4]-[C;H0;D4;+0:1](-[CH3;D1;+0:6])(-[C:2]-[C:3])-[C:10]-[CH2;D2;+0:7]-[C:8]-[C:9] | 75 | [{"value": 75.0, "product": "C(CCCCCCCCC)C(C)(CCCCCCCCCC)CCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | One mole of tri-n-decylmethylchloride was added to 0.75 liters of methylene chloride and the solution was blanketed with nitrogen and cooled to 0° C. 0.33 moles of trimethylaluminum was then added and the mixture was allowed to warm to room temperature. The mixture was slowly quenched with 50 ml of water followed by wa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | null | null | null | null | C(Cl)Cl | 0 | null | CCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC>C(Cl)Cl>CCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a7e187e142942fdb6f461d846f40942 | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC>>CCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCC | C(CCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCC.C[Al](C)C>>C(CCCCCCCCC)C(C)(CCCCCCCCCC)CCCCCCCCCC | O[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11... | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC | CCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCC | null | [Ti](Cl)(Cl)(Cl)Cl | C(Cl)Cl | Miscellaneous | OtherReaction | 11d17e43de92be7fa6f46d5cbef5874ff365848c27d02336596ae498740a47ba | 96b5e5e1e667b20dc45eb811e44eb97b30bb7bfac720a7b7a090312707dfb175 | null | O-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:4]-[C;H0;D4;+0:1](-[CH3;D1;+0:6])(-[C:2]-[C:3])-[C:10]-[CH2;D2;+0:7]-[C:8]-[C:9] | 70 | [{"value": 70.0, "product": "C(CCCCCCCCC)C(C)(CCCCCCCCCC)CCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2.5 | HOUR | Alternatively, the 0.1 moles of the synthesized tri-n-decylcarbinol was added to 0.2 liters of methylene chloride. The mixture was covered with a blanket of nitrogen and cooled to 0° C. 0.050 mole titanium tetrachloride was added to the mixture and the solution was stirred 2-3 hours at 0° C. 0.066 mole trimethylaluminu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | null | null | null | null | [Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl | 0 | 2.5 | CCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>CCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53f58a0bd1b3472b91143912053c2870 | CCCCCCCCBr.CCOC(=O)OCC>>CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC | Cl.C(CCCCCCC)Br.[Mg].C(OCC)(OCC)=O>>C(CCCCCCC)C(O)(CCCCCCCC)CCCCCCCC | Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O([CH2:2][CH3:1])[C:9](O[CH2:3][CH3:6])=[O:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:10])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26] | CCCCCCCCBr.CCOC(=O)OCC | CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC | null | null | C(C)OCC | C-C Coupling | OtherReaction | 8706ba12a6e3eac34bcc4e6f93267fb45dbd62c681eb88a043e053be354fdd53 | 66c8a44d5e8977ee5c977d626a3446a6c88153f3dc208477947005725264b4ae | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[CH2;D2;+0:5]-O-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-[CH2;D2;+0:8]-[CH3;D1;+0:9]>>[C:10]-[C:11]-[C;H0;D4;+0:6](-[OH;D1;+0:7])(-[C:12]-[C:13]-[CH2;D2;+0:9]-[C:14]-[C:15]-[CH2;D2;+0:8]-[CH2;D2;+0:5]-[C;D1;H3:4])-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | 30 | CELSIUS | 1 | HOUR | This compound may be prepared in the following manner. Three moles of n-octylbromide are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester | Tertiary alcohol | null | null | null | Br- | C(C)OCC | 30 | 1 | CCCCCCCCBr.CCOC(=O)OCC>C(C)OCC>CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-108d826840d345cdb28e811cd9a5ff6a | CCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCC[CH2][Mg][Br].CCOC(=O)OCC>>CCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC | Cl.C(CCCCCCCCC)[Mg]Br.C(C)OC(OCC)=O.C(CCCCCCCCCCCCC)[Mg]Br>>C(CCCCCCCCC)C(O)(CCCCCCCCCCCCCC)CCCCCCCCCC | [Br][Mg][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[Br][Mg][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O([C:15](O[CH2:35][CH3:27])=[O:16])[CH2:28][CH3:29]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH... | CCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCC[CH2][Mg][Br].CCOC(=O)OCC | CCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC | null | null | C(C)OCC | C-C Coupling | OtherReaction | 62964fd1377eac5f0eb7f51aea42b9f3e2d3ca0f07b95736432e18531304a33d | 624e8b17a308e03f3e6939ffdcbdcca4c9cec90af9e7aef377156454a167fe61 | null | [Br]-[Mg]-[CH2;D2;+0:1]-[C:2]-[C:3].[Br]-[Mg]-[CH2;D2;+0:4]-[C:5]-[C:6].[CH3;D1;+0:7]-[CH2;D2;+0:8]-O-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-O-[CH2;D2;+0:11]-[CH3;D1;+0:12]>>[C:13]-[C:14]-[CH2;D2;+0:8]-[C;D1;H3:15].[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[CH2;D2;+0:4]-[C:5]-[C:6])-[CH2;D2;+0:7]-[CH2;D2;+0:1... | null | [] | 30 | CELSIUS | 1 | HOUR | Decylmagnesium bromide (0.66 mole) in ethyl ether is slowly added to 0.33 moles of diethylcarbonate in 100 ml ethyl ether and stirred for one hour at 30° C. (nitrogen atmosphere). Tetradecylmagnesium bromide (0.33 moles) is slowly added to the solution and stirred for one hour at 30° C. The mixture is then slowly poure... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Magnesium halide.Carbonic Ester | Tertiary alcohol | null | null | null | null | C(C)OCC | 30 | 1 | CCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCC[CH2][Mg][Br].CCOC(=O)OCC>C(C)OCC>CCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3272ce8059be4591a93fe2fa3200dcab | CCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC.Cl>>CCCCCCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC | Cl.C(CCCCCCCCC)C(O)(CCCCCCCCCCCCCC)CCCCCCCCCC.[Cl-].[Ca+2].