dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f218942ee1f4928a90ada5177e921b7 | NCc1ccccc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>O=C1Cc2cc(S(=O)(=O)NCc3ccccc3)ccc2N1 | Cl.ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.C(C1=CC=CC=C1)N.N1=CC=CC=C1>>C(C1=CC=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.Cl[S:7]([c:6]1[cH:5][c:4]2[c:20]([cH:19][cH:18]1)[NH:21][C:2](=[O:1])[CH2:3]2)(=[O:8])=[O:9]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[NH:21]1 | NCc1ccccc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | O=C1Cc2cc(S(=O)(=O)NCc3ccccc3)ccc2N1 | null | null | ClCCl.C(C)(=O)OCC | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2cc(S(=O)(=O)NCc3ccccc3)ccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[C:8]-[c:9])-[c:4](:[c:5]):[c:6] | 66.1 | [{"value": 66.0, "product": "C(C1=CC=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "C(C1=CC=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), benzylamine (0.918 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and acidified with 1 N hydrochloric acid (16 mL). The organic layer was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | HCl | ClCCl.C(C)(=O)OCC | null | 4 | NCc1ccccc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl.C(C)(=O)OCC>O=C1Cc2cc(S(=O)(=O)NCc3ccccc3)ccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b80eeb8993cb48e39afe93a6e754ca1a | NCc1ccc(F)cc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>O=C1Cc2cc(S(=O)(=O)NCc3ccc(F)cc3)ccc2N1 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.FC1=CC=C(CN)C=C1.N1=CC=CC=C1>>FC1=CC=C(CNS(=O)(=O)C=2C=C3CC(NC3=CC2)=O)C=C1 | [NH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.Cl[S:7]([c:6]1[cH:5][c:4]2[c:21]([cH:20][cH:19]1)[NH:22][C:2](=[O:1])[CH2:3]2)(=[O:8])=[O:9]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][CH2:11][c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[cH:19][cH:20][c:21]2[NH:22]1 | NCc1ccc(F)cc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | O=C1Cc2cc(S(=O)(=O)NCc3ccc(F)cc3)ccc2N1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2cc(S(=O)(=O)NCc3ccccc3)ccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[C:8]-[c:9])-[c:4](:[c:5]):[c:6] | 84 | [{"value": 84.0, "product": "FC1=CC=C(CNS(=O)(=O)C=2C=C3CC(NC3=CC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 5-chlorosulfonyl-2-oxindole (5.0 g), 4-fluorobenzylamine (3.0 mL) and pyridine (3.5 mL) in dichloromethane (30 mL) was stirred at room temperature for 4 hours. The precipitate was filtered, washed with dichloromethane and dried to give 5.8 g (84%) of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-fluoro-... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | HCl | ClCCl | null | 4 | NCc1ccc(F)cc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl>O=C1Cc2cc(S(=O)(=O)NCc3ccc(F)cc3)ccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9512e5995e1e4f05808eeea03d9e3e61 | Nc1cccc(Cl)c1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>O=C1Cc2cc(S(=O)(=O)Nc3cccc(Cl)c3)ccc2N1 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.ClC=1C=C(N)C=CC1.N1=CC=CC=C1>>ClC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1.Cl[S:7]([c:6]1[cH:5][c:4]2[c:20]([cH:19][cH:18]1)[NH:21][C:2](=[O:1])[CH2:3]2)(=[O:8])=[O:9]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]3)[cH:18][cH:19][c:20]2[NH:21]1 | Nc1cccc(Cl)c1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | O=C1Cc2cc(S(=O)(=O)Nc3cccc(Cl)c3)ccc2N1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2cc(S(=O)(=O)Nc3ccccc3)ccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 74 | [{"value": 74.0, "product": "ClC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of 5-chlorosulfonyl-2-oxindole (5 g), 3-chloroaniline (2.74 mL) and pyridine (3.5 mL) in dichloromethane (30 mL) was stirred at room temperature for overnight. The precipitate was filtered, washed with dichloromethane and dried to give 5.2 g (74%) 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chloro-pheny... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | HCl | ClCCl | null | 8 | Nc1cccc(Cl)c1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl>O=C1Cc2cc(S(=O)(=O)Nc3cccc(Cl)c3)ccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b71dcc59c17f45b0a42c35086404e79c | COc1ccccc1N.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>COc1ccccc1NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.COC=1C(=CC=CC1)N.N1=CC=CC=C1>>COC1=C(C=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[CH2:19][C:20](=[O:21])[NH:22]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[CH2:19][C:20](=[O:21])[NH:22]2 | COc1ccccc1N.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | COc1ccccc1NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2cc(S(=O)(=O)Nc3ccccc3)ccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 37 | [{"value": 37.0, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-chlorosulfonyl-2-oxindole (3 g), o-anisidine (1.8 mL) and pyridine (2.1 mL) in dichloromethane (20 mL) was stirred at room temperature for overnight at which time the red color solid was present. The solid was filtered, washed with ethanol and dried under vacuum to yield 1.5 g (37%) of 2-oxo-2,3-dihydro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HCl | ClCCl | null | null | COc1ccccc1N.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl>COc1ccccc1NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-49d25400c31f48409a84e78483e89006 | Nc1cccnc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.NC=1C=NC=CC1>>N1=CC(=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [NH2:10][c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1.Cl[S:7]([c:6]1[cH:5][c:4]2[c:19]([cH:18][cH:17]1)[NH:20][C:2](=[O:1])[CH2:3]2)(=[O:8])=[O:9]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[cH:17][cH:18][c:19]2[NH:20]1 | Nc1cccnc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12])-[c:4](:[c:5]):[c:6] | 38 | [{"value": 38.0, "product": "N1=CC(=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.4, "product": "N1=CC(=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-chlorosulfonyl-2-oxindole (3 g) and 3-aminopyridine (1.46 g) in pyridine (15 mL) was stirred at room temperature for overnight at which time the brown color solid was present. The precipitate was filtered, washed with ethanol and dried under vacuum to yield 1.4 g (38%) of 2-oxo-2,3-dihydro-1H-indole-5-s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2.c1ccncc1 | HCl | N1=CC=CC=C1 | null | null | Nc1cccnc1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>N1=CC=CC=C1>O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-761f226795de4ac6b0c3118f5cfe2d33 | COCCN.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>COCCNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.COCCN.N1=CC=CC=C1>>COCCNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][C:16](=[O:17])[NH:18]2>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][C:16](=[O:17])[NH:18]2 | COCCN.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | COCCNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2ccccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 33 | [{"value": 33.0, "product": "COCCNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-chlorosulfonyl-2-oxindole (5 g), 2-methoxyethylamine (2.25 mL) and pyridine (7 mL) in dichloromethane (30 mL) was stirred at room temperature for 4 hours. The reaction was concentrated and dichloromethane (15 mL) was added. The precipitate was filtered, washed with dichloromethane and dried to give 1.9 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2 | HCl | ClCCl | null | null | COCCN.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl>COCCNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4fe8631dc68e4b4fafdf204b79c372cd | O=C1Cc2ccccc2N1.O=S(=O)(O)Cl>>O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | ClS(=O)(=O)O.N1C(CC2=CC=CC=C12)=O>>ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:11][cH:12][c:13]2[NH:14]1.O[S:7](=[O:8])(=[O:9])[Cl:10]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([S:7](=[O:8])(=[O:9])[Cl:10])[cH:11][cH:12][c:13]2[NH:14]1 | O=C1Cc2ccccc2N1.O=S(=O)(O)Cl | O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | null | null | O | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 1d9d5a8f3073ec09a40a230cbc17ee68db12527a82342f5e24b541bcc0969ba1 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | O=C1Cc2ccccc2N1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 50 | [{"value": 50.0, "product": "ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a 100 mL flask charged with 27 mL of chlorosulfonic acid, 13.3 g of 2-oxindole was added slowly. The reaction temperature was maintained below 30° C. during the addition. After the addition, the reaction mixture was stirred at room temperature for 1.5 hour, heated to 68° C. for 1 hour, cooled, and poured into water.... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HO- | O | null | 1.5 | O=C1Cc2ccccc2N1.O=S(=O)(O)Cl>O>O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b820d9b2cbf24448ad491e3ac1473356 | O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1.[NH4+]>>NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.[OH-].[NH4+]>>NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | Cl[S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:12](=[O:13])[NH:14]2.[NH4+:1]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:12](=[O:13])[NH:14]2 | O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1.[NH4+] | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | null | null | C(C)O | Acylation | OtherReaction | 672a14b4f1ef0b966898e1b4c118f241f21df1d6e087372155b9d0c840dac61f | 29e1633db8f1f00444181a0bcac91d574ed806fddf9165be4c8478fc32a80994 | O=C1Cc2ccccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 20 | [{"value": 20.0, "product": "NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 5-Chlorosulfonyl-2-oxindole (2.1 g) was added to 10 mL of ammonium hydroxide in 10 mL of ethanol and stirred at room temperature overnight. The mixture was concentrated and the solid collected by vacuum filtration to give 0.4 g (20% yield) of 5-aminosulfonyl-2-oxindole as an off-white solid.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2 | HCl | C(C)O | null | 8 | O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1.[NH4+]>C(C)O>NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc2860086c3648638a6b6a5ca5490ccd | CN.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.CN>>CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [CH3:1][NH2:2].Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:13](=[O:14])[NH:15]2>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:13](=[O:14])[NH:15]2 | CN.