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-cb6871243aa046c0acd17a0fc444cdcb | C=C(C)CCl.CCCCCCCCCCCCCCO.O=C(OO)c1cccc(Cl)c1>>CCCCCCCCCCCCCCOCC1(C)CO1 | C(CCCCCCCCCCCCC)O.[H-].[Na+].C(C(C)=C)Cl.ClC1=CC(=CC=C1)C(=O)OO>>O1CC1(COCCCCCCCCCCCCCC)C | Cl[CH2:16][C:17]([CH3:18])=[CH2:19].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].O=C(O[OH:20])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1([CH3:18])[CH2:19][O:2... | C=C(C)CCl.CCCCCCCCCCCCCCO.O=C(OO)c1cccc(Cl)c1 | CCCCCCCCCCCCCCOCC1(C)CO1 | null | null | CN(C=O)C.ClCCl.O | Heteroatom Alkylation and Arylation | OtherReaction | f67fee1378ff9e29a7ec8914e82defd9e3495ac250ed6031b1fd098a2ace357d | f33536a6cbdd7c0e99b2e1466416f23e4a04749846e1248994131907e4409a93 | C1CO1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH2;D1;+0:4].Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:5]):c:1.[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1 | 79.5 | [{"value": 79.4, "product": "O1CC1(COCCCCCCCCCCCCCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "O1CC1(COCCCCCCCCCCCCCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 15 | HOUR | A 200-ml flask equipped with a stirrer was charged with 10 g (46.6 mmol) of tetradecanol, 50 ml of dimethylformamide, 2.86 g (71.5 mmol) of 60% NaH and 5.96 g (65.8 mmol) of methallyl chloride. The contents were stirred at 60° C. for 15 hours. After completion of the reaction, the reaction mixture was added with water ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary alcohol.Peroxide.Vinyl | Ether.Ether | c1ccccc1 | C1CO1 | C1CO1 | HCl | CN(C=O)C.ClCCl.O | 60 | 15 | C=C(C)CCl.CCCCCCCCCCCCCCO.O=C(OO)c1cccc(Cl)c1>CN(C=O)C.ClCCl.O>CCCCCCCCCCCCCCOCC1(C)CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40839e5adad8417b8a69e675e27185ad | CCCCCCCCCCCCCCOCC1(C)CO1.NCCO>>CCCCCCCCCCCCCCOCC(C)(O)CNCCO | C(O)CN.O1CC1(COCCCCCCCCCCCCCC)C>>OCCNCC(COCCCCCCCCCCCCCC)(O)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1([CH3:18])[O:19][CH2:20]1.[NH2:21][CH2:22][CH2:23][OH:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]([CH3:18])([OH... | CCCCCCCCCCCCCCOCC1(C)CO1.NCCO | CCCCCCCCCCCCCCOCC(C)(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 09dcc949ba57c1c8aa9b0ec8a5f2d0bd08582df941541cfb30cc229d76954460 | 981ed0456dddd8dd6daddb49af97a2d7d93f8ca3d6b01c65314714af406e7930 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1(-[C;D1;H3:6])-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:4]-[C:5](-[C;D1;H3:6])(-[OH;D1;+0:8])-[CH2;D2;+0:7]-[NH;D2;+0:3]-[C:2]-[C:1] | 68 | [{"value": 68.0, "product": "OCCNCC(COCCCCCCCCCCCCCC)(O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "OCCNCC(COCCCCCCCCCCCCCC)(O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 100-ml flask equipped with a stirrer and dropping funnel was then charged with 16.8 g (280 mmol) of ethanolamine and 15 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 5.00 g (17.6 mmol) of 1,2-epoxy-2-methyl-3-tetradecyloxypropane was added dropwise over 3 hours. The contents were stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Tertiary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCCCCCCCCCCCOCC1(C)CO1.NCCO>C(C)O>CCCCCCCCCCCCCCOCC(C)(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9a01b6c4e7348f3b4a477b1d53347a8 | CCCCCCCCCCCCCCOCC1CO1.NCCCO>>CCCCCCCCCCCCCCOCC(O)CNCCCO | C(C1CO1)OCCCCCCCCCCCCCC.NCCCO>>OCCCNCC(COCCCCCCCCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]1[O:18][CH2:19]1.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]([OH:18])[CH2:... | CCCCCCCCCCCCCCOCC1CO1.NCCCO | CCCCCCCCCCCCCCOCC(O)CNCCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 135 | [{"value": 92.0, "product": "OCCCNCC(COCCCCCCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 135.0, "product": "OCCCNCC(COCCCCCCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 300-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 25.1 g (0.33 mol) of 3-amino-1-propanol and 6.00 g of ethanol, and the contents were heated and stirred at 80° C. in a nitrogen atmosphere. After 9.00 g (33 mmol) of tetradecyl glycidyl ether were added dropwise over 2 hours, the r... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCCCCCCCCCCCOCC1CO1.NCCCO>C(C)O>CCCCCCCCCCCCCCOCC(O)CNCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d521726c64849569940c6f7bb84cf4f | CCCCCCCCCCCCCCOCC1CO1.CCO.NCC(=O)O>>CCCCCCCCCCCCOCC(C)(O)CCNCCO | C(C1CO1)OCCCCCCCCCCCCCC.C(C)O.NCC(=O)O.[OH-].[Na+].C(C)O.Cl>>OCCNCCC(COCCCCCCCCCCCC)(O)C | C(C[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]1[O:17][CH2:18]1)[CH2:2][CH3:1].O[CH2:19][CH3:16].O=[C:22]([CH2:21][NH2:20])[OH:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][C:15]([CH3:16])([OH:17])[CH2:18][CH2... | CCCCCCCCCCCCCCOCC1CO1.CCO.NCC(=O)O | CCCCCCCCCCCCOCC(C)(O)CCNCCO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 6421f63ee64704188eacd859707a492b167f8b99570829447d4f950d0da28cc4 | eb72a91262031d72ce374b3d0d4d73595d6a629341524b46dda84055f634c18f | null | O-[CH2;D2;+0:1]-[CH3;D1;+0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[C:5]-[NH2;D1;+0:6].[#8:7]-[C:8]-[CH;D3;+0:9]1-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-1.[C:12]-[C:13]-[CH2;D2;+0:14]-C-C-[CH2;D2;+0:15]-[C;D1;H3:16]>>[#8:7]-[C:8]-[C;H0;D4;+0:9](-[CH3;D1;+0:2])(-[OH;D1;+0:11])-[CH2;D2;+0:10]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[CH2;D2;+... | 30.7 | [{"value": 30.7, "product": "OCCNCCC(COCCCCCCCCCCCC)(O)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 300-ml two-necked flask equipped with a stirrer was charged with 7.51 g (0.1 mol) of glycine, 8.3 g (0.1 mol) of 48% NaOH and 200 ml of ethanol. While stirring the mixture at 80° C., an ethanol solution of 2.70 g (10 mmol) of tetradecyl glycidyl ether was added, and the resultant mixture was stirred for 3 hours. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary alcohol.Primary amine | Primary alcohol.Tertiary alcohol.Secondary amine | C1CO1 | null | null | HO- | null | 80 | null | CCCCCCCCCCCCCCOCC1CO1.CCO.NCC(=O)O>>CCCCCCCCCCCCOCC(C)(O)CCNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c432984f9d54ac78349420a214a1024 | CCCCCCCCCCCCCCOCC(O)CNCCO.O=P(O)(O)O>>CCCCCCCCCCCCCCOCC(O)CNCCOP(=O)([O-])O | C(C1CO1)OCCCCCCCCCCCCCC.C(O)CN.O1CCCC1.P(O)(O)(O)=O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.OCCNCC(COCCCCCCCCCCCCCC)O.[OH-].[Na+].[Na]>>P(=O)(OCCNCC(COCCCCCCCCCCCCCC)O)([O-])O.[Na+] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]([OH:18])[CH2:19][NH:20][CH2:21][CH2:22][OH:23].O[P:24](=[O:25])([OH:26])[OH:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:... | CCCCCCCCCCCCCCOCC(O)CNCCO.O=P(O)(O)O | CCCCCCCCCCCCCCOCC(O)CNCCOP(=O)([O-])O | null | null | O | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | null | O-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;D1;H1:3])-[OH;D1;+0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[P;H0;D4;+0:1](-[O-;H0;D1:4])(=[O;D1;H0:2])-[O;D1;H1:3] | 36.2 | [{"value": 34.9, "product": "P(=O)(OCCNCC(COCCCCCCCCCCCCCC)O)([O-])O.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.2, "product": "P(=O)(OCCNCC(COCCCCCCCCCCCCCC)O)([O-])O.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A 300-ml flask equipped with a stirrer was charged with 5.13 g (14.8 mmol) of 3-(2-hydroxyethylamino)-1-tetradecyloxy-2-propanol prepared from tetradecyl glycidyl ether and ethanolamine in the same manner as in Preparation Example 14, and 70 mol of tetrahydrofuran, 1.95 g (16.9 mmol) of 85% phosphoric acid and 3.54 g (... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | null | HO- | O | null | 0.5 | CCCCCCCCCCCCCCOCC(O)CNCCO.O=P(O)(O)O>O>CCCCCCCCCCCCCCOCC(O)CNCCOP(=O)([O-])O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-540e2d8dfa8f4e3c817851023a8dc240 | CBr.CCCCCCC(O)CCCCCCCCCCCCC(O)CN(C)CCO.CCCCCCC(O)CCCCCCCCCCCOCC1CO1>>CCCCCCC(O)CCCCCCCCCCCCC(O)C[N+](C)(C)CC(C)O.[Br-] | CN(CCO)CC(CCCCCCCCCCCCC(CCCCCC)O)O.C(C1CO1)OCCCCCCCCCCCC(CCCCCC)O.CNCCO.COCC(CN(C)CCO)O.CBr>>[Br-].OC(C[N+](CC(CCCCCCCCCCCCC(CCCCCC)O)O)(C)C)C | [CH3:26][Br:31].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:22])[CH2:23][N:24]([CH3:25])[CH2:27][CH2:28][OH:30].CCCCCCC(O)CCCCCCCCCCCOCC1O[CH2:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH... | CBr.CCCCCCC(O)CCCCCCCCCCCCC(O)CN(C)CCO.CCCCCCC(O)CCCCCCCCCCCOCC1CO1 | CCCCCCC(O)CCCCCCCCCCCCC(O)C[N+](C)(C)CC(C)O.[Br-] | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 655d5e15669199b985c336dee1e41bbd5c253d27b8f38540e39e955cb16b7ff2 | 749391d1c8d87bf3231b7e96c58a053d5f8d292ffc23c83916e5cf24297c51a5 | null | C-C-C-C-C-C-C(-O)-C-C-C-C-C-C-C-C-C-C-C-O-C-C1-O-[CH2;D2;+0:1]-1.[Br;H0;D1;+0:2]-[CH3;D1;+0:3].[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C:8]-[CH2;D2;+0:9]-[O;D1;H1:10]>>[Br-;H0;D0:2].[C:4]-[C:5]-[N+;H0;D4:6](-[C;D1;H3:7])(-[CH3;D1;+0:3])-[C:8]-[CH;D3;+0:9](-[CH3;D1;+0:1])-[O;D1;H1:10] | 90 | [{"value": 90.0, "product": "[Br-].OC(C[N+](CC(CCCCCCCCCCCCC(CCCCCC)O)O)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[N-Methyl-N-(2-hydroxyethyl)amino]-3-(12-hydroxyoctadecyl)-2-propanol was first prepared from 12-hydroxyoctadecyl glycidyl ether and N-methylethanolamine in the same manner as in the preparation of N-(3-methoxy-2-hydroxy-propyl)-N-methyl-2-hydroxyethylamine in Preparation Example 24. A 200-ml autoclave was charged wi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol.Tertiary amine | Secondary alcohol | C1CO1 | null | null | HO- | C(C)OCC | null | null | CBr.CCCCCCC(O)CCCCCCCCCCCCC(O)CN(C)CCO.CCCCCCC(O)CCCCCCCCCCCOCC1CO1>C(C)OCC>CCCCCCC(O)CCCCCCCCCCCCC(O)C[N+](C)(C)CC(C)O.[Br-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80c2effe4d3141839b36b2e47237d5ac | CCCCCCCCCCCCCCCCC1CO1.NCCO>>CCCCCCCCCCCCCCCCC(O)CNCCO | C(O)CN.C(C)O.O1CC1CCCCCCCCCCCCCCCC>>OCCNCC(CCCCCCCCCCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:18][CH2:19]1.[NH2:20][CH2:21][CH2:22][OH:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[CH2:19][... | CCCCCCCCCCCCCCCCC1CO1.NCCO | CCCCCCCCCCCCCCCCC(O)CNCCO | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 74.6 | [{"value": 74.6, "product": "OCCNCC(CCCCCCCCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "OCCNCC(CCCCCCCCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 300-ml flask equipped with a stirrer and a dropping funnel was charged with 45.8 g (0.75 mol) of ethanolamine and 9 g of ethanol. While stirring the mixture at 80° C., 13.4 g (50 mmol) of 1,2-epoxyoctadecane were added dropwise over 2 hours. Water was added to the resultant reaction mixture, and white crystals formed... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | O | 80 | null | CCCCCCCCCCCCCCCCC1CO1.NCCO>O>CCCCCCCCCCCCCCCCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b816d25167cf4c2ca0b10e123324d743 | CCCCCCCCCCCCCCCCC1CO1.CNCCO>>CCCCCCCCCCCCCCCCC(O)CN(C)CCO | O1CC1CCCCCCCCCCCCCCCC.CNCCO>>OCCN(C)CC(CCCCCCCCCCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:18][CH2:19]1.[NH:20]([CH3:21])[CH2:22][CH2:23][OH:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])... | CCCCCCCCCCCCCCCCC1CO1.CNCCO | CCCCCCCCCCCCCCCCC(O)CN(C)CCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[C:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:5]-[C:6](-[OH;D1;+0:8])-[CH2;D2;+0:7]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[C:2]-[C:1] | 67 | [{"value": 67.0, "product": "OCCN(C)CC(CCCCCCCCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.9, "product": "OCCN(C)CC(CCCCCCCCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | A 300-ml flask equipped with a stirrer was charged with 26.85 g (0.1 mol) of 1,2-epoxyoctadecane, 7.51 g (0.1 mol) of N-methylethanolamine and 50 ml of ethanol, and the contents were stirred at 80° C. for 18 hours. After the solvent was distilled off under reduced pressure, the resultant residue was purified by column ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | null | null | C(C)O | 80 | 18 | CCCCCCCCCCCCCCCCC1CO1.CNCCO>C(C)O>CCCCCCCCCCCCCCCCC(O)CN(C)CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e403979772a141b9b46f8ea7de5203df | CCCCCCCCCCCCCCOCC1OC1(C)C.NCCO>>CCCCCCCCCCCCCCOCC(NCCO)C(C)(C)O | C(O)CN.C(CCCCCCCCCCCCC)OCC1C(C)(C)O1>>OCCNC(C(C)(O)C)COCCCCCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]1[C:22]([CH3:23])([CH3:24])[O:25]1.[NH2:18][CH2:19][CH2:20][OH:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]([NH... | CCCCCCCCCCCCCCOCC1OC1(C)C.NCCO | CCCCCCCCCCCCCCOCC(NCCO)C(C)(C)O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 09dcc949ba57c1c8aa9b0ec8a5f2d0bd08582df941541cfb30cc229d76954460 | 981ed0456dddd8dd6daddb49af97a2d7d93f8ca3d6b01c65314714af406e7930 | null | [#8:1]-[C:2]-[CH;D3;+0:3]1-[O;H0;D2;+0:4]-[C:5]-1(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[NH;D2;+0:10]-[C:9]-[C:8])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[OH;D1;+0:4] | 58 | [{"value": 58.0, "product": "OCCNC(C(C)(O)C)COCCCCCCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.8, "product": "OCCNC(C(C)(O)C)COCCCCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 100-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 15.3 g (16.7 mmol) of ethanolamine and 5.0 g of ethanol. While heating and stirring the mixture at 80° C. in a nitrogen atmosphere, an ethanol solution of 5.00 g (16.7 mmol) of 1-tetradecyloxy-3-methyl-2-butene oxide was added drop... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Tertiary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCCCCCCCCCCCOCC1OC1(C)C.NCCO>C(C)O>CCCCCCCCCCCCCCOCC(NCCO)C(C)(C)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70a4eebe93b24ba3bd4111e18405dbfa | CCCCCCCCC=CCCCCCCCC(=O)NCCO>>CCCCCCCCC=CCCCCCCCCNCCO | [OH-].[K+].C(CCCCCCCC=CCCCCCCCC)(=O)NCCO.[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N>>C(CCCCCCCC=CCCCCCCCC)NCCO | O=[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[NH:19][CH2:20][CH2:21][OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH... | CCCCCCCCC=CCCCCCCCC(=O)NCCO | CCCCCCCCC=CCCCCCCCCNCCO | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | null | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[C:3] | 65 | [{"value": 65.0, "product": "C(CCCCCCCC=CCCCCCCCC)NCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "C(CCCCCCCC=CCCCCCCCC)NCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | A 100-ml eggplant type flask equipped with a stirrer was charged with 1.40 g (37.2 mmol) of LiAlH4 and 30 ml of tetrahydrofuran. While heating and stirring the contents at room temperature in an N2 atmosphere, a tetrahydrofuran solution of 1.67 g (5.12 mmol) of N-(9-octadecenoyl)ethanolamine was added dropwise over 10 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | null | Other | O1CCCC1 | 60 | 16 | CCCCCCCCC=CCCCCCCCC(=O)NCCO>O1CCCC1>CCCCCCCCC=CCCCCCCCCNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9575b1a855c84db398427cd5e89360d1 | CS(C)=O.O=CCCCCCCCCCCCCCCOC1CCCCO1>>C=CCCCCCCCCCCCCCCOC1CCCCO1 | O1C(CCCC1)OCCCCCCCCCCCCCCC=O.CS(=O)C.N#N.[H-].[Na+].CS(=O)C.O>>O1C(CCCC1)OCCCCCCCCCCCCCCC=C | CS(=O)[CH3:1].O=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][O:23]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:... | CS(C)=O.O=CCCCCCCCCCCCCCCOC1CCCCO1 | C=CCCCCCCCCCCCCCCOC1CCCCO1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | C-C Coupling | OtherReaction | 5cfb75c6bab693235daf0ac5fd1246c85d26339c8533fb46cd8a376b6da4a918 | 5aa2b06974507c8a8025fd53b24b8c1d2de573e1740ff1857bc2886b8646feca | C1CCOCC1 | C-S(=O)-[CH3;D1;+0:1].O=[CH;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH;D2;+0:2]=[CH2;D1;+0:1] | 46 | [{"value": 46.0, "product": "O1C(CCCC1)OCCCCCCCCCCCCCCC=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A 300-ml three-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 40 ml of dimethyl sulfoxide and 1.2 g (30 mmol) of 60% sodium hydride. The contents were stirred at 75° C. for 1.5 hours in an N2 atmosphere and then cooled to room temperature. To this mixture, a solution of 8.93 g ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Sulfoxide | Allyl | null | null | C1CCOCC1 | Other | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | null | 0.5 | CS(C)=O.O=CCCCCCCCCCCCCCCOC1CCCCO1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>C=CCCCCCCCCCCCCCCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c54f235e113e4ef68f3a56e016403a66 | NCCO.OCCCCCCCCCCCCCCC1CO1>>OCCCCCCCCCCCCCCC(O)CNCCO | O1CC1CCCCCCCCCCCCCCO.C(O)CN.N#N.C(O)CN>>OCCNCC(CCCCCCCCCCCCCCO)O | [NH2:19][CH2:20][CH2:21][OH:22].[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]1[O:17][CH2:18]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:17])[CH2:18][NH:19][CH2:20][CH2... | NCCO.OCCCCCCCCCCCCCCC1CO1 | OCCCCCCCCCCCCCCC(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 68 | [{"value": 68.0, "product": "OCCNCC(CCCCCCCCCCCCCCO)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "OCCNCC(CCCCCCCCCCCCCCO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 50-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.14 g (68 mmol) of ethanolamine and 0.8 g of ethanol. While heating and stirring the mixture at 80° C. in an N2 atmosphere, an ethanol solution of 0.87 g (3.4 mmol) of 1,2-epoxy-16-hexadecanol was added dropwise over 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | null | null | NCCO.OCCCCCCCCCCCCCCC1CO1>C(C)O>OCCCCCCCCCCCCCCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-314181a292b147ec995c4191958340db | O=C1CCCCCCCCCCCCCCCO1.OCCNCCO>>O=C(CCCCCCCCCCCCCCCO)N(CCO)CCO | N(CCO)CCO.C1CCCCCCCC(=O)OCCCCCCC1>>OCCN(C(CCCCCCCCCCCCCCCO)=O)CCO | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]1.[NH:19]([CH2:20][CH2:21][OH:22])[CH2:23][CH2:24][OH:25]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:1... | O=C1CCCCCCCCCCCCCCCO1.OCCNCCO | O=C(CCCCCCCCCCCCCCCO)N(CCO)CCO | null | C[O-].[Na+] | O | Acylation | OtherReaction | d0669d32ff95853a71a1e4f52e404d304c90e5a3ad7f5c6454f90efa0c0695d9 | ff1ec1760b35133bcda3889e4f778444bc5783bb8e80db6e68552e7362fe2c9f | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[C:12]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C:4]-[C:5])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[C:12].[C:6]-[C:7]-[OH;D1;+0:8] | 82 | [{"value": 82.0, "product": "OCCN(C(CCCCCCCCCCCCCCCO)=O)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "OCCN(C(CCCCCCCCCCCCCCCO)=O)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | A 200-ml flask equipped with a stirrer was charged with 16.6 g (158 mmol) of diethanolamine and 20.1 g (79 mmol) of cyclohexadecanolide, to which 0.21 g (3.9 mmol) of sodium methoxide was added. The contents were stirred at 80° C. for 18 hours. After completion of the reaction, water was added, and solids deposited wer... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide.Primary alcohol | C1CCCCCCCCOCCCCCCC1 | null | null | null | C[O-].[Na+].O | 80 | 18 | O=C1CCCCCCCCCCCCCCCO1.OCCNCCO>C[O-].[Na+].O>O=C(CCCCCCCCCCCCCCCO)N(CCO)CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f7c05078e24046a8887d238bff8b0c4f | O=C(CCCCCCCCCCCCCCCO)N(CCO)CCO>>OCCCCCCCCCCCCCCCCN(CCO)CCO | [OH-].[K+].N#N.OCCN(C(CCCCCCCCCCCCCCCO)=O)CCO.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>OCCN(CCO)CCCCCCCCCCCCCCCCO | O=[C: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][OH:1])[N:18]([CH2:19][CH2:20][OH:21])[CH2:22][CH2:23][OH:24]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH... | O=C(CCCCCCCCCCCCCCCO)N(CCO)CCO | OCCCCCCCCCCCCCCCCN(CCO)CCO | null | null | O1CCCC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | null | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[#7:4](-[C:5])-[C:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[#7:4](-[C:5])-[C:6] | 62 | [{"value": 62.0, "product": "OCCN(CCO)CCCCCCCCCCCCCCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "OCCN(CCO)CCCCCCCCCCCCCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 18 | HOUR | A 500-ml flask equipped with a stirrer and reflux condenser was charged with 3.01 g (79.3 mmol) of LiAlH4 and 200 ml of tetrahydrofuran. While stirring the mixture at room temperature in an N2 atmosphere, 5.00 g (13.9 mmol) of N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide were added, followed by stirring at 65° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | null | Other | O1CCCC1 | 65 | 18 | O=C(CCCCCCCCCCCCCCCO)N(CCO)CCO>O1CCCC1>OCCCCCCCCCCCCCCCCN(CCO)CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1fba45c98c28483dbc24abfca08ff922 | COC(=O)CCCCCCCCCCCCCCCOC1CCCCO1.OCCNCCO>>OCCNCCCCCCCCCCCCCCCCOC1CCCCO1 | C1CCCCCCCC(=O)OCCCCCCC1.C(O)CN.O1C(CCCC1)OCCCCCCCCCCCCCCCC(=O)OC.N(CCO)CCO>>OCCNCCCCCCCCCCCCCCCCOC1OCCCC1 | COC(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1.OC[CH2:5][NH:4][CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:... | COC(=O)CCCCCCCCCCCCCCCOC1CCCCO1.OCCNCCO | OCCNCCCCCCCCCCCCCCCCOC1CCCCO1 | null | null | null | C-C Coupling | OtherReaction | c6e6f8431a2f95e212ca1ff22e794af539e5b288412b6c9354d640c48d89ad58 | 28126b46b6bfdfc96be770904d9dbbbb023c790c30cc393f36b178a45fe2e52f | C1CCOCC1 | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3].O-C-[CH2;D2;+0:4]-[#7:5]-[C:6]>>[C:6]-[#7:5]-[CH2;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | A reaction was conducted in the same manner as in Preparation Example 37 except that ethanolamine and methyl 16-(2-tetrahydropyranyloxy)hexadecanate were used in place of diethanolamine and cyclohexadecanolide, respectively, in Preparation Example 37, thereby obtaining the title compound (IId-4).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | null | null | null | C1CCOCC1 | HO- | null | null | null | COC(=O)CCCCCCCCCCCCCCCOC1CCCCO1.OCCNCCO>>OCCNCCCCCCCCCCCCCCCCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-050e689426f84409ae62ef62ee510e60 | CCCCCCCCCCCCCCSCC1CO1.NCCO>>CCCCCCCCCCCCCCSCC(O)CNCCO | C(O)CN.C(CCCCCCCCCCCCC)SCC1CO1>>OCCNCC(CSCCCCCCCCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][CH2:16][CH:17]1[O:18][CH2:19]1.[NH2:20][CH2:21][CH2:22][OH:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][CH2:16][CH:17]([OH:18])[CH2:19][NH:2... | CCCCCCCCCCCCCCSCC1CO1.NCCO | CCCCCCCCCCCCCCSCC(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 91 | [{"value": 91.0, "product": "OCCNCC(CSCCCCCCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "OCCNCC(CSCCCCCCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 300-ml flask equipped with a stirrer and dropping funnel was charged with 61.1 g (1 mol) of ethanolamine and 61 g of ethanol. While stirring the contents at 80° C., a solution of 14.3 g (50 mmol) of 1-tetradecylthio-2,3-epoxypropane in 30 g ethanol was added dropwise over 3 hours. After completion of the dropping, th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCCCCCCCCCCCSCC1CO1.NCCO>C(C)O>CCCCCCCCCCCCCCSCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a88b93c6dde7436aafafe69ae2775345 | CCCCCCCCCCCCCC(=O)OCC1CO1.CNCCO>>CCCCCCCCCCCCCC(=O)OCC(O)CN(C)CCO | CNCCO.C(CCCCCCCCCCCCC)(=O)OCC1CO1>>C(CCCCCCCCCCCCC)(=O)OCC(CN(C)CCO)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[O:16][CH2:17][CH:18]1[O:19][CH2:20]1.[NH:21]([CH3:22])[CH2:23][CH2:24][OH:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[O:16][CH2:17][CH:18... | CCCCCCCCCCCCCC(=O)OCC1CO1.CNCCO | CCCCCCCCCCCCCC(=O)OCC(O)CN(C)CCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[C:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:5]-[C:6](-[OH;D1;+0:8])-[CH2;D2;+0:7]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[C:2]-[C:1] | 60.8 | [{"value": 60.8, "product": "C(CCCCCCCCCCCCC)(=O)OCC(CN(C)CCO)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "C(CCCCCCCCCCCCC)(=O)OCC(CN(C)CCO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A 100-ml flask equipped with a stirrer and dropping funnel was charged with 6.01 g (80 mmol) of N-methylethanolamine, 50 ml of ethanol and 22.8 g (80 mmol) of glycidyl tetradecanate, and the contents were stirred at 80° C. for 2 hours. The resultant reaction mixture was concentrated under reduced pressure, and the resi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | null | null | C(C)O | 80 | 2 | CCCCCCCCCCCCCC(=O)OCC1CO1.CNCCO>C(C)O>CCCCCCCCCCCCCC(=O)OCC(O)CN(C)CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4e7d6fabfea64e0cb15c31ea61de1db0 | CC(O)NCCN.CCCCCCC(O)CCCCCCCCCCC(=O)OCC>>CCCCCCC(O)CCCCCCCCCCC(=O)NCCNCCO | OC(CCCCCCCCCCC(=O)OCC)CCCCCC.NCCNC(C)O.C[O-].[Na+].N#N>>OCCNCCNC(CCCCCCCCCCC(CCCCCC)O)=O | [NH2:21][CH2:22][CH2:23][NH:24][CH:25]([CH3:26])[OH:27].CCO[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:8])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:1... | CC(O)NCCN.CCCCCCC(O)CCCCCCCCCCC(=O)OCC | CCCCCCC(O)CCCCCCCCCCC(=O)NCCNCCO | null | null | C1CCOC1.O | Acylation | OtherReaction | 077654e25b1463cc2f90add0637d4cfbbe7d9928abe034ea0ed574169e01e19c | e8f6313ae381d127459d5b4a3f52751700bf2be0d0c8db3d4e4c0ac77993682f | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[CH3;D1;+0:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[#7:8]-[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10]-[C:9]-[#7:8]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[OH;D1;+0:7] | 737.2 | [{"value": 74.0, "product": "OCCNCCNC(CCCCCCCCCCC(CCCCCC)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 737.2, "product": "OCCNCCNC(CCCCCCCCCCC(CCCCCC)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 30-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 2.08 g (20 mmol) of aminoethylaminoethanol and 0.054 g (1 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a solution of 3.29 g (10 mmol) of ethyl 12-hydroxystearate in 10 ml of THF was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Primary amine | Secondary amide.Primary alcohol | null | null | null | HO- | C1CCOC1.O | null | null | CC(O)NCCN.CCCCCCC(O)CCCCCCCCCCC(=O)OCC>C1CCOC1.O>CCCCCCC(O)CCCCCCCCCCC(=O)NCCNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-336388df5b80425486bbf74ea75cd7c9 | C=CC(O)CCCCCCCCCC.O=C(OO)c1cccc(Cl)c1>>CCCCCCCCCCC(O)C1CO1 | C=CC(CCCCCCCCCC)O.ClC1=CC(=CC=C1)C(=O)OO.C1=CC=CC=C1>>O1CC1C(CCCCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH:13]=[CH2:14].O=C(O[OH:15])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH:13]1[CH2:14][O:15]1 | C=CC(O)CCCCCCCCCC.O=C(OO)c1cccc(Cl)c1 | CCCCCCCCCCC(O)C1CO1 | null | null | CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | d136da1ba89cbec8282600d9bfdb623a2c13519ce4d37a4560f0218659f5ffb4 | f75e65b0e5496a37782761dec7855d157e425ce81d4a868786f212e1339acdbf | C1CO1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[C:3](-[O;D1;H1:4])-[CH;D2;+0:5]=[CH2;D1;+0:6]>>[C:2]-[C:3](-[O;D1;H1:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:1]-1 | 74 | [{"value": 74.0, "product": "O1CC1C(CCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.9, "product": "O1CC1C(CCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A 500-ml flask equipped with a stirrer was charged with 23.8 g (0.12 mol) of 1-tridecen-3-ol, 25.0 g (0.145 mol) of m-chloroperbenzoic acid and 250 ml of benzene, and the contents were stirred at room temperature for 48 hours. After completion of the reaction, 200 ml of hexane. Solids deposited were separated by filtra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Vinyl | Ether | c1ccccc1 | C1CO1 | C1CO1 | HCl | CCCCCC | null | 48 | C=CC(O)CCCCCCCCCC.O=C(OO)c1cccc(Cl)c1>CCCCCC>CCCCCCCCCCC(O)C1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5b031bc712c84f05b17662207d4f72dd | CCCCCCCCCCC(O)C1CO1.NCc1ccccc1>>CCCCCCCCCCC(O)C(O)CNCc1ccccc1 | C(C1=CC=CC=C1)N.O1CC1C(CCCCCCCCCC)O>>C(C1=CC=CC=C1)NCC(C(CCCCCCCCCC)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH:13]1[O:14][CH2:15]1.[NH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH:13]([OH:14])[CH2:15][NH:16][CH2:17][c:18]1[cH:19][cH:20][... | CCCCCCCCCCC(O)C1CO1.NCc1ccccc1 | CCCCCCCCCCC(O)C(O)CNCc1ccccc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccccc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[NH;D2;+0:5]-[C:6]-[c:7] | 72 | [{"value": 72.0, "product": "C(C1=CC=CC=C1)NCC(C(CCCCCCCCCC)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "C(C1=CC=CC=C1)NCC(C(CCCCCCCCCC)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A 500-ml flask equipped with a stirrer was charged with 107 g (1 mol) of benzylamine, to which a solution of 5.2 g (71 mmol) of 1,2-epoxy-3-tridecanol in 170 ml of dioxane was added dropwise over 2 hours. After completion of the dropping, a reaction was conducted further for 12 hours at 80° C. Dioxane and excess benzyl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1 | null | O1CCOCC1 | null | 12 | CCCCCCCCCCC(O)C1CO1.NCc1ccccc1>O1CCOCC1>CCCCCCCCCCC(O)C(O)CNCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f171f3959e24ce6acc5b2cc1ccb94f6 | CCCCCCCCCCCCCCCCC1CO1>>CCCCCCCCCCCCCCCCC(O)CN | C(C1=CC=CC=C1)N.O1CC1CCCCCCCCCCCCCCCC>>NCC(CCCCCCCCCCCCCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:18][CH2:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[CH2:19][NH2:20] | CCCCCCCCCCCCCCCCC1CO1 | CCCCCCCCCCCCCCCCC(O)CN | null | null | null | Functional Group Addition | OtherReaction | e8f483baa1df50dc51ca71356091d0aab082bd6a57d18118803efcf9c9bd74a4 | 604c2cde89ba21cccea5848b25fc4ba515e46430643c268de3fdecd95de94a50 | null | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[N;D1;H2:5] | 83.1 | [{"value": 83.0, "product": "NCC(CCCCCCCCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "NCC(CCCCCCCCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 12 | HOUR | A 500-ml flask equipped with a stirrer was charged with 160 g (1.5 mol) of benzylamine, to which 29 g (0.11 mol) of 1,2-epoxyoctadecane were added dropwise over 3 hours while stirring at 100° C. Stirring was conducted further for 12 hours at 100° C. Benzyl alcohol was distilled off under reduced pressure, and the resid... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol.Primary amine | C1CO1 | null | null | Other | null | 100 | 12 | CCCCCCCCCCCCCCCCC1CO1>>CCCCCCCCCCCCCCCCC(O)CN |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cb7b361a66f24faab6f6db5494adcd1b | C1=COCCC1.CCCCCCCCCCCCCCCCC(O)CO>>CCCCCCCCCCCCCCCCC(O)COC1CCCCO1 | C(=O)(O)[O-].[Na+].C(C(CCCCCCCCCCCCCCCC)O)O.C1(=CC=C(C=C1)S(=O)(=O)O)C.O1CCCC=C1>>O1C(CCCC1)OCC(CCCCCCCCCCCCCCCC)O | [CH:21]1=[CH:22][CH2:23][CH2:24][CH2:25][O:26]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[CH2:19][OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][... | C1=COCCC1.CCCCCCCCCCCCCCCCC(O)CO | CCCCCCCCCCCCCCCCC(O)COC1CCCCO1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 29 | [{"value": 29.0, "product": "O1C(CCCC1)OCC(CCCCCCCCCCCCCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "O1C(CCCC1)OCC(CCCCCCCCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1-liter flask equipped with a stirrer and dropping funnel was charged with 20 g (70 mmol) of octadecane-1,2-diol, 0.7 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane. While stirring the contents at room temperature, 5.9 g (70 mmol) of dihydropyran were added dropwise. After stirring the mixture a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | ClCCl | null | null | C1=COCCC1.CCCCCCCCCCCCCCCCC(O)CO>ClCCl>CCCCCCCCCCCCCCCCC(O)COC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c24607cade224f55921e8fa774f3f6f4 | COC(=O)CCCCCCCCCCCO.NCC(O)CN>>NCC(O)CNC(=O)CCCCCCCCCCCO | OCCCCCCCCCCCC(=O)OC.NCC(CN)O.N#N>>NCC(CNC(CCCCCCCCCCCO)=O)O | CO[C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].[NH2:1][CH2:2][CH:3]([OH:4])[CH2:5][NH2:6]>>[NH2:1][CH2:2][CH:3]([OH:4])[CH2:5][NH:6][C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20] | COC(=O)CCCCCCCCCCCO.NCC(O)CN | NCC(O)CNC(=O)CCCCCCCCCCCO | null | C[O-].[Na+] | C1CCOC1 | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 75.7 | [{"value": 75.0, "product": "NCC(CNC(CCCCCCCCCCCO)=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "NCC(CNC(CCCCCCCCCCCO)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 100-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 9.39 g (104 mmol) of 1,3-diamino-2-propanol and 0.047 g (0.87 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a THF solution of 4.00 g (17.4 mmol) of methyl 12-hydroxydodecanate was a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | null | HO- | C[O-].[Na+].C1CCOC1 | null | null | COC(=O)CCCCCCCCCCCO.NCC(O)CN>C[O-].[Na+].C1CCOC1>NCC(O)CNC(=O)CCCCCCCCCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5222a695140643c8a668e63555fad359 | CC1(C)CCC(C)(C)c2cc3cc(Br)ccc3cc21.CCOC(=O)c1csc(Br)c1>>CCOC(=O)c1csc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c1 | CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)Br)C.[Mg].BrC=1SC=C(C1)C(=O)OCC>>CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)C=1SC=C(C1)C(=O)OCC)C | Br[c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15]3[c:16]([cH:17][c:18]2[cH:19]1)[C:20]([CH3:21])([CH3:22])[CH2:23][CH2:24][C:25]3([CH3:26])[CH3:27].Br[c:9]1[s:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[cH:14][c:15]4[c:16]([cH:1... | CC1(C)CCC(C)(C)c2cc3cc(Br)ccc3cc21.CCOC(=O)c1csc(Br)c1 | CCOC(=O)c1csc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c1 | null | Cl[Ni]Cl.CCN(CC)CCOC=1C=CC(=CC1)CC=2C=CC=CC2.Cl.[Cl-].[Zn+2].[Cl-] | C1CCOC1 | C-C Coupling | Negishi | f674f2dc28578b12b308e7cbd9921fcbada13b86e3e7229d39e6fd04933df713 | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1csc(-c2ccc3cc4c(cc3c2)CCCC4)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9](-[C:10](-[#8:11])=[O;D1;H0:12]):[c:13]:1>>[#8:11]-[C:10](=[O;D1;H0:12])-[c:9]1:[c:13]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#16;a:7]:[c:8]:1 | null | [] | null | null | 1 | HOUR | A solution of 9.5 g (30 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-bromoanthracene was added dropwise to a suspension of 724 mg (30 mmol) of magnesium in 10 ml of THF. Once the addition was completed, the mixture was heated at reflux for one hour. At room temperature 4.1 g (30 mmol) of anhydrous zinc chloride we... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccc2cc3c(cc2c1)CCCC3.c1ccsc1 | c1ccsc1.c1ccc2cc3c(cc2c1)CCCC3 | c1ccsc1.c1ccc2cc3c(cc2c1)CCCC3 | Br- | Cl[Ni]Cl.CCN(CC)CCOC=1C=CC(=CC1)CC=2C=CC=CC2.Cl.[Cl-].[Zn+2].[Cl-].C1CCOC1 | null | 1 | CC1(C)CCC(C)(C)c2cc3cc(Br)ccc3cc21.CCOC(=O)c1csc(Br)c1>Cl[Ni]Cl.CCN(CC)CCOC=1C=CC(=CC1)CC=2C=CC=CC2.Cl.[Cl-].[Zn+2].[Cl-].C1CCOC1>CCOC(=O)c1csc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66e0b8dbf3514265bd84740660b01c23 | CCOC(=O)c1csc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c1>>CC1(C)CCC(C)(C)c2cc3cc(-c4cc(C(=O)O)cs4)ccc3cc21 | CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)C=1SC=C(C1)C(=O)OCC)C.[OH-].[Na+]>>CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)C=1SC=C(C1)C(=O)O)C | CC[O:19][C:17]([c:16]1[cH:15][c:14](-[c:13]2[cH:12][c:11]3[cH:10][c:9]4[c:26]([cH:25][c:24]3[cH:23][cH:22]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]4([CH3:7])[CH3:8])[s:21][cH:20]1)=[O:18]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][c:16]([C:17](=[O:18... | CCOC(=O)c1csc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c1 | CC1(C)CCC(C)(C)c2cc3cc(-c4cc(C(=O)O)cs4)ccc3cc21 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1csc(-c2ccc3cc4c(cc3c2)CCCC4)c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 6.3 g (16 mmol) of the ester prepared in Example 1 and 100 ml of a 2N methanolic sodium hydroxide solution were introduced into a round-bottomed flask and the mixture was heated at reflux for one hour. The reaction medium was evaporated to dryness, the residue taken up in water, acidified to pH 1 with concentrated hydr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2cc3c(cc2c1)CCCC3.c1ccsc1 | Other | null | null | null | CCOC(=O)c1csc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c1>>CC1(C)CCC(C)(C)c2cc3cc(-c4cc(C(=O)O)cs4)ccc3cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c0764d0c4c24228988989f273084ebb | O=C(Cl)C(Cl)(Cl)Cl.c1cc[nH]c1>>O=C(c1ccc[nH]1)C(Cl)(Cl)Cl | C([O-])([O-])=O.[K+].[K+].ClC(C(=O)Cl)(Cl)Cl.N1C=CC=C1>>ClC(C(=O)C=1NC=CC1)(Cl)Cl | Cl[C:2](=[O:1])[C:8]([Cl:9])([Cl:10])[Cl:11].[cH:3]1[cH:4][cH:5][cH:6][nH:7]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][nH:7]1)[C:8]([Cl:9])([Cl:10])[Cl:11] | O=C(Cl)C(Cl)(Cl)Cl.c1cc[nH]c1 | O=C(c1ccc[nH]1)C(Cl)(Cl)Cl | null | null | O.C(C)OCC | C-C Coupling | Friedel-Crafts acylation | 701d21b652ce6d90463464dd21d4d87caf603bff2f60e1ad8fa59cfd59145f4f | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1cc[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[#7;a:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])(-[Cl;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:11]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1 | null | [] | null | null | 1 | HOUR | 45 g (247 mmol) of trichloroacetyl chloride and 100 ml of ethyl ether were introduced into a three-necked flask. A solution of 15.4 g (230 mmol) of pyrrole in 100 ml of ethyl ether was added dropwise and the mixture was stirred at room temperature for one hour, then a solution of 20 g of potassium carbonate in 60 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HCl | O.C(C)OCC | null | 1 | O=C(Cl)C(Cl)(Cl)Cl.c1cc[nH]c1>O.C(C)OCC>O=C(c1ccc[nH]1)C(Cl)(Cl)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f9353d568ba495d9d6fa8a66d2c0875 | CO.O=C(c1cc(I)c[nH]1)C(Cl)(Cl)Cl>>COC(=O)c1cc(I)c[nH]1 | IC=1C=C(NC1)C(C(Cl)(Cl)Cl)=O.CO.C[O-].