[Cl-]>>C(CCCCCCCCC)C(CCCCCCCCCCCCCC)(CCCCCCCCCC)Cl | O[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[ClH:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]... | CCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC.Cl | CCCCCCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC | null | null | C(Cl)Cl | Miscellaneous | Alcohol to chloride_HCl | 06eab52f623b8fb0d86400eecae376db031ba5e5becb07a748e186ad18f204bc | 34c38d962daad1da1e92c0e4cf09f41371ed52dbd062ebc36fca2e0c616df50b | null | O-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[C:6]-[C:7].[ClH;D0;+0:8]>>[C:3]-[C:2]-[C;H0;D4;+0:1](-[Cl;H0;D1;+0:8])(-[C:4]-[C:5])-[C:6]-[C:7] | null | [] | null | null | null | null | One mole of di-n-decyl-n-tetradecylcarbinol is added to 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Tertiary halide | null | null | null | HO- | C(Cl)Cl | null | null | CCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCC.Cl>C(Cl)Cl>CCCCCCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a5409deb6a74c57b3451bf511fe1b1f | CCCCCCCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCC[CH2][Mg][Br].CCOC(=O)OCC>>CCCCCCCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCCCCCC | C(CCCCCCCCC)[Mg]Br.C(CCCCCCCCCCCCCCCCCC)[Mg]Br.C(C)OC(OCC)=O.Cl.C(CCCCCCCCCCCCC)[Mg]Br>>C(CCCCCCCCCCCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCCCCCC | [Br][Mg][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[Br][Mg][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].[Br][Mg][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26... | CCCCCCCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCC[CH2][Mg][Br].CCOC(=O)OCC | CCCCCCCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCCCCCC | null | null | C(C)OCC | C-C Coupling | OtherReaction | 2ff6284ae5c29aecab9688c38dab5c3f668b289ce7880f1ed4e891928aae5c9e | 628a23618f2baf89036e21fa6db53ec245ef0b967c8fb58f9713610e1454506d | null | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-O-C-C.[Br]-[Mg]-[CH2;D2;+0:3]-[C:4]-[C:5].[Br]-[Mg]-[CH2;D2;+0:6]-[C:7]-[C:8].[Br]-[Mg]-[CH2;D2;+0:9]-[C:10]-[C:11]>>[C:5]-[C:4]-[CH2;D2;+0:3]-[C;H0;D4;+0:1](-[OH;D1;+0:2])(-[CH2;D2;+0:9]-[C:10]-[C:11])-[CH2;D2;+0:6]-[C:7]-[C:8] | null | [] | 30 | CELSIUS | 1 | HOUR | n-Nonadecylmagnesium bromide (0.33 moles) in ethyl ether is slowly added to 0.33 mole of diethylcarbonate in 100 ml diethyl ether and stirred for one hour at 30° C. (nitrogen atmosphere). n-Tetradecylmagnesium bromide (0.33 mole) is slowly added to the solution and stirred for one hour at 30° C. n-Decylmagnesium bromid... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Magnesium halide.Magnesium halide.Carbonic Ester | Tertiary alcohol | null | null | null | HBr.Mg | C(C)OCC | 30 | 1 | CCCCCCCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCCCCCC[CH2][Mg][Br].CCCCCCCCC[CH2][Mg][Br].CCOC(=O)OCC>C(C)OCC>CCCCCCCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5357024e5ff4448eabdc6f4dbebdfb2c | CCCCCCCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCCCCCC.Cl>>CCCCCCCCCCCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCCCCCC | Cl.C(CCCCCCCCCCCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCCCCCC.[Cl-].[Ca+2].[Cl-]>>C(CCCCCCCCCCCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCCCCCC)Cl | O[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:4... | CCCCCCCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCCCCCC.Cl | CCCCCCCCCCCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCCCCCC | null | null | C(Cl)Cl | Miscellaneous | Alcohol to chloride_HCl | 06eab52f623b8fb0d86400eecae376db031ba5e5becb07a748e186ad18f204bc | 34c38d962daad1da1e92c0e4cf09f41371ed52dbd062ebc36fca2e0c616df50b | null | O-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[C:6]-[C:7].[ClH;D0;+0:8]>>[C:3]-[C:2]-[C;H0;D4;+0:1](-[Cl;H0;D1;+0:8])(-[C:4]-[C:5])-[C:6]-[C:7] | null | [] | null | null | null | null | One mole of n-nonadecyl-n-tetradecyl-n-decylcarbinol is added to 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried wit... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Tertiary halide | null | null | null | HO- | C(Cl)Cl | null | null | CCCCCCCCCCCCCCCCCCCC(O)(CCCCCCCCCC)CCCCCCCCCCCCCC.Cl>C(Cl)Cl>CCCCCCCCCCCCCCCCCCCC(Cl)(CCCCCCCCCC)CCCCCCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ccded561afe0424fa8a1fedcae175ed7 | CC1(C)Oc2cc3c(cc2O1)OC(C)(C)O3.O=C=O>>CC1(C)Oc2cc3c(c(C(=O)O)c2O1)OC(C)(C)O3 | [OH-].[Na+].CC1(OC2=C(O1)C=C1C(OC(O1)(C)C)=C2)C.C(CCC)[Li].C(=O)=O>>CC1(OC2=C(O1)C(=C1C(OC(O1)(C)C)=C2)C(=O)O)C | [CH3:1][C:2]1([CH3:3])[O:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][c:13]2[O:14]1)[O:15][C:16]([CH3:17])([CH3:18])[O:19]3.[C:10](=[O:11])=[O:12]>>[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[cH:6][c:7]3[c:8]([c:9]([C:10](=[O:11])[OH:12])[c:13]2[O:14]1)[O:15][C:16]([CH3:17])([CH3:18])[O:19]3 | CC1(C)Oc2cc3c(cc2O1)OC(C)(C)O3.O=C=O | CC1(C)Oc2cc3c(c(C(=O)O)c2O1)OC(C)(C)O3 | null | null | C1CCOC1.O.CCCCCC | Acylation | OtherReaction | a86cfdbc7f612158eb74004352ed48cb5636d9157f80b8a4084730d2d59c5e2c | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1c2c(cc3c1OCO3)OCO2 | [#8:1]1-[C:2]-[#8:3]-[c:4]:[c:5]-1:[cH;D2;+0:6]:[c:7]1:[c:8]-[#8:9]-[C:10]-[#8:11]-1.[O;D1;H0:12]=[C;H0;D2;+0:13]=[O;H0;D1;+0:14]>>[O;D1;H0:12]=[C;H0;D3;+0:13](-[OH;D1;+0:14])-[c;H0;D3;+0:6](:[c:5]1:[c:4]-[#8:3]-[C:2]-[#8:1]-1):[c:7]1:[c:8]-[#8:9]-[C:10]-[#8:11]-1 | null | [] | -20 | CELSIUS | 8 | HOUR | 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole (10.0 g, 45.0 mmol; prepared according to WO-91/12024) was dissolved in dry THF (200 mL) under an argon atmosphere. The solution was cooled to -20° C. and n-butyllithium (20.0 mL, 50.0 mmol) in hexane was added. After attaining ambient temperature, the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1OCO3)OCO2 | null | C1CCOC1.O.CCCCCC | -20 | 8 | CC1(C)Oc2cc3c(cc2O1)OC(C)(C)O3.O=C=O>C1CCOC1.O.CCCCCC>CC1(C)Oc2cc3c(c(C(=O)O)c2O1)OC(C)(C)O3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b748cc817d6e4b11bba391ca0648edaa | CC1(C)Oc2cc3c(c(C(=O)O)c2O1)OC(C)(C)O3.CI>>COC(=O)c1c2c(cc3c1OC(C)(C)O3)OC(C)(C)O2 | CC1(OC2=C(O1)C(=C1C(OC(O1)(C)C)=C2)C(=O)O)C.C([O-])([O-])=O.[K+].