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | null | null | O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2ccccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 88 | [{"value": 88.0, "product": "CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 3.38 g of 5-chlorosulfonyl-2-oxindole in 10 mL of 2 M methylamine in tetrahydrofuran was stirred at room temperature for 4 hours at which time a white solid was present. The precipitate was collected by vacuum filtration, washed twice with 5 mL of water each time and dried under vacuum at 40° C. overnig... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2 | HCl | O1CCCC1 | null | 4 | CN.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>O1CCCC1>CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c04674d1561d4ba9821fdd21961b06c9 | CNC.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.CNC>>CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C | [CH3:1][NH:2][CH3:3].Cl[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][C:14](=[O:15])[NH:16]2>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][C:14](=[O:15])[NH:16]2 | CNC.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2 | null | null | CO | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C1Cc2ccccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 79 | [{"value": 79.0, "product": "CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 2.3 g of 5-chlorosulfonyl-2-oxindole in 10 mL of 2 M dimethylamine in methanol was stirred at room temperature for 4 hours at which time a white solid was present. The precipitate was collected by vacuum filtration, washed with 5 mL of 1 N sodium hydroxide and 5 mL of 1 N hydrochloric acid and dried und... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccc2c(c1)CCN2 | HCl | CO | null | 4 | CNC.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>CO>CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8db5f9b6624f4568a95dc50f93c1c1cd | CC(C)N.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>CC(C)NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.C(C)(C)N.N1=CC=CC=C1>>C(C)(C)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [CH3:1][CH:2]([CH3:3])[NH2:4].Cl[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][C:15](=[O:16])[NH:17]2>>[CH3:1][CH:2]([CH3:3])[NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][C:15](=[O:16])[NH:17]2 | CC(C)N.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | CC(C)NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1Cc2ccccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 45.5 | [{"value": 45.0, "product": "C(C)(C)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.5, "product": "C(C)(C)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 3 g of 5-chlorosulfonyl-2-oxindole, 1.15 g of isopropylamine and 1.2 mL of pyridine in 50 mL of dichloromethane was stirred at room temperature for 4 hours at which time a white solid was present. The precipitate was collected by vacuum filtration. The solids were slurry-washed with hot ethanol, cooled,... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCN2 | HCl | ClCCl | null | 4 | CC(C)N.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl>CC(C)NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8fff4cc818e435b81ea9979252c47a9 | O=C1Cc2cc(Br)ccc2N1.OB(O)c1ccccc1>>O=C1Cc2cc(-c3ccccc3)ccc2N1 | C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C2CC(NC2=CC1)=O.C(C)O>>C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O | Br[c:6]1[cH:5][c:4]2[c:15]([cH:14][cH:13]1)[NH:16][C:2](=[O:1])[CH2:3]2.OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[cH:13][cH:14][c:15]2[NH:16]1 | O=C1Cc2cc(Br)ccc2N1.OB(O)c1ccccc1 | O=C1Cc2cc(-c3ccccc3)ccc2N1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[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] | 77.3 | [{"value": 77.0, "product": "C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 12 | HOUR | 5-Bromo-2-oxindole (5 g, 23.5 mmol) was dissolved in 110 mL of toluene and 110 mL of ethanol with stirring and a little heating. Tetrakis(triphenylphosphine)-palladium(0) (1.9 g, 1.6 mmol) was added followed by a 2 M aq. solution of sodium carbonate (40 mL, 80 mmol). To this mixture benzene boronic acid (3.7 g, 30.6 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)(=O)OCC | 100 | 12 | O=C1Cc2cc(Br)ccc2N1.OB(O)c1ccccc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)(=O)OCC>O=C1Cc2cc(-c3ccccc3)ccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a35eb37090d4673953f933d414f1791 | O=C1Cc2ccc(Br)cc2N1.OB(O)c1cccnc1>>O=C1Cc2ccc(-c3cccnc3)cc2N1 | C([O-])([O-])=O.[Na+].[Na+].C(CC)(O)O.N1=CC(=CC=C1)B(O)O.C(C)O.BrC1=CC=C2CC(NC2=C1)=O>>N1=CC(=CC=C1)C1=CC=C2CC(NC2=C1)=O | Br[c:7]1[cH:6][cH:5][c:4]2[c:15]([cH:14]1)[NH:16][C:2](=[O:1])[CH2:3]2.OB(O)[c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][n:12][cH:13]3)[cH:14][c:15]2[NH:16]1 | O=C1Cc2ccc(Br)cc2N1.OB(O)c1cccnc1 | O=C1Cc2ccc(-c3cccnc3)cc2N1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | a91ebef74c819bbf975cd59349af7e75fd7403a76d7a54fde0217a7e75825ae7 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2ccc(-c3cccnc3)cc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[#7:4]):[c:5]:[c:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:1>>[#7:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:1):[c:5]:[c:6] | 42 | [{"value": 42.0, "product": "N1=CC(=CC=C1)C1=CC=C2CC(NC2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.0, "product": "N1=CC(=CC=C1)C1=CC=C2CC(NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL of toluene and 60 mL of ethanol with stirring and a little heating tetrakis(triphenyl-phosphine)palladium(0) (2.3 g, 1.9 mmol) was added followed by a 2 M aqueous solution of sodium carbonate (50 mL, 100 mmol) and pyridine-3-boronic acid propane di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccncc1 | c1ccc2c(c1)CCN2.c1ccncc1 | c1ccc2c(c1)CCN2.c1ccncc1 | HBr.B | C1(=CC=CC=C1)C.C(C)(=O)OCC | 100 | null | O=C1Cc2ccc(Br)cc2N1.OB(O)c1cccnc1>C1(=CC=CC=C1)C.C(C)(=O)OCC>O=C1Cc2ccc(-c3cccnc3)cc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55ea1a3635b74f3a8ec5c8236a434314 | O=[N+]([O-])c1cc(Br)ccc1F.OB(O)c1ccccc1>>O=[N+]([O-])c1cc(-c2ccccc2)ccc1F | C1(=CC=CC=C1)B(O)O.BrC=1C=CC(=C(C1)[N+](=O)[O-])F.C([O-])([O-])=O.[Na+].[Na+]>>FC1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=O)[O-] | Br[c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:15]([F:16])[cH:14][cH:13]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15]1[F:16] | O=[N+]([O-])c1cc(Br)ccc1F.OB(O)c1ccccc1 | O=[N+]([O-])c1cc(-c2ccccc2)ccc1F | 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)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[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] | 96.2 | [{"value": 96.0, "product": "FC1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.2, "product": "FC1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetrakis(triphenylphosphine)palladium (0.8 g) was added to a mixture of benzeneboronic acid (3.1 g), 5-bromo-2-fluoronitrobenzene (5 g) and 22 mL of 2 M sodium carbonate solution in toluene (50 mL) and ethanol (50 mL). The mixture was heated to reflux for 2 hours, concentrated, and the residue was extracted twice with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | 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)O | null | null | O=[N+]([O-])c1cc(Br)ccc1F.OB(O)c1ccccc1>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)O>O=[N+]([O-])c1cc(-c2ccccc2)ccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93f14a92d7b948aeb7136339faf59c3b | COC(=O)CC(=O)OC.O=[N+]([O-])c1cc(-c2ccccc2)ccc1F>>COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2)cc1[N+](=O)[O-] | FC1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=O)[O-].C(CC(=O)OC)(=O)OC.[H-].[Na+]>>COC(C(C(=O)OC)C1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=O)[O-])=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[O:8][CH3:9].F[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[N+:22](=[O:23])[O-:24]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[N+:... | COC(=O)CC(=O)OC.O=[N+]([O-])c1cc(-c2ccccc2)ccc1F | COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2)cc1[N+](=O)[O-] | null | null | CS(=O)C | C-C Coupling | OtherReaction | 5a1171068c2a10d196160f01101b1c97354196d6923cfc455c6b686284d6c6f2 | c0fb657475d92a5e1ab643a3f03921ebe4d047c8d805f98b012a5df3f9fb1f6c | c1ccc(-c2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[C:9](=[O;D1;H0:10])-[#8:8]-[C;D1;H3:7])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]):[c:2]:[c:3] | null | [] | 100 | CELSIUS | null | null | Dimethyl malonate (10 mL) in 25 mL of dimethylsulfoxide was added dropwise to 3.5 g of sodium hydride suspended in 25 mL of dimethylsulfoxide and the mixture heated at 100° C. for 10 minutes. The mixture was cooled to room temperature and 4.7 g of 4-fluoro-3-nitrobiphenyl in 25 mL of dimethylsulfoxide was added. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CS(=O)C | 100 | null | COC(=O)CC(=O)OC.O=[N+]([O-])c1cc(-c2ccccc2)ccc1F>CS(=O)C>COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72684266cfd64a47babebee184279430 | O=C(O)Cc1ccc(-c2ccccc2)cc1[N+](=O)[O-]>>O=C1Cc2ccc(-c3ccccc3)cc2N1 | [N+](=O)([O-])C=1C=C(C=CC1CC(=O)O)C1=CC=CC=C1>>C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O | O=[N+:16]([O-])[c:15]1[c:4]([CH2:3][C:2](O)=[O:1])[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][c:15]2[NH:16]1 | O=C(O)Cc1ccc(-c2ccccc2)cc1[N+](=O)[O-] | O=C1Cc2ccc(-c3ccccc3)cc2N1 | null | [Fe] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | e98c7e13a0e22318df8d26b28a8117bfb6ce0313bb5b14de92a87461040b8923 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Cc2ccc(-c3ccccc3)cc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[c:5](-[N+;H0;D3:6](=O)-[O-]):[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[c:4]:[c:5](:[c:7])-[NH;D2;+0:6]-1 | 93 | [{"value": 93.0, "product": "C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Iron chips (2.6 g) were added all at once to 4.5 g of 3-nitrobiphenyl-4-acetic acid in 40 mL of acetic acid. The mixture was heated to reflux for 2 hours, concentrated to dryness and taken up in ethyl acetate. The solids were removed by filtration and the filtrate was washed twice with 1 N hydrochloric acid and brine a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1 | Other | [Fe].C(C)(=O)O | null | null | O=C(O)Cc1ccc(-c2ccccc2)cc1[N+](=O)[O-]>[Fe].C(C)(=O)O>O=C1Cc2ccc(-c3ccccc3)cc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95c0514ee8dd40ee8d7b1d05041a7485 | COC(=O)CC(=O)OC.COc1ccccc1-c1ccc(F)c([N+](=O)[O-])c1>>COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2OC)cc1[N+](=O)[O-] | FC1=C(C=C(C=C1)C1=C(C=CC=C1)OC)[N+](=O)[O-].C(CC(=O)OC)(=O)OC.[H-].