[Na+]>>IC=1C=C(NC1)C(=O)OC | [CH3:1][OH:2].ClC(Cl)(Cl)[C:3](=[O:4])[c:5]1[cH:6][c:7]([I:8])[cH:9][nH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([I:8])[cH:9][nH:10]1 | CO.O=C(c1cc(I)c[nH]1)C(Cl)(Cl)Cl | COC(=O)c1cc(I)c[nH]1 | null | null | O.C(C)OCC | Acylation | OtherReaction | bb2341d143935ccc8065bdd4084fedbad20e7f48b8013bb1e9d80700631fc60c | 23a2adf82de85a40ec60d39fbe3e80820c3a8dd06055de3d3c5fde7651211013 | c1cc[nH]c1 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 4 | HOUR | 8.2 g (24 mmol) of 4-iodo-2-trichloroacetylpyrrole and 100 ml of methanol were introduced into a round-bottomed flask and 2 g (36 mmol) of sodium methoxide were added. The mixture was stirred at room temperature for four hours, the reaction medium evaporated to dryness, and the residue obtained taken up in water and et... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ketone.Methanol | Ester | null | null | c1cc[nH]c1 | HCl | O.C(C)OCC | null | 4 | CO.O=C(c1cc(I)c[nH]1)C(Cl)(Cl)Cl>O.C(C)OCC>COC(=O)c1cc(I)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8254c501c8dc491b8f88eae119f49eae | CI.COC(=O)c1cc(I)c[nH]1>>COC(=O)c1cc(I)cn1C | O.[H-].[Na+].IC=1C=C(NC1)C(=O)OC.IC>>CN1C(=CC(=C1)I)C(=O)OC | I[CH3:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([I:8])[cH:9][nH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([I:8])[cH:9][n:10]1[CH3:11] | CI.COC(=O)c1cc(I)c[nH]1 | COC(=O)c1cc(I)cn1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9ead09c93a8a9d57f887a48202e25076c1ec25be9e5b61e0648504d88c26cda6 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1cc[nH]c1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH3;D1;+0:1] | null | [] | null | null | null | null | 780 mg (25.9 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 6.5 g (25.9 mmol) of methyl 4-iodo-2-pyrrolecarboxylate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 2.1 ml (33.6 mmol) of iodomethane were then ad... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HI | CN(C)C=O | null | null | CI.COC(=O)c1cc(I)c[nH]1>CN(C)C=O>COC(=O)c1cc(I)cn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-205c29c6463642c4a3ef2726db5ff6fc | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.COC(=O)c1cc(I)cn1C>>COC(=O)c1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cn1C | CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)B(O)O)C.C([O-])([O-])=O.[K+].[K+].CN1C(=CC(=C1)I)C(=O)OC>>CN1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC | OB(O)[c:8]1[cH:9][cH:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][c:16]2[cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]3([CH3:24])[CH3:25].I[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:27]([CH3:28])[cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[cH:12][c:13]4[c:14]([cH:15][c:16]3[... | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.COC(=O)c1cc(I)cn1C | COC(=O)c1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cn1C | null | null | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 1ae6c8ac07df41724f89d3a167e7b6589b8a63a41abe6b2b281e91283bac64b7 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(-c2ccc3cc4c(cc3c2)CCCC4)c[nH]1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C;D1;H3:4]):[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[c:9]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:[#7;a:3]:1-[C;D1;H3:4] | 47 | [{"value": 47.0, "product": "CN1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.9, "product": "CN1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 231 mg (0.2 mml) of tetrakis-(triphenylphosphine)palladium (0), 50 ml of toluene and 1.75 g (6.6 mmol) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate were introduced into a three-necked flask and under a nitrogen stream and the mixture was stirred at room temperature for 20 minutes. 2.8 g (10 mmol) of 5,6,7,8-tetrahydr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc3c(cc2c1)CCCC3.c1cc[nH]c1 | c1cc[nH]c1.c1ccc2cc3c(cc2c1)CCCC3 | c1cc[nH]c1.c1ccc2cc3c(cc2c1)CCCC3 | HI.B | C1(=CC=CC=C1)C | null | 0.333333 | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.COC(=O)c1cc(I)cn1C>C1(=CC=CC=C1)C>COC(=O)c1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cn1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9af6adb5c534d1a86a82222f63dd4ec | CI.COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1O>>COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1OC | O.[H-].[Na+].OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C.IC>>COC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C | I[CH3:30].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[cH:13][c:14]4[c:15]([cH:16][c:17]3[cH:18]2)[C:19]([CH3:20])([CH3:21])[CH2:22][CH2:23][C:24]4([CH3:25])[CH3:26])[cH:27][c:28]1[OH:29]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[cH:13][c:14]4[c:15](... | CI.COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1O | COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(-c2ccc3cc4c(cc3c2)CCCC4)cc1 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH3;D1;+0:1]):[c:8] | null | [] | null | null | null | null | 130 mg (4.2 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 1.6 g (4.2 mmol) of methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 340 μ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2cc3c(cc2c1)CCCC3 | HI | CN(C)C=O | null | null | CI.COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1O>CN(C)C=O>COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b7fc3759f58e4209a7cf0781050443b3 | BrCc1ccccc1.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2>>Brc1ccc2cc(OCc3ccccc3)c(C34CC5CC(CC(C5)C3)C4)cc2c1 | C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O.C(C1=CC=CC=C1)Br>>C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=CC=C2 | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[Br:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([OH:8])[c:16]([C:17]34[CH2:18][CH:19]5[CH2:20][CH:21]([CH2:22][CH:23]([CH2:24]5)[CH2:25]3)[CH2:26]4)[cH:27][c:28]2[cH:29]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:... | BrCc1ccccc1.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2 | Brc1ccc2cc(OCc3ccccc3)c(C34CC5CC(CC(C5)C3)C4)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cc3ccccc3cc2C23CC4CC(CC(C4)C2)C3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 80 | [{"value": 80.0, "product": "C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 11, by reacting 12.5 g (35 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene with 5 ml (42 mmol) of benzyl bromide, 12.5 g (80%) of the expected compound of melting point 150°-151° C. were obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HBr | null | null | null | BrCc1ccccc1.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2>>Brc1ccc2cc(OCc3ccccc3)c(C34CC5CC(CC(C5)C3)C4)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0bc171163cc04932b98554480b9c571f | COC(=O)c1ccc(I)cc1O.OB(O)c1ccc2cc(OCc3ccccc3)c(C34CC5CC(CC(C5)C3)C4)cc2c1>>COC(=O)c1ccc(-c2ccc3cc(OCc4ccccc4)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1O | C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)B(O)O)OCC2=CC=CC=C2.OC1=C(C(=O)OC)C=CC(=C1)I>>OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCC1=CC=CC=C1)C12CC3CC(CC(C1)C3)C2 | I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:38]([OH:39])[cH:37]1.OB(O)[c:9]1[cH:10][cH:11][c:12]2[cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]([C:24]34[CH2:25][CH:26]5[CH2:27][CH:28]([CH2:29][CH:30]([CH2:31]5)[CH2:32]3)[CH2:33]4)[cH:34][c:35]2[cH:36]1>>[CH3:1][O:2][C:3](=[O:4]... | COC(=O)c1ccc(I)cc1O.OB(O)c1ccc2cc(OCc3ccccc3)c(C34CC5CC(CC(C5)C3)C4)cc2c1 | COC(=O)c1ccc(-c2ccc3cc(OCc4ccccc4)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 44300e12668e13575bd83146e75f4d99efe4beab23be02dbe4dd7587e7e6a7cd | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(COc2cc3ccc(-c4ccccc4)cc3cc2C23CC4CC(CC(C4)C2)C3)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 36.2 | [{"value": 36.0, "product": "OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCC1=CC=CC=C1)C12CC3CC(CC(C1)C3)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.2, "product": "OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCC1=CC=CC=C1)C12CC3CC(CC(C1)C3)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Following the basic procedure of Example 7(f), by reacting 5.52 g (13.4 mmol) of 7-(1-adamantyl)-6-benzyloxy-2-naphthylboronic acid with 2.46 g (8.8 mmol) of methyl 2-hydroxy-4-iodobenzoate, 1.65 g (36%) of the expected compound was obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HI.B | null | null | null | COC(=O)c1ccc(I)cc1O.OB(O)c1ccc2cc(OCc3ccccc3)c(C34CC5CC(CC(C5)C3)C4)cc2c1>>COC(=O)c1ccc(-c2ccc3cc(OCc4ccccc4)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dbade7089fdb4aeda06e0dbd6d0e1ec8 | CCCCCCI.COC(=O)c1ccc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1O>>CCCCCCOc1cc2ccc(-c3ccc(C(=O)OC)c(O)c3)cc2cc1C12CC3CC(CC(C3)C1)C2 | OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)O)C12CC3CC(CC(C1)C3)C2.ICCCCCC>>OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCCCCCC)C12CC3CC(CC(C1)C3)C2 | I[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:7][c:8]1[cH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[O:20][CH3:21])[c:22]([OH:23])[cH:24]3)[cH:25][c:26]2[cH:27][c:28]1[C:29]12[CH2:30][CH:31]3[CH2:32][CH:33]([CH2:34][CH:35]([CH2:36]3)[CH2:37]1)[CH2:38]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2... | CCCCCCI.COC(=O)c1ccc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1O | CCCCCCOc1cc2ccc(-c3ccc(C(=O)OC)c(O)c3)cc2cc1C12CC3CC(CC(C3)C1)C2 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccc3ccc(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 55 | [{"value": 55.0, "product": "OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCCCCCC)C12CC3CC(CC(C1)C3)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.6, "product": "OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCCCCCC)C12CC3CC(CC(C1)C3)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 11, by reacting 430 mg (1 mmol) of methyl 2-hydroxy-4-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]benzoate with 180 μl (1.2 mmol) of 6-iodohexane, 280 mg (55%) of methyl 2-hydroxy-4-[7-(1-adamantyl)-6-hexyloxy-2-naphthyl]benzoate were obtained.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HI | null | null | null | CCCCCCI.COC(=O)c1ccc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1O>>CCCCCCOc1cc2ccc(-c3ccc(C(=O)OC)c(O)c3)cc2cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a85735f44d44b4dad4458afbbf407f8 | COC(=O)c1ccc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1.COCCOCCl>>COCCOCOc1cc2ccc(-c3ccc(C(=O)OC)cc3)cc2cc1C12CC3CC(CC(C3)C1)C2 | C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C2=CC=C(C(=O)OC)C=C2)O.COCCOCCl>>C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C2=CC=C(C(=O)OC)C=C2)OCOCCOC | [OH:7][c:8]1[cH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[O:20][CH3:21])[cH:22][cH:23]3)[cH:24][c:25]2[cH:26][c:27]1[C:28]12[CH2:29][CH:30]3[CH2:31][CH:32]([CH2:33][CH:34]([CH2:35]3)[CH2:36]1)[CH2:37]2.Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7]... | COC(=O)c1ccc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1.COCCOCCl | COCCOCOc1cc2ccc(-c3ccc(C(=O)OC)cc3)cc2cc1C12CC3CC(CC(C3)C1)C2 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccc(-c2ccc3ccc(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 55 | [{"value": 55.0, "product": "C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C2=CC=C(C(=O)OC)C=C2)OCOCCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.1, "product": "C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C2=CC=C(C(=O)OC)C=C2)OCOCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 12, by reacting 980 mg (2.4 mmol) of methyl 4-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]benzoate with 330 μl (28.6 mmol) of methoxyethoxymethyl chloride, 650 mg (55%) of the expected compound were obtained in the form of an oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccc2ccccc2c1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HCl | null | null | null | COC(=O)c1ccc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)cc1.COCCOCCl>>COCCOCOc1cc2ccc(-c3ccc(C(=O)OC)cc3)cc2cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-af764768aabb4d659aa7d8d3f6f94944 | Cc1cc(C(=O)O)ccc1N.[I-]>>Cc1cc(C(=O)O)ccc1I | [I-].[K+].S(O)(O)(=O)=O.N(=O)[O-].[Na+].CC=1C=C(C(=O)O)C=CC1N.S(O)(O)(=O)=O>>CC=1C=C(C(=O)O)C=CC1I | N[c:10]1[c:2]([CH3:1])[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9]1.[I-:11]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9][c:10]1[I:11] | Cc1cc(C(=O)O)ccc1N.[I-] | Cc1cc(C(=O)O)ccc1I | null | [Cu](I)I | O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | f4fea6a3c7b007f3829d29d893f3499a4094808c0f3b2211f4c3483919a690d8 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[I-;H0;D0:7]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[I;H0;D1;+0:7]):[c:2]:[c:3] | null | [] | null | null | 2 | HOUR | 20 g (0.132 mol) of 3-methyl-4-aminobenzoic acid and 175 ml of sulfuric acid (20%) were introduced into a three-necked flask. At -10° C., a solution of 11.9 g (0.172 mol) of sodium nitrite in 50 ml of water was added dropwise and the mixture was stirred for two hours. This solution was introduced dropwise via a droppin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Cu](I)I.O.C(C)(=O)OCC | null | 2 | Cc1cc(C(=O)O)ccc1N.[I-]>[Cu](I)I.O.C(C)(=O)OCC>Cc1cc(C(=O)O)ccc1I |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9664b54f4f6141978a503b896b8ef7fd | CO.Cc1cc(C(=O)O)ccc1I>>COC(=O)c1ccc(I)c(C)c1 | CC=1C=C(C(=O)O)C=CC1I.CO.S(O)(O)(=O)=O>>CC=1C=C(C(=O)OC)C=CC1I | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([I:9])[c:10]([CH3:11])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([I:9])[c:10]([CH3:11])[cH:12]1 | CO.Cc1cc(C(=O)O)ccc1I | COC(=O)c1ccc(I)c(C)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 24.4 g (0.093 mol) of 3-methyl-4-iodobenzoic acid and 250 ml of methanol were introduced into a round-bottomed flask and 2.5 ml of concentrated sulfuric acid were added dropwise. The mixture was heated at reflux for twelve hours, the reaction medium evaporated, taken up in ethyl acetate and water, the organic phase dec... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Cc1cc(C(=O)O)ccc1I>>COC(=O)c1ccc(I)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7949d567ab7542a8990b7bcf17a467de | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.COC(=O)c1ccc(I)c(C)c1>>COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c(C)c1 | CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)B(O)O)C.CC=1C=C(C(=O)OC)C=CC1I>>CC=1C=C(C(=O)OC)C=CC1C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C | OB(O)[c:9]1[cH:10][cH:11][c:12]2[cH:13][c:14]3[c:15]([cH:16][c:17]2[cH:18]1)[C:19]([CH3:20])([CH3:21])[CH2:22][CH2:23][C:24]3([CH3:25])[CH3:26].I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:29][c:27]1[CH3:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[cH:13][c:14]4[c:15]([cH... | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.COC(=O)c1ccc(I)c(C)c1 | COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c(C)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | bf3685ce01b232e2a6a72cf78778682668414933f5a01822d81318d82da577bf | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc4c(cc3c2)CCCC4)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | 53 | [{"value": 53.0, "product": "CC=1C=C(C(=O)OC)C=CC1C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "CC=1C=C(C(=O)OC)C=CC1C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 7(f), by reacting 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid with 1.84 g (6.7 mmol) of methyl 3-methyl-4-iodobenzoate, 1.37 g (53%) of methyl 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate was obtained in the form of a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc3c(cc2c1)CCCC3.c1ccccc1 | c1ccccc1.c1ccc2cc3c(cc2c1)CCCC3 | c1ccccc1.c1ccc2cc3c(cc2c1)CCCC3 | HI.B | null | null | null | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.COC(=O)c1ccc(I)c(C)c1>>COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5fa351dbe3ea452bbf01e7f31dec9368 | CCCI.COC(=O)c1cc(I)c[nH]1>>CCCn1cc(I)cc1C(=O)OC | IC=1C=C(NC1)C(=O)OC.ICCC>>C(CC)N1C(=CC(=C1)I)C(=O)OC | I[CH2:3][CH2:2][CH3:1].[nH:4]1[cH:5][c:6]([I:7])[cH:8][c:9]1[C:10](=[O:11])[O:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][c:6]([I:7])[cH:8][c:9]1[C:10](=[O:11])[O:12][CH3:13] | CCCI.COC(=O)c1cc(I)c[nH]1 | CCCn1cc(I)cc1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ed81cee7c9cb1b5c2931f1dacbfdcf63d83b311ec7685759e6b229eee13149ed | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1cc[nH]c1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | 64.7 | [{"value": 64.0, "product": "C(CC)N1C(=CC(=C1)I)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "C(CC)N1C(=CC(=C1)I)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 7(d), by reacting 1.96 g (7.8 mmol) of methyl 4-iodo-2-pyrrolecarboxylate with 940 μl (9.6 mmol) of 3-iodopropane, 1.48 g (64%) of methyl N-propyl-4-iodo-2-pyrrolecarboxylate was obtained in the form of a slightly yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HI | null | null | null | CCCI.COC(=O)c1cc(I)c[nH]1>>CCCn1cc(I)cc1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-00a204d0f65b435cab8a71dca632e9c7 | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.CCCn1cc(I)cc1C(=O)OC>>CCCn1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1C(=O)OC | CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)B(O)O)C.C(CC)N1C(=CC(=C1)I)C(=O)OC>>C(CC)N1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC | OB(O)[c:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]3[c:13]([cH:14][c:15]2[cH:16]1)[C:17]([CH3:18])([CH3:19])[CH2:20][CH2:21][C:22]3([CH3:23])[CH3:24].I[c:6]1[cH:5][n:4]([CH2:3][CH2:2][CH3:1])[c:26]([C:27](=[O:28])[O:29][CH3:30])[cH:25]1>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][c:12]4[c:13]([cH:... | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.CCCn1cc(I)cc1C(=O)OC | CCCn1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1C(=O)OC | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 1ae6c8ac07df41724f89d3a167e7b6589b8a63a41abe6b2b281e91283bac64b7 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(-c2ccc3cc4c(cc3c2)CCCC4)c[nH]1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[#7;a:7](-[C:8]):[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:9]:[#7;a:7]:1-[C:8] | 22.3 | [{"value": 22.0, "product": "C(CC)N1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.3, "product": "C(CC)N1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 7(f), by reacting 1.7 g (6 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid with 1.47 g (5 mmol) of methyl N-propyl-4-iodo-2-pyrrolecarboxylate, 450 mg (22%) of methyl N-propyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate were ob... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc3c(cc2c1)CCCC3.c1cc[nH]c1 | c1cc[nH]c1.c1ccc2cc3c(cc2c1)CCCC3 | c1cc[nH]c1.c1ccc2cc3c(cc2c1)CCCC3 | HI.B | null | null | null | CC1(C)CCC(C)(C)c2cc3cc(B(O)O)ccc3cc21.CCCn1cc(I)cc1C(=O)OC>>CCCn1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-02728028cd2a48e7adeea22530388872 | CCCI.COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1O>>CCCOc1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)ccc1C(=O)OC | OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C.ICCC>>C(CC)OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C | I[CH2:3][CH2:2][CH3:1].[OH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[cH:12][c:13]4[c:14]([cH:15][c:16]3[cH:17]2)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]4([CH3:24])[CH3:25])[cH:26][cH:27][c:28]1[C:29](=[O:30])[O:31][CH3:32]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[cH:12][c:1... | CCCI.COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1O | CCCOc1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)ccc1C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccc3cc4c(cc3c2)CCCC4)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:10] | 54 | [{"value": 54.0, "product": "C(CC)OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "C(CC)OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 12, by reacting 2 g (5.1 mmol) of methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate with 600 μl (6.1 mmol) of 3-iodopropane, 1.16 g (54%) of methyl 2-propyloxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate was obtained.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2cc3c(cc2c1)CCCC3 | HI | null | null | null | CCCI.COC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)cc1O>>CCCOc1cc(-c2ccc3cc4c(cc3c2)C(C)(C)CCC4(C)C)ccc1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f03bd0e627354ee4a55f5536f5f04cf4 | Fc1ccc(CBr)cc1.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2>>Fc1ccc(COc2cc3ccc(Br)cc3cc2C23CC4CC(CC(C4)C2)C3)cc1 | C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O.FC1=CC=C(CBr)C=C1>>C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=C(C=C2)F | Br[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:30][cH:29]1.[OH:7][c:8]1[cH:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[cH:17][c:18]1[C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][CH:25]([CH2:26]3)[CH2:27]1)[CH2:28]2>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][O:7][c:8]2[cH:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15]... | Fc1ccc(CBr)cc1.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2 | Fc1ccc(COc2cc3ccc(Br)cc3cc2C23CC4CC(CC(C4)C2)C3)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cc3ccccc3cc2C23CC4CC(CC(C4)C2)C3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 86 | [{"value": 86.0, "product": "C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the basic procedure of Example 11, by reacting 1.1 g (3 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene with 420 μl (3,3 mmol) of 4-fluorobenzyl bromide, 1.2 g (86%) of the expected compound was obtained in the form of a colorless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2ccccc2c1.C1C2CC3CC1CC(C2)C3 | HBr | null | null | null | Fc1ccc(CBr)cc1.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2>>Fc1ccc(COc2cc3ccc(Br)cc3cc2C23CC4CC(CC(C4)C2)C3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a18ffbdb8f6b474a86827045ded0ce46 | CC(C)(C)[Si](C)(C)Cl.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2>>CC(C)(C)[Si](C)(C)Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2 | [Si](C)(C)(C(C)(C)C)Cl.C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O.CN(C)C=O.C(C)N(CC)CC>>C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O[Si](C)(C)C(C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[cH:18][c:19]1[C:20]12[CH2:21][CH:22]3[CH2:23][CH:24]([CH2:25][CH:26]([CH2:27]3)[CH2:28]1)[CH2:29]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][c:11]2[cH:12][cH:13]... | CC(C)(C)[Si](C)(C)Cl.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2 | CC(C)(C)[Si](C)(C)Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2 | null | CN(C1=CC=NC=C1)C | O | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccc2cc(C34CC5CC(CC(C5)C3)C4)ccc2c1 | 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].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[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;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 12 | HOUR | 11.9 g (33.3 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene, 120 ml of DMF, 5.1 ml (36.6 mmol) of triethylamine and 203 mg of 4-dimethylaminopyridine were introduced successively into a three-necked flask. A solution of 5.52 g (36.6 mmol) of tert-butyldimethylsilyl chloride was added dropwise and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2ccccc2c1.C1C2CC3CC1CC(C2)C3 | HCl | CN(C1=CC=NC=C1)C.O | null | 12 | CC(C)(C)[Si](C)(C)Cl.Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2>CN(C1=CC=NC=C1)C.O>CC(C)(C)[Si](C)(C)Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3150c5b19251400f94abae6bc2510c0b | CC(C)(C)[Si](C)(C)Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2.OBO>>CC(C)(C)[Si](C)(C)Oc1cc2ccc(B(O)O)cc2cc1C12CC3CC(CC(C3)C1)C2 | C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O[Si](C)(C)C(C)(C)C.B(O)O>>C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)B(O)O)O[Si](C)(C)C(C)(C)C | Br[c:14]1[cH:13][cH:12][c:11]2[cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:21]([C:22]34[CH2:23][CH:24]5[CH2:25][CH:26]([CH2:27][CH:28]([CH2:29]5)[CH2:30]3)[CH2:31]4)[cH:20][c:19]2[cH:18]1.[BH:15]([OH:16])[OH:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][c:1... | CC(C)(C)[Si](C)(C)Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2.OBO | CC(C)(C)[Si](C)(C)Oc1cc2ccc(B(O)O)cc2cc1C12CC3CC(CC(C3)C1)C2 | null | null | null | Miscellaneous | OtherReaction | 5e14c0418b5489193c2f9cab37a1ee7bed4f0fe7e58c5c9713c9fa95392c1e02 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc2cc(C34CC5CC(CC(C5)C3)C4)ccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H1:6]-[BH;D2;+0:7]-[O;D1;H1:8]>>[O;D1;H1:6]-[B;H0;D3;+0:7](-[O;D1;H1:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | Following the basic procedure of Example 7(e), beginning with 11.9 g (25.4 mmol) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene, 8.37 g (75%) of the expected boronic acid of melting point 221°-222° C. were obtained.
Conditions: See reaction.notes.procedure_details.
Workup: were obtained | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1.C1C2CC3CC1CC(C2)C3 | HBr | null | null | null | CC(C)(C)[Si](C)(C)Oc1cc2ccc(Br)cc2cc1C12CC3CC(CC(C3)C1)C2.OBO>>CC(C)(C)[Si](C)(C)Oc1cc2ccc(B(O)O)cc2cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd8eb0b6bec94543a29935506ffa1165 | CCOC(=O)c1csc(-c2ccc3cc(O[Si](C)(C)C(C)(C)C)c(C45CC6CC(CC(C6)C4)C5)cc3c2)c1>>CCOC(=O)c1csc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)c1 | C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C=2SC=C(C2)C(=O)OCC)O[Si](C)(C)C(C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>>C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C=2SC=C(C2)C(=O)OCC)O | CC(C)(C)[Si](C)(C)[O:16][c:15]1[cH:14][c:13]2[cH:12][cH:11][c:10](-[c:9]3[s:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:31]3)[cH:30][c:29]2[cH:28][c:17]1[C:18]12[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23][CH:24]([CH2:25]3)[CH2:26]1)[CH2:27]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9](-[c:10]2[cH:11][cH... | CCOC(=O)c1csc(-c2ccc3cc(O[Si](C)(C)C(C)(C)C)c(C45CC6CC(CC(C6)C4)C5)cc3c2)c1 | CCOC(=O)c1csc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)c1 | null | null | C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | c1csc(-c2ccc3ccc(C45CC6CC(CC(C6)C4)C5)cc3c2)c1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | 8.29 g (15.2 mmol) of ethyl 2-[7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-naphthyl]-4-thiophenecarboxylate and 60 ml of THF were introduced into a round-bottomed flask. A solution of 15.2 ml (16.6 mmol) of tetrabutylammonium fluoride in THF (1.1N) was added dropwise and the mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccsc1.c1ccc2ccccc2c1.C1C2CC3CC1CC(C2)C3 | Other | C1CCOC1 | null | 2 | CCOC(=O)c1csc(-c2ccc3cc(O[Si](C)(C)C(C)(C)C)c(C45CC6CC(CC(C6)C4)C5)cc3c2)c1>C1CCOC1>CCOC(=O)c1csc(-c2ccc3cc(O)c(C45CC6CC(CC(C6)C4)C5)cc3c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20b7c42ff39d4f27aff2e357d5541bd7 | CC(=O)Oc1cc(OC(C)=O)cc(C(=O)O)c1.CCC(N)C(N)=O>>CCC(O)c1cc(O)cc(O)c1 | C(C)(=O)OC=1C=C(C(=O)O)C=C(C1)OC(C)=O.OCC(C)(CO)CO.C(=C)[Si](C=C)(C=C)C=C.OC1=CC=C(C=C1)C(C)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O.C(CN)N.N=O.OCC(CO)(CO)CO.NC(C(=O)N)CC>>OC=1C=C(C(CC)O)C=C(C1)O | CC(=O)[O:8][c:7]1[cH:6][c:5](C(=O)[OH:4])[cH:12][c:10]([O:11]C(C)=O)[cH:9]1.NC(=O)[CH:3](N)[CH2:2][CH3:1]>>[CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([OH:8])[cH:9][c:10]([OH:11])[cH:12]1 | CC(=O)Oc1cc(OC(C)=O)cc(C(=O)O)c1.CCC(N)C(N)=O | CCC(O)c1cc(O)cc(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2c2d1c8b68ffa1b974d0bfc3253fc7eccb45d9de1ab9e2c57e4e8b38819e81d8 | 68f8d4f234bd8dc2e62e327d389484b226fe14658d99e9cae7ce55e67399ce26 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-C(=O)-[OH;D1;+0:5]):[c:6]:[c:7](-[O;H0;D2;+0:8]-C(-C)=O):[c:9]:1.N-C(=O)-[CH;D3;+0:10](-N)-[C:11]-[C;D1;H3:12]>>[C;D1;H3:12]-[C:11]-[CH;D3;+0:10](-[OH;D1;+0:5])-[c;H0;D3;+0:4]1:[c:3]:[c:2](-[OH;D1;+0:1]):[c:9]:[c:7](-[OH;D1;+0:8]):[c:6]:1 | null | [] | null | null | null | null | The dendrimers of the present invention can be selected as toner additives, for example, as illustrated in the documents mentioned herein. Dendrimers are known, and can be considered radially symmetrical molecules of a STARBURST™ topology comprised of an initiator core, such as nitrogen, ethylenediimine, silicon, and t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester.Primary amide.Primary amine | Secondary alcohol.Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)Oc1cc(OC(C)=O)cc(C(=O)O)c1.CCC(N)C(N)=O>>CCC(O)c1cc(O)cc(O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d0e79d3004cd4cb5a98d3c999a726a05 | N#CCc1ccc(F)cc1.O=[N+]([O-])c1ccccc1>>Fc1ccc(-c2onc3ccccc23)cc1 | FC1=CC=C(C=C1)CC#N.[OH-].[Na+].[N+](=O)([O-])C1=CC=CC=C1>>FC1=CC=C(C=C1)C=1ON=C2C1C=CC=C2 | N#C[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:16][cH:15]1.O=[N+:8]([O-:7])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[o:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][cH:16]1 | N#CCc1ccc(F)cc1.O=[N+]([O-])c1ccccc1 | Fc1ccc(-c2onc3ccccc23)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 0f22d84b2a4c2a0e4579a9b5d1adb0e1a3a85c6a163e0b5818a361e01201e52a | b0095d38e0fbba4b05f88363393446922ef1c66394cfc608f7c1cd4fc808583a | c1ccc(-c2onc3ccccc23)cc1 | N#C-[CH2;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].O=[N+;H0;D3:7](-[O-;H0;D1:8])-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[c:10]:[c:9]1:[n;H0;D2;+0:7]:[o;H0;D2;+0:8]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[c;H0;D3;+0:11]:1:[c:12]:[c:13] | null | [] | null | null | 9 | HOUR | A total of 50.7 g (0.375 mol) of 4-fluorophenyl-acetonitrile is slowly added to a vigorously stirred, room-temperature solution of 150 g (3.75 mol) of sodium hydroxide in 750 ml of absolute methanol. After solution is complete, 46 g (0.374 mol) of nitrobenzene is slowly added. The resulting solution is warmed to 65°-70... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitro group | null | c1ccccc1 | c1ccc2nocc2c1 | c1ccccc1.c1ccc2nocc2c1 | HO- | CO | null | 9 | N#CCc1ccc(F)cc1.O=[N+]([O-])c1ccccc1>CO>Fc1ccc(-c2onc3ccccc23)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-92bc8cb4ed55424491eb833aaed1c16a | Fc1ccc(-c2onc3ccccc23)cc1>>Nc1ccccc1C(=O)c1ccc(F)cc1 | FC1=CC=C(C=C1)C=1ON=C2C1C=CC=C2>>NC1=C(C(=O)C2=CC=C(C=C2)F)C=CC=C1 | [n:1]1[c:2]2[cH:3][cH:4][cH:5][cH:6][c:7]2[c:8](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[o:9]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | Fc1ccc(-c2onc3ccccc23)cc1 | Nc1ccccc1C(=O)c1ccc(F)cc1 | null | [Pd] | O1CCCC1.C(C)N(CC)CC | Miscellaneous | OtherReaction | 63dfc430e67d3a7ada3c7e8f6e094ee16a92b905651085a196381d3119990ee1 | 2e99338cc955e46b2c0e811178d7128dca9a68ef9fbb467724eba7220efe12b0 | O=C(c1ccccc1)c1ccccc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[o;H0;D2;+0:5]:[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:11]:[c:12]>>[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:11]:[c:12]):[c:10] | null | [] | null | null | null | null | To a suspension of (16) (42.6 g, 0.2 mol) in 750 ml of dry tetrahydrofuran (THF) and 20 ml of triethylamine is added 5% palladium on charcoal (6 g). The vigorously stirred suspension is flushed with hydrogen gas and stirred at room temperature under a hydrogen atmosphere until absorption of hydrogen ceases (approximate... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Primary amine | c1ccc2nocc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | [Pd].O1CCCC1.C(C)N(CC)CC | null | null | Fc1ccc(-c2onc3ccccc23)cc1>[Pd].O1CCCC1.C(C)N(CC)CC>Nc1ccccc1C(=O)c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-505bc94ed0b24d42b247b9173702273a | CC(=O)c1ccc(F)cc1.Nc1ccccc1C(=O)c1ccc(F)cc1>>Fc1ccc(-c2cc(-c3ccc(F)cc3)c3ccccc3n2)cc1 | NC1=C(C(=O)C2=CC=C(C=C2)F)C=CC=C1.CC(=O)C1=CC=C(C=C1)F.O.C=1(C(=CC=CC1)S(=O)(=O)O)C>>FC1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=C1)C1=CC=C(C=C1)F | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:24][cH:23]1)[CH3:7].O=[C:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[NH2:22]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[n:22]2... | CC(=O)c1ccc(F)cc1.Nc1ccccc1C(=O)c1ccc(F)cc1 | Fc1ccc(-c2cc(-c3ccc(F)cc3)c3ccccc3n2)cc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | ef62a17cf5af6b6a9400c0546d94e169af6c90ed68e6730786f9942d0bd5f3dc | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].O=[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:16]:[c:15]:[c;H0;D3;+0:14](-[c;H0;D3;+0:8]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[n;H0;D2;+0:12]:... | null | [] | 200 | CELSIUS | null | null | A flask is loaded with (17) (21.5 g, 0.1 mol), 4-fluoroacetophenone (13.8 g, 0.1 mol), and toluene sulfonic acid monohydrate (3.8 g, 0.02 mol). The flask is heated to 200° C. and the water of condensation removed. After water evolution ceased, the mixture is cooled and the crude solid product is crushed and washed with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HO- | O | 200 | null | CC(=O)c1ccc(F)cc1.Nc1ccccc1C(=O)c1ccc(F)cc1>O>Fc1ccc(-c2cc(-c3ccc(F)cc3)c3ccccc3n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48ed68423d4a4e7fb6e576167938191c | Cl.Cl>>ClCCl.N | N1=CC=CC=C1.CC(C)(C)[Si](C)(C)Cl.N[C@@H](CC1=CNC=N1)CO.[H-].[Na+].Cl.Cl.N[C@@H](CC1=CNC=N1)CO>>N.C(Cl)Cl.N[C@@H](CC1=CNC=N1)CO | [ClH:1].[ClH:3]>>[Cl:1][CH2:2][Cl:3].[NH3:4] | Cl.Cl | ClCCl.N | null | null | CN(C)C=O.CCCCCC | Functional Group Addition | OtherReaction | 41523ea8a56e473f35c21479a8332be3a39833fcdb7794bb86c8a0176356dde0 | ffcace6ec62222cc441f032155f7c26a7f18918e26f8fa19eef390df174a1801 | null | [ClH;D0;+0:1].[ClH;D0;+0:2]>>[Cl;H0;D1;+0:1]-[C:3]-[Cl;H0;D1;+0:2] | null | [] | null | null | 1.5 | HOUR | TBDMS protected histidinol 14--To a stirred solution of 205 mg (5.1 mmol) of NaH washed 3× with hexane, under argon, in 3.0 mL DMF was added in portions 500 mg (2.3 mmol) of histidinol dihydrochloride, resulting in moderate gas evolution. The solution was stirred for 1.5 h, then 1.8 mL (23 mmol) of anhydrous pyridine a... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary halide.Primary halide | null | null | null | Other | CN(C)C=O.CCCCCC | null | 1.5 | Cl.Cl>CN(C)C=O.CCCCCC>ClCCl.N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58e35fa5d3104b07bb1cd637b9c2a80b | CC(CN)(CN)CN.O=C1CCCO1>>CC1(CN)CN=C2CCCN2C1 | C1(CCCO1)=O.[Cl-].[NH4+].NCC(C)(CN)CN>>NCC1(CN=C2N(C1)CCC2)C | [CH3:1][C:2]([CH2:3][NH2:4])([CH2:5][NH2:6])[CH2:12][NH2:11].O=[C:7]1O[CH2:10][CH2:9][CH2:8]1>>[CH3:1][C:2]1([CH2:3][NH2:4])[CH2:5][N:6]=[C:7]2[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12]1 | CC(CN)(CN)CN.O=C1CCCO1 | CC1(CN)CN=C2CCCN2C1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 1d8e04e574d96100d365a352017d9cbd9eb21df9423d7eccd6549a60899f558c | 278cd8e31d8f48c7f944b77ce78ef7ba21405ad243ad2b6be0edc47e13497c28 | C1CN=C2CCCN2C1 | O=[C;H0;D3;+0:1]1-O-[CH2;D2;+0:2]-[C:3]-[C:4]-1.[NH2;D1;+0:5]-[C:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:6]1-[C:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]2-[C:4]-[C:3]-[CH2;D2;+0:2]-[N;H0;D3;+0:5]-1-2 | null | [] | 250 | CELSIUS | 1.5 | HOUR | A mixture of 21.03 g (0.24 mol) of γ-butyrolactone and 1.31 g (24 mmol) of ammonium chloride in 114.5 g (0.98 mol) of 1,1,1-tris(aminomethyl)ethane was heated at 250° C. in an autoclave. After 1.5 h, the mixture was cooled and the excess amine and the water formed were removed by distillation. The residue was distilled... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | Tertiary amine | C1CCOC1 | C1CN=C2CCCN2C1 | C1CN=C2CCCN2C1 | HO- | O | 250 | 1.5 | CC(CN)(CN)CN.O=C1CCCO1>O>CC1(CN)CN=C2CCCN2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54fc6a8a376c4fd9a41d798a9116e90e | CC(=O)c1c(C)cc(C)cc1C.CCOC(=O)C(=O)OCC>>CCOC(=O)C(=O)CC(=O)c1c(C)cc(C)cc1C | CC1=C(C(=CC(=C1)C)C)C(C)=O.C(C(=O)OCC)(=O)OCC.[H-].