[K+].CI>>COC(=O)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C | [OH:2][C:3](=[O:4])[c:5]1[c:6]2[c:7]([cH:8][c:9]3[c:10]1[O:11][C:12]([CH3:13])([CH3:14])[O:15]3)[O:16][C:17]([CH3:18])([CH3:19])[O:20]2.I[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[c:7]([cH:8][c:9]3[c:10]1[O:11][C:12]([CH3:13])([CH3:14])[O:15]3)[O:16][C:17]([CH3:18])([CH3:19])[O:20]2 | CC1(C)Oc2cc3c(c(C(=O)O)c2O1)OC(C)(C)O3.CI | COC(=O)c1c2c(cc3c1OC(C)(C)O3)OC(C)(C)O2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1c2c(cc3c1OCO3)OCO2 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 88.3 | [{"value": 88.0, "product": "COC(=O)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.3, "product": "COC(=O)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 8 | HOUR | 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic acid (10.0 g, 38.0 mmol) was dissolved in dry DMF (100 mL). Potassium carbonate (15.2 g, 110.0 mmol) was added and the reaction was heated to 55° C. for 30 min. After cooling to ambient temperature, methyl iodide (15.6 g, 110.0 mmol) was added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1c2c(cc3c1OCO3)OCO2 | HI | CN(C)C=O | 55 | 8 | CC1(C)Oc2cc3c(c(C(=O)O)c2O1)OC(C)(C)O3.CI>CN(C)C=O>COC(=O)c1c2c(cc3c1OC(C)(C)O3)OC(C)(C)O2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6735643c3b9e41779184084c922223ce | CC1(C)Sc2cc3c(cc2S1)SC(C)(C)S3.COC(=O)c1c2c(cc3c1OC(C)(C)O3)OC(C)(C)O2.[Li][CH2]CCC>>CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 | CC1(SC2=C(S1)C=C1C(SC(S1)(C)C)=C2)C.C(CCC)[Li].COC(=O)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C>>CC1(SC2=C(S1)C(=C1C(SC(S1)(C)C)=C2)C(O)(C2=C1C(OC(O1)(C)C)=CC1=C2OC(O1)(C)C)C1=C2C(SC(S2)(C)C)=CC2=C1SC(S2)(C)C)C | [CH3:1][C:19]1([CH3:21])[S:18][c:33]2[cH:28][c:29]3[c:30]([cH:31][c:32]2[S:38]1)[S:39][C:40]([CH3:26])([CH3:41])[S:43]3.O([C:10](=[O:11])[c:12]1[c:13]2[c:14]([cH:15][c:16]3[c:17]1[O:45][C:24]([CH3:3])([CH3:44])[O:4]3)[O:46][C:47]([CH3:48])([CH3:49])[O:50]2)[CH3:20].[Li][CH2:35][CH2:36][CH2:2][CH3:5]>>[CH3:1][C:2]1([CH3... | CC1(C)Sc2cc3c(cc2S1)SC(C)(C)S3.COC(=O)c1c2c(cc3c1OC(C)(C)O3)OC(C)(C)O2.[Li][CH2]CCC | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | e452af76f0455ab1d8513150fcc164c0fb93545642074ba0071ff3502d56f9e2 | eb8a988e87dd1193fc0c80512a94e5e30ef7d7055d9620e213ba0a6c44aa617d | c1c2c(c(C(c3c4c(cc5c3SCS5)SCS4)c3c4c(cc5c3SCS5)SCS4)c3c1OCO3)OCO2 | [C;D1;H3:1]-[C;H0;D4;+0:2]1(-[CH3;D1;+0:3])-[S;H0;D2;+0:4]-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[c:7]3:[c:8](:[c:9]:[c:10]:2-[S;H0;D2;+0:11]-1)-[#16:12]-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[CH3;D1;+0:15])-[#16:16]-3.[C;D1;H3:17]-[C:18]1(-[C;D1;H3:19])-[O;H0;D2;+0:20]-[c;H0;D3;+0:21]2:[c:22]:[c;H0;D3;+0:23]3:[c;H0;D3;+0:24](:[c:25]... | 44 | [{"value": 44.0, "product": "CC1(SC2=C(S1)C(=C1C(SC(S1)(C)C)=C2)C(O)(C2=C1C(OC(O1)(C)C)=CC1=C2OC(O1)(C)C)C1=C2C(SC(S2)(C)C)=CC2=C1SC(S2)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dithiole (2.86 g, 10 mmol; prepared according to WO-91/12024) was dissolved in anhydrous THF (75 mL) and cooled to -70° C. n-Butyllithium (4.4 mL, 2.5M in hexane) was added. The reaction mixture was allowed to reach ambient temperature. 4-Methoxycarbonyl-2,2,6,6-tetramethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Ether.Ether.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Alkyl lithium | Ether.Ether.Ether.Ether.Tertiary alcohol.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | Li | C1CCOC1 | null | 1 | CC1(C)Sc2cc3c(cc2S1)SC(C)(C)S3.COC(=O)c1c2c(cc3c1OC(C)(C)O3)OC(C)(C)O2.[Li][CH2]CCC>C1CCOC1>CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a322f043809404b8fb31f9aa2d7aec3 | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3.CCOC(=O)OCC.CN(C)CCN(C)C.[Li][C](C)(C)C>>CCOC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OCC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c4c(c(C(=O)OCC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 | C(C)(C)(C)[Li].CN(C)CCN(C)C.CC1(SC2=C(S1)C(=C1C(SC(S1)(C)C)=C2)C(O)(C2=C1C(OC(O1)(C)C)=CC1=C2OC(O1)(C)C)C1=C2C(SC(S2)(C)C)=CC2=C1SC(S2)(C)C)C.C(OCC)(OCC)=O>>C(C)OC(=O)C1=C2SC(SC2=C(C=2SC(SC21)(C)C)C(O)(C2=C1C(OC(O1)(C)C)=C(C1=C2OC(O1)(C)C)C(=O)OCC)C1=C2C(SC(S2)(C)C)=C(C2=C1SC(S2)(C)C)C(=O)OCC)(C)C | C[C:40]1([CH3:41])[O:5][c:54]2[c:9]([C:10]([OH:11])([c:12]3[c:13]4[c:14]([cH:15][c:21]5[c:22]3[S:23][C:24]([CH3:25])([CH3:26])[S:27]5)[S:28][C:29]([CH3:30])([CH3:31])[S:32]4)[c:33]3[c:34]4[c:35]([cH:36][c:42]5[c:43]3[S:44][C:45]([CH3:46])([CH3:47])[S:48]5)[S:49][C:50]([CH3:51])([CH3:52])[S:53]4)[c:8]3[c:7]([cH:6][c:37]... | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3.CCOC(=O)OCC.CN(C)CCN(C)C.[Li][C](C)(C)C | CCOC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OCC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c4c(c(C(=O)OCC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 | null | null | C1=CC=CC=C1 | Acylation | OtherReaction | 5fcb5e4cfee0f50a20faa57213b39d23f0a1ab10fa059a32f7eaeddb4458f2f7 | 6a804c132f059daed8d566da6ea8362db9e5aae9e5436ad52cf3e05a9944fcad | c1c2c(c(C(c3c4c(cc5c3SCS5)SCS4)c3c4c(cc5c3SCS5)SCS4)c3c1OCO3)OCO2 | C-N(-C)-C-C-N(-C)-[CH3;D1;+0:1].C-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[#8:4]-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[c:7]3:[c:8](:[c:9](-[C:10]):[c;H0;D3;+0:11]:2-[O;H0;D2;+0:12]-1)-[#8:13]-[C:14]-[#8:15]-3.[#16:16]1-[C:17]-[#16:18]-[c:19](:[c:20]-1):[cH;D2;+0:21]:[c:22]1:[c:23]-[#16:24]-[C:25]-[#16:26]-1.[#16:27]1-[C:28]-[#16:29]-[c:... | null | [] | null | null | 1.5 | HOUR | Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)methanol (0.50 g, 0.61 mmol) was dissolved in dry benzene (6.0 mL) under an atmosphere of argon. t-Butyllitium (2.44 mL, 1.5M in pentane) and TMEDA (0.545 mL, 3.66 mmol) were added. The re... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ether.Ether.Tertiary amine.Tertiary amine.Alkyl lithium | Ester.Ester.Ester.Ether.Ether | c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | Li | C1=CC=CC=C1 | null | 1.5 | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3.CCOC(=O)OCC.CN(C)CCN(C)C.