[Na+]>>COC1=C(C=CC=C1)C1=CC(=C(C=C1)C(C(=O)OC)C(=O)OC)[N+](=O)[O-] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[O:8][CH3:9].F[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20][CH3:21])[cH:22][c:23]1[N+:24](=[O:25])[O-:26]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[O:20][... | COC(=O)CC(=O)OC.COc1ccccc1-c1ccc(F)c([N+](=O)[O-])c1 | COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2OC)cc1[N+](=O)[O-] | null | null | CS(=O)C | C-C Coupling | OtherReaction | 5a1171068c2a10d196160f01101b1c97354196d6923cfc455c6b686284d6c6f2 | c0fb657475d92a5e1ab643a3f03921ebe4d047c8d805f98b012a5df3f9fb1f6c | c1ccc(-c2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[C:9](=[O;D1;H0:10])-[#8:8]-[C;D1;H3:7])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]):[c:2]:[c:3] | null | [] | 100 | CELSIUS | null | null | Dimethyl malonate (14 mL) was added dropwise to 2.9 g of sodium hydride suspended in 50 mL of dimethylsulfoxide. The mixture was heated at 100° C. for 15 minutes and cooled to room temperature. Crude 4-fluoro-2′-methoxy-3-nitrobiphenyl in 60 mL of dimethylsulfoxide was added and the mixture was heated at 100° C. for 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CS(=O)C | 100 | null | COC(=O)CC(=O)OC.COc1ccccc1-c1ccc(F)c([N+](=O)[O-])c1>CS(=O)C>COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2OC)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47b2bfe7d4eb4a989b1b246f46f8e9fa | COc1ccccc1-c1ccc(CC(=O)O)c([N+](=O)[O-])c1>>COc1ccccc1-c1ccc2c(c1)NC(=O)C2 | COC1=C(C=CC=C1)C1=CC(=C(C=C1)CC(=O)O)[N+](=O)[O-]>>COC1=C(C=CC=C1)C1=CC=C2CC(NC2=C1)=O | O=[N+:15]([O-])[c:13]1[c:12]([CH2:18][C:16](O)=[O:17])[cH:11][cH:10][c:9](-[c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[NH:15][C:16](=[O:17])[CH2:18]2 | COc1ccccc1-c1ccc(CC(=O)O)c([N+](=O)[O-])c1 | COc1ccccc1-c1ccc2c(c1)NC(=O)C2 | null | [Fe] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | e98c7e13a0e22318df8d26b28a8117bfb6ce0313bb5b14de92a87461040b8923 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Cc2ccc(-c3ccccc3)cc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[c:5](-[N+;H0;D3:6](=O)-[O-]):[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[c:4]:[c:5](:[c:7])-[NH;D2;+0:6]-1 | 69 | [{"value": 69.0, "product": "COC1=C(C=CC=C1)C1=CC=C2CC(NC2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "COC1=C(C=CC=C1)C1=CC=C2CC(NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Iron chips (5 g) were added in one portion to 9.8 g of 2′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL of glacial acetic acid and heated to 100° C. for 3 hours. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1 N hy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2 | Other | [Fe].C(C)(=O)O | 100 | null | COc1ccccc1-c1ccc(CC(=O)O)c([N+](=O)[O-])c1>[Fe].C(C)(=O)O>COc1ccccc1-c1ccc2c(c1)NC(=O)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0aedcfaa8c0a46d5b70cbff208230660 | COc1cccc(B(O)O)c1.O=[N+]([O-])c1cc(Br)ccc1F>>COc1cccc(-c2ccc(F)c([N+](=O)[O-])c2)c1 | COC=1C=C(C=CC1)B(O)O.BrC=1C=CC(=C(C1)[N+](=O)[O-])F.C([O-])([O-])=O.[Na+].[Na+]>>FC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)[N+](=O)[O-] | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18]1.Br[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[cH:18]1 | COc1cccc(B(O)O)c1.O=[N+]([O-])c1cc(Br)ccc1F | COc1cccc(-c2ccc(F)c([N+](=O)[O-])c2)c1 | 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 | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[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:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 77 | [{"value": 77.0, "product": "FC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "FC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetrakis(triphenylphosphine)palladium (0.7 g) was added to a mixture of 3.8 g of 3-methoxyphenylboronic acid, 5 g of 5-bromo-2-fluoronitrobenzene and 11 mL of 2 M sodium carbonate solution in 100 mL of toluene. The mixture was heated to reflux for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | 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.O.C1(=CC=CC=C1)C | null | null | COc1cccc(B(O)O)c1.O=[N+]([O-])c1cc(Br)ccc1F>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.O.C1(=CC=CC=C1)C>COc1cccc(-c2ccc(F)c([N+](=O)[O-])c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec1c217554b04edcb37dde22329173fb | COc1cccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)c1>>COc1cccc(-c2ccc3c(c2)NC(=O)C3)c1 | COC=1C=C(C=CC1)C1=CC(=C(C=C1)CC(=O)O)[N+](=O)[O-]>>COC=1C=C(C=CC1)C1=CC=C2CC(NC2=C1)=O | O=[N+:14]([O-])[c:12]1[c:11]([CH2:17][C:15](O)=[O:16])[cH:10][cH:9][c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18]2)[cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[NH:14][C:15](=[O:16])[CH2:17]3)[cH:18]1 | COc1cccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)c1 | COc1cccc(-c2ccc3c(c2)NC(=O)C3)c1 | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | e98c7e13a0e22318df8d26b28a8117bfb6ce0313bb5b14de92a87461040b8923 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Cc2ccc(-c3ccccc3)cc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[c:5](-[N+;H0;D3:6](=O)-[O-]):[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[c:4]:[c:5](:[c:7])-[NH;D2;+0:6]-1 | 75 | [{"value": 75.0, "product": "COC=1C=C(C=CC1)C1=CC=C2CC(NC2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "COC=1C=C(C=CC1)C1=CC=C2CC(NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3′-Methoxy-3-nitrobiphenyl-4-acetic acid (5.2 g) was dissolved in methanol and hydrogenated over 0.8 g of 10% palladium on carbon for 3 hours at room temperature. The catalyst was removed by filtration, washed with methanol and the filtrates combined and concentrated to give a brown solid. The solid was purified by col... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2 | Other | [Pd].CO | null | null | COc1cccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)c1>[Pd].CO>COc1cccc(-c2ccc3c(c2)NC(=O)C3)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40cd27683e8240bf9bb68ae563315f45 | COc1ccc(B(O)O)cc1.O=[N+]([O-])c1cc(Br)ccc1F>>COc1ccc(-c2ccc(F)c([N+](=O)[O-])c2)cc1 | COC1=CC=C(C=C1)B(O)O.BrC=1C=CC(=C(C1)[N+](=O)[O-])F.C([O-])([O-])=O.[Na+].[Na+]>>FC1=C(C=C(C=C1)C1=CC=C(C=C1)OC)[N+](=O)[O-] | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1.Br[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]2)[cH:17][cH:18]1 | COc1ccc(B(O)O)cc1.O=[N+]([O-])c1cc(Br)ccc1F | COc1ccc(-c2ccc(F)c([N+](=O)[O-])c2)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)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[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: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] | null | [] | null | null | null | null | Tetrakis(triphenylphosphine)palladium (1 g) was added to a mixture of 5 g of 4-methoxyphenylboronic acid, 6.6 g of 5-bromo-2-fluoronitrobenzene and 30 mL of 2 M sodium carbonate solution in 50 mL of toluene and 50 mL of ethanol. The mixture was heated to reflux for 2 hours, concentrated, and the residue extracted twice... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | 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)O | null | null | COc1ccc(B(O)O)cc1.O=[N+]([O-])c1cc(Br)ccc1F>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)O>COc1ccc(-c2ccc(F)c([N+](=O)[O-])c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9b374d7d7684b1a8263159d26e065d4 | COc1ccc(-c2ccc(C(C(=O)[O-])C(=O)[O-])c([N+](=O)[O-])c2)cc1>>COc1ccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)cc1 | COC1=CC=C(C=C1)C1=CC(=C(C=C1)C(C(=O)[O-])C(=O)[O-])[N+](=O)[O-]>>COC1=CC=C(C=C1)C1=CC(=C(C=C1)CC(=O)O)[N+](=O)[O-] | O=C([O-])[CH:11]([c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]2)[cH:19][c:15]1[N+:16](=[O:17])[O-:18])[C:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH2:11][C:12](=[O:13])[OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[cH:20][cH:21]1 | COc1ccc(-c2ccc(C(C(=O)[O-])C(=O)[O-])c([N+](=O)[O-])c2)cc1 | COc1ccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)cc1 | null | null | Cl | Reduction | OtherReaction | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | c1ccc(-c2ccccc2)cc1 | O=C(-[O-])-[CH;D3;+0:1](-[C:2](-[O-;H0;D1:3])=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[O;D1;H0:4]=[C:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Crude 4′-methoxy-3-nitro-biphenyl-4-malonate was heated at 100° C. in 60 mL of 6 N hydrochloric acid for 15 hours and cooled. The precipitate was collected by filtration, washed with water and hexane, and dried to give 7.2 g of crude 4′-methoxy-3-nitrobiphenyl-4-acetic acid as a light tan solid.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | Cl | null | null | COc1ccc(-c2ccc(C(C(=O)[O-])C(=O)[O-])c([N+](=O)[O-])c2)cc1>Cl>COc1ccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c22e35016f334ef985010b8adb49a67a | COc1ccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)cc1>>COc1ccc(-c2ccc3c(c2)NC(=O)C3)cc1 | COC1=CC=C(C=C1)C1=CC(=C(C=C1)CC(=O)O)[N+](=O)[O-]>>COC1=CC=C(C=C1)C1=CC=C2CC(NC2=C1)=O | O=[N+:13]([O-])[c:11]1[c:10]([CH2:16][C:14](O)=[O:15])[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[NH:13][C:14](=[O:15])[CH2:16]3)[cH:17][cH:18]1 | COc1ccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)cc1 | COc1ccc(-c2ccc3c(c2)NC(=O)C3)cc1 | null | [Fe] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | e98c7e13a0e22318df8d26b28a8117bfb6ce0313bb5b14de92a87461040b8923 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Cc2ccc(-c3ccccc3)cc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[c:5](-[N+;H0;D3:6](=O)-[O-]):[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[c:4]:[c:5](:[c:7])-[NH;D2;+0:6]-1 | 54 | [{"value": 54.0, "product": "COC1=CC=C(C=C1)C1=CC=C2CC(NC2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": "COC1=CC=C(C=C1)C1=CC=C2CC(NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Iron chips (3.6 g) were added in one portion to 7.2 g of 4′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL of glacial acetic acid and heated at 100° C. overnight. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1 N hy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2 | Other | [Fe].C(C)(=O)O | 100 | null | COc1ccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)cc1>[Fe].C(C)(=O)O>COc1ccc(-c2ccc3c(c2)NC(=O)C3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-be65052310f24bffa8ad90b56f56a7dc | COc1ccc(N)cc1Cl.O=C1Cc2c(cccc2C(=O)O)N1>>COc1ccc(NC(=O)c2cccc3c2CC(=O)N3)cc1Cl | O=C1NC=2C=CC=C(C2C1)C(=O)O.ClC=1C=C(C=CC1OC)N.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>ClC=1C=C(C=CC1OC)NC(=O)C=1C=2CC(NC2C=CC1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:20][c:21]1[Cl:22].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[CH2:16][C:17](=[O:18])[NH:19]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[CH2:16][C:17](=[O:18])[NH:19]3)[cH:20][c:21]1[Cl:22] | COc1ccc(N)cc1Cl.O=C1Cc2c(cccc2C(=O)O)N1 | COc1ccc(NC(=O)c2cccc3c2CC(=O)N3)cc1Cl | null | CN(C1=CC=NC=C1)C | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1Cc2c(cccc2C(=O)Nc2ccccc2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 72 | HOUR | To a solution of 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (200 mg, 1.13 mmol) and 3-chloro-4-methoxy-phenylamine (178 mg, 1.13 mmol) in dimethylformamide (15 mL) at room temperature benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent 997 mg, 2.26 mmol) was added followed by 4-dimeth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C.C(C)(=O)OCC | null | 72 | COc1ccc(N)cc1Cl.O=C1Cc2c(cccc2C(=O)O)N1>CN(C1=CC=NC=C1)C.CN(C=O)C.C(C)(=O)OCC>COc1ccc(NC(=O)c2cccc3c2CC(=O)N3)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-086f2bea67084563aeccecbb77a52574 | CCN.O=C1Cc2c(cccc2C(=O)O)N1>>CCNC(=O)c1cccc2c1CC(=O)N2 | C(C)N.C(=O)(O)C1=C2CC(NC2=CC=C1)=O.