[Na+]>>O=C(C(=O)OCC)CC(C1=C(C=C(C=C1C)C)C)=O | [CH3:8][C:9](=[O:10])[c:11]1[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]1[CH3:19].CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]1[CH3:19] | CC(=O)c1c(C)cc(C)cc1C.CCOC(=O)C(=O)OCC | CCOC(=O)C(=O)CC(=O)c1c(C)cc(C)cc1C | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 75e47111412c372865b4b8c2556a24f38f2daf372ab5522938a6e976b4732185 | 907e247f98c28f5bcc369b20fadcc26c24574c2b68d4b59762f1e8515d373c02 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10] | 66.7 | [{"value": 66.7, "product": "O=C(C(=O)OCC)CC(C1=C(C=C(C=C1C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2', 4', 6'-trimethylacetophenone (15 g, 92.6 mmol) and diethyl oxalate (20 g, 139 mmol) in 500 mL of anhydrous toluene was cautiously added 7.4 g of NaH (60% dispersion in mineral oil). The reaction mixture was slowly heated to reflux under N2. It was refluxed for about 20 minutes, then cooled, poured ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone.Ketone | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)c1c(C)cc(C)cc1C.CCOC(=O)C(=O)OCC>C1(=CC=CC=C1)C>CCOC(=O)C(=O)CC(=O)c1c(C)cc(C)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9ea025a9a0a4f688e80e240ea0b34ac | CCOC(=O)C(=O)CC(=O)c1c(C)cc(C)cc1C.O=N[O-]>>CCOC(=O)C(=O)C(=NO)C(=O)c1c(C)cc(C)cc1C | O=C(C(=O)OCC)CC(C1=C(C=C(C=C1C)C)C)=O.Cl.N(=O)[O-].[Na+]>>O=C(C(=O)OCC)C(C(C1=C(C=C(C=C1C)C)C)=O)=NO | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:11](=[O:12])[c:13]1[c:14]([CH3:15])[cH:16][c:17]([CH3:18])[cH:19][c:20]1[CH3:21].O=[N:9][O-:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[C:8](=[N:9][OH:10])[C:11](=[O:12])[c:13]1[c:14]([CH3:15])[cH:16][c:17]([CH3:18])[cH:19][c:20]1[CH3:21] | CCOC(=O)C(=O)CC(=O)c1c(C)cc(C)cc1C.O=N[O-] | CCOC(=O)C(=O)C(=NO)C(=O)c1c(C)cc(C)cc1C | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 9638fdacd8d405b0a44d1ce6aba3da753854cff65501b5a57f0aafc95fc4c4f0 | d3bd726ddd957b1a2366e6bbf86ce90af8c1a91be2fc86e65360edda049ba84b | c1ccccc1 | O=[N;H0;D2;+0:1]-[O-;H0;D1:2].[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[N;H0;D2;+0:1]-[OH;D1;+0:2])-[C:10](=[O;D1;H0:11])-[c:12] | null | [] | null | null | null | null | N2O3 gas was slowly passed into a stirred solution of the product of step A (16.2 g) in 300 mL of ethanol until the disappearance of starting material was confirmed by TLC. N2O3 gas was generated by the dropwise addition of 12N aqueous HCl solution into an aqueous slurry of NaNO2. The solvent was removed from the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Nitroso | Ketone.Ketone.Oxime | null | null | c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)C(=O)CC(=O)c1c(C)cc(C)cc1C.O=N[O-]>C(C)O>CCOC(=O)C(=O)C(=NO)C(=O)c1c(C)cc(C)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-75a3caa0644f40ee90d13cb00258ca5f | CCOC(=O)C(=O)C(=NO)C(=O)c1c(C)cc(C)cc1C.CNN>>CCOC(=O)c1nn(C)c(-c2c(C)cc(C)cc2C)c1N | O=C(C(=O)OCC)C(C(C1=C(C=C(C=C1C)C)C)=O)=NO.Cl.CNN>>NC=1C(=NN(C1C1=C(C=C(C=C1C)C)C)C)C(=O)OCC | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:20]([C:10](=O)[c:11]1[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]1[CH3:19])=[N:21]O.[NH2:7][NH:8][CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][n:8]([CH3:9])[c:10](-[c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17][c:18]2[CH3:19])[c:20]1[NH2:21] | CCOC(=O)C(=O)C(=NO)C(=O)c1c(C)cc(C)cc1C.CNN | CCOC(=O)c1nn(C)c(-c2c(C)cc(C)cc2C)c1N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | e4c6ec0e05e1c203106a5b5aa997e8a1ccd7f76a640bd7c557c3b58ce08a8ce3 | 5d820015a1c4befea2445c7bdac96cc1fe907ff48e6873810c167772c5bb36e5 | c1ccc(-c2ccn[nH]2)cc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5](-[C;D1;H3:6]):[c:7]):[c:8](-[C;D1;H3:9]):[c:10])-[C;H0;D3;+0:11](=O)-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15].[C;D1;H3:16]-[NH;D2;+0:17]-[NH2;D1;+0:18]>>[C:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:11]1:[n;H0;D2;+0:18]:[n;H0;D3;+0:17](-[C;D1;H3:1... | 78.9 | [{"value": 78.9, "product": "NC=1C(=NN(C1C1=C(C=C(C=C1C)C)C)C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of the product of step B (4.0 g, 13.8 mmol) and 1.6 mL of 12N hydrochloric acid in 100 mL of methanol was added dropwise 0.63 g of methyl hydrazine at 0° C. The reaction mixture was stirred at room temperature 4 hours, and then concentrated. The resulting residue was partitioned between water and ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone.Ester.Oxime | Ester.Primary amine | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HO- | CO | null | 4 | CCOC(=O)C(=O)C(=NO)C(=O)c1c(C)cc(C)cc1C.CNN>CO>CCOC(=O)c1nn(C)c(-c2c(C)cc(C)cc2C)c1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0a66d17f4434d27b82b139747ba9e7b | CCCBr.CCCNc1nc(C)nc2c(-c3c(C)cc(C)cc3C)n(C)nc12>>CCCN(CCC)c1nc(C)nc2c(-c3c(C)cc(C)cc3C)n(C)nc12 | C(CC)NC=1C=2C(N=C(N1)C)=C(N(N2)C)C2=C(C=C(C=C2C)C)C.[OH-].[K+].BrCCC>>C(CC)N(C=1C=2C(N=C(N1)C)=C(N(N2)C)C2=C(C=C(C=C2C)C)C)CCC | Br[CH2:5][CH2:6][CH3:7].[CH3:1][CH2:2][CH2:3][NH:4][c:8]1[n:9][c:10]([CH3:11])[n:12][c:13]2[c:14](-[c:15]3[c:16]([CH3:17])[cH:18][c:19]([CH3:20])[cH:21][c:22]3[CH3:23])[n:24]([CH3:25])[n:26][c:27]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[c:8]1[n:9][c:10]([CH3:11])[n:12][c:13]2[c:14](-[c:15]3[c:16]([CH3:17])... | CCCBr.CCCNc1nc(C)nc2c(-c3c(C)cc(C)cc3C)n(C)nc12 | CCCN(CCC)c1nc(C)nc2c(-c3c(C)cc(C)cc3C)n(C)nc12 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2[nH]nc3cncnc23)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[#7;a:13]:[#7;a:14]:[c:15]:2:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[#7;a:13]:[#7;a:14]:[c:15]:2:1 | null | [] | 60 | CELSIUS | null | null | A mixture of the product of step F (400 mg, 1.2 mmol), powder KOH (1.0 g) and 1-bromopropane (1 mL) in 2 mL of DMSO was heated at 60° C. for 8 hours. The excess bromopropane was then evaporated. The mixture was partitioned between water and ether. The aqueous layer was separated and extracted with ether. The combined e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ncc2n[nH]cc2n1 | HBr | CS(=O)C | 60 | null | CCCBr.CCCNc1nc(C)nc2c(-c3c(C)cc(C)cc3C)n(C)nc12>CS(=O)C>CCCN(CCC)c1nc(C)nc2c(-c3c(C)cc(C)cc3C)n(C)nc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-564b28fa70ee43db9e87ffa6d6c4d4e6 | CC1(NC(=O)OC(C)(C)C)CCN(c2nccc(Cl)n2)CC1>>CC1(N)CCN(c2nccc(Cl)n2)CC1 | C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)NC1(CCN(CC1)C1=NC=CC(=N1)Cl)C.[OH-].[Na+]>>NC1(CCN(CC1)C1=NC=CC(=N1)Cl)C | CC(C)(C)OC(=O)[NH:3][C:2]1([CH3:1])[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][c:11]([Cl:12])[n:13]2)[CH2:14][CH2:15]1>>[CH3:1][C:2]1([NH2:3])[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][c:11]([Cl:12])[n:13]2)[CH2:14][CH2:15]1 | CC1(NC(=O)OC(C)(C)C)CCN(c2nccc(Cl)n2)CC1 | CC1(N)CCN(c2nccc(Cl)n2)CC1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cnc(N2CCCCC2)nc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C:4])-[C:5]>>[C:4]-[C:2](-[C;D1;H3:3])(-[NH2;D1;+0:1])-[C:5] | null | [] | null | null | 1 | HOUR | A solution of 2.22 g (0.0068 mol) of 4-t-butoxycarbonylamino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine (step c) in 25 ml of anhydrous methylene chloride is cooled under a nitrogen atmosphere and 5 ml of anisole and 25 ml of trifluoroacetic acid are added slowly. The mixture is stirred for 1 hour at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]CC1.c1cncnc1 | HO- | C(Cl)Cl | null | 1 | CC1(NC(=O)OC(C)(C)C)CCN(c2nccc(Cl)n2)CC1>C(Cl)Cl>CC1(N)CCN(c2nccc(Cl)n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b6be6f155af94436ba0e8bfe5bd8a6cd | CC1(NC(=O)OC(C)(C)C)CCN(c2ccnc(Cl)n2)CC1>>CC1(N)CCN(c2ccnc(Cl)n2)CC1 | C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)NC1(CCN(CC1)C1=NC(=NC=C1)Cl)C.[OH-].[Na+]>>NC1(CCN(CC1)C1=NC(=NC=C1)Cl)C | CC(C)(C)OC(=O)[NH:3][C:2]1([CH3:1])[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[n:13]2)[CH2:14][CH2:15]1>>[CH3:1][C:2]1([NH2:3])[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][n:10][c:11]([Cl:12])[n:13]2)[CH2:14][CH2:15]1 | CC1(NC(=O)OC(C)(C)C)CCN(c2ccnc(Cl)n2)CC1 | CC1(N)CCN(c2ccnc(Cl)n2)CC1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(N2CCCCC2)ncn1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C:4])-[C:5]>>[C:4]-[C:2](-[C;D1;H3:3])(-[NH2;D1;+0:1])-[C:5] | null | [] | null | null | 1 | HOUR | The procedure described in Example 2 is followed up to the end of step (c). A solution of 6.81 g (0.021 mol) of 4-t-butoxycarbonylamino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine (step c) in 80 ml of anhydrous methylene chloride is cooled under a nitrogen atmosphere and 16.4 ml of anisole and 83 ml of trifluoroaceti... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]CC1.c1cncnc1 | HO- | C(Cl)Cl | null | 1 | CC1(NC(=O)OC(C)(C)C)CCN(c2ccnc(Cl)n2)CC1>C(Cl)Cl>CC1(N)CCN(c2ccnc(Cl)n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4c3ca7fee7ca4cb68a75ae1c5be3919e | Cc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>Cc1ccc(C(=O)Cl)cc1 | CC1=CC=C(C(=O)O)C=C1.S(=O)(Cl)Cl>>CC1=CC=C(C(=O)Cl)C=C1 | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:10][cH:9]1)=[O:7].O=S(Cl)[Cl:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[Cl:8])[cH:9][cH:10]1 | Cc1ccc(C(=O)O)cc1.O=S(Cl)Cl | Cc1ccc(C(=O)Cl)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 4-Methylbenzoyl chloride was prepared in a conventional manner from 4-methylbenzoic acid and thionyl chloride and after excess thionyl chloride was distilled off, was used as the crude product in the side chain chlorination.
Conditions: See reaction.notes.procedure_details.
Workup: after excess thionyl chloride was dis... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | Cc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>Cc1ccc(C(=O)Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9c7d389a33241bbb79d7412a80e13bc | CCCCCCCCCCOc1cnc(-c2ccc(C=CCCO)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(CCCCO)cc2)nc1 | OCCC=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC.[H][H].[H][H]>>OCCCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]=[CH:21][CH2:22][CH2:23][OH:24])[cH:25][cH:26]2)[n:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:... | CCCCCCCCCCOc1cnc(-c2ccc(C=CCCO)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(CCCCO)cc2)nc1 | null | [Pd] | O1CCCC1 | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(-c2ncccn2)cc1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99 | [{"value": 99.0, "product": "OCCCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.38 g (1 mmol) of the thus obtained 2-(4-(4-hydroxy-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of tetrahydrofuran, added with 0.05 g of 10% Pd/C and subjected to a hydrogenation reaction in a hydrogen atmosphere under normal pressure. The reaction was stopped when about 25 ml of hydrogen was consum... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cncnc1.c1ccccc1 | null | [Pd].O1CCCC1 | null | null | CCCCCCCCCCOc1cnc(-c2ccc(C=CCCO)cc2)nc1>[Pd].O1CCCC1>CCCCCCCCCCOc1cnc(-c2ccc(CCCCO)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8266c5cd4a68414b8c3137da7bc01eef | CCCCCCCCCCOc1cnc(-c2ccc(C(C)=O)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1 | [BH4-].[Na+].C(C)(=O)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC.C(C)O.C(Cl)(Cl)Cl>>OC(C)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])=[O:22])[cH:23][cH:24]2)[n:25][cH:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19... | CCCCCCCCCCOc1cnc(-c2ccc(C(C)=O)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1 | null | null | O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2ncccn2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 100.3 | [{"value": 100.0, "product": "OC(C)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "OC(C)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 35.5 g (0.1 mo1) of 2-(4-acetylphenyl)-5-decyloxypyrimidine, 300 ml of ethanol and 300 ml of chloroform were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 2.8 g (0.075 mol) of sodium borohydride was added at 30°-40° C. and the mixture was stirred at the same temperature for 4 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1cncnc1.c1ccccc1 | null | O | null | 4 | CCCCCCCCCCOc1cnc(-c2ccc(C(C)=O)cc2)nc1>O>CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01a269bda00c4ee495d089d890ae2b6c | CCCCCCCCCCOc1cnc(-c2ccc(C(C)OC(C)=O)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1 | C(C)(=O)OC(C)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC>>OC(C)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC | CC(=O)[O:22][CH:20]([c:19]1[cH:18][cH:17][c:16](-[c:15]2[n:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:26][n:25]2)[cH:24][cH:23]1)[CH3:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18... | CCCCCCCCCCOc1cnc(-c2ccc(C(C)OC(C)=O)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1 | null | null | [OH-].[Na+].CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | c1ccc(-c2ncccn2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])-[c:4]>>[C;D1;H3:3]-[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 30 | CELSIUS | 2 | HOUR | 4 g of the above product (-)-(4-(1-acetoxyethyl) phenyl)-5-decyloxypyrimidine was dissolved in a mixture of 50 ml of methanol and 10 ml of a 20% sodium hydroxide solution, stirred at 30° C. for 2 hours and hydrolyzed, and the resulting reaction solution was extracted by adding 200 ml of water and 200 ml of toluene, fol... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1cncnc1.c1ccccc1 | HO- | [OH-].[Na+].CO | 30 | 2 | CCCCCCCCCCOc1cnc(-c2ccc(C(C)OC(C)=O)cc2)nc1>[OH-].[Na+].CO>CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa775880ee5b480896f2619381c4dc7e | CCCCCCCCCCOc1cnc(-c2ccc(C=CC(O)C(F)(F)F)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(C=CC(OCCCC)C(F)(F)F)cc2)nc1 | OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F>>C(CCC)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]=[CH:21][CH:22]([OH:23])[C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]2)[n:34][cH:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:1... | CCCCCCCCCCOc1cnc(-c2ccc(C=CC(O)C(F)(F)F)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(C=CC(OCCCC)C(F)(F)F)cc2)nc1 | null | [Ag]=O | C(CCC)I | Functional Group Interconversion | OtherReaction | 1f8b4f749d7b68e358abf6dadca641af7be42cbed7d6129cc817b66a2815d76b | 1986048cb9f2a7cc7e0c9d12b7a8bd2e76fdd82b5837c7e5982a2b2c413cbea0 | c1ccc(-c2ncccn2)cc1 | [C:1]-[#8:2]-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[c:6](-[c:7]):[n;H0;D2;+0:8]:[cH;D2;+0:9]:1.[F;D1;H0:10]-[C:11](-[F;D1;H0:12])(-[F;D1;H0:13])-[C:14](-[OH;D1;+0:15])-[C:16]=[C:17]-[c:18]>>[C:1]-[#8:2]-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[c:6](-[c:7]):[n;H0;D2;+0:8]:[c:19]:1.[C:20]-[C:21]-[CH2;D2;+0:9]-[O;H0;D2;+0:15]-[C:14](-[C:... | 173.7 | [{"value": 173.7, "product": "C(CCC)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | 1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 5 ml of butyl iodide. The solution was added with 3 g of silver oxide and stirred at 25°-30° C. for 4 days. The reaction mixture was cleared of silver oxide by filtration and concentrated under reduced pressure, and th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ether.Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | Other | [Ag]=O.C(CCC)I | null | 96 | CCCCCCCCCCOc1cnc(-c2ccc(C=CC(O)C(F)(F)F)cc2)nc1>[Ag]=O.C(CCC)I>CCCCCCCCCCOc1cnc(-c2ccc(C=CC(OCCCC)C(F)(F)F)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a527bf234aeb411088cf0a7588b93b15 | CCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(C=CC(O)C(F)(F)F)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(C=CC(OC(=O)CCC)C(F)(F)F)cc2)nc1 | OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F.C(CCC)(=O)Cl>>C(CCC)(=O)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F | Cl[C:24](=[O:25])[CH2:26][CH2:27][CH3:28].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]=[CH:21][CH:22]([OH:23])[C:29]([F:30])([F:31])[F:32])[cH:33][cH:34]2)[n:35][cH:36]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2... | CCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(C=CC(O)C(F)(F)F)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(C=CC(OC(=O)CCC)C(F)(F)F)cc2)nc1 | null | null | C1(=CC=CC=C1)C.N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc(-c2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[F;D1;H0:5]-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:9](-[OH;D1;+0:10])-[C:11]=[C:12]-[c:13]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9](-[C:11]=[C:12]-[c:13])-[C:6](-[F;D1;H0:5])(-[F;D1;H0:7])-[F;D1;H0:8] | 93.1 | [{"value": 93.1, "product": "C(CCC)(=O)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine. The solution was added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1cncnc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.N1=CC=CC=C1 | null | 4 | CCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(C=CC(O)C(F)(F)F)cc2)nc1>C1(=CC=CC=C1)C.N1=CC=CC=C1>CCCCCCCCCCOc1cnc(-c2ccc(C=CC(OC(=O)CCC)C(F)(F)F)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5085d0f6c9584e6a85f4d46b48c68abb | CCCCCCCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(CCCC(O)C(F)(F)F)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(CCCC(OC(=O)CCCCCCCC)C(F)(F)F)cc2)nc1 | OC(CCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F.C(CCCCCCCC)(=O)Cl>>C(CCCCCCCC)(=O)OC(CCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F | Cl[C:25](=[O:26])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH2:20][CH2:21][CH2:22][CH:23]([OH:24])[C:35]([F:36])([F:37])[F:38])[cH:39][cH:40]2)[n:41][cH:42]1>>[CH3... | CCCCCCCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(CCCC(O)C(F)(F)F)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(CCCC(OC(=O)CCCCCCCC)C(F)(F)F)cc2)nc1 | null | null | C1(=CC=CC=C1)C.N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc(-c2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11] | null | [] | null | null | null | null | 1.1 g (2.5 mmol) of (-)-2-(4-(4-hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine was dissolved in 10 ml of pyridine, followed by addition of 0.53 g (3 mmol) of nonanoyl chloride and 2-hour reaction at 20°-30° C. The reaction mixture was diluted with 100 ml of toluene, and the toluene layer was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1cncnc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.N1=CC=CC=C1 | null | null | CCCCCCCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(CCCC(O)C(F)(F)F)cc2)nc1>C1(=CC=CC=C1)C.N1=CC=CC=C1>CCCCCCCCCCOc1cnc(-c2ccc(CCCC(OC(=O)CCCCCCCC)C(F)(F)F)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9b515fcf22a54464836bc78f7d1d5c2e | CCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(C=CC(C)O)cc2)nc1>>CCCCCCCCCCOc1cnc(-c2ccc(C=CC(C)OC(=O)CCC)cc2)nc1 | OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C.C(CCC)(=O)Cl>>C(CCC)(=O)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C | Cl[C:25](=[O:26])[CH2:27][CH2:28][CH3:29].