[Li][C](C)(C)C>C1=CC=CC=C1>CCOC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OCC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c4c(c(C(=O)OCC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20a28c547f764190864154877d314000 | CC1(C)Sc2cc3c(cc2S1)SC(C)(C)S3.CI.O=C=O>>COC(=O)c1c2c(cc3c1SC(C)(C)S3)SC(C)(C)S2 | C(=O)=O.CI.C([O-])([O-])=O.[K+].[K+].C(CCC)[Li].CC1(SC2=C(S1)C=C1C(SC(S1)(C)C)=C2)C>>COC(=O)C1=C2C(SC(S2)(C)C)=CC2=C1SC(S2)(C)C | [cH:5]1[c:7]2[c:6]([cH:8][c:9]3[c:10]1[S:11][C:12]([CH3:13])([CH3:14])[S:15]3)[S:20][C:17]([CH3:18])([CH3:19])[S:16]2.I[CH3:1].[O:2]=[C:3]=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[c:7]([cH:8][c:9]3[c:10]1[S:11][C:12]([CH3:13])([CH3:14])[S:15]3)[S:16][C:17]([CH3:18])([CH3:19])[S:20]2 | CC1(C)Sc2cc3c(cc2S1)SC(C)(C)S3.CI.O=C=O | COC(=O)c1c2c(cc3c1SC(C)(C)S3)SC(C)(C)S2 | null | null | CN(C)C=O.CCOCC | Acylation | OtherReaction | 2ac4ae5ad8e7f510ba480690120240df76ffe7841789a7c2d284c6c1b9c4fea5 | c0da44b11e2071417522771b259351ca8046db346df1eea32c3b5ee03a22b629 | c1c2c(cc3c1SCS3)SCS2 | I-[CH3;D1;+0:1].[#16:2]1-[C:3]-[#16:4]-[c:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:7]3:[c;H0;D3;+0:8](:[cH;D2;+0:9]:[c:10]:2-1)-[#16:11]-[C:12]-[#16:13]-3.[O;D1;H0:14]=[C;H0;D2;+0:15]=[O;H0;D1;+0:16]>>[CH3;D1;+0:1]-[O;H0;D2;+0:16]-[C;H0;D3;+0:15](=[O;D1;H0:14])-[c;H0;D3;+0:9]1:[c:10]2:[c:5](:[cH;D2;+0:6]:[c;H0;D3;+0:8]3:[c;H0;D3;+... | null | [] | null | null | 30 | MINUTE | 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole (2.0 g, 6.98 mmol) was dissolved in dry ether (50.0 mL) in a dry, argon filled reaction flask. n-Butyllithium (3.07 mL, 2.5M in hexane) was added and the reaction mixture was stirred for 30 min. The solution was poured onto solid carbon dioxide and, after stirring... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Carbon dioxide | Ester.Monosulfide.Monosulfide | c1c2c(cc3c1SCS3)SCS2 | c1c2c(cc3c1SCS3)SCS2 | c1c2c(cc3c1SCS3)SCS2 | HI | CN(C)C=O.CCOCC | null | 0.5 | CC1(C)Sc2cc3c(cc2S1)SC(C)(C)S3.CI.O=C=O>CN(C)C=O.CCOCC>COC(=O)c1c2c(cc3c1SC(C)(C)S3)SC(C)(C)S2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-760fc340b5b24bef86b0fc2c43979b8e | CC1(C)Oc2cc3c(cc2O1)OC(C)(C)O3.COC(=O)c1c2c(cc3c1SC(C)(C)S3)SC(C)(C)S2.O.[Li][CH2]CCC>>CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 | C(CCC)[Li].CC1(OC2=C(O1)C=C1C(OC(O1)(C)C)=C2)C.O.COC(=O)C1=C2C(SC(S2)(C)C)=CC2=C1SC(S2)(C)C>>CC1(OC2=C(O1)C(=C1C(OC(O1)(C)C)=C2)C(O)(C2=C1C(SC(S1)(C)C)=CC1=C2SC(S1)(C)C)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C)C | [CH3:1][C:2]1([CH3:3])[O:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][c:44]2[O:45]1)[O:23][C:24]([CH3:25])([CH3:26])[O:50]3.[C:10](=[O:11])([c:12]1[c:13]2[c:30]([cH:31][c:32]3[c:33]1[S:34][C:35]([CH3:29])([CH3:36])[S:38]3)[S:39][C:40]([CH3:28])([CH3:41])[S:43]2)[O:18][CH3:19].[OH2:22].[Li][CH2:14][CH2:16][CH2:17][CH3:20]>>[CH3:1][... | CC1(C)Oc2cc3c(cc2O1)OC(C)(C)O3.COC(=O)c1c2c(cc3c1SC(C)(C)S3)SC(C)(C)S2.O.[Li][CH2]CCC | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 | null | null | CCOCC | Aromatic Heterocycle Formation | OtherReaction | 3c9731cefac7ec6dac7be3711a5cf7750a2196eba6b63fa29411637f97d9f49c | fcf18322b4fb6ad88995c1972b82afb060297e4ba9bf7c0f58733510d9731900 | c1c2c(c(C(c3c4c(cc5c3OCO5)OCO4)c3c4c(cc5c3SCS5)SCS4)c3c1OCO3)OCO2 | [C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[c:7]3:[c:8](:[c:9]:[c:10]:2-[O;H0;D2;+0:11]-1)-[#8:12]-[C:13]-[#8:14]-3.[C;D1;H3:15]-[C;H0;D4;+0:16]1(-[CH3;D1;+0:17])-[#16:18]-[c;H0;D3;+0:19]2:[c:20](:[c:21]:[c;H0;D3;+0:22]3:[c;H0;D3;+0:23](:[c;H0;D3;+0:24]:2-[C;H0;D3;+0:25](=[O;H... | null | [] | 0 | CELSIUS | 15 | MINUTE | 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole (5.15 g, 23.2 mmol) was dissolved in dry ether (40.0 mL) in a dried, argon filled reaction vessel. The solution was cooled to 0° C. and n-butyllithium (9.29 mL, 2.5M in hexane) was added. After stirring for 15 min at ambient temperature, the mixture was cooled to 0... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Alkyl lithium | Ether.Ether.Ether.Ether.Ether.Ether.Tertiary alcohol.Monosulfide.Monosulfide.Monosulfide.Monosulfide | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2 | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | Li | CCOCC | 0 | 0.25 | CC1(C)Oc2cc3c(cc2O1)OC(C)(C)O3.COC(=O)c1c2c(cc3c1SC(C)(C)S3)SC(C)(C)S2.O.[Li][CH2]CCC>CCOCC>CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c35abaa1aed4412e96a4c1b72c7b8021 | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3.CN(C)CCN(C)C.O=C=O>>CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)O)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)O)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c(c2C(=O)O)OC(C)(C)O3)O1 | C(=O)=O.CN(C)CCN(C)C.C(C)(C)(C)[Li].CC1(OC2=C(O1)C(=C1C(OC(O1)(C)C)=C2)C(O)(C2=C1C(SC(S1)(C)C)=CC1=C2SC(S1)(C)C)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C)C>>C(=O)(O)C1=C2OC(OC2=C(C=2OC(OC21)(C)C)C(O)(C2=C1C(SC(S1)(C)C)=C(C1=C2SC(S1)(C)C)C(=O)O)C1=C2C(OC(O2)(C)C)=C(C2=C1OC(O2)(C)C)C(=O)O)(C)C | [CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([c:7]([C:8]([OH:9])([c:10]3[c:11]4[c:12]([cH:13][c:17]5[c:18]3[O:19][C:20]([CH3:21])([CH3:22])[O:23]5)[O:24][C:25]([CH3:26])([CH3:27])[O:28]4)[c:29]3[c:30]4[c:31]([cH:32][c:36]5[c:37]3[S:38][C:39]([CH3:40])([CH3:41])[S:42]5)[S:43][C:44]([CH3:45])([CH3:46])[S:47]4)[c:49]3[c:48]([cH... | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3.CN(C)CCN(C)C.O=C=O | CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)O)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)O)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c(c2C(=O)O)OC(C)(C)O3)O1 | null | null | CCOCC.C1CCCCC1 | Acylation | OtherReaction | e74a997982e87f10791fe4f45689589c2ddca68356fd6979f0c8c39fdbbfedde | cbf0082711680dd33e04480d9b3cd8c3c0149eebf11600a58f74f5586b00ceaa | c1c2c(c(C(c3c4c(cc5c3OCO5)OCO4)c3c4c(cc5c3SCS5)SCS4)c3c1OCO3)OCO2 | C-N(-C)-C-C-N(-C)-[CH3;D1;+0:1].