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=C5)N=N4.F[P-](F)(F)(F)(F)F>>C(C)NC(=O)C=1C=2CC(NC2C=CC1)=O | [CH3:1][CH2:2][NH2:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[CH2:12][C:13](=[O:14])[NH:15]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[CH2:12][C:13](=[O:14])[NH:15]2 | CCN.O=C1Cc2c(cccc2C(=O)O)N1 | CCNC(=O)c1cccc2c1CC(=O)N2 | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1Cc2ccccc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[NH2;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 65.3 | [{"value": 65.0, "product": "C(C)NC(=O)C=1C=2CC(NC2C=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "C(C)NC(=O)C=1C=2CC(NC2C=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Ethylamine (2.1 mL of 2.0 M solution in tetrahydrofuran, 4.2 mmol) was added dropwise to a suspension of 4-carboxy-2-oxindole (380 mg, 2.1 mmol) in dimethylformamide (8 mL), followed by 4-dimethylaminopyridine (385 mg, 3.15 mmol) and PyBOP (2.185 g, 4.2 mmol). The mixture was stirred at room temperature for 6 hrs. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCN2 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 6 | CCN.O=C1Cc2c(cccc2C(=O)O)N1>CN(C1=CC=NC=C1)C.CN(C=O)C>CCNC(=O)c1cccc2c1CC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5d42876c3b7492fa6b2aad18e23ba11 | O=Cc1ccccc1.OCCO>>c1ccc(C2OCCO2)cc1 | C(C1=CC=CC=C1)=O.C(CO)O.O>>C1(=CC=CC=C1)C1OCCO1 | [cH:1]1[cH:2][cH:3][c:4]([CH:5]=[O:6])[cH:10][cH:11]1.O[CH2:7][CH2:8][OH:9]>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[O:6][CH2:7][CH2:8][O:9]2)[cH:10][cH:11]1 | O=Cc1ccccc1.OCCO | c1ccc(C2OCCO2)cc1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc(C2OCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1):[c:8] | 89 | [{"value": 89.0, "product": "C1(=CC=CC=C1)C1OCCO1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "C1(=CC=CC=C1)C1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500-mL three-necked flask equipped with a reflux condenser having a Dean-Stark water trap was charged with 5.0 g of benzaldehyde, 29.3 g of ethylene glycol, 0.09 g of p-toluenesulfonic acid monohydrate and 250 mL of benzene, and the contents were refluxed for 21 h. The resultant reaction solution was allowed to stand... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccccc1.C1COCO1 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=C1 | null | null | O=Cc1ccccc1.OCCO>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=C1>c1ccc(C2OCCO2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93912b0f9c4e4dadbfc0baf5ed7206e6 | O=Cc1ccccc1.OCCO>>c1ccc(C2OCCO2)cc1 | C(C1=CC=CC=C1)=O.C(CO)O.O>>C1(=CC=CC=C1)C1OCCO1 | [cH:1]1[cH:2][cH:3][c:4]([CH:5]=[O:6])[cH:10][cH:11]1.O[CH2:7][CH2:8][OH:9]>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[O:6][CH2:7][CH2:8][O:9]2)[cH:10][cH:11]1 | O=Cc1ccccc1.OCCO | c1ccc(C2OCCO2)cc1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc(C2OCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1):[c:8] | 89 | [{"value": 89.0, "product": "C1(=CC=CC=C1)C1OCCO1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "C1(=CC=CC=C1)C1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500-mL three-necked flask equipped with a reflux condenser having a Dean-Stark water trap was charged with 5.0 g of benzaldehyde, 29.3 g of ethylene glycol, 0.09 g of p-toluenesulfonic acid monohydrate and 250 mL of benzene, and the contents were refluxed for 21 h. The resultant reaction solution was allowed to stand... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccccc1.C1COCO1 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=C1 | null | null | O=Cc1ccccc1.OCCO>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=C1>c1ccc(C2OCCO2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fecd8c4325a044fe9432bcdb6bfcaf63 | C=CC.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>>CC(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 | C=1(C(=CC=C2CCCCC12)C1=CC=2CCCCC2C=C1)O.C=CC.C=1(C(=CC=C2CCCCC12)C1=CC=2CCCCC2C=C1)O>>C(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1 | [CH2:1]=[CH:2][CH3:3].[cH:4]1[cH:5][c:6]2[c:7]([c:8]([OH:9])[c:10]1-[c:11]1[cH:12][cH:13][c:14]3[c:15]([cH:16]1)[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:21][CH2:22][CH2:23][CH2:24]2>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([OH:9])[c:10]1-[c:11]1[cH:12][cH:13][c:14]3[c:15]([cH:16]1)[CH2:17][CH2:18][CH2:19][CH2... | C=CC.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2 | CC(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 | null | O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] | C=1(C(=CC=CC1)C)C | C-C Coupling | Friedel-Crafts alkylation | ec8f21b326d83472ee4b10e7d20a55a7273fffbc535eac62ffaaea718d36de52 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1cc2c(cc1-c1ccc3c(c1)CCCC3)CCCC2 | [C;D1;H3:1]-[CH;D2;+0:2]=[CH2;D1;+0:3].[c:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[c:4]):[c:6] | 42 | [{"value": 42.0, "product": "C(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (30.0 g), xylene (5 ml) and phosphotungstic acid (1.5 g) was heated to 140° C. To the mixture was added propylene (8.9 g) slowly via a dry-ice condenser. GC analysis of the reaction mixture indicated that 98% conversion of the 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | null | O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].C=1(C(=CC=CC1)C)C | 140 | null | C=CC.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].C=1(C(=CC=CC1)C)C>CC(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-366fafc4eb344e6ebc2c03201dcde3fe | C=CC.Clc1ccc(Cl)cc1.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>>CC(C)c1cc2c(cc1-c1c(C(C)C)cc3c(c1O)CCCC3)CCCC2 | C=1(C(=CC=C2CCCCC12)C1=CC=2CCCCC2C=C1)O.C1=CC(=CC=C1Cl)Cl.C=CC>>C(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1C(C)C | [CH:2](=[CH2:3])[CH3:14].Clc1c[cH:13][c:12](Cl)c[cH:1]1.[cH:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1-[c:10]1[cH:11][cH:15][c:16]3[c:17]([c:18]1[OH:19])[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH2:24][CH2:25][CH2:26][CH2:27]2>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1-[c:10]1[c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][... | C=CC.Clc1ccc(Cl)cc1.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2 | CC(C)c1cc2c(cc1-c1c(C(C)C)cc3c(c1O)CCCC3)CCCC2 | null | O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] | null | C-C Coupling | OtherReaction | 22b6bb8d84b60d31f45107e068d2c7f6a47a8bbb4ec121f47047d6d567bb8a05 | 6085f512e278c1c48c257e40fa8895f511b6c14f22cbc4a119e27edc859a5be0 | c1cc2c(cc1-c1ccc3c(c1)CCCC3)CCCC2 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:c:c(-Cl):[cH;D2;+0:3]:c:1.[CH2;D1;+0:4]=[CH;D2;+0:5]-[CH3;D1;+0:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10](-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]):[c:16]>>[CH3;D1;+0:2]-[CH;D3;+0:1](-[CH3;D1;+0:6])-[c;H0;D3;+0:9](:[c:8]:[c:7]):[c:10](-[c:11](:[c:12]):[c;H0;D3;+0:13](-[CH;D3;+0:5](-[CH3;D1;... | null | [] | 130 | CELSIUS | null | null | A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (44.0 g), dichlorobenzene (10 ml) and phosphotungstic acid (2.3 g) was heated to 130° C. To the mixture was added excess propylene via a dry-ice condenser. The reaction was monitored by GC analysis. The reaction mixture contained 6% of monoisopropylated product... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Vinyl | null | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | Other | O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] | 130 | null | C=CC.Clc1ccc(Cl)cc1.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W]>CC(C)c1cc2c(cc1-c1c(C(C)C)cc3c(c1O)CCCC3)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77786d6651e545b5b9146ffe454cfdf6 | C1=CCCC1.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>>Oc1c2c(cc(C3CCCC3)c1-c1cc3c(cc1C1CCCC1)CCCC3)CCCC2 | C=1(C(=CC=C2CCCCC12)C1=CC=2CCCCC2C=C1)O.C1=CCCC1>>C1(CCCC1)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1C1CCCC1 | [CH:19]1=[CH:20][CH2:21][CH2:22][CH2:23]1.[OH:1][c:2]1[c:3]2[c:4]([cH:5][cH:6][c:12]1-[c:7]1[cH:14][c:13]3[c:15]([cH:26][cH:25]1)[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:28][CH2:29][CH2:30][CH2:31]2>>[OH:1][c:2]1[c:3]2[c:4]([cH:5][c:6]([CH:7]3[CH2:8][CH2:9][CH2:10][CH2:11]3)[c:12]1-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]... | C1=CCCC1.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2 | Oc1c2c(cc(C3CCCC3)c1-c1cc3c(cc1C1CCCC1)CCCC3)CCCC2 | null | O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] | null | C-C Coupling | OtherReaction | 53496ddc706f3c3b0b9bdeb7dff6105fa36d9e1fa2ad53fb753e3e4cb9578828 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1c2c(cc(C3CCCC3)c1-c1cc3c(cc1C1CCCC1)CCCC3)CCCC2 | [C:1]1-[C:2]-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[O;D1;H1:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[c;H0;D3;+0:15]2:[c;H0;D3;+0:16](:[cH;D2;+0:17]:[cH;D2;+0:18]:1)-[CH2;D2;+0:19]-[C:20]-[C:21]-[CH2;D2;+0:22]-2>>[O;D1;H1:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11](-[CH;D... | 42 | [{"value": 42.0, "product": "C1(CCCC1)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1C1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.3, "product": "C1(CCCC1)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1C1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binapthol (48 g), phosphotungstic acid (2.4 g) and cyclopentene (58 g) was charged into a Hastelloy reactor. The reactor was heated to 180 C for 40 hours. The mixture was purified by column chromatography (silica gel, eluting with 2% ethyl acetate/hexane) to yield 29.5 g ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCC1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | C1CCCC1.C1CCCC1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | C1CCCC1.C1CCCC1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | Other | O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] | null | null | C1=CCCC1.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W]>Oc1c2c(cc(C3CCCC3)c1-c1cc3c(cc1C1CCCC1)CCCC3)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-04a94cb311e24ec1addae5f01600a743 | CC(C)OS(C)(=O)=O.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>>CC(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 | C=1(C(=CC=C2CCCCC12)C1=CC=2CCCCC2C=C1)O.CS(=O)(=O)OC(C)C>>C(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1 | CS(=O)(=O)O[CH:2]([CH3:1])[CH3:3].