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]=[CH:21][CH:22]([CH3:23])[OH:24])[cH:30][cH:31]2)[n:32][cH:33]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O... | CCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(C=CC(C)O)cc2)nc1 | CCCCCCCCCCOc1cnc(-c2ccc(C=CC(C)OC(=O)CCC)cc2)nc1 | null | null | C1(=CC=CC=C1)C.N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc(-c2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[C:6](-[OH;D1;+0:7])-[C:8]=[C:9]-[c:10]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6](-[C;D1;H3:5])-[C:8]=[C:9]-[c:10] | 88.7 | [{"value": 88.7, "product": "C(CCC)(=O)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1.0 g of (-)-2-(4-(3-hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine, added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1cncnc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.N1=CC=CC=C1 | null | 4 | CCCC(=O)Cl.CCCCCCCCCCOc1cnc(-c2ccc(C=CC(C)O)cc2)nc1>C1(=CC=CC=C1)C.N1=CC=CC=C1>CCCCCCCCCCOc1cnc(-c2ccc(C=CC(C)OC(=O)CCC)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db70288e9ca54cb89358931186bc5974 | N#[N+]c1ccc(Cl)cc1.Nc1cc(Cl)nc(N)n1>>Nc1nc(N)c(N=Nc2ccc(Cl)cc2)c(Cl)n1 | ClC1=NC(=NC(=C1)N)N.C(C)(=O)[O-].[Na+].[Cl-].ClC1=CC=C(C=C1)[N+]#N>>ClC1=C(C(=NC(=N1)N)N)N=NC1=CC=C(C=C1)Cl | [N:7]#[N+:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.[NH2:1][c:2]1[n:3][c:4]([NH2:5])[cH:6][c:16]([Cl:17])[n:18]1>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]([N:7]=[N:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16]([Cl:17])[n:18]1 | N#[N+]c1ccc(Cl)cc1.Nc1cc(Cl)nc(N)n1 | Nc1nc(N)c(N=Nc2ccc(Cl)cc2)c(Cl)n1 | null | null | C(C)(=O)O.O | Functional Group Addition | OtherReaction | 59dbef215a5e5b8c943f9f2b2cb274bbf73bcb989858c51965027a5e963c218e | 2c6cd95d4efa78d9d3de76e13585ebc8f102df9229b31c028b4deed5aad0dd25 | c1ccc(N=Nc2cncnc2)cc1 | [Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[cH;D2;+0:8]:1.[N;H0;D1;+0:9]#[N+;H0;D2:10]-[c:11](:[c:12]):[c:13]>>[Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[c;H0;D3;+0:8]:1-[N;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | 41.4 | [{"value": 41.4, "product": "ClC1=C(C(=NC(=N1)N)N)N=NC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a suspension of 4-chloro-2,6-diaminopyrimidine (21.68 g, 0.150 mol) in water (750 ml) and acetic acid (750 ml) was added sodium acetate (300 g). Solution occurred after stirring for 20 minutes, and then the solution of 4-chlorobenzenediazonium chloride (0.166 mol) was added with cooling over 30 minutes at a rate tha... | 10.6084/m9.figshare.5104873.v1 | null | null | Diazene | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | null | C(C)(=O)O.O | null | 0.333333 | N#[N+]c1ccc(Cl)cc1.Nc1cc(Cl)nc(N)n1>C(C)(=O)O.O>Nc1nc(N)c(N=Nc2ccc(Cl)cc2)c(Cl)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-63652823dab044f195e03b0122ca1c8d | Nc1nc(N)c(N=Nc2ccc(Cl)cc2)c(Cl)n1>>Nc1nc(N)c(N)c(Cl)n1 | ClC1=C(C(=NC(=N1)N)N)N=NC1=CC=C(C=C1)Cl>>ClC1=C(C(=NC(=N1)N)N)N | Clc1ccc(N=[N:7][c:6]2[c:4]([NH2:5])[n:3][c:2]([NH2:1])[n:10][c:8]2[Cl:9])cc1>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]([NH2:7])[c:8]([Cl:9])[n:10]1 | Nc1nc(N)c(N=Nc2ccc(Cl)cc2)c(Cl)n1 | Nc1nc(N)c(N)c(Cl)n1 | null | [Zn] | C(C)(=O)O.C(C)O.O | Deprotection | OtherReaction | 0722c3cf3c652bcadbf2fd556ba1691a180af92ae74607c0f7d0965c24b92a49 | 16b76cc963cfd15c080c900b77fa1174c8de86c98ea02220734eaeb14bc96073 | c1cncnc1 | Cl-c1:c:c:c(-N=[N;H0;D2;+0:1]-[c:2]2:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2-[Cl;D1;H0:9]):c:c:1>>[Cl;D1;H0:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:3](-[N;D1;H2:4]):[c:2]:1-[NH2;D1;+0:1] | 75.7 | [{"value": 75.7, "product": "ClC1=C(C(=NC(=N1)N)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A suspension of 6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidinediamine (24.55 g, 0.0906 mol) in ethanol (640 ml), water (640 ml) and acetic acid (64 ml) was heated to 70° under nitrogen. Zinc dust (75 g) was added slowly over 1 hour, and then the reaction was stirred an additional hour at 70°. Then the reaction was coo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Diazene | Primary amine | c1ccccc1 | null | c1cncnc1 | HCl | [Zn].C(C)(=O)O.C(C)O.O | null | 72 | Nc1nc(N)c(N=Nc2ccc(Cl)cc2)c(Cl)n1>[Zn].C(C)(=O)O.C(C)O.O>Nc1nc(N)c(N)c(Cl)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b26f3f6bab4540adb2aaf83c30a9a560 | N#Cc1ccc2[nH]cc(CCCCCl)c2c1.NC(=O)c1cc2cc(N3CCNCC3)ccc2o1>>N#Cc1ccc2[nH]cc(CCCCN3CCN(c4ccc5oc(C(N)=O)cc5c4)CC3)c2c1 | N1(CCNCC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1.ClCCCCC1=CNC2=CC=C(C=C12)C#N>>C(#N)C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C=1C=CC2=C(C=C(O2)C(N)=O)C1 | Cl[CH2:13][CH2:12][CH2:11][CH2:10][c:9]1[cH:8][nH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:33][c:32]21.[NH:14]1[CH2:15][CH2:16][N:17]([c:18]2[cH:19][cH:20][c:21]3[o:22][c:23]([C:24]([NH2:25])=[O:26])[cH:27][c:28]3[cH:29]2)[CH2:30][CH2:31]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][... | N#Cc1ccc2[nH]cc(CCCCCl)c2c1.NC(=O)c1cc2cc(N3CCNCC3)ccc2o1 | N#Cc1ccc2[nH]cc(CCCCN3CCN(c4ccc5oc(C(N)=O)cc5c4)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(CCCCN3CCN(c4ccc5occc5c4)CC3)c[nH]c2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | 5-(1-piperazinyl)benzofuran-2-carboxamide or a corresponding salt is reacted with 3-(4-chlorobutyl)-5-cyanoindole to give 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine and optionally then converted into its acid addition salt.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccc2occc2c1 | HCl | null | null | null | N#Cc1ccc2[nH]cc(CCCCCl)c2c1.NC(=O)c1cc2cc(N3CCNCC3)ccc2o1>>N#Cc1ccc2[nH]cc(CCCCN3CCN(c4ccc5oc(C(N)=O)cc5c4)CC3)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fb1ddf8127a44d35bcac2a8bffbfe5d1 | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2o1>>CCOC(=O)c1cc2cc(N)ccc2o1 | [N+](=O)([O-])C=1C=CC2=C(C=C(O2)C(=O)OCC)C1>>NC=1C=CC2=C(C=C(O2)C(=O)OCC)C1 | O=[N+:11]([O-])[c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:15][c:14]2[cH:13][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[o:15]1 | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 | CCOC(=O)c1cc2cc(N)ccc2o1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2occc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 2.3 g of ethyl 5-nitrobenzofuran-2-carboxylate in 60 ml of methanol is hydrogenated in the presence of Raney nickel. The catalyst is filtered off and the solution is concentrated. After customary working up, ethyl 5-aminobenzofuran-2-carboxylate, Rf 0.1 (dichloromethane/ethanol 9.5:0.5) obtained; hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2occc2c1 | Other | [Ni].CO | null | null | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2o1>[Ni].CO>CCOC(=O)c1cc2cc(N)ccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d431b55cb724be5bee26d49a4283c0c | CCOC(=O)c1cc2cc(N3CCN(C(=O)OC(C)(C)C)CC3)ccc2o1.NC=O>>CC(C)(C)OC(=O)N1CCN(c2ccc3oc(C(N)=O)cc3c2)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=CC2=C(C=C(O2)C(=O)OCC)C1.C(=O)N>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1 | CCO[C:18]([c:17]1[o:16][c:15]2[cH:14][cH:13][c:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]3)[cH:23][c:22]2[cH:21]1)=[O:20].O=C[NH2:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]3[o:16][c:17]([C:18]([NH2:1... | CCOC(=O)c1cc2cc(N3CCN(C(=O)OC(C)(C)C)CC3)ccc2o1.NC=O | CC(C)(C)OC(=O)N1CCN(c2ccc3oc(C(N)=O)cc3c2)CC1 | null | null | CN1C(CCC1)=O | Acylation | OtherReaction | 8485ff0c27805637c203a0305c6b23f92c4eeb142cc0b7710a60928ccd98fb24 | 6966630ca7488e58a1b66dece4d4906c351d42d1615b3e81f8c9466448df6023 | c1cc2cc(N3CCNCC3)ccc2o1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].O=C-[NH2;D1;+0:7]>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | A solution of 3 g of ethyl 5-(4-tert-butoxycarbonyl-1-piperazinyl)benzofuran-2-carboxylate in 100 ml of N-methylpyrrolidone is stirred for 5 hours with 1 g of formamide and 3 g of sodium alkoxide. After customary working up, 5-(4-tert-butoxycarbonyl-1-piperazinyl)benzofuran-2-carboxamide, m.p. 198°-200°, is obtained.
C... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amide | Primary amide | null | null | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HO- | CN1C(CCC1)=O | null | null | CCOC(=O)c1cc2cc(N3CCN(C(=O)OC(C)(C)C)CC3)ccc2o1.NC=O>CN1C(CCC1)=O>CC(C)(C)OC(=O)N1CCN(c2ccc3oc(C(N)=O)cc3c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9767918db3564609a907b285260c24dc | CCOC(=O)c1cc2cc(N3CCNCC3)ccc2o1.ClCc1ccccc1>>CCOC(=O)c1cc2cc(N3CCN(Cc4ccccc4)CC3)ccc2o1 | N1(CCNCC1)C=1C=CC2=C(C=C(O2)C(=O)OCC)C1.C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)N1CCN(CC1)C=1C=CC2=C(C=C(O2)C(=O)OCC)C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([N:11]3[CH2:12][CH2:13][NH:14][CH2:22][CH2:23]3)[cH:24][cH:25][c:26]2[o:27]1.Cl[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][c:16]4[cH:17][cH:18][cH... | CCOC(=O)c1cc2cc(N3CCNCC3)ccc2o1.ClCc1ccccc1 | CCOC(=O)c1cc2cc(N3CCN(Cc4ccccc4)CC3)ccc2o1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCN(c3ccc4occc4c3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | null | [] | null | null | 2 | HOUR | A solution of 1 g of ethyl 5-(1-piperazinyl)-benzofuran-2-carboxylate in 50 ml of dichloromethane is treated with 1 g of benzyl chloride and stirred for 2 hours. After customary working up, ethyl 5-(4-benzyl-1-piperazinyl)benzofuran-2-carboxylate, m.p. 219°-222°, is obtained.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | ClCCl | null | 2 | CCOC(=O)c1cc2cc(N3CCNCC3)ccc2o1.ClCc1ccccc1>ClCCl>CCOC(=O)c1cc2cc(N3CCN(Cc4ccccc4)CC3)ccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5c1249063ad41ecb9a886e640b8e144 | CC(C)(C)OC(=O)N1CCN(c2ccc3oc(C(N)=O)cc3c2)CC1>>NC(=O)c1cc2cc(N3CCNCC3)ccc2o1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1>>N1(CCNCC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][N:9]([c:8]2[cH:7][c:6]3[cH:5][c:4]([C:2]([NH2:1])=[O:3])[o:18][c:17]3[cH:16][cH:15]2)[CH2:14][CH2:13]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[cH:7][c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16][c:17]2[o:18]1 | CC(C)(C)OC(=O)N1CCN(c2ccc3oc(C(N)=O)cc3c2)CC1 | NC(=O)c1cc2cc(N3CCNCC3)ccc2o1 | null | null | Cl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc2cc(N3CCNCC3)ccc2o1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 1 g of 5-(4-tert-butoxycarbonyl-1-piperazinyl)-benzofuran-2-carboxamide is dissolved in 50 ml of methanolic HCl and stirred for I hour. After customary working up, 5-(1-piperazinyl)benzofuran-2-carboxamide, m.p. 252°-255°, is obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2occc2c1.C1C[NH]CCN1 | HO- | Cl | null | null | CC(C)(C)OC(=O)N1CCN(c2ccc3oc(C(N)=O)cc3c2)CC1>Cl>NC(=O)c1cc2cc(N3CCNCC3)ccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-185abfaba55a4edabda0c165062f3325 | COc1ccc(Cc2nccc3cc(OC)c(OC)cc23)cc1OC.O=C(CBr)c1ccccc1>>Br.c1ccc2c(c1)ccn1cccc21 | COC=1C=CC(=CC1OC)CC2=C3C=C(C(=CC3=CC=N2)OC)OC.Cl.COC=1C=CC(=CC1OC)CC2=C3C=C(C(=CC3=CC=N2)OC)OC.C(C(=O)C1=CC=CC=C1)Br>>C=1C=CN2C1C1=CC=CC=C1C=C2.COC=1C=CC(=CC1OC)CC2=C3C=C(C(=CC3=CC=N2)OC)OC.Br | COc1ccc(C[c:36]2c3cc(OC)c(OC)c[c:31]3[cH:33][cH:34][n:35]2)cc1OC.O=[C:38]([CH2:37][Br:1])[c:39]1[cH:30][cH:29][cH:28][cH:27][cH:32]1>>[BrH:1].[cH:27]1[cH:28][cH:29][c:30]2[c:31]([cH:32]1)[cH:33][cH:34][n:35]1[cH:36][cH:37][cH:38][c:39]21 | COc1ccc(Cc2nccc3cc(OC)c(OC)cc23)cc1OC.O=C(CBr)c1ccccc1 | Br.c1ccc2c(c1)ccn1cccc21 | null | null | CC(=O)C | Miscellaneous | OtherReaction | 5b1557426c466a1800a826fc8905b45ce8b0bd3b7b5a14fabf8103068e10bab9 | 7619af0a64bd8308938008ca62032f343612f5b288c90b81bdc8a457a3d66263 | c1ccc2c(c1)ccn1cccc21 | C-O-c1:c:c:c(-C-[c;H0;D3;+0:1]2:[n;H0;D2;+0:2]:[c:3]:[c:4]:[c;H0;D3;+0:5]3:c:c(-O-C):c(-O-C):c:c:3:2):c:c:1-O-C.O=[C;H0;D3;+0:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:8])-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1>>[BrH;D0;+0:8].[c:13]1:[c:12]:[c:11]:[c;H0;D3;+0:10]2:[c;H0;D3;+0:5](:[c:4]:[c:3]:[n;H0;D3;+... | 97 | [{"value": 97.0, "product": "C=1C=CN2C1C1=CC=CC=C1C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A series of novel pyrrolo[2,1-a]isoquinoline dyes was prepared from readily available starting materials via a simple synthetic pathway. One such starting material is papaverine, a naturally occurring alkaloid that is relatively inexpensive and commercially available as its hydrochloride salt. Papaverine hydrochloride ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether.Ether.Ether.Ether | null | c1ccccc1.c1ccc2cnccc2c1.c1ccccc1 | c1ccc2c(c1)ccn1cccc21 | c1ccc2c(c1)ccn1cccc21 | HO- | CC(=O)C | null | null | COc1ccc(Cc2nccc3cc(OC)c(OC)cc23)cc1OC.O=C(CBr)c1ccccc1>CC(=O)C>Br.c1ccc2c(c1)ccn1cccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-138236e224a34c72b9402d81270c32cc | CC(=O)OC(C)(C)C.NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)O>>CC(C)(C)OC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1 | [OH-].[Na+].C(=O)(OCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)O.C(C)(=O)OC(C)(C)C.Cl(=O)(=O)(=O)O>>C(=O)(OCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)OC(C)(C)C | CC(=O)O[C:2]([CH3:1])([CH3:3])[CH3:4].[OH:5][C:6](=[O:7])[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[NH:14][C:15](=[O:16])[O:17][CH2:18][c... | CC(=O)OC(C)(C)C.NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)O | CC(C)(C)OC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 5d0917103c940f1e5ac32fa703bc10c45f3a69de0aac06714163499c8044ed5e | 55fd932a5ab5c250a820c8abdb02fe030ad2f5c333e3caf54ef6d66281c0b519 | c1ccccc1 | C-C(=O)-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4] | null | [] | null | null | 8 | HOUR | A mixture of 25 g of Nα-CBZ-L-lysine from Sigma, where CBZ is benzyloxycarbonyl, 250 mL of t-butyl acetate and 14 mL of 70% perchloric acid was vigorously mixed until all solids were dissolved. After stirring overnight, 375 mL of ethyl acetate was added followed by 250 mL of water. The pH of the aqueous layer was raise... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester | null | null | c1ccccc1 | HO- | O.C(C)(=O)OCC | null | 8 | CC(=O)OC(C)(C)C.NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)O>O.C(C)(=O)OCC>CC(C)(C)OC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fcbfd11331bc48daad13c3d9090822ab | C=O.CC(C)(C)OC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1>>CN(C)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C | C=O.C(=O)(OCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)OC(C)(C)C.[BH3-]C#N.[Na+]>>CN(NCCCC[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C)C | O=[CH2:1].[NH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27]>>[CH3:1][N:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH... | C=O.CC(C)(C)OC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1 | CN(C)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C | null | [Cl-].[Cl-].[Zn+2] | CO | Functional Group Interconversion | OtherReaction | 027108093d66f25b96db02c2a96d84c4d6959ed84baaa7e0f661b3cbc1d5d2a6 | 470057d9808f6000905d55406490a6d808be0a7d893d79207ff5fea327996f07 | c1ccccc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH2;D1;+0:4]>>[C:2]-[C:3]-[NH;D2;+0:4]-[#7:5](-[C;D1;H3:6])-[CH3;D1;+0:1] | null | [] | null | null | 1 | HOUR | A mixture consisting of 3.7 (27.2 mmol) of ZnCl2, 3.2 g (53 mmol) of NaCNBH3 and 60 mL of methanol was prepared to which was added a solution of 18 g (51.7 mmol) of the amine 1 in 180 mL of methanol. After cooling to 10°-15° C. 12.4 mL of 37% formaldehyde (165 mmol) was added dropwise over a 2-3 minute period. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Hydrazine | null | null | c1ccccc1 | null | [Cl-].[Cl-].[Zn+2].CO | null | 1 | C=O.CC(C)(C)OC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1>[Cl-].[Cl-].[Zn+2].CO>CN(C)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2d46e70de5c24d3e972efa60da2d0c9b | CN(C)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C.OO>>CN(C)NCCCC[C@@H](C(=O)OC(C)(C)C)[NH+]([O-])C(=O)OCc1ccccc1 | CN(NCCCC[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C)C.OO.OO>>CN(NCCCC[C@H]([NH+](C(=O)OCC1=CC=CC=C1)[O-])C(=O)OC(C)(C)C)C | [CH3:1][N:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[NH:17][C:19](=[O:20])[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.O[OH:18]>>[CH3:1][N:2]([CH3:3])[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15]... | CN(C)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C.OO | CN(C)NCCCC[C@@H](C(=O)OC(C)(C)C)[NH+]([O-])C(=O)OCc1ccccc1 | null | null | CO | Functional Group Interconversion | OtherReaction | ffa3c246ed1677fbed02d8b0540bad4c5b5bb5053711032730364292798a0d94 | 783c90bfee8f176c85f19a00da30e47da456c4a5f1236b20aa29c1dddcde7e75 | c1ccccc1 | O-[OH;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7](-[C:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15]>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[NH+;D3:6](-[O-;H0;D1:1])-[C:7](-[C:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15] | null | [] | 60 | CELSIUS | 48 | HOUR | A solution of 25.3 g of dimethylamine 2, 7.9 mL of 30% hydrogen peroxide and 150 mL of methanol was stirred for 5 h after which an additional 7.9 g of 30% hydrogen peroxide was added. The reaction was allowed to stir for 48 h and monitored by silica gel TLC, eluting with solvent A. A 1 mL aqueous slurry of approximatel... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Peroxide | null | null | null | c1ccccc1 | HO- | CO | 60 | 48 | CN(C)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C.OO>CO>CN(C)NCCCC[C@@H](C(=O)OC(C)(C)C)[NH+]([O-])C(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c6890bb15744174b710f1c89858ac54 | CCCCOC(=O)C(CCc1c[n+](CCCCC(NC(=O)OCc2ccccc2)C(=O)OC(C)(C)C)cc(O)c1CC(NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C)NC(=O)OCc1ccccc1>>N[C@H](CCCC[n+]1cc(O)c(C[C@H](N)C(=O)O)c(CC[C@H](N)C(=O)O)c1)C(=O)[O-] | OC=1C=[N+](C=C(C1CC(C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1)CCC(C(=O)OCCCC)NC(=O)OCC1=CC=CC=C1)CCCCC(C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1.Br>>C1=C(C(=C(C=[N+]1CCCC[C@H](C(=O)[O-])N)O)C[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N | CCCC[O:25][C:23]([CH:21]([CH2:20][CH2:19][c:18]1[c:11]([CH2:12][CH:13]([NH:14]C(=O)OCc2ccccc2)[C:15](=[O:16])[O:17]C(C)(C)C)[c:9]([OH:10])[cH:8][n+:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([NH:1]C(=O)OCc2ccccc2)[C:27](=[O:28])[O:29]C(C)(C)C)[cH:26]1)[NH:22]C(=O)OCc1ccccc1)=[O:24]>>[NH2:1][C@H:2]([CH2:3][CH2:4][CH2:5][CH2:... | CCCCOC(=O)C(CCc1c[n+](CCCCC(NC(=O)OCc2ccccc2)C(=O)OC(C)(C)C)cc(O)c1CC(NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C)NC(=O)OCc1ccccc1 | N[C@H](CCCC[n+]1cc(O)c(C[C@H](N)C(=O)O)c(CC[C@H](N)C(=O)O)c1)C(=O)[O-] | null | null | null | Miscellaneous | OtherReaction | 75990981b45ceb497d1737383df43bfbb9cf97e893baf9d9696871101496658c | b71332cca5f7165c9a25a4c1883c32cfb1bcc76f89d47889d4ed1d741b4da989 | c1cc[nH+]cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4](-[C:5]-[C:6])-[NH;D2;+0:7]-C(=O)-O-C-c1:c:c:c:c:c:1.C-C(-C)(-C)-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[C:12]-[c:13])-[NH;D2;+0:14]-C(=O)-O-C-c1:c:c:c:c:c:1.C-C-C-C-[O;H0;D2;+0:15]-[C:16](=[O;D1;H0:17])-[CH;D3;+0:18](-[C:19]-[C:20])-[NH;D2;+0:21]-C... | null | [] | null | null | null | null | reacting the pyridinium salt prepared in step (c) with HBr in an appropriate solvent to provide deoxypyridinoline.