[O;D1;H1:2]-[C:3](-[c:4]1:[c:5]2:[c:6](:[cH;D2;+0:7]:[c:8]3:[c:9]:1-[#8:10]-[C:11]-[#8:12]-3)-[#8:13]-[C:14]-[#8:15]-2)(-[c:16]1:[c:17]2:[c:18](:[cH;D2;+0:19]:[c:20]3:[c:21]:1-[#16:22]-[C:23]-[#16:24]-3)-[#16:25]-[C:26]-[#16:27]-2)-[c;H0;D3;+0:28]1:[c:29]2:[c:30](:[cH;D2;+0:31]:[c;H0;D3;... | null | [] | null | null | 20 | MINUTE | Dry TMEDA (1.21 mL, 8.04 mmol) and t-butyllithium (5.36 mL, 1.5M in pentane) were dissolved in dry cyclohexane (12 mL) at 0° C. Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(2,2,6,6-tetramethyl benzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol (0.608 g, 0.804 mmol) was then added at ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amine.Tertiary amine.Carbon dioxide | Carboxylic acid.Carboxylic acid.Carboxylic acid.Ether.Ether | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | Other | CCOCC.C1CCCCC1 | null | 0.333333 | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3.CN(C)CCN(C)C.O=C=O>CCOCC.C1CCCCC1>CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)O)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)O)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c(c2C(=O)O)OC(C)(C)O3)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71815a1699b6445f9f96283c7d73efe0 | COC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2>>COC(=O)c1c2c(c(C(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 | COC(=O)C1=C2OC(OC2=C(C=2OC(OC21)(C)C)C(O)(C2=C1C(SC(S1)(C)C)=C(C1=C2SC(S1)(C)C)C(=O)OC)C1=C2C(OC(O2)(C)C)=C(C2=C1OC(O2)(C)C)C(=O)OC)(C)C.B(F)(F)F.CCOCC.[Sn](Cl)Cl>>COC(=O)C1=C2OC(OC2=C(C=2OC(OC21)(C)C)C(C2=C1C(SC(S1)(C)C)=C(C1=C2SC(S1)(C)C)C(=O)OC)C1=C2C(OC(O2)(C)C)=C(C2=C1OC(O2)(C)C)C(=O)OC)(C)C | O[C:9]([c:8]1[c:7]2[c:6]([c:5]([C:3]([O:2][CH3:1])=[O:4])[c:51]3[c:50]1[O:56][C:53]([CH3:54])([CH3:55])[O:52]3)[O:61][C:58]([CH3:59])([CH3:60])[O:57]2)([c:10]1[c:11]2[c:12]([c:13]([C:14](=[O:15])[O:16][CH3:17])[c:18]3[c:19]1[O:20][C:21]([CH3:22])([CH3:23])[O:24]3)[O:25][C:26]([CH3:27])([CH3:28])[O:29]2)[c:30]1[c:31]2[c... | COC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 | COC(=O)c1c2c(c(C(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 | null | [Zn] | null | Reduction | OtherReaction | c74e766e62dea6513290ab98d06521c92685074430a200193315f473ed0037ec | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1c2c(c(C(c3c4c(cc5c3OCO5)OCO4)c3c4c(cc5c3SCS5)SCS4)c3c1OCO3)OCO2 | O-[C;H0;D4;+0:1](-[c:2](:[c:3]-[#8:4]):[c:5]-[#8:6])(-[c:7](:[c:8]-[#16:9]):[c:10]-[#16:11])-[c:12](:[c:13]-[#8:14]):[c:15]-[#8:16]>>[#16:11]-[c:10]:[c:7](-[CH;D3;+0:1](-[c:2](:[c:3]-[#8:4]):[c:5]-[#8:6])-[c:12](:[c:13]-[#8:14]):[c:15]-[#8:16]):[c:8]-[#16:9] | null | [] | null | null | null | null | Bis-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol (5 mg, 0.005 mmol) was dissolved in dry, degassed acetonitrile under an argon atmosphere. BF3.Et2O (2.0 μL, 0.011 mmol) and tin(II) chloride (3.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | null | null | c1c2c(cc3c1OCO3)OCO2.c1c2c(cc3c1SCS3)SCS2.c1c2c(cc3c1OCO3)OCO2 | Other | [Zn] | null | null | COC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2>[Zn]>COC(=O)c1c2c(c(C(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a6d6748b1df4808a57a14672a9c86dc | CC(=O)OCC1(COC(C)=O)Sc2cc3c(cc2S1)SC(COC(C)=O)(COC(C)=O)S3>>OCC1(CO)Sc2cc3c(cc2S1)SC(CO)(CO)S3 | C(C)(=O)OCC1(SC2=C(S1)C=C1C(SC(S1)(COC(C)=O)COC(C)=O)=C2)COC(C)=O.C(=O)([O-])[O-].[K+].[K+]>>OCC1(SC2=C(S1)C=C1C(SC(S1)(CO)CO)=C2)CO | CC(=O)[O:1][CH2:2][C:3]1([CH2:4][O:5]C(C)=O)[S:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]2[S:13]1)[S:14][C:15]([CH2:16][O:17]C(C)=O)([CH2:18][O:19]C(C)=O)[S:20]3>>[OH:1][CH2:2][C:3]1([CH2:4][OH:5])[S:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]2[S:13]1)[S:14][C:15]([CH2:16][OH:17])([CH2:18][OH:19])[S:20]3 | CC(=O)OCC1(COC(C)=O)Sc2cc3c(cc2S1)SC(COC(C)=O)(COC(C)=O)S3 | OCC1(CO)Sc2cc3c(cc2S1)SC(CO)(CO)S3 | null | null | CO | Reduction | OtherReaction | 73cc08f15920db4ea0923c3b24e1a4c6d7380b91c4b3106d69889f1d89e036a6 | db6f6d98b99f51adabbd240fbce698bfbe6fd62e873120ade7beae025e5657bb | c1c2c(cc3c1SCS3)SCS2 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](-[C:4]-[O;H0;D2;+0:5]-C(-C)=O)(-[#16:6])-[#16:7].C-C(=O)-[O;H0;D2;+0:8]-[C:9]-[C:10](-[C:11]-[O;H0;D2;+0:12]-C(-C)=O)(-[#16:13])-[#16:14]>>[#16:13]-[C:10](-[C:9]-[OH;D1;+0:8])(-[C:11]-[OH;D1;+0:12])-[#16:14].[#16:6]-[C:3](-[C:2]-[OH;D1;+0:1])(-[C:4]-[OH;D1;+0:5])-[#16:7] | null | [] | null | null | null | null | 2,2,6,6-Tetra(acetoxymethyl)benzo[1,2-d:4,5-d']bis(1,3)dithiole (1.8 g, 3.5 mmol) and K2CO3 (1.9 g) were stirred in methanol (100 mL) for 1 h at ambient temperature. The solvent was evaporated and water (100 mL) was added. The mixture was neutralized (2M HCl) and the precipitate was collected.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol | null | null | c1c2c(cc3c1SCS3)SCS2 | HO- | CO | null | null | CC(=O)OCC1(COC(C)=O)Sc2cc3c(cc2S1)SC(COC(C)=O)(COC(C)=O)S3>CO>OCC1(CO)Sc2cc3c(cc2S1)SC(CO)(CO)S3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3fd18c20fe384f209c75449594a77dfc | CC1(C)Oc2cc3c(cc2S1)SC(C)(C)O3.C[Si](C)(C)Cl>>CC1(C)Oc2c(cc3c(c2[Si](C)(C)C)OC(C)(C)S3)S1 | CC1(OC=2C(S1)=CC=1SC(OC1C2)(C)C)C.C(CCC)[Li].Cl[Si](C)(C)C>>C[Si](C1=C2C(SC(O2)(C)C)=CC=2SC(OC21)(C)C)(C)C | [CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([cH:7][c:8]3[c:9]([cH:10]2)[O:15][C:16]([CH3:17])([CH3:18])[S:19]3)[S:20]1.Cl[Si:11]([CH3:12])([CH3:13])[CH3:14]>>[CH3:1][C:2]1([CH3:3])[O:4][c:5]2[c:6]([cH:7][c:8]3[c:9]([c:10]2[Si:11]([CH3:12])([CH3:13])[CH3:14])[O:15][C:16]([CH3:17])([CH3:18])[S:19]3)[S:20]1 | CC1(C)Oc2cc3c(cc2S1)SC(C)(C)O3.C[Si](C)(C)Cl | CC1(C)Oc2c(cc3c(c2[Si](C)(C)C)OC(C)(C)S3)S1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 4d920506285c00399efb181b4ec00c0f33dc1bce9f2dbd24ac119a8845500b75 | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | c1c2c(cc3c1OCS3)SCO2 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[#16:5]1-[C:6]-[#8:7]-[c:8](:[c:9]-1):[cH;D2;+0:10]:[c:11]1:[c:12]-[#16:13]-[C:14]-[#8:15]-1>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:10](:[c:11]1:[c:12]-[#16:13]-[C:14]-[#8:15]-1):[c:8]1:[c:9]-[#16:5]-[C:6]-[#8:7]-1 | null | [] | null | null | 15 | MINUTE | The reaction was performed under an argon atmosphere using deoxygenated solvents. 