[cH:4]1[cH:5][c:6]2[c:7]([c:8]([OH:9])[c:10]1-[c:11]1[cH:12][cH:13][c:14]3[c:15]([cH:16]1)[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:21][CH2:22][CH2:23][CH2:24]2>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([OH:9])[c:10]1-[c:11]1[cH:12][cH:13][c:14]3[c:15]([cH:16]1)[CH2:17][CH2:18]... | CC(C)OS(C)(=O)=O.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2 | CC(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 | null | [O-]S(=O)(=O)C(F)(F)F.[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F | C(Cl)(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 44609fac1e6df793c8f50b67261b725863114e1015df0f037137a23bf9c07168 | b041d6622af412448d337accfca176f1c793181140e2fc4a55aecc4778a24787 | c1cc2c(cc1-c1ccc3c(c1)CCCC3)CCCC2 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[c:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[c:4]):[c:6] | 78 | [{"value": 78.0, "product": "C(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (2 g, 6.8 mmol), isopropyl methanesulfonate (5.5 mmol), scandium triflate (0.34 g, 5 mol %), and carbon tetrachloride (10 ml) was brought to reflux under argon. After 18 hours, GC indicated 65% conversion to give 78% desired product. Additional isopropyl methan... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | MsOH.HO- | [O-]S(=O)(=O)C(F)(F)F.[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.C(Cl)(Cl)(Cl)Cl | null | 18 | CC(C)OS(C)(=O)=O.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>[O-]S(=O)(=O)C(F)(F)F.[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.C(Cl)(Cl)(Cl)Cl>CC(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71922025b2c742d789cbad502858e85d | CC(C)(C)O.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>>CC(C)(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 | C=1(C(=CC=C2CCCCC12)C1=CC=2CCCCC2C=C1)O.C(C)(C)(C)O.FC(S(=O)(=O)O)(F)F>>C(C)(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1 | O[C:2]([CH3:1])([CH3:3])[CH3:4].[cH:5]1[cH:6][c:7]2[c:8]([c:9]([OH:10])[c:11]1-[c:12]1[cH:13][cH:14][c:15]3[c:16]([cH:17]1)[CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:22][CH2:23][CH2:24][CH2:25]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]2[c:8]([c:9]([OH:10])[c:11]1-[c:12]1[cH:13][cH:14][c:15]3[c:16]([cH:17]1)[CH2:18]... | CC(C)(C)O.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2 | CC(C)(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 | null | null | ClC1=C(C=CC=C1)Cl.CCOCC.O | C-C Coupling | OtherReaction | 9f30c6b466cec7957c45c711887e472599839277737f74ab7afb6bbfcc2a2cf4 | 80806390361076ffee90cd775b1e87663148d08d65f5b27bdd06ebc36de07186 | c1cc2c(cc1-c1ccc3c(c1)CCCC3)CCCC2 | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[c:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:2]-[C;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[c:5]):[c:7] | 61.6 | [{"value": 61.6, "product": "C(C)(C)(C)C1=C(C(=C2CCCCC2=C1)O)C1=CC=2CCCCC2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (1.0 g, 3.4 mmol), tert-butyl alcohol (1.4 g), trifluoromethanesulfonic acid (0.04 g) was dissolved in 2 ml 1,2-dichlorobenzene. The mixture was heated at 120° C. for 2.5 hours. GC showed 97% conversion to 87% mono-butylated product, and 10% bis-butylated produ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | HO- | ClC1=C(C=CC=C1)Cl.CCOCC.O | 120 | null | CC(C)(C)O.Oc1c(-c2ccc3c(c2)CCCC3)ccc2c1CCCC2>ClC1=C(C=CC=C1)Cl.CCOCC.O>CC(C)(C)c1cc2c(c(O)c1-c1ccc3c(c1)CCCC3)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4a78a9a85ece421eb143a32bead65125 | C1COCCN1.CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCC(=O)O)C[C@H]2C[C@H]1O>>CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCCN3CCOCC3)C[C@H]2C[C@H]1O | [Cl-].[NH4+].C(=O)(O)CCC\C=C\1/C[C@H]2C[C@H]([C@@H]([C@H]2C1)\C=C\[C@H](C(CC#CC)C)O)O.C(=O)(N1C=NC=C1)N1C=NC=C1.N1CCOCC1>>O1CCN(CC1)CCCC\C=C\1/C[C@H]2C[C@H]([C@@H]([C@H]2C1)\C=C\[C@H](C(CC#CC)C)O)O | [NH:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1.O=[C:19](O)[CH2:18][CH2:17][CH2:16]/[CH:15]=[C:14]1/[CH2:13][C@@H:12]2[C@@H:11](/[CH:10]=[CH:9]/[C@H:7]([CH:5]([CH2:4][C:3]#[C:2][CH3:1])[CH3:6])[OH:8])[C@H:29]([OH:30])[CH2:28][C@@H:27]2[CH2:26]1>>[CH3:1][C:2]#[C:3][CH2:4][CH:5]([CH3:6])[C@H:7]([OH:8])/[CH:9]=[CH:10]/[C@... | C1COCCN1.CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCC(=O)O)C[C@H]2C[C@H]1O | CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCCN3CCOCC3)C[C@H]2C[C@H]1O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c60b8c5e8ed4f8735a6d92335f9d058f7ab0d9365e1bd9f6b6322ce378b11144 | 5fb52ddc67e52a472f28d69e60f3ac94989e70b5307ac3fa95fe53e87c1d2696 | C(\CCCCN1CCOCC1)=C1\C[C@H]2CCC[C@H]2C1 | O-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[#8:4]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]-[#8:4]-[C:9]-[C:8]-1 | 40 | [{"value": 40.0, "product": "O1CCN(CC1)CCCC\\C=C\\1/C[C@H]2C[C@H]([C@@H]([C@H]2C1)\\C=C\\[C@H](C(CC#CC)C)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.4, "product": "O1CCN(CC1)CCCC\\C=C\\1/C[C@H]2C[C@H]([C@@H]([C@H]2C1)\\C=C\\[C@H](C(CC#CC)C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | 50 | CELSIUS | 1.5 | HOUR | 20 mg of (1S,2R,3R,5S)-7-[(E)-4-carboxybutylidene]-2-[(3S,1E)-3-hydroxy-4-methyl-6-octyne-1-enyl]-3-hydroxybicyclo[3.3.0]octane was taken and dissolved in 2 mL of dimethylformamide. After addition of 20 mg of 1,1′-carbonyldiimidazole, it was stirred at 50° C. for 1.5 hours. It was then cooled to ambient temperature, an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1C[C@H]2CCC[C@H]2C1.C1COCC[NH]1 | Other | CN(C=O)C | 50 | 1.5 | C1COCCN1.CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCC(=O)O)C[C@H]2C[C@H]1O>CN(C=O)C>CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCCN3CCOCC3)C[C@H]2C[C@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4f667ad199b4df4a69d9ad291606bb7 | C1COCCN1.CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2c3cccc(CCCC(=O)O)c3O[C@H]2C[C@H]1O>>CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2c3cccc(CCCCN4CCOCC4)c3O[C@H]2C[C@H]1O | [Cl-].[NH4+].O[C@H]1[C@@H]([C@@H]2[C@@H](OC3=C2C=CC=C3CCCC(=O)O)C1)\C=C\[C@H](C(CC#CC)C)O.C(=O)(N1C=NC=C1)N1C=NC=C1.N1CCOCC1>>O[C@H]1[C@@H]([C@@H]2[C@@H](OC3=C2C=CC=C3CCCCN3CCOCC3)C1)\C=C\[C@H](C(CC#CC)C)O | [NH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.O=[C:21](O)[CH2:20][CH2:19][CH2:18][c:17]1[cH:16][cH:15][cH:14][c:13]2[c:28]1[O:29][C@@H:30]1[C@H:12]2[C@@H:11](/[CH:10]=[CH:9]/[C@H:7]([CH:5]([CH2:4][C:3]#[C:2][CH3:1])[CH3:6])[OH:8])[C@H:32]([OH:33])[CH2:31]1>>[CH3:1][C:2]#[C:3][CH2:4][CH:5]([CH3:6])[C@H:7]([OH:8])/[CH:... | C1COCCN1.CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2c3cccc(CCCC(=O)O)c3O[C@H]2C[C@H]1O | CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2c3cccc(CCCCN4CCOCC4)c3O[C@H]2C[C@H]1O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c60b8c5e8ed4f8735a6d92335f9d058f7ab0d9365e1bd9f6b6322ce378b11144 | 5fb52ddc67e52a472f28d69e60f3ac94989e70b5307ac3fa95fe53e87c1d2696 | c1cc(CCCCN2CCOCC2)c2c(c1)[C@@H]1CCC[C@@H]1O2 | O-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[#8:4]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]-[#8:4]-[C:9]-[C:8]-1 | 48 | [{"value": 48.0, "product": "O[C@H]1[C@@H]([C@@H]2[C@@H](OC3=C2C=CC=C3CCCCN3CCOCC3)C1)\\C=C\\[C@H](C(CC#CC)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "O[C@H]1[C@@H]([C@@H]2[C@@H](OC3=C2C=CC=C3CCCCN3CCOCC3)C1)\\C=C\\[C@H](C(CC#CC)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | 50 | CELSIUS | 1 | HOUR | 10 mg of (1R,2R,3aS,8bS)-2,3,3a,8b-tetrahydro-2-hydroxy-1-[(3S,1E)-3-hydroxy-4-methyl-1-octene-6-ynyl]-5-(3-carboxypropyl)-1H-cyclopenta[b]benzofuran was taken and was dissolved in 2 mL of dimethylformamide. After addition of 8.1 mg of 1,1′-carbonyldiimidazole, it was stirred at 50° C. for 1 hour. It was cooled to ambi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccc2c(c1)O[C@H]1CCC[C@@H]21 | Other | CN(C=O)C | 50 | 1 | C1COCCN1.CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2c3cccc(CCCC(=O)O)c3O[C@H]2C[C@H]1O>CN(C=O)C>CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2c3cccc(CCCCN4CCOCC4)c3O[C@H]2C[C@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af70023515324f95bea882d743822d1c | CI.Cc1cc(Br)ccc1N>>CNc1ccc(Br)cc1C | BrC1=CC(=C(N)C=C1)C.C(=O)([O-])[O-].[K+].[K+].IC>>CNC1=C(C=C(C=C1)Br)C | I[CH3:1].[NH2:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[CH3:10]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[CH3:10] | CI.Cc1cc(Br)ccc1N | CNc1ccc(Br)cc1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 3c2788b3f372b76c1d2ee0d77963cb247b210aa8a28e76637b4e731826c4252a | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccccc1 | I-[CH3;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 14 | HOUR | To a solution of 2.03 g (10.91 mmol) of 4-bromo-2-methylaniline in 40 ml of DMF was added 2.07 g (14.98 mmol) of K2CO3 and 0.63 ml (10.12 mmol) of iodomethane, and the mixture was stirred at room temperature for 14 hours. After this time, the reaction mixture was quenched by the addition of a saturated aqueous solution... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccccc1 | HI | CN(C)C=O | null | 14 | CI.Cc1cc(Br)ccc1N>CN(C)C=O>CNc1ccc(Br)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7de15a5b80d4d3ca1aea6c4a4e5da0b | CNc1ccc(Br)cc1C.COc1ccc(CCl)cc1>>COc1ccc(CN(C)c2ccc(Br)cc2C)cc1 | COC1=CC=C(CCl)C=C1.CNC1=C(C=C(C=C1)Br)C.[H-].[Na+]>>CN(C1=C(C=C(C=C1)Br)C)CC1=CC=C(C=C1)OC | [NH:8]([CH3:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]1[CH3:17].Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH3:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[CH3:17])[cH:18][cH:19]1 | CNc1ccc(Br)cc1C.COc1ccc(CCl)cc1 | COc1ccc(CN(C)c2ccc(Br)cc2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CNc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:7](:[c:8]):[c:9] | null | [] | null | null | 0.5 | HOUR | To a solution of 2.7 g (13.57 mmol) of N-methyl-4-bromo-2-methylaniline in 20 ml of DMF at room temperature was added 608 mg (15.2 mmol) of NaH and the mixture was stirred at room temperature for 0.5 h. After this time, 2.05 ml (15.1 mmol) of 4-methoxybenzyl chloride was added and the reaction mixture was heated to 60°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 0.5 | CNc1ccc(Br)cc1C.COc1ccc(CCl)cc1>CN(C)C=O>COc1ccc(CN(C)c2ccc(Br)cc2C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41d4930a785649b8835252e9e1c4c3e2 | Cc1cc(Br)ccc1N(C)S(=O)(=O)c1ccccc1.O=C(c1ccccc1)C(F)(F)F>>CNc1ccc(C(O)(c2ccccc2)C(F)(F)F)cc1C | C(=O)(C(F)(F)F)O.FC(C(=O)C1=CC=CC=C1)(F)F.BrC1=CC(=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C)C.[Li]C(C)(C)C>>FC(C(O)(C1=CC=CC=C1)C1=CC(=C(C=C1)NC)C)(F)F | O=S(=O)(c1ccccc1)[N:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6](Br)[cH:19][c:20]1[CH3:21].