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Carbamic ester.Ester.Ester.Ester.Ether.Ether.Ether.Boc.Boc | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1=CC=[NH+]C=C1 | HO- | null | null | null | CCCCOC(=O)C(CCc1c[n+](CCCCC(NC(=O)OCc2ccccc2)C(=O)OC(C)(C)C)cc(O)c1CC(NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C)NC(=O)OCc1ccccc1>>N[C@H](CCCC[n+]1cc(O)c(C[C@H](N)C(=O)O)c(CC[C@H](N)C(=O)O)c1)C(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5cabef20e3d4416cbf3328a8863028c7 | CC#N.c1ccc2c(c1)CC1OC21>>N[C@@H]1c2ccccc2C[C@@H]1O | C(C)#N.CS(=O)(=O)O.C12C(CC3=CC=CC=C13)O2.O>>N[C@H]1[C@H](CC2=CC=CC=C12)O | CC#[N:1].[CH:2]12[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[CH2:9][CH:10]1[O:11]2>>[NH2:1][C@@H:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C@@H:10]1[OH:11] | CC#N.c1ccc2c(c1)CC1OC21 | N[C@@H]1c2ccccc2C[C@@H]1O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | c326310fbe6c4c9ff3a0833bf4c39adac3f31aec1ac88f4c5a37342c4ef31146 | 133fdcfd54a50b782beb091526e7c313f29970d3e8558cf65178b1c05b908815 | c1ccc2c(c1)CCC2 | C-C#[N;H0;D1;+0:1].[c:2]:[c:3]1:[c:4]-[C:5]-[CH;D3;+0:6]2-[O;H0;D2;+0:7]-[CH;D3;+0:8]-2-1>>[NH2;D1;+0:1]-[C@H;D3;+0:8]1-[C@@H;D3;+0:6](-[OH;D1;+0:7])-[C:5]-[c:4]:[c:3]-1:[c:2] | null | [] | -20 | CELSIUS | null | null | Indene oxide (117 g) diluted to a total volume of 600 mL in methylene chloride was diluted with acetonitrile (600 mL) and cooled to -20° C. Methanesulfonic acid (114 mL) was then added. The mixture was warmed to 25° C. and aged for 2 h. Water (600 mL) was added and the mixture heated at 45° C. for 5 h. The organic phas... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Secondary alcohol.Primary amine | c1ccc2c(c1)CC1OC21 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | C(Cl)Cl | -20 | null | CC#N.c1ccc2c(c1)CC1OC21>C(Cl)Cl>N[C@@H]1c2ccccc2C[C@@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d0c32a5746a47be8dab7284d54a01f0 | CC#N.O[C@@H]1Cc2ccccc2[C@H]1O>>N[C@@H]1c2ccccc2C[C@@H]1O | [OH-].[Na+].S(O)(O)(=O)=O.[C@@H]1([C@@H](CC2=CC=CC=C12)O)O.C(C)#N.C(C)#N.O>>N[C@H]1[C@H](CC2=CC=CC=C12)O | CC#[N:1].O[C@@H:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C@H:10]1[OH:11]>>[NH2:1][C@@H:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C@@H:10]1[OH:11] | CC#N.O[C@@H]1Cc2ccccc2[C@H]1O | N[C@@H]1c2ccccc2C[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d881d6d5d211f65d417c36b0d4968906c9ad252517a54e2b64bea808b0ba8aac | 67fd49cf09a1a174c541805acde8e33a68a7d1aea9b7b149523a970b84a1b277 | c1ccc2c(c1)CCC2 | C-C#[N;H0;D1;+0:1].O-[C@H;D3;+0:2]1-[C:3](-[O;D1;H1:4])-[C:5]-[c:6]:[c:7]-1:[c:8]>>[NH2;D1;+0:1]-[C@H;D3;+0:2]1-[C:3](-[O;D1;H1:4])-[C:5]-[c:6]:[c:7]-1:[c:8] | 63 | [{"value": 63.0, "product": "N[C@H]1[C@H](CC2=CC=CC=C12)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C., and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary alcohol | Primary amine | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | null | 0 | null | CC#N.O[C@@H]1Cc2ccccc2[C@H]1O>>N[C@@H]1c2ccccc2C[C@@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bb4572950e154c0d8d7ae87ec0fb230d | CC#N.O[C@@H]1c2ccccc2C[C@@H]1O>>N[C@@H]1c2ccccc2C[C@@H]1O | [C@@H]1([C@H](CC2=CC=CC=C12)O)O.C(C)#N.S(O)(O)(=O)=O.O>>N[C@H]1[C@H](CC2=CC=CC=C12)O | CC#[N:1].O[C@@H:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C@@H:10]1[OH:11]>>[NH2:1][C@@H:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C@@H:10]1[OH:11] | CC#N.O[C@@H]1c2ccccc2C[C@@H]1O | N[C@@H]1c2ccccc2C[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d881d6d5d211f65d417c36b0d4968906c9ad252517a54e2b64bea808b0ba8aac | 67fd49cf09a1a174c541805acde8e33a68a7d1aea9b7b149523a970b84a1b277 | c1ccc2c(c1)CCC2 | C-C#[N;H0;D1;+0:1].O-[C@H;D3;+0:2]1-[C:3](-[O;D1;H1:4])-[C:5]-[c:6]:[c:7]-1:[c:8]>>[NH2;D1;+0:1]-[C@H;D3;+0:2]1-[C:3](-[O;D1;H1:4])-[C:5]-[c:6]:[c:7]-1:[c:8] | null | [] | -40 | CELSIUS | 1 | HOUR | Cis-1,2-indandiol (1.0 g) was dissolved in acetonitrile (20 mL), cooled to -40° C., and fuming sulfuric acid (21% SO3, 0.8 mL) was added. The mixture was aged for 1 hour with gradual warming to 0° C. Water was added and the mixture heated to 80° C. for 1 hour to provide an aqueous solution of cis-1-amino-2-indanol.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary alcohol | Primary amine | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | null | -40 | 1 | CC#N.O[C@@H]1c2ccccc2C[C@@H]1O>>N[C@@H]1c2ccccc2C[C@@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f5c19c1716b641f7a3721e4238a2fc65 | CCCC1CCC(c2ccc([Si](OC)(OC)OC)cc2)CC1.Fc1ccc(Br)cc1F>>CCCC1CCC(c2ccc(-c3ccc(F)c(F)c3)cc2)CC1 | FC=1C=C(C=CC1F)Br.O.C(CC)C1CCC(CC1)C1=CC=C(C=C1)[Si](OC)(OC)OC.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>C(CC)C1CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C=C1)F)F | CO[Si](OC)(OC)[c:11]1[cH:10][cH:9][c:8]([CH:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][CH3:1])[CH2:23][CH2:22]2)[cH:21][cH:20]1.Br[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]1>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]3)[... | CCCC1CCC(c2ccc([Si](OC)(OC)OC)cc2)CC1.Fc1ccc(Br)cc1F | CCCC1CCC(c2ccc(-c3ccc(F)c(F)c3)cc2)CC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 6c7e46f037db2db13a9d5119176e5c1599bfbcc866048f620c21387f17020f61 | 2856e130876f022e74efbbf6704a31362bbcc6a09b5f3423754264b3ad894840 | c1ccc(-c2ccc(C3CCCCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-O-[Si](-O-C)(-O-C)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 94.5 | [{"value": 40.0, "product": "C(CC)C1CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C=C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "C(CC)C1CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To 0.645 g (2 mmol) of 4-(4-propylcyclohexyl)-phenyltrimethoxysilane (Ih) was added 2.1 ml of TBAF (2.1 mmol, 1M in THF) under nitrogen, and the mixture was stirred at room temperature for 30 minutes. After the solvent was removed under reduced pressure, a solution of 3,4-difluorobromobenzene (0.463 g, 2.4 mmol) in tol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Silyl protective group | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | 0.5 | CCCC1CCC(c2ccc([Si](OC)(OC)OC)cc2)CC1.Fc1ccc(Br)cc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CCCC1CCC(c2ccc(-c3ccc(F)c(F)c3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-605c87dbb48f48b79511bcb4086ebb7c | FC(F)=C(F)C(F)(F)F.O=S(=O)=O>>O=S1(=O)OC(F)(F)C1(F)C(F)(F)F | OS(=O)(=O)O.O=S(=O)=O.FC(C(=C(F)F)F)(F)F>>C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F | [C:5]([F:6])([F:7])=[C:8]([F:9])[C:10]([F:11])([F:12])[F:13].[O:1]=[S:2](=[O:3])=[O:4]>>[O:1]=[S:2]1(=[O:3])[O:4][C:5]([F:6])([F:7])[C:8]1([F:9])[C:10]([F:11])([F:12])[F:13] | FC(F)=C(F)C(F)(F)F.O=S(=O)=O | O=S1(=O)OC(F)(F)C1(F)C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc11a660dfe158b2f097d9ced0e7160496bf1a7a654f488480d20094b26f97c9 | d984d1e98d50ababc2f79015fe04137f1ee62396665577d69700bd725f0b5290 | O=S1(=O)CCO1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D3;+0:5](-[F;D1;H0:6])=[C;H0;D3;+0:7](-[F;D1;H0:8])-[F;D1;H0:9].[O;D1;H0:10]=[S;H0;D3;+0:11](=[O;D1;H0:12])=[O;H0;D1;+0:13]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:5]1(-[F;D1;H0:6])-[C;H0;D4;+0:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[O;H0;D2;+0:13]-[S;H0;D4... | 66 | [{"value": 66.0, "product": "C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | -45 | CELSIUS | 9 | MINUTE | A 100 mL Parr™ reactor was charged with 63.8 g of 65% oleum (0.52 mole SO3), cooled to -45° C., evacuated, and then charged with 62 grams (0.44 mole) liquid hexafluoropropene from a cold trap (-78° C.). The reaction mixture was allowed to warm to room temperature. At 20° C. a slight exotherm was observed which increase... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide | Tertiary halide.Tertiary halide.Tertiary halide.Sulfonate | null | C1CSO1 | C1CSO1 | null | null | -45 | 0.15 | FC(F)=C(F)C(F)(F)F.O=S(=O)=O>>O=S1(=O)OC(F)(F)C1(F)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88d4144d85e8491ea90668f6b8fef2a3 | FC(F)=C(F)C(F)(F)F.O=S(=O)=O>>O=S1(=O)OC(F)(F)C1(F)C(F)(F)F | OS(=O)(=O)O.O=S(=O)=O.FC(C(=C(F)F)F)(F)F.FC(C(=C(F)F)F)(F)F>>C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F | [C:5]([F:6])([F:7])=[C:8]([F:9])[C:10]([F:11])([F:12])[F:13].[O:1]=[S:2](=[O:3])=[O:4]>>[O:1]=[S:2]1(=[O:3])[O:4][C:5]([F:6])([F:7])[C:8]1([F:9])[C:10]([F:11])([F:12])[F:13] | FC(F)=C(F)C(F)(F)F.O=S(=O)=O | O=S1(=O)OC(F)(F)C1(F)C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc11a660dfe158b2f097d9ced0e7160496bf1a7a654f488480d20094b26f97c9 | d984d1e98d50ababc2f79015fe04137f1ee62396665577d69700bd725f0b5290 | O=S1(=O)CCO1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D3;+0:5](-[F;D1;H0:6])=[C;H0;D3;+0:7](-[F;D1;H0:8])-[F;D1;H0:9].[O;D1;H0:10]=[S;H0;D3;+0:11](=[O;D1;H0:12])=[O;H0;D1;+0:13]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:5]1(-[F;D1;H0:6])-[C;H0;D4;+0:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[O;H0;D2;+0:13]-[S;H0;D4... | 62 | [{"value": 62.0, "product": "C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.8, "product": "C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 43 | CELSIUS | null | null | Using essentially the procedure of Example 1, the reactor was charged with 33.8 g of 67 wt. % oleum (0.28 mole SO3) and 58.0 g hexafluoropropene. After the initial exotherm (max. pressure 896 kPa at 39° C.) the mixture was heated for 13 hours at 43° C. The reactor was vented of excess hexafluoropropene (16.0 g recovere... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide | Tertiary halide.Tertiary halide.Tertiary halide.Sulfonate | null | C1CSO1 | C1CSO1 | null | null | 43 | null | FC(F)=C(F)C(F)(F)F.O=S(=O)=O>>O=S1(=O)OC(F)(F)C1(F)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42930046cadb48d6957e758ac989945a | FC(F)=C(F)C(F)(F)F.O=S(=O)=O>>O=S1(=O)OC(F)(F)C1(F)C(F)(F)F | FC(C(=C(F)F)F)(F)F.OS(=O)(=O)O.O=S(=O)=O>>C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F | [C:5]([F:6])([F:7])=[C:8]([F:9])[C:10]([F:11])([F:12])[F:13].[O:1]=[S:2](=[O:3])=[O:4]>>[O:1]=[S:2]1(=[O:3])[O:4][C:5]([F:6])([F:7])[C:8]1([F:9])[C:10]([F:11])([F:12])[F:13] | FC(F)=C(F)C(F)(F)F.O=S(=O)=O | O=S1(=O)OC(F)(F)C1(F)C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc11a660dfe158b2f097d9ced0e7160496bf1a7a654f488480d20094b26f97c9 | d984d1e98d50ababc2f79015fe04137f1ee62396665577d69700bd725f0b5290 | O=S1(=O)CCO1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D3;+0:5](-[F;D1;H0:6])=[C;H0;D3;+0:7](-[F;D1;H0:8])-[F;D1;H0:9].[O;D1;H0:10]=[S;H0;D3;+0:11](=[O;D1;H0:12])=[O;H0;D1;+0:13]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:5]1(-[F;D1;H0:6])-[C;H0;D4;+0:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[O;H0;D2;+0:13]-[S;H0;D4... | 65 | [{"value": 65.0, "product": "C1(C(OS1(=O)=O)(F)F)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | Using essentially the procedure of Example 1, the reactor was charged with 44.7 g hexafluoropropene, 45.9 g of 67 wt. % oleum and 41.5 g Fluorinert FC-77™. The reaction mixture was heated at 50° C. for 6 hours. The reactor was vented of excess HFP and the sultone layer (95.0 g) was separated and distilled to provide th... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide | Tertiary halide.Tertiary halide.Tertiary halide.Sulfonate | null | C1CSO1 | C1CSO1 | null | null | 50 | null | FC(F)=C(F)C(F)(F)F.O=S(=O)=O>>O=S1(=O)OC(F)(F)C1(F)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66f1b1423ff84fd0aecb09103bf3af98 | CCCC(=O)CC(=O)OCC.Oc1cc(O)cc(O)c1>>CCCc1cc(=O)oc2cc(O)cc(O)c12 | C1(O)=CC(O)=CC(O)=C1.C(CCC)(=O)CC(=O)OCC.FC(S(=O)(=O)O)(F)F>>OC1=C2C(=CC(OC2=CC(=C1)O)=O)CCC | CCO[C:6]([CH2:5][C:4](=O)[CH2:3][CH2:2][CH3:1])=[O:7].[OH:8][c:9]1[cH:10][c:11]([OH:12])[cH:13][c:14]([OH:15])[cH:16]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6](=[O:7])[o:8][c:9]2[cH:10][c:11]([OH:12])[cH:13][c:14]([OH:15])[c:16]12 | CCCC(=O)CC(=O)OCC.Oc1cc(O)cc(O)c1 | CCCc1cc(=O)oc2cc(O)cc(O)c12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73bb7365a8a6e9bc003da4fff3edbd064895960a48b91098cfd38bf6af202cd2 | 89a9e45776dbe9070f40025f4f55f2a7b9907ff5b9cebad1727718d85938e303 | O=c1ccc2ccccc2o1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]-[C:6].[O;D1;H1:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[C:6]-[C:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[o;H0;D2;+0:12]:[c:11](:[c:13]):[c;H0;D3;+0:10]:1:[c:8](-[O;D1;H1:7]):[c:9] | 99.1 | [{"value": 99.0, "product": "OC1=C2C(=CC(OC2=CC(=C1)O)=O)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.1, "product": "OC1=C2C(=CC(OC2=CC(=C1)O)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of anhydrous phloroglucinol (20.0 g, 0.159 mol) in ethyl butrylacetate (26.3 g; 0.167 mol) was added over 30 min to 50 g of constantly stirred trifluoromethanesulfonic acid cooled in an ice bath. A drying tube was then fined to the reaction vessel and the mixture was stirred for 16h at 25° C., after which ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Aromatic alcohol | null | c1ccccc1 | c1ccc2cccoc2c1 | c1ccc2cccoc2c1 | HO- | O | null | null | CCCC(=O)CC(=O)OCC.Oc1cc(O)cc(O)c1>O>CCCc1cc(=O)oc2cc(O)cc(O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6edcc2e8e3744c608ae582a2c614eb39 | CCOC(=O)CN1Cc2ccccc2C[C@H](N2C(=O)c3ccccc3C2=O)C1=O.O=C(Cl)OCc1ccccc1>>CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O | C(C)N(CC)CC.C(C1=CC=CC=C1)OC(=O)Cl.C1(C=2C(C(N1[C@@H]1C(N(CC3=C(C1)C=CC=C3)CC(=O)OCC)=O)=O)=CC=CC2)=O.C(C)O>>C1(=CC=CC=C1)COC(=O)N[C@@H]1C(N(CC2=C(C1)C=CC=C2)CC(=O)OCC)=O | O=C1c2ccccc2C(=O)[N:17]1[C@H:16]1[CH2:15][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[CH2:8][N:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:28]1=[O:29].Cl[C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]... | CCOC(=O)CN1Cc2ccccc2C[C@H](N2C(=O)c3ccccc3C2=O)C1=O.O=C(Cl)OCc1ccccc1 | CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC.O.NN | Protection | OtherReaction | fe3102b6b408f3d3825eb2b8e397463241cc48fe0961b1edbc9ae90e981158d6 | 1040b538a38b728279e7919c87da3a9c1d00e9f692e311a76ca8b5e574dd287d | O=C(N[C@H]1Cc2ccccc2CNC1=O)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O=C1-[N;H0;D3;+0:5](-[C:6](-[C:7])-[C:8](=[O;D1;H0:9])-[#7:10](-[C:11]-[C:12](-[#8:13])=[O;D1;H0:14])-[C:15])-C(=O)-c2:c:c:c:c:c:2-1>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]-[#7:10](-[C:15])-[C:8](=[O;D1;H0:9])-[C:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:7... | null | [] | 0 | CELSIUS | 2 | HOUR | A solution of (S)-1,3,4,5-tetrahydro-4-phthalimido-3-oxo-2H-2-benzazepine-2-acetic acid, ethyl ester (1.67 g., 4.26 mmol.) in 1.0M hydrazine hydrate in ethanol (9.0 ml., 9.0 mmol.) was stirred at room temperature under argon for 36 hours. The mixture was diluted with an equal volume of ethyl acetate, filtered and filtr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Substituted dicarboximide | Carbamic ester | c1ccc2c(c1)C[NH]C2 | null | c1ccc2c(c1)CCC[NH]C2.c1ccccc1 | HCl | C1(=CC=CC=C1)C.C(C)(=O)OCC.O.NN | 0 | 2 | CCOC(=O)CN1Cc2ccccc2C[C@H](N2C(=O)c3ccccc3C2=O)C1=O.O=C(Cl)OCc1ccccc1>C1(=CC=CC=C1)C.C(C)(=O)OCC.O.NN>CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2956910e6964c68a222931d19fd2abc | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1ccccc1F>>CC(C)(C)OC(=O)N[C@@H](COc1ccccc1[N+](=O)[O-])C(=O)O | [H-].[Na+].FC1=C(C=CC=C1)[N+](=O)[O-].C(Cl)Cl.CC(C)(OC(=O)N[C@@H](CO)C(=O)O)C>>CC(C)(OC(=O)N[C@@H](COC1=C(C=CC=C1)[N+](=O)[O-])C(=O)O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][OH:11])[C:21](=[O:22])[OH:23].F[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20])[C:21](... | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1ccccc1F | CC(C)(C)OC(=O)N[C@@H](COc1ccccc1[N+](=O)[O-])C(=O)O | null | null | CN(C=O)C.CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[C:10]-[C:11]-[OH;D1;+0:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]-[C:8](=[O;D1;H0:7])-[O;D1;H1:9]):[c:2]:[c:3] | null | [] | null | null | null | null | A solution of N-[(1,1-dimethylethoxy)carbonyl]-L-serine (24.3 g., 0.118 mole) in dry dimethylformamide (25 ml.) was added dropwise over a period of 1.0 hour to a cooled (0°, ice-salt bath) suspension of 60% sodium hydride (10.1 g., 0.25 mole) in dry dimethylformamide (200 ml.) and stirring was continued at 0° until the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C=O)C.CO.C(C)(=O)O | null | null | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1ccccc1F>CN(C=O)C.CO.C(C)(=O)O>CC(C)(C)OC(=O)N[C@@H](COc1ccccc1[N+](=O)[O-])C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-34f0afde778d417c9ab448469c03bc23 | CCOC(=O)CBr.O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1>>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OCc2ccccc2)CSC[C@H]1c1ccccc1 | [OH-].[K+].BrCC(=O)OCC.BrCC(=O)OCC.C1(=CC=CC=C1)[C@@H]1CSC[C@@H](C(N1)=O)NC(=O)OCC1=CC=CC=C1>>O=C1N([C@@H](CSC[C@@H]1NC(=O)OCC1=CC=CC=C1)C1=CC=CC=C1)CC(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][S:23][CH2:24][C@H:25]1[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O... | CCOC(=O)CBr.O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1 | CCOC(=O)CN1C(=O)[C@@H](NC(=O)OCc2ccccc2)CSC[C@H]1c1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)(=O)OCC.O1CCCC1.S(=O)(=O)([O-])[O-].