2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole (6.0 g, 23.6 mmol) was dissolved in dry THF (120 mL). The mixture was cooled on an ice-bath and n-butyllithium (10.8 mL, 2.5M in hexane) was added dropwise over 10 min. After 15 min... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1c2c(cc3c1OCS3)SCO2 | c1c2c(cc3c1OCS3)SCO2 | c1c2c(cc3c1OCS3)SCO2 | HCl | C1CCOC1 | null | 0.25 | CC1(C)Oc2cc3c(cc2S1)SC(C)(C)O3.C[Si](C)(C)Cl>C1CCOC1>CC1(C)Oc2c(cc3c(c2[Si](C)(C)C)OC(C)(C)S3)S1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3f677304111d45a7802ed37ac3c6141c | CC1(C)Oc2c(c(C(O)(c3c4c(c([Si](C)(C)C)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c([Si](C)(C)C)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2[Si](C)(C)C)OC(C)(C)S3)S1>>CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)O6)OC(C)(C)S5)c4c5c(cc6c4SC(C)(C)O6)OC(C)(C)S5)c2S1)SC(C)(C)O3 | C(=O)(O)[O-].[Na+].[I-].[Na+].Cl[Si](C)(C)C.C[Si](C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C1SC(OC1=C(C1=C2SC(O1)(C)C)[Si](C)(C)C)(C)C)C1=C2SC(OC2=C(C2=C1SC(O2)(C)C)[Si](C)(C)C)(C)C)(C)C>>CC1(OC=2C(S1)=C(C=1SC(OC1C2)(C)C)C(O)(C2=C1SC(OC1=CC1=C2SC(O1)(C)C)(C)C)C1=C2SC(OC2=CC2=C1SC(O2)(C)C)(C)C)C | C[Si](C)(C)[c:6]1[c:5]2[c:44]([c:9]([C:10]([OH:11])([c:12]3[c:13]4[c:14]([c:15]([Si](C)(C)C)[c:16]5[c:17]3[S:18][C:19]([CH3:20])([CH3:21])[O:22]5)[O:23][C:24]([CH3:25])([CH3:26])[S:27]4)[c:28]3[c:29]4[c:30]([c:31]([Si](C)(C)C)[c:32]5[c:33]3[S:34][C:35]([CH3:36])([CH3:37])[O:38]5)[O:39][C:40]([CH3:41])([CH3:42])[S:43]4)... | CC1(C)Oc2c(c(C(O)(c3c4c(c([Si](C)(C)C)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c([Si](C)(C)C)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2[Si](C)(C)C)OC(C)(C)S3)S1 | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)O6)OC(C)(C)S5)c4c5c(cc6c4SC(C)(C)O6)OC(C)(C)S5)c2S1)SC(C)(C)O3 | null | null | C(C)#N | Miscellaneous | OtherReaction | afe9566dd4aa30908e30516c808e43d3b8eee858237c95b927f53c5eda9e4b43 | f3322e71c3e92cdc73f7ed164c490ee5862b18cfe67e54f1ba9ef731a52db4b7 | c1c2c(c(C(c3c4c(cc5c3SCO5)OCS4)c3c4c(cc5c3SCO5)OCS4)c3c1OCS3)SCO2 | C-[Si](-C)(-C)-[c;H0;D3;+0:1](:[c:2]1:[c:3]-[#16:4]-[C:5]-[#8:6]-1):[c:7]1:[c:8]-[#16:9]-[C:10]-[#8:11]-1.C-[Si](-C)(-C)-[c;H0;D3;+0:12](:[c:13]1:[c:14]-[#16:15]-[C:16]-[#8:17]-1):[c:18]1:[c:19]-[#16:20]-[C:21]-[#8:22]-1.C-[Si](-C)(-C)-[c;H0;D3;+0:23](:[c:24]1:[c:25]-[#16:26]-[C:27]-[#8:28]-1):[c:29]1:[c:30]-[#16:31]-[... | null | [] | null | null | 20 | MINUTE | Tris-(8-trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol (0.62 g, 0.62 mmol) was dissolved in acetonitrile (150 mL). Sodium iodide (0.75 g, 6.0 mmol) and chlorotrimethylsilane (0.65 g, 6.0 mmol) was added in one portion. The mixture was stirred for 20 min and then poured onto diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group.Silyl protective group.Silyl protective group | null | c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2 | c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2 | c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2 | Other | C(C)#N | null | 0.333333 | CC1(C)Oc2c(c(C(O)(c3c4c(c([Si](C)(C)C)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c([Si](C)(C)C)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2[Si](C)(C)C)OC(C)(C)S3)S1>C(C)#N>CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4SC(C)(C)O6)OC(C)(C)S5)c4c5c(cc6c4SC(C)(C)O6)OC(C)(C)S5)c2S1)SC(C)(C)O3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9d46f1258cf4095bcf66afa8b7bb539 | CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)Cl)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c(C(=O)Cl)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2C(=O)Cl)OC(C)(C)S3)S1.OCCNCCO>>CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)N(CCO)CCO)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c(C(=O)N(CCO)CCO)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2C(=O)N(CCO)CCO)OC(C)(C)S3)S1 | ClC(=O)C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C1SC(OC1=C(C1=C2SC(O1)(C)C)C(=O)Cl)(C)C)C1=C2SC(OC2=C(C2=C1SC(O2)(C)C)C(=O)Cl)(C)C.OCCNCCO>>OCCN(C(=O)C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C1SC(OC1=C(C1=C2SC(O1)(C)C)C(=O)N(CCO)CCO)(C)C)C1=C2SC(OC2=C(C2=C1SC(O2)(C)C)C(=O)N(CCO)CCO)(C)C)CCO | Cl[C:14]([c:13]1[c:12]2[c:11]([c:10]([C:8]([c:7]3[c:6]4[c:5]([c:62]([C:63](Cl)=[O:64])[c:61]5[c:60]3[S:76][C:73]([CH3:74])([CH3:75])[O:72]5)[O:4][C:2]([CH3:3])([CH3:42])[S:77]4)([OH:9])[c:35]3[c:36]4[c:37]([c:38]([C:39](Cl)=[O:40])[c:48]5[c:49]3[S:50][C:51]([CH3:1])([CH3:21])[O:54]5)[O:55][C:56]([CH3:57])([CH3:58])[S:5... | CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)Cl)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c(C(=O)Cl)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2C(=O)Cl)OC(C)(C)S3)S1.OCCNCCO | CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)N(CCO)CCO)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c(C(=O)N(CCO)CCO)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2C(=O)N(CCO)CCO)OC(C)(C)S3)S1 | null | null | C1=CC=CC=C1.O | Acylation | OtherReaction | d2ac129f39631fe97b426d032dbc96ae91fd7b43567819c49127adcf67e2462c | d83b6db80199c7edcb8f196b1f0ce5b10cd1c761c76ee97e489bb5b2ef866b36 | c1c2c(c(C(c3c4c(cc5c3SCO5)OCS4)c3c4c(cc5c3SCO5)OCS4)c3c1OCS3)SCO2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]-[#8:5]):[c:6]-[#8:7].Cl-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]-[#8:12]):[c:13]1:[c:14]-[#16:15]-[C;H0;D4;+0:16](-[C;D1;H3:17])(-[CH3;D1;+0:18])-[#8:19]-1.Cl-[C;H0;D3;+0:20](=[O;D1;H0:21])-[c:22](:[c:23]-[#8:24]):[c:25]1:[c:26]-[#16:27]-[C;H0;D4;+0:28](-[CH3;D1;+0:29])(-... | 