[C:7](=[O:8])([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15]([F:16])([F:17])[F:18]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[C:15]([F:16])([F:17])[F:18])[cH:19][c:20]1[CH3:21] | Cc1cc(Br)ccc1N(C)S(=O)(=O)c1ccccc1.O=C(c1ccccc1)C(F)(F)F | CNc1ccc(C(O)(c2ccccc2)C(F)(F)F)cc1C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | dede6ff79bd7f869797072aa63f73523791693b80f650aaa4ee655b252853c55 | a54fb2b4a2d4c4f9e6988da61f3d85e6e8274065bcf7838ffd7a40da5a580474 | c1ccc(Cc2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[N;H0;D3;+0:5](-[C;D1;H3:6])-S(=O)(=O)-c2:c:c:c:c:c:2):[c:7]:[c:8]:1.[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[c:15](:[c:16]):[c:17]>>[C;D1;H3:6]-[NH;D2;+0:5]-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:13](-[OH;D1;+0:14])(-[c:15](:[c:16... | null | [] | -78 | CELSIUS | 0.5 | HOUR | To a solution of 1.03 g (3.23 mmol) of N-(4-bromo-2-methylphenyl)-N-methyl-benzenesulfonamide in 30 ml THF at −78° C. was added dropwise 3.9 ml (6.63 mmol) of a 1.7M solution of tert-BuLi in hexanes and the resultant mixture was stirred at −78° C. for 0.5 h. To this mixture was then added 0.66 ml (4.7 mmol) of 2,2,2-tr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Tertiary amine | Tertiary alcohol.Secondary amine | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C1CCOC1 | -78 | 0.5 | Cc1cc(Br)ccc1N(C)S(=O)(=O)c1ccccc1.O=C(c1ccccc1)C(F)(F)F>C1CCOC1>CNc1ccc(C(O)(c2ccccc2)C(F)(F)F)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5753627b79654a82b0b98a7cd4b39a1f | CNc1ccc(C(O)(c2cccc(C(F)(F)F)c2)C(CF)(CF)CF)cc1C.O=S(=O)(Cl)c1ccccc1>>Cc1cc(C(O)(c2cccc(C(F)(F)F)c2)C(F)(F)F)ccc1N(C)S(=O)(=O)c1ccccc1 | FCC(C(O)(C1=CC(=CC=C1)C(F)(F)F)C1=CC(=C(C=C1)NC)C)(CF)CF.C1(=CC=CC=C1)S(=O)(=O)Cl>>CN(S(=O)(=O)C1=CC=CC=C1)C1=C(C=C(C=C1)C(C(F)(F)F)(C1=CC(=CC=C1)C(F)(F)F)O)C | C([C:17](C[F:19])(C[F:20])[C:5]([c:4]1[cH:3][c:2]([CH3:1])[c:23]([NH:24][CH3:25])[cH:22][cH:21]1)([OH:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[F:18].Cl[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([OH:6])([c:7]2[cH:8][cH:9][cH:10][c:... | CNc1ccc(C(O)(c2cccc(C(F)(F)F)c2)C(CF)(CF)CF)cc1C.O=S(=O)(Cl)c1ccccc1 | Cc1cc(C(O)(c2cccc(C(F)(F)F)c2)C(F)(F)F)ccc1N(C)S(=O)(=O)c1ccccc1 | null | null | null | Acylation | OtherReaction | 123b2137a06084a4b3c1a6013c0cd92a1ec9938b1392d2a38e8a451464e6aa7c | 0ac24d1a131e4ca9cf43f5228ce6ad99b7d350ee17451e901421de0c21e61ca4 | O=S(=O)(Nc1ccc(Cc2ccccc2)cc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11].[F;H0;D1;+0:12]-C-[C;H0;D4;+0:13](-C-[F;H0;D1;+0:14])(-C-[F;H0;D1;+0:15])-[C:16](-[O;D1;H1:17])(-[c:18])-[c:19]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-... | null | [] | null | null | null | null | The title compound was prepared from 2,2,2-trifluoromethyl-1-(3-methyl-4-methylaminophenyl)-1-(3-trifluoromethyl-phenyl)-ethanol (Step A) and benzenesulfonyl chloride using the procedure described in Example 1, Step D. 1H-NMR (CDCl3) δ 2.41 (s, 3H), 3.15 (s, 3H), 6.64 (d, J=8.4 Hz, 1H), 7.18 (brs, 1H), 7.42 (brs, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary halide.Secondary amine.Sulfonyl halide | Trifluoro group.Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CNc1ccc(C(O)(c2cccc(C(F)(F)F)c2)C(CF)(CF)CF)cc1C.O=S(=O)(Cl)c1ccccc1>>Cc1cc(C(O)(c2cccc(C(F)(F)F)c2)C(F)(F)F)ccc1N(C)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56c612ddbb804f2eaca1a9a515e8f4cf | CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.Clc1cc[c]([Mg][Br])cc1>>CN(c1ccc(C(O)(c2ccc(Cl)cc2)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C(F)(F)F)=O.ClC1=CC=C(C=C1)[Mg]Br>>ClC1=CC=C(C=C1)C(C(F)(F)F)(O)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | [CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1)[S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[Br][Mg][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:... | CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.Clc1cc[c]([Mg][Br])cc1 | CN(c1ccc(C(O)(c2ccc(Cl)cc2)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Grignard from ketone to alcohol | 181fdd58eba73242b2de454099edbf422e18f2a0a3f78d67208494cf1d83905c | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | O=S(=O)(Nc1ccc(Cc2ccccc2)cc1)c1ccccc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 4 | HOUR | To a solution of 0.2 g of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide in 10 mL of THF were added 0.7 mL of a 1M solution 4-chlorophenyl magnesium bromide at −78° C. The resulting mixture was stirred at −78° C. for 4 hr. After this time, the reaction mixture was quenched by the addition of a saturated aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Br-.Mg | C1CCOC1 | -78 | 4 | CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.Clc1cc[c]([Mg][Br])cc1>C1CCOC1>CN(c1ccc(C(O)(c2ccc(Cl)cc2)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-068cd57809ed447eb08a6bef3d7309e1 | CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.COCn1ccnc1>>COCn1ccnc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C(F)(F)F)=O.COCN1C=NC=C1.C(CCC)[Li]>>CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C(F)(F)F)(C=1N(C=CN1)COC)O | [C:9](=[O:10])([c:11]1[cH:12][cH:13][c:14]([N:15]([CH3:16])[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1)[C:28]([F:29])([F:30])[F:31].[CH3:1][O:2][CH2:3][n:4]1[cH:5][cH:6][n:7][cH:8]1>>[CH3:1][O:2][CH2:3][n:4]1[cH:5][cH:6][n:7][c:8]1[C:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([N:15]... | CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.COCn1ccnc1 | COCn1ccnc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 6437c5442b1284778f29095577cfe2e46b8a5b4ae4a931f781e1b4367639985a | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | O=S(=O)(Nc1ccc(Cc2ncc[nH]2)cc1)c1ccccc1 | [C:1]-[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[cH;D2;+0:6]:1.[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13](:[c:14]):[c:15]>>[C:1]-[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:11](-[OH;D1;+0:12])(-[c:13](:[c:14]):[c:15])-[C:8](-[F;D1;H0:7])(-[F;D1;H0:9])-[F;D1;H0:10] | null | [] | null | null | 14 | HOUR | To a solution of 55 mg (0.49 mmol) of 1-methoxymethyl-1H-imidazole in 5 ml of THF at −78° C. was added 0.20 ml (0.50 mmol) of a 2.5 M solution of n-butyllithium in hexanes and the resultant mixture was stirred at −78° C. for 30 mins. After this time, a solution of 160 mg (0.47 mmol) of N-methyl-N-(4-trifluoroacetyl-phe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | 14 | CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.COCn1ccnc1>C1CCOC1>COCn1ccnc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-272692371c074155b8e4bdc7870a2a38 | C#Cc1ccccc1.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>>CN(c1ccc(C(O)(C#Cc2ccccc2)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C(F)(F)F)=O.C1(=CC=CC=C1)C#C.[Li]CCCC>>OC(C#CC1=CC=CC=C1)(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | [CH:9]#[C:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([C:9]#[C:10][c:11]2[cH:12][cH:13][cH:14][cH:15][... | C#Cc1ccccc1.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | CN(c1ccc(C(O)(C#Cc2ccccc2)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2ddb79a55c34731f669ca9c81c37bd79ca03c4be0b8aa443046efbe4fb65f2a7 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | O=S(=O)(Nc1ccc(CC#Cc2ccccc2)cc1)c1ccccc1 | [CH;D1;+0:1]#[C:2]-[c:3].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[C;H0;D2;+0:1]#[C:2]-[c:3])-[c:10](:[c:11]):[c:12] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of 0.18 g of phenylacetylene (1.75 mmol) in 5 mL of THF was added dropwise 0.76 mL of n-BuLi (2.5M in hexane) at −78° C. The color of the solution turned dark blue and the mixture was stirred at −78° C. for 30 min. Then 0.5 g of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1CCOC1 | -78 | 0.5 | C#Cc1ccccc1.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>C1CCOC1>CN(c1ccc(C(O)(C#Cc2ccccc2)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9173a36377bb49c8a9885055e531babe | C#CC(F)(F)F.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>>CN(c1ccc(C(O)(C#CC(F)(F)F)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C(F)(F)F)=O.FC(C#C)(F)F>>CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C#CC(F)(F)F)(C(F)(F)F)O | [CH:9]#[C:10][C:11]([F:12])([F:13])[F:14].[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1)[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([C:9]#[C:10][C:11]([F:12])([F:13])[F:14])[C:15]([F:16])([F:17])... | C#CC(F)(F)F.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | CN(c1ccc(C(O)(C#CC(F)(F)F)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 2ddb79a55c34731f669ca9c81c37bd79ca03c4be0b8aa443046efbe4fb65f2a7 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | O=S(=O)(Nc1ccccc1)c1ccccc1 | [CH;D1;+0:1]#[C:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13](:[c:14]):[c:15]>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:2]#[C;H0;D2;+0:1]-[C;H0;D4;+0:11](-[OH;D1;+0:12])(-[c:13](:[c:14]):[c:15])-[C:8](-[F;D1;H0:7])(-[F;D1... | null | [] | null | null | null | null | The compound was prepared from N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A) and 3,3,3-trifluoroprop-1-yne following the procedure described in Example 29. 1H NMR (CDCl3) δ 3.19 (s, 3H), 4.30 (br s, 1H), 7.11–7.63 (m, 9H). Mass Spectrum (CI+) m/e=438 (M+1).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | null | null | c1ccccc1.c1ccccc1 | null | null | null | null | C#CC(F)(F)F.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>>CN(c1ccc(C(O)(C#CC(F)(F)F)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86d8cb05cde84ed19ba311853bb41f4b | C#CCC(C)C.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>>CC(C)CC#CC(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | CN(S(=O)(=O)C1=CC=CC=C1)C1=CC=C(C=C1)C(C(F)(F)F)=O.CC(CC#C)C>>OC(C#CCC(C)C)(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C:5]#[CH:6].[C:7](=[O:8])([c:9]1[cH:10][cH:11][c:12]([N:13]([CH3:14])[S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1)[C:26]([F:27])([F:28])[F:29]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5]#[C:6][C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12]([N:13]([CH3:14])[S:15](=[O... | C#CCC(C)C.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | CC(C)CC#CC(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | null | C-C Coupling | OtherReaction | 2ddb79a55c34731f669ca9c81c37bd79ca03c4be0b8aa443046efbe4fb65f2a7 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | O=S(=O)(Nc1ccccc1)c1ccccc1 | [C:1]-[C:2]#[CH;D1;+0:3].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[C:1]-[C:2]#[C;H0;D2;+0:3]-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[c:10](:[c:11]):[c:12])-[C:5](-[F;D1;H0:4])(-[F;D1;H0:6])-[F;D1;H0:7] | null | [] | null | null | null | null | The compound was prepared from N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A) and 4-methyl-pent-1-yne following the procedure described in Example 29. 1H NMR (CDCl3) δ 1.01 (d, J=6.6 Hz, 6H), 1.90 (sept, J=6.6 Hz, 1H), 2.21 (d, J=7.7 Hz, 2H), 3.17 (s, 3H), 3.24 (br s, 1H), 7.12–7.68 (m, 9... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | null | null | c1ccccc1.c1ccccc1 | null | null | null | null | C#CCC(C)C.CN(c1ccc(C(=O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>>CC(C)CC#CC(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a2989db33d445c4b96af396a0efd1b0 | NC1CCCC1.O=C(c1ccc(F)cc1)C(F)(F)F>>O=C(c1ccc(NC2CCCC2)cc1)C(F)(F)F | FC(C(=O)C1=CC=C(C=C1)F)(F)F.C(C)N(CC)CC.C1(CCCC1)N>>C1(CCCC1)NC1=CC=C(C=C1)C(C(F)(F)F)=O | [NH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1.F[c:6]1[cH:5][cH:4][c:3]([C:2](=[O:1])[C:15]([F:16])([F:17])[F:18])[cH:14][cH:13]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][cH:14]1)[C:15]([F:16])([F:17])[F:18] | NC1CCCC1.O=C(c1ccc(F)cc1)C(F)(F)F | O=C(c1ccc(NC2CCCC2)cc1)C(F)(F)F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9] | null | [] | null | null | null | null | To a mixture of 3.94 g of 2,2,2,4′-tetrafluoroacetophenone (20.5 mmol) and 3.35 ml triethylamine (24.0 mmol) in 40 ml of acetonitrile at 0° C. were added 5.9 ml of cyclopentylamine (59.8 mmol). The reaction was allowed to warm to room temperature and then heated to reflux for 14 h. After this time the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCC1 | HF | C(C)#N | null | null | NC1CCCC1.O=C(c1ccc(F)cc1)C(F)(F)F>C(C)#N>O=C(c1ccc(NC2CCCC2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-905bcbd6cf02468cae9f1104f7cb26a1 | C#Cc1ccccc1.O=C(c1ccc(NC2CCCC2)cc1)C(F)(F)F>>OC(C#Cc1ccccc1)(c1ccc(NC2CCCC2)cc1)C(F)(F)F | C1(CCCC1)NC1=CC=C(C=C1)C(C(F)(F)F)=O.C1(=CC=CC=C1)C#C.C(CCC)[Li]>>C1(CCCC1)NC1=CC=C(C=C1)C(C(F)(F)F)(C#CC1=CC=CC=C1)O | [CH:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:1]=[C:2]([c:11]1[cH:12][cH:13][c:14]([NH:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1)[C:23]([F:24])([F:25])[F:26]>>[OH:1][C:2]([C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)([c:11]1[cH:12][cH:13][c:14]([NH:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2... | C#Cc1ccccc1.O=C(c1ccc(NC2CCCC2)cc1)C(F)(F)F | OC(C#Cc1ccccc1)(c1ccc(NC2CCCC2)cc1)C(F)(F)F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2ddb79a55c34731f669ca9c81c37bd79ca03c4be0b8aa443046efbe4fb65f2a7 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | C(#Cc1ccccc1)Cc1ccc(NC2CCCC2)cc1 | [CH;D1;+0:1]#[C:2]-[c:3].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[C;H0;D2;+0:1]#[C:2]-[c:3])-[c:10](:[c:11]):[c:12] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of 0.4 ml of phenylacetylene (3.6 mmol in 10 ml of THF at −78° C. was added 1.9 ml (4.75 mmol) of a 2.5 M solution of n-butyllithium in hexanes. The color of the solution turned dark blue and the reaction mixture was stirred at −78° C. for 30 min. After this time, a solution of 450 mg of 1-(4-cyclopentyla... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | null | null | c1ccccc1.c1ccccc1.C1CCCC1 | null | C1CCOC1 | -78 | 0.5 | C#Cc1ccccc1.O=C(c1ccc(NC2CCCC2)cc1)C(F)(F)F>C1CCOC1>OC(C#Cc1ccccc1)(c1ccc(NC2CCCC2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a44c26cf9d6443bda601b2b6b77d0b6c | O=S(=O)(Cl)c1cc(Cl)ccc1Cl.OC(C#Cc1ccccc1)(c1ccc(NC2CCCC2)cc1)C(F)(F)F>>O=S(=O)(c1cc(Cl)ccc1Cl)N(c1ccc(C(O)(C#Cc2ccccc2)C(F)(F)F)cc1)C1CCCC1 | C1(CCCC1)NC1=CC=C(C=C1)C(C(F)(F)F)(C#CC1=CC=CC=C1)O.ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl>>ClC1=C(C=C(C=C1)Cl)S(=O)(=O)N(C1=CC=C(C=C1)C(C#CC1=CC=CC=C1)(C(F)(F)F)O)C1CCCC1 | Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[Cl:11].[NH:12]([c:13]1[cH:14][cH:15][c:16]([C:17]([OH:18])([C:19]#[C:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]1)[CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][c:6]([Cl:7])[cH... | O=S(=O)(Cl)c1cc(Cl)ccc1Cl.OC(C#Cc1ccccc1)(c1ccc(NC2CCCC2)cc1)C(F)(F)F | O=S(=O)(c1cc(Cl)ccc1Cl)N(c1ccc(C(O)(C#Cc2ccccc2)C(F)(F)F)cc1)C1CCCC1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N(c1ccc(CC#Cc2ccccc2)cc1)C1CCCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:13]>>[C:7]-[C:8](-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:13] | null | [] | 70 | CELSIUS | null | null | A mixture of 53 mg of 2-(4-cyclopentylamino-phenyl)-1,1,1-trifluoro-4-phenyl-but-3-yn-2-ol (0.15 mmol) and 44 mg of 2,5-dichlorobenzenesulfonyl chloride (0.18 mmol) in 0.2 ml of pyridine was heated to 70° C. for 14 hours. After this time the reaction mixture was allowed to cool to room temperature, quenched by the addi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCC1 | HCl | N1=CC=CC=C1 | 70 | null | O=S(=O)(Cl)c1cc(Cl)ccc1Cl.OC(C#Cc1ccccc1)(c1ccc(NC2CCCC2)cc1)C(F)(F)F>N1=CC=CC=C1>O=S(=O)(c1cc(Cl)ccc1Cl)N(c1ccc(C(O)(C#Cc2ccccc2)C(F)(F)F)cc1)C1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab4cba9ad83843d2a764bfbec7274330 | CC(C)CN.O=S(=O)(Cl)c1ccccc1>>CC(C)CNS(=O)(=O)c1ccccc1 | C(C(C)C)N.C(C)N(CC)CC.C1(=CC=CC=C1)S(=O)(=O)Cl>>C(C(C)C)NS(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | CC(C)CN.O=S(=O)(Cl)c1ccccc1 | CC(C)CNS(=O)(=O)c1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 4.14 g of isobutylamine (56.6 mmol) and 2.86 g of triethylamine (28.3 mmol) in 40 mL of CH2Cl2 was slowly added 5.0 g of benzenesulfonyl chloride (28.3 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min and then at rt for 1 hr. 150 mL of CH2Cl2 were added, and the organic layer was wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.5 | CC(C)CN.O=S(=O)(Cl)c1ccccc1>C(Cl)Cl>CC(C)CNS(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3bc4ba7f6bb4a54a7d11f396736f8e8 | CC(C)CN(c1ccc(C(O)(C#CC(=O)O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.CN>>CNC(=O)C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | C1(=CC=CC=C1)S(=O)(=O)N(C1=CC=C(C=C1)C(C#CC(=O)O)(C(F)(F)F)O)CC(C)C.CN.Cl.CN(CCCN=C=NCC)C>>CNC(C#CC(C(F)(F)F)(O)C1=CC=C(C=C1)N(CC(C)C)S(=O)(=O)C1=CC=CC=C1)=O | O[C:3](=[O:4])[C:5]#[C:6][C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1)[C:29]([F:30])([F:31])[F:32].[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[C:5]#[C:6][C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12]([N:13]... | CC(C)CN(c1ccc(C(O)(C#CC(=O)O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.CN | CNC(=O)C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=S(=O)(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]#[C:4]-[C:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C:5]-[C:4]#[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 16 | HOUR | 0.2 g of 4-[4-(benzenesulfonyl-isobutyl-amino)-phenyl]-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid (see Example 69; 0.439 mmol) and 0.26 mL of methylamine (2M in THF) were combined in 3 mL of CH2Cl2 at rt. 0.1 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.527 mmol) was added. The resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 16 | CC(C)CN(c1ccc(C(O)(C#CC(=O)O)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1.CN>C(Cl)Cl>CNC(=O)C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68c1b2678fec4a839319799f6101cb08 | CC(C)CN(c1ccc(C(O)(C#C[Si](C)(C)C)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>>C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | OC(C#C[Si](C)(C)C)(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)CC(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OC(C#C)(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)CC(C)C | C[Si](C)(C)[C:1]#[C:2][C:3]([OH:4])([c:5]1[cH:6][cH:7][c:8]([N:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1)[C:25]([F:26])([F:27])[F:28]>>[CH:1]#[C:2][C:3]([OH:4])([c:5]1[cH:6][cH:7][c:8]([N:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[S:14](=[O:15])(... | CC(C)CN(c1ccc(C(O)(C#C[Si](C)(C)C)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | C(Cl)Cl.C1CCOC1 | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | O=S(=O)(Nc1ccccc1)c1ccccc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[C:3]>>[C:3]-[C:2]#[CH;D1;+0:1] | null | [] | null | null | 1 | HOUR | To a solution of 0.25 g (0.51 mmol) of N-[4-(1-hydroxy-1-trifluoromethyl-3-trimethylsilanyl-prop-2-ynyl)-phenyl]-N-isobutyl-benzenesulfonamide (Example 74) in 6 mL of CH2Cl2 was added 0.4 mL of a 1 M solution of tetrabutylammonium fluoride in THF. The mixture was stirred at room temperature for 1 hour. CH2Cl2 (60 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.c1ccccc1 | Other | C(Cl)Cl.C1CCOC1 | null | 1 | CC(C)CN(c1ccc(C(O)(C#C[Si](C)(C)C)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1>C(Cl)Cl.C1CCOC1>C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b6978f8aa5c4493b9190309ea64498e | Brc1ccc2ccccc2c1.C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F>>CC(C)CN(c1ccc(C(O)(C#Cc2cccc3ccccc23)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | BrC1=CC2=CC=CC=C2C=C1.O.C(=O)([O-])[O-].[K+].[K+].OC(C#C)(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)CC(C)C>>OC(C#CC1=CC=CC2=CC=CC=C12)(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)CC(C)C | Br[c:15]1[cH:14][c:23]2[c:18]([cH:17][cH:16]1)[cH:19][cH:20][cH:21][cH:22]2.[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([c:6]1[cH:7][cH:8][c:9]([C:10]([OH:11])([C:12]#[CH:13])[C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]1)[S:30](=[O:31])(=[O:32])[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([c:6]... | Brc1ccc2ccccc2c1.C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | CC(C)CN(c1ccc(C(O)(C#Cc2cccc3ccccc23)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 | null | [Pd].[Cu]I | COCCOC | C-C Coupling | OtherReaction | 427d52803b094b22f8f109b6c17c82e6ccc9792ebeaad9bc5ad19cad543470b3 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=S(=O)(Nc1ccc(CC#Cc2cccc3ccccc23)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]):[cH;D2;+0:7]:1.[C:8]-[C:9]#[CH;D1;+0:10]>>[C:8]-[C:9]#[C;H0;D2;+0:10]-[c;H0;D3;+0:7]1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6] | null | [] | null | null | 30 | MINUTE | 80.6 mg (0.39 mmol) 2-Bromonaphthalene, 21 mg palladium on carbon (10% Pd), 74.1 mg (0.39 mmol) copper (I) iodide, and 135 mg (0.98 mmol) K2CO3 were combined 2 mL of DME and 2 mL of water and the resulting mixture was stirred at room temperature for 30 min. A solution of 80 mg (0.2 mmol) of N-[4-(1-hydroxy-1-trifluorom... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | HBr | [Pd].[Cu]I.COCCOC | null | 0.5 | Brc1ccc2ccccc2c1.C#CC(O)(c1ccc(N(CC(C)C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F>[Pd].[Cu]I.COCCOC>CC(C)CN(c1ccc(C(O)(C#Cc2cccc3ccccc23)C(F)(F)F)cc1)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9e8b955dadb4be390e459aed7fa1256 | CCOCCBr.O=C(c1ccc[nH]1)C(F)(F)F>>CCOCCn1cccc1C(=O)C(F)(F)F | [H-].[Na+].FC(C(=O)C=1NC=CC1)(F)F.C(C)OCCBr>>C(C)OCCN1C(=CC=C1)C(C(F)(F)F)=O | Br[CH2:5][CH2:4][O:3][CH2:2][CH3:1].