[Mg+2] | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 448d2a9bdfd31665de19d5d708bf0615b1c0dce8080afe65ff0e19354a21937a | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#16:6]-[C:7]-[C:8](-[c:9])-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[C:13]>>[#16:6]-[C:7]-[C:8](-[c:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:11](=[O;D1;H0:12])-[C:13] | null | [] | null | null | null | null | A solution of (3R-cis)-tetrahydro-3-phenyl-6-[[(phenylmethoxy)carbonyl]amino]-1,4-thiazepin-5(4H)-one (1.16 g., 3.25 mmol) [prepared as described by Yanagisawa et al., J. Med. Chem., Vol. 30, p. 1984-1991 (1987)] in distilled tetrahydrofuran (30 ml.), under an atmosphere of argon, was cooled to 0° C. and treated with p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CNCCSC1 | C1C[NH]CCSC1 | C1C[NH]CCSC1.c1ccccc1.c1ccccc1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.O1CCCC1.S(=O)(=O)([O-])[O-].[Mg+2] | null | null | CCOC(=O)CBr.O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.O1CCCC1.S(=O)(=O)([O-])[O-].[Mg+2]>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OCc2ccccc2)CSC[C@H]1c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-89c19946194d4a158a9cbb1375586293 | N[C@@H](Cc1ccccc1)C(=O)O.[Br-]>>O=C(O)[C@@H](Br)Cc1ccccc1 | N(=O)[O-].[Na+].C1(=CC=CC=C1)C.N[C@@H](CC1=CC=CC=C1)C(=O)O.[Br-].[K+]>>Br[C@H](C(=O)O)CC1=CC=CC=C1 | N[C@H:4]([C:2](=[O:1])[OH:3])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[Br-:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([Br:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.[Br-] | O=C(O)[C@@H](Br)Cc1ccccc1 | null | null | C(C)(=O)O.S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 117344ae409beae3589a30d5997369184f62edb887830bd6b795e8dfdf82920d | 9544d3c5449a12cdcbad58c02e82937c94837ec7c67e3baf5ab21c8ae3b17e42 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | 1 | HOUR | A solution of L-phenylalanine (30.0 g., 0.175 mole) and potassium bromide (73.5 g., 0.618 mole) in 2.5N sulfuric acid (365 ml.) was cooled down to 0° (ice-salt bath) and treated portionwise with sodium nitrite (19.3 g., 0.28 mole) over a period of 1.0 hour. Stirring was continued for 1.0 hour at 0° and at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary halide | null | null | c1ccccc1 | Other | C(C)(=O)O.S(O)(O)(=O)=O | null | 1 | N[C@@H](Cc1ccccc1)C(=O)O.[Br-]>C(C)(=O)O.S(O)(O)(=O)=O>O=C(O)[C@@H](Br)Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d26e1da8640f4b3bb9f977d4faa64c80 | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=[N+]([O-])c1ccccc1F>>C[C@@H](Oc1ccccc1[N+](=O)[O-])[C@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)(OC(=O)N[C@@H]([C@H](O)C)C(=O)O)C.[H-].[Na+].FC1=C(C=CC=C1)[N+](=O)[O-]>>CC(C)(OC(=O)N[C@@H]([C@H](OC1=C(C=CC=C1)[N+](=O)[O-])C)C(=O)O)C | [CH3:1][C@@H:2]([OH:3])[C@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:22](=[O:23])[OH:24].F[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[CH3:1][C@@H:2]([O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12])[C@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:... | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=[N+]([O-])c1ccccc1F | C[C@@H](Oc1ccccc1[N+](=O)[O-])[C@H](NC(=O)OC(C)(C)C)C(=O)O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fc6e1b465ae75176f3fa192a660d0d622bdf538cea285b0e2b9dc00b273004b2 | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[C:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C:8](-[C;D1;H3:7])-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[c:2]:[c:3] | null | [] | 0 | CELSIUS | null | null | A solution of N-[(1,1-dimethylethoxy)carbonyl]-L-threonine (5.02 g., 22.9 mmol.) in dry dimethylformamide (10 ml.) was added dropwise over a period of 30 minutes to a cooled (0° C.) suspension of 60% sodium hydride (1.93 g., 48.25 mmol., 2.11 eq.) in dry dimethylformamide (40 ml.). The reaction was stirred at 0° C. unt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C=O)C | 0 | null | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=[N+]([O-])c1ccccc1F>CN(C=O)C>C[C@@H](Oc1ccccc1[N+](=O)[O-])[C@H](NC(=O)OC(C)(C)C)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9bbf79d4ce94d02ab717ad740996fe9 | CO.N[C@@H](CCCCO)C(=O)O>>COC(=O)[C@@H](N)CCCCO | N[C@H](C(=O)O)CCCCO.Cl.CO>>Cl.N[C@H](C(=O)OC)CCCCO | [CH3:1][OH:2].O[C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11] | CO.N[C@@H](CCCCO)C(=O)O | COC(=O)[C@@H](N)CCCCO | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[N;D1;H2:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C:4]-[C:3](-[N;D1;H2:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 2.5 | HOUR | A slurry of (S)-2-amino-6-hydroxyhexanoic acid (2.42 g., 16.4 mmole) in dry methanol (60 ml.) was treated with gaseous hydrogen chloride until the mixture began to reflux. The homogeneous solution was then stirred at room temperature for 2.5 hours. The solvent was stripped and the residue azeotroped three times with to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | null | HO- | null | null | 2.5 | CO.N[C@@H](CCCCO)C(=O)O>>COC(=O)[C@@H](N)CCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64ae065485524aae852fadf8328767e1 | CCOC(=O)CN.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>>CCCC[C@@H](C(=O)NCC(=O)OCC)N1C(=O)c2ccccc2C1=O | Cl.NCC(=O)OCC.CN1CCOCC1.C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O.OC1=CC=CC=2NN=NC21>>C1(C=2C(C(N1[C@H](C(=O)NCC(=O)OCC)CCCC)=O)=CC=CC2)=O | [NH2:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH3:14].O[CH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]([C:6](O)=[O:7])[N:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][C@@H:5]([C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH3:14])[N:15]1[C:16](=[O:17])[c:18]2[cH:1... | CCOC(=O)CN.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | CCCC[C@@H](C(=O)NCC(=O)OCC)N1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C | Acylation | OtherReaction | 0417a24920227ec1bd95566b2c81b0ce9679eff3bca069621b0123bac13830c8 | a1b92777bbff0323f68374ba2bb35d2b7447e9327d1247846bdecf2f4bf4b05b | O=C1NC(=O)c2ccccc21 | O-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5](-[#7:6](-[C:7]=[O;D1;H0:8])-[C:9]=[O;D1;H0:10])-[C;H0;D3;+0:11](-O)=[O;D1;H0:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[NH2;D1;+0:18]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[NH;D2;+0:18]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:5](-[C:4]-[C:3]-[C:2]-[CH3;D1;+0:1])-[#7:6](-[C... | null | [] | null | null | 5 | MINUTE | A slurry of glycine, ethyl ester, hydrochloride salt (2.718 g, 19.5 mmol.) in dimethylformamide (36 ml.) was treated with 4-methyl morpholine (2.60 ml., 2.39 g., 23.6 mmol.) and stirred at room temperature for 5 minutes. The mixture was then treated with (S)-2-phthalimido-6-hydroxyhexanoic acid (4.50 g., 16.2 mmol.) an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2 | HO- | CN(C=O)C | null | 0.083333 | CCOC(=O)CN.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>CN(C=O)C>CCCC[C@@H](C(=O)NCC(=O)OCC)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a4951c4532f4cb2bdd53951628d0ded | C=CC(=O)OCC.[N-]=[N+]=NC1CCc2ccccc2NC1=O>>CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21 | N(=[N+]=[N-])C1C(NC2=C(CC1)C=CC=C2)=O.C(C=C)(=O)OCC.C(C)(C)(C)O.[K]>>N(=[N+]=[N-])C1C(N(C2=C(CC1)C=CC=C2)CCC(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[NH:8]1[C:9](=[O:10])[CH:11]([N:12]=[N+:13]=[N-:14])[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[C:9](=[O:10])[CH:11]([N:12]=[N+:13]=[N-:14])[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | C=CC(=O)OCC.[N-]=[N+]=NC1CCc2ccccc2NC1=O | CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21 | null | null | O1CCCC1.C(C)(C)(C)O.O1CCCC1 | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | ba7c4bd71d9dac9254c12d0209ebbe315a4f74699e256502917bd8de51885203 | 91e54cd6e65f2c08b5c1a8b4338c7ceefc90d4eb91eb55b2313d1887e8793e60 | O=C1CCCc2ccccc2N1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:7]-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[C:1])-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A solution of 3-azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one [prepared as described by Watthey et al., J. Med. Chem., 28, p. 1511-15156 (1985)] in tetrahydrofuran/tert-butanol was cooled to 0° C. and treated with ethyl acrylate and 1N tert-butanol, potassium salt/tetrahydrofuran according to the procedure of Example ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Vinyl | Ester.Tertiary amide | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)CCCC[NH]2 | null | O1CCCC1.C(C)(C)(C)O.O1CCCC1 | null | null | C=CC(=O)OCC.[N-]=[N+]=NC1CCc2ccccc2NC1=O>O1CCCC1.C(C)(C)(C)O.O1CCCC1>CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d269152a14054777a8d6f6accb67dec8 | CC(C)(C)OC(=O)NN.CCOC(=O)CBr>>CCOC(=O)CNNC(=O)OC(C)(C)C | C(C)N(CC)CC.C(C)N(CC)CC.BrCC(=O)OCC.C(C)N(CC)CC.N(N)C(=O)OC(C)(C)C.BrCC(=O)OCC.BrCC(=O)OCC>>CC(C)(OC(=O)NNCC(=O)OCC)C | [NH2:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15] | CC(C)(C)OC(=O)NN.CCOC(=O)CBr | CCOC(=O)CNNC(=O)OC(C)(C)C | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | a10280ad95ed368c75fdf1d65f9c7b02199bd814b62740ab81803f6da82dc483 | 150ef5d6000fad15b6e5d9a7d488fe3ba905820f4205bfb36d0ee312b4df76ec | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[NH2;D1;+0:14]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[NH;D2;+0:14]-[#7:13]-[C:11](=[O;D1;H0:12])-[#8:10]-[C:7](-[C;D1;H3:6])(-[C;D1;H3:8])-[C;D1;H3:9] | null | [] | null | null | null | null | Triethylamine (13.94 ml., 0.1 mol.) was added to a solution of hydrazine carboxylic acid, 1,1-dimethylethyl ester (13.216 g., 0.1 mole) in benzene (100 ml.), followed by the addition of ethyl bromoacetate (11.09 ml., 0.1 mol.). The reaction mixture was refluxed (oil bath, 95°-100° C.) for 14 hours, after which triethyl... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide | Acylhydrazine.Ester | null | null | null | HBr | C1=CC=CC=C1 | null | null | CC(C)(C)OC(=O)NN.CCOC(=O)CBr>C1=CC=CC=C1>CCOC(=O)CNNC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fcdfc14041c342599ff1c5287314bf6b | CCCC[C@@H](N)C(=O)O.[Br-]>>CCCC[C@H](Br)C(=O)O | [Br-].[K+].N[C@H](CCCC)C(=O)O.N(=O)[O-].[Na+]>>Br[C@H](C(=O)O)CCCC | N[C@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:7](=[O:8])[OH:9].[Br-:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([Br:6])[C:7](=[O:8])[OH:9] | CCCC[C@@H](N)C(=O)O.[Br-] | CCCC[C@H](Br)C(=O)O | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 117344ae409beae3589a30d5997369184f62edb887830bd6b795e8dfdf82920d | 9544d3c5449a12cdcbad58c02e82937c94837ec7c67e3baf5ab21c8ae3b17e42 | null | N-[C@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[C@@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | -10 | CELSIUS | 1 | HOUR | Potassium bromide (15.9 g., .133 mmol.) was added to a stirred solution of D-norleucine (5.0 g., 38 mmol.) in 2.5N sulfuric acid (77 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (3.94 g., 57 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary halide | null | null | null | Other | S(O)(O)(=O)=O | -10 | 1 | CCCC[C@@H](N)C(=O)O.[Br-]>S(O)(O)(=O)=O>CCCC[C@H](Br)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2dd08204e1ab4e3cac55386d2d7fb4fa | CC(=Cc1ccccc1)C(=O)O>>CC(Cc1ccccc1)C(=O)O | CC(C(=O)O)=CC1=CC=CC=C1>>CC(C(=O)O)CC1=CC=CC=C1 | [CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12] | CC(=Cc1ccccc1)C(=O)O | CC(Cc1ccccc1)C(=O)O | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | null | null | A solution of α-methyl cinnamic acid (10.0 g., 61.7 mmol.) in dry methanol (250 ml.) was treated with 10% palladium on carbon and hydrogenated (balloon used) at room temperature for 16 hours. The reaction mixture was diluted with methanol (250 ml.), filtered through a Celite pad in a millipore unit, washing the pad wel... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | [Pd].CO | null | null | CC(=Cc1ccccc1)C(=O)O>[Pd].CO>CC(Cc1ccccc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0ab2ffb190f41a3906168de2e0367c1 | BrCc1ccccc1.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>>O=C(OCc1ccccc1)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | C([O-])([O-])=O.[Cs+].[Cs+].C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O.C(C1=CC=CC=C1)Br>>C1(C=2C(C(N1[C@H](C(=O)OCC1=CC=CC=C1)CCCCO)=O)=CC=CC2)=O | Br[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:1]=[C:2]([OH:3])[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:17]1[C:18... | BrCc1ccccc1.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | O=C(OCc1ccccc1)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(CN1C(=O)c2ccccc2C1=O)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | A slurry of cesium carbonate (3.819 g, 11.7 mmol.) and (S)-2-phthalimido-6-hydroxyhexanoic acid (6.00 g, 21.6 mmol.) in dimethylformamide (60 ml.) was treated with benzyl bromide (3.30 ml., 4.75 g., 27.7 mmol.). After stirring at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and water.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HBr | CN(C=O)C | null | 2 | BrCc1ccccc1.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>CN(C=O)C>O=C(OCc1ccccc1)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-efe923230555472e8f595617781b5290 | CI.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>>COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O.C([O-])([O-])=O.[Cs+].[Cs+].CI>>C1(C=2C(C(N1[C@H](C(=O)OC)CCCCO)=O)=CC=CC2)=O | I[CH3:1].[OH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21] | CI.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | O=C1NC(=O)c2ccccc21 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 196 | [{"value": 196.0, "product": "C1(C=2C(C(N1[C@H](C(=O)OC)CCCCO)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed succes... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2c(c1)C[NH]C2 | HI | CN(C=O)C.C(C)(=O)OCC | null | 2 | CI.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>CN(C=O)C.C(C)(=O)OCC>COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-276860cf665e4f20bd9d6fbcfc7e8c12 | CCOC(=O)CBr.C[C@@H]1CCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1>>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCC[C@H]1C | CC(C)(OC(=O)N[C@@H]1C(N[C@@H](CCC1)C)=O)C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].BrCC(=O)OCC>>CC(C)(OC(=O)N[C@@H]1C(N([C@@H](CCC1)C)CC(=O)OCC)=O)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20][CH2:21][C@H:22]1[CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH... | CCOC(=O)CBr.C[C@@H]1CCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1 | CCOC(=O)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCC[C@H]1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 21efda898581b4e7e1b0a01b07328527522c0c899fbfe8483d7f4fdc1f9e273c | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C1CCCCCN1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C:12]>>[C:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:10](-[C;D1;H3:11])-[C:12] | null | [] | null | null | 30 | MINUTE | A solution of (3S-cis)-hexahydro-3-[[(1,1-dimethylethoxy)carbonyl]amino]-7-methyl-2H-azepin-2-one [prepared as described in Example 64(f), 500 mg., 2.06 mmol.] in tetrahydrofuran (13 ml.) at room temperature under argon was treated dropwise with 1.0M lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 ml., 2.7 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1 | HBr | O1CCCC1 | null | 0.5 | CCOC(=O)CBr.C[C@@H]1CCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1>O1CCCC1>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCC[C@H]1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6701048b9aed462d813326f7541d1d53 | CC(C)NC(C)C.ClCCCCBr.O=C(O)C1CCCC1>>CC(C)[N-]C(C)C.O=C(O)C1(CCCCCl)CCCC1.[Li+] | BrCCCCCl.C1(CCCC1)C(=O)O.C(C)(C)NC(C)C.C(CCC)[Li]>>C(C)(C)[N-]C(C)C.[Li+].ClCCCCC1(CCCC1)C(=O)O | [CH3:1][CH:2]([CH3:3])[NH:4][CH:5]([CH3:6])[CH3:7].Br[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].[O:8]=[C:9]([OH:10])[CH:11]1[CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[N-:4][CH:5]([CH3:6])[CH3:7].[O:8]=[C:9]([OH:10])[C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][CH2:19][CH2:20]1.[Li+:21] | CC(C)NC(C)C.ClCCCCBr.O=C(O)C1CCCC1 | CC(C)[N-]C(C)C.O=C(O)C1(CCCCCl)CCCC1.[Li+] | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 77153b7242f8754879e3f0b886657cd5957a50555e81a521ab32e496bf739211 | 9ba1e0467902f373f7806da8e18ec7a85760b64f74aa649da2579d00e73d9ca4 | C1CCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])-[NH;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[O;D1;H0:11]=[C:12](-[O;D1;H1:13])-[CH;D3;+0:14]1-[C:15]-[C:16]-[C:17]-[C:18]-1>>[C;D1;H3:4]-[C:5](-[C;D1;H3:6])-[N-;H0;D2:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:14]1(-[C:12](=[O... | null | [] | -74 | CELSIUS | 15 | MINUTE | A solution of lithium diisopropylamide was prepared under nitrogen from diisopropylamine (31.0 ml., 220 mmol.) and n-butyl lithium (1.5M in hexane, 88.0 ml., 220 mmol.) in tetrahydrofuran (80 ml.), maintaining the temperature between -3° C. -1° C. After stirring 15 minutes, cyclopentanecarboxylic acid (11.4 g., 100 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | null | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | O1CCCC1 | -74 | 0.25 | CC(C)NC(C)C.ClCCCCBr.O=C(O)C1CCCC1>O1CCCC1>CC(C)[N-]C(C)C.O=C(O)C1(CCCCCl)CCCC1.[Li+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-765f7e8377cb44718d3884bdc87dc102 | CCCCC.CCOCC.CCOCC>>O=C1CCCCCC12CCCC2 | C(C)(C)(C)[Li].CCOCC.CCOCC.CCCCC>>C1CCCC12C(CCCCC2)=O | [CH3:8][CH2:12][CH2:11][CH2:10][CH3:9].C([O:1][CH2:2][CH3:3])[CH3:5].CCO[CH2:7][CH3:6]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][CH2:11][CH2:12]2 | CCCCC.CCOCC.CCOCC | O=C1CCCCCC12CCCC2 | null | null | null | Acylation | OtherReaction | 7f9c56080232237cb2af9c91b9ac11dba4e3d417835241b7fb2a95600fe5c061 | 71cd9ffc2461c2b8f2c58f8e59f7f0e3e5cc0afbee292adb82f64bbd7fde8e75 | O=C1CCCCCC12CCCC2 | C-C-O-[CH2;D2;+0:1]-[CH3;D1;+0:2].[CH3;D1;+0:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-C-[CH3;D1;+0:6].[CH3;D1;+0:7]-[C:8]-[C:9]-[C:10]-[CH3;D1;+0:11]>>[O;H0;D1;+0:5]=[C;H0;D3;+0:4]1-[CH2;D2;+0:3]-[C:12]-[CH2;D2;+0:6]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:7]-12-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-2 | null | [] | -100 | CELSIUS | null | null | t-Butyl lithium (1.7M in pentane, 20.0 ml., 34 mmol.) was slowly added to ether (38 ml.) at -20° C. as the reaction was further cooled to -100° C. in a methanol/dry ice/liquid nitrogen bath. To this -100° C. solution was added the product from part (c) (5.0 g., 16.1 mmol.) in 2:1 ether/pentane (3 ml.) over 35 minutes, ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | null | C1CCCC2(CC1)CCCC2 | C1CCCC2(CC1)CCCC2 | HO- | null | -100 | null | CCCCC.CCOCC.CCOCC>>O=C1CCCCCC12CCCC2 |
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