63.4 | [{"value": 60.0, "product": "OCCN(C(=O)C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C1SC(OC1=C(C1=C2SC(O1)(C)C)C(=O)N(CCO)CCO)(C)C)C1=C2SC(OC2=C(C2=C1SC(O2)(C)C)C(=O)N(CCO)CCO)(C)C)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "OCCN(C(=O)C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C... | null | null | 8 | HOUR | Tris-(8-chlorocarbonyl-2,2,6,6-tetramethyl-benzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol (0.80 g, 0.80 mmol) was dissolved in benzene (200 mL). A solution of of bis(2-hydroxyethyl)amine (8.0 g, 48 mmol) in water (200 mL) was added and after vigorous stirring overnight, the mixture was transferred to a separatory f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Acyl halide.Ether.Ether.Secondary amine.Monosulfide.Monosulfide | Ether.Ether.Tertiary amide.Tertiary amide.Tertiary amide.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Monosulfide.Monosulfide | c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2 | c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2 | c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2.c1c2c(cc3c1OCS3)SCO2 | null | C1=CC=CC=C1.O | null | 8 | CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)Cl)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c(C(=O)Cl)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2C(=O)Cl)OC(C)(C)S3)S1.OCCNCCO>C1=CC=CC=C1.O>CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)N(CCO)CCO)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c4c(c(C(=O)N(CCO)CCO)c5c3SC(C)(C)O5)OC(C)(C)S4)c3c(c2C(=O)N(CCO)CCO)OC(C)(C)S3)S1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-98343e58e325465bbbaa7fdb2b6a1ac0 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1ccc(Br)cc1>>Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cc1 | BrC1=CC=C(C=C1)C.CC1(CCC(C2=CC(=CC=C12)Br)=O)C.CC1(CCC(C2=CC(=CC=C12)Br)=O)C>>C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)Br)(C)C)C | O=[C:6]1[CH2:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]21.Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[cH:19][cH:20]1 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1ccc(Br)cc1 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cc1 | null | null | C1CCOC1.C(C)OC(C)=O | C-C Coupling | OtherReaction | 2fbbf41647a8c4f0278c25fbcfbace1cdbb174312495bfebc071a73b393e6788 | 554b1bee1ccf92984990164979ec7aaf354dc2a70796dc88c3036796633e99e1 | C1=C(c2ccccc2)c2ccccc2CC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[C;H0;D3;+0:6]1-[CH2;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[c:12]:[c:11]1:[c:10]-[C:9]-[C:8]-[CH;D2;+0:7]=[C;H0;D3;+0:6]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | To a mixture of Mg metal (650 mg, 27 mmol) in THF (20 mL) was added 4-bromotoluene (5.3 g, 31 mmol) in THF (40 mL). The mixture was stirred for 2 hours at ambient temperature and heated to 70° C. for 30 minutes. After cooling to ambient temperature, 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A) (2.1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | null | c1ccc2c(c1)CCCC2.c1ccccc1 | c1ccccc1.C1=Cc2ccccc2CC1 | c1ccccc1.C1=Cc2ccccc2CC1 | HBr | C1CCOC1.C(C)OC(C)=O | null | 2 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1ccc(Br)cc1>C1CCOC1.C(C)OC(C)=O>Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf0cea00f0c14b87bedbeafd627d9061 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cc1.O=C=O>>Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)cc1 | C(=O)=O.[Li]C(C)(C)C.CCCCC.C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)Br)(C)C)C.C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)Br)(C)C)C.CN(C=O)C>>C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C)C | Br[c:15]1[cH:14][cH:13][c:12]2[c:19]([cH:18]1)[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1)=[CH:7][CH2:8][C:9]2([CH3:10])[CH3:11].O=[C:16]=[O:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][c:19]32)[cH:20][cH:21]1 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cc1.O=C=O | Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)cc1 | null | null | C1CCOC1.C(C)OC(C)=O | C-C Coupling | OtherReaction | b4070cec8a084380200c9a64a85dcebfacf7487a23558ab094a57ef7a0675fac | c0100ab7b5bcec44798faf2d53320d9c2adb8a4e38bf9019653825fce736fb17 | C1=C(c2ccccc2)c2ccccc2CC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].O=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:2]:[c:3] | null | [] | null | null | null | null | To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Aldehyde | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | c1ccccc1.C1=Cc2ccccc2CC1 | Br- | C1CCOC1.C(C)OC(C)=O | null | null | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cc1.O=C=O>C1CCOC1.C(C)OC(C)=O>Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b0e8d298ae64c8b9df10e43febd3af1 | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)cc1>>CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)cc2)=CCC3(C)C)CC(OC)OC)cc1 | C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.[Li]CCCC.CCCCCC.C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C)C.C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C)C>>COC(C/C(=C\C1=CC=C2C(CC=C(C2=C1)C1=CC=C(C=C1)C)(C)C)/C1=CC=C(C(=O)OCC)C=C1)OC | CCOP(=O)(OCC)[C:32]([CH2:31][CH2:10][c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:38][cH:37]1)([O:33][CH3:34])[O:35][CH3:36].O=[CH:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([c:19]1[cH:20][cH:21][c:22]([CH3:23])[cH:24][cH:25]1)=[CH:26][CH2:27][C:28]2([CH3:29])[CH3:30]>>[CH3:1][CH2:2][O:3][C:4]... | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)cc1 | CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)cc2)=CCC3(C)C)CC(OC)OC)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2b2f01a2a3c2f6ea43954e1fcfb38220499a98de93d92d3a033fa1127e06f89d | 3598948eace7341b2f4800001ea9b7b5ac95eb54b4840cc8e83ad3a3413fcab8 | C1=C(c2ccccc2)c2cc(/C=C/c3ccccc3)ccc2CC1 | C-C-O-P(=O)(-O-C-C)-[C;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10].O=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:3]-[#8:2]-[CH;D3;+0:1](-[#8:4]-[C;D1;H3:5])-[C:6]/[C;H0;D3;+0:7](=[CH;D2;+0:11]\[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 1.5 | HOUR | To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 350 mg, 0.9 mmol, available in accordance with EPO Application No. 0 210 929 published on Feb. 4, 1987), in THF (9 mL), was added n-BuLi in hexane (1.6M solution, 0.7 mL, 1.1 mmol). The mixture was stirred for 1.5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether | Ether.Ether | null | null | c1ccccc1.c1ccccc1.C1=Cc2ccccc2CC1 | HO- | C1CCOC1 | null | 1.5 | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)cc1>C1CCOC1>CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)cc2)=CCC3(C)C)CC(OC)OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-da975157105744468fa3d3bb8edc1433 | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)cc2)=CCC4(C)C)cc1>>Cc1ccc(C2=CCC(C)(C)c3cc4cccc(-c5ccc(C(=O)O)cc5)c4cc32)cc1 | C1(=CC=C(C=C1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)OCC)C=C1)(C)C)C.C1(=CC=C(C=C1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)OCC)C=C1)(C)C)C.CO.[Li+].[OH-].Cl>>C1(=CC=C(C=C1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)O)C=C1)(C)C)C | CC[O:25][C:23]([c:22]1[cH:21][cH:20][c:19](-[c:18]2[cH:17][cH:16][cH:15][c:14]3[cH:13][c:12]4[c:30]([cH:29][c:28]32)[C:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)=[CH:7][CH2:8][C:9]4([CH3:10])[CH3:11])[cH:27][cH:26]1)=[O:24]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH... | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)cc2)=CCC4(C)C)cc1 | Cc1ccc(C2=CCC(C)(C)c3cc4cccc(-c5ccc(C(=O)O)cc5)c4cc32)cc1 | null | null | CCOCC.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=C(c2ccccc2)c2cc3c(-c4ccccc4)cccc3cc2CC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 16 | HOUR | To a degassed solution of ethyl 4-[1(tol-4-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 1, 35 mg, 0.08 mmol), in THF (1.5 mL) and MeOH (1.5 mL) was added LiOH (1M solution in water, 0.3 mL, 0.3 mmol). The mixture was stirred at ambient temperature for 16 hours, diluted with ether (60 mL). The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1=Cc2cc3ccccc3cc2CC1.c1ccccc1 | Other | CCOCC.C1CCOC1 | null | 16 | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)cc2)=CCC4(C)C)cc1>CCOCC.C1CCOC1>Cc1ccc(C2=CCC(C)(C)c3cc4cccc(-c5ccc(C(=O)O)cc5)c4cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1181981a49704b02b7381620902d58eb | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1cccs1>>Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)s1 | CC1(CCC(C2=CC(=CC=C12)Br)=O)C.CC1(CCC(C2=CC(=CC=C12)Br)=O)C.CC=1SC=CC1.[Li]CCCC>>CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C | O=[C:6]1[CH2:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]21.[CH3:1][c:2]1[cH:3][cH:4][cH:5][s:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[s:19]1 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1cccs1 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)s1 | null | null | CCOCC.C(C)OC(C)=O.C1CCOC1 | C-C Coupling | OtherReaction | 89330b8a34552186e5f49cfb277c70aa6a06cd6639f780a165e8aac713b088a2 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C1=C(c2cccs2)c2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[#16;a:8]1:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1>>[c:7]:[c:6]1:[c:5]-[C:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1]-1-[c;H0;D3;+0:12]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1 | 62.3 | [{"value": 62.3, "product": "CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | To a cold (-78° C.) solution of 2-methylthiophene (800 mg, 8.1 mmol) in THF (10 mL) was added n-BuLi (1.6M solution in hexane, 5 mL). The mixture was stirred for 1.5 hours and transferred to a cold (-78° C.) flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.63 g, 6.5 mmol), in THF (15... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCC2.c1ccsc1 | c1ccsc1.C1=Cc2ccccc2CC1 | c1ccsc1.C1=Cc2ccccc2CC1 | HO- | CCOCC.C(C)OC(C)=O.C1CCOC1 | 0 | 1.5 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1cccs1>CCOCC.C(C)OC(C)=O.C1CCOC1>Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4955e9d4488f4c70a01e631513107eb7 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)s1.O=C=O>>Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)s1 | CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C.CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C.[Li]C(C)(C)C.CCCCC.C(=O)=O.CN(C)C=O>>CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C | Br[c:15]1[cH:14][cH:13][c:12]2[c:19]([cH:18]1)[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[s:20]1)=[CH:7][CH2:8][C:9]2([CH3:10])[CH3:11].O=[C:16]=[O:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][c:19]32)[s:20]1 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)s1.O=C=O | Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)s1 | null | null | C1CCOC1.CCOCC | C-C Coupling | OtherReaction | b4070cec8a084380200c9a64a85dcebfacf7487a23558ab094a57ef7a0675fac | c0100ab7b5bcec44798faf2d53320d9c2adb8a4e38bf9019653825fce736fb17 | C1=C(c2cccs2)c2ccccc2CC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].O=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:2]:[c:3] | null | [] | null | null | 15 | MINUTE | To a cold (-78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replace... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Aldehyde | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | c1ccsc1.C1=Cc2ccccc2CC1 | Br- | C1CCOC1.CCOCC | null | 0.25 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)s1.O=C=O>C1CCOC1.CCOCC>Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)s1 |
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