[nH:6]1[cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[C:13]([F:14])([F:15])[F:16]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[C:13]([F:14])([F:15])[F:16] | CCOCCBr.O=C(c1ccc[nH]1)C(F)(F)F | CCOCCn1cccc1C(=O)C(F)(F)F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 161a14961e9f1b305dfb4891994ad58540b58501680f8eb4ba76ad15e1e7cb96 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1cc[nH]c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]:[c:10]:1-[C:8](=[O;D1;H0:9])-[C:5](-[F;D1;H0:4])(-[F;D1;H0:6])-[F;D1;H0:7] | null | [] | 0 | CELSIUS | 1 | HOUR | To a suspension of 268 mg (6.70 mmol) of NaH (60% dispersion in oil) in 20 mL DMF at 0° C. was added 1.01 g (6.19 mmol) of 2-(trifluoroacteyl)pyrrole and the mixture was stirred at 0° C. for 1 h. After this time, 765 μL (6.51 mmol) of 2-bromoethyl ethyl ether was added and the mixture was warmed to 60° C. and stirred f... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1 | HBr | CN(C)C=O | 0 | 1 | CCOCCBr.O=C(c1ccc[nH]1)C(F)(F)F>CN(C)C=O>CCOCCn1cccc1C(=O)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1e33565cabe49e5b2004b2758236b11 | CNc1ccc(Br)cc1.O=S(=O)(Cl)c1ccccc1>>CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1 | BrC1=CC=C(NC)C=C1.C1(=CC=CC=C1)S(=O)(=O)Cl>>BrC1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | [CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CNc1ccc(Br)cc1.O=S(=O)(Cl)c1ccccc1 | CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1 | null | null | N1=CC=CC=C1 | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) secondary amine | f885e88ea942f3030166da4c7f20dfb8bf6f1e152c7507d56458611df7dc3120 | 971e620478d668662a3bf915b510f5704d42a595d6ca9c67de007bd5d7063a75 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of 0.61 g (3.3 mmol) of 4-bromo-N-methylaniline and 0.5 mL (3.92 mmol) of benzenesulfonyl chloride in 5 mL of pyridine was stirred for 12 h at rt. After that time the pyridine was removed by azeotropic distillation with heptane. The residue was purified by chromatography on silica (hexanes:EtOAc, 9:1) to giv... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | CNc1ccc(Br)cc1.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1>CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cbf5c4679a00474b8f5f7f699350d347 | CCOCCn1cccc1C(=O)C(F)(F)F.CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1>>CCOCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | C(C)OCCN1C(=CC=C1)C(C(F)(F)F)=O.BrC1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C.[Li]C(C)(C)C>>C(C)OCCN1C(=CC=C1)C(C(F)(F)F)(O)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[C:30]([F:31])([F:32])[F:33].Br[c:13]1[cH:14][cH:15][c:16]([N:17]([CH3:18])[S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]1[C:11]([OH:12])([... | CCOCCn1cccc1C(=O)C(F)(F)F.CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1 | CCOCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | CCOCC.CCCCC.C1CCOC1 | C-C Coupling | Grignard_alcohol | 23831eb2f5100c758a065f977b2daac4728a2009a2a7f37e9b01c50283e9e583 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | O=S(=O)(Nc1ccc(Cc2ccc[nH]2)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7](:[c:8]):[c:9](-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]):[c:16]>>[C:6]-[#7;a:7](:[c:8]):[c:9](-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15... | null | [] | null | null | null | null | To a solution of 75 mg (0.23 mmol) of N-(4-bromophenyl)-N-methyl-benzenesulfonamide in 4 mL of Et2O at −78° C. was added dropwise 285 μL (0.49 mmol) of a 1.7 M solution of tert-BuLi in pentane and the resultant mixture was stirred at −78° C. for 10 min. To this mixture was then added a solution of 81 mg (0.34 mmol) of ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1 | c1ccccc1 | c1ccc[nH]1.c1ccccc1.c1ccccc1 | Br- | CCOCC.CCCCC.C1CCOC1 | null | null | CCOCCn1cccc1C(=O)C(F)(F)F.CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1>CCOCC.CCCCC.C1CCOC1>CCOCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ae3e8692b2f4f589d0a29c32af72885 | CI.COCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F>>COCCn1cccc1C(OC)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | [H-].[Na+].COCCN1C(=CC=C1)C(C(F)(F)F)(O)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C.IC>>COCCN1C(=CC=C1)C(C(F)(F)F)(OC)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | I[CH3:12].[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][cH:8][c:9]1[C:10]([OH:11])([c:13]1[cH:14][cH:15][c:16]([N:17]([CH3:18])[S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29]1)[C:30]([F:31])([F:32])[F:33]>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][cH:8][c:9]1[C:10]([O:11][CH3:12])([... | CI.COCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | COCCn1cccc1C(OC)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | cd10a9010f842ab825b304bd2965f17f9c39c4c64e5fc6cd91306ae51817de0d | 9271b713ded6954f3329c61a211042ac37c82b3aff1b62cb455035e69339dd27 | O=S(=O)(Nc1ccc(Cc2ccc[nH]2)cc1)c1ccccc1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4](-[OH;D1;+0:5])(-[c:6])-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10]>>[#7;a:2]:[c:3]-[C:4](-[c:6])(-[O;H0;D2;+0:5]-[CH3;D1;+0:1])-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10] | null | [] | 0 | CELSIUS | 35 | MINUTE | To a suspension of 3.8 mg of NaH (0.10 mmol) in 3 mL of DMF at 0° C. was added 32 mg of N-(4-{-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide (Example 79, 0.068 mmol) and the reaction mixture was stirred at 0° C. for 35 min. 6 μL of iodomethane (0.089 mmol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | c1ccc[nH]1.c1ccccc1.c1ccccc1 | HI | CN(C)C=O | 0 | 0.583333 | CI.COCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F>CN(C)C=O>COCCn1cccc1C(OC)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c4550540a824d66b849dd341f27b37d | CCOCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F>>CCOCCn1cccc1C(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | B(F)(F)F.CCOCC.C(C)OCCN1C(=CC=C1)C(C(F)(F)F)(O)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C.C(C)[SiH](CC)CC>>C(C)OCCN1C(=CC=C1)C(C(F)(F)F)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | O[C:11]([c:10]1[n:6]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])[cH:7][cH:8][cH:9]1)([c:12]1[cH:13][cH:14][c:15]([N:16]([CH3:17])[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1)[C:29]([F:30])([F:31])[F:32]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]1[CH:11]([c:12]1[cH:13]... | CCOCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | CCOCCn1cccc1C(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F | null | null | C(Cl)Cl | Reduction | OtherReaction | c74e766e62dea6513290ab98d06521c92685074430a200193315f473ed0037ec | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | O=S(=O)(Nc1ccc(Cc2ccc[nH]2)cc1)c1ccccc1 | O-[C;H0;D4;+0:1](-[c:2](:[c:3]):[#7;a:4](-[C:5]):[c:6])(-[c:7](:[c:8]):[c:9])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]>>[C:5]-[#7;a:4](:[c:6]):[c:2](-[CH;D3;+0:1](-[c:7](:[c:8]):[c:9])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:3] | null | [] | null | null | 1.75 | HOUR | To a solution of 32 mg (0.07 mmol) of N-(4-{1-[1-(2-ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide (Example 78) in 2 mL of CH2Cl2 at 0° C. were added 1.05 mL (6.57 mmol) of triethylsilane followed by 167 μL (1.32 mmol) of boron trifluoride diethyl etherate dropwise. The... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | null | null | c1ccc[nH]1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 1.75 | CCOCCn1cccc1C(O)(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F>C(Cl)Cl>CCOCCn1cccc1C(c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32943dafa0ec4be9a66701c171835240 | CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1.COCCn1cccc1C=O>>COCCn1cccc1C(O)c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 | COCCN1C(=CC=C1)C=O.BrC1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C.[Li]C(C)(C)C>>OC(C=1N(C=CC1)CCOC)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | Br[c:12]1[cH:13][cH:14][c:15]([N:16]([CH3:17])[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][cH:8][c:9]1[CH:10]=[O:11]>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][cH:8][c:9]1[CH:10]([OH:11])[c:12]1[cH:13][cH:14][c:15]([N:16]([CH3:17])[S... | CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1.COCCn1cccc1C=O | COCCn1cccc1C(O)c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 | null | null | CCCCC.C1CCOC1 | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | O=S(=O)(Nc1ccc(Cc2ccc[nH]2)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7;a:7](:[c:8]):[c:9](-[CH;D2;+0:10]=[O;H0;D1;+0:11]):[c:12]>>[C:6]-[#7;a:7](:[c:8]):[c:9](-[CH;D3;+0:10](-[OH;D1;+0:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12] | null | [] | -30 | CELSIUS | null | null | To a solution of 1.49 g (4.59 mmol) of N-(4-bromophenyl)-N-methyl benzenesulfonamide (Example 78, Step C) in 37.5 mL THF at −78° C. was added dropwise 5.94 mL (10.10 mmol) of a 1.7 M solution of tert-BuLi in pentane and the resultant mixture was stirred at −78° C. for 15 min. To this mixture was then added a solution o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccc[nH]1.c1ccccc1.c1ccccc1 | Br- | CCCCC.C1CCOC1 | -30 | null | CN(c1ccc(Br)cc1)S(=O)(=O)c1ccccc1.COCCn1cccc1C=O>CCCCC.C1CCOC1>COCCn1cccc1C(O)c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5de3c28587d841a49d898ee79598a074 | COCCn1cccc1C(O)c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1>>COCCn1cccc1Cc1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 | B(F)(F)F.CCOCC.OC(C=1N(C=CC1)CCOC)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C.C(C)[SiH](CC)CC>>COCCN1C(=CC=C1)CC1=CC=C(C=C1)N(S(=O)(=O)C1=CC=CC=C1)C | O[CH:10]([c:9]1[n:5]([CH2:4][CH2:3][O:2][CH3:1])[cH:6][cH:7][cH:8]1)[c:11]1[cH:12][cH:13][c:14]([N:15]([CH3:16])[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][cH:8][c:9]1[CH2:10][c:11]1[cH:12][cH:13][c:14]([N:15]([CH3:16])[S:17](=[O:18])... | COCCn1cccc1C(O)c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 | COCCn1cccc1Cc1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 | null | null | C(Cl)Cl | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | O=S(=O)(Nc1ccc(Cc2ccc[nH]2)cc1)c1ccccc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[#7;a:7](-[C:8]):[c:9]>>[C:8]-[#7;a:7](:[c:9]):[c:5](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:6] | null | [] | null | null | 2.5 | HOUR | To a solution of 16 mg (0.04 mmol) of N-(4-{1-hydroxy-1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide (Example 93) in 1.5 mL CH2Cl2 at 0° C. were added 620 μL (3.88 mmol) of triethylsilane followed by 100 μL (0.79 mmol) of boron trifluoride diethyl etherate dropwise. The mixture was wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccc[nH]1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 2.5 | COCCn1cccc1C(O)c1ccc(N(C)S(=O)(=O)c2ccccc2)cc1>C(Cl)Cl>COCCn1cccc1Cc1ccc(N(C)S(=O)(=O)c2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-57535bf7c107433c9e25a290b71400a3 | C=C(CCl)CCl.CC(=O)c1ccc(O)c(CS(=O)(=O)c2ccccc2)c1>>C=C(CCl)COc1ccc(C(=O)OC)cc1CS(=O)(=O)c1ccccc1 | C([O-])([O-])=O.[K+].[K+].ClCC(=C)CCl.OC1=C(C=C(C=C1)C(C)=O)CS(=O)(=O)C1=CC=CC=C1.CN(C=O)C.Cl>>ClCC(COC1=C(C=C(C(=O)OC)C=C1)CS(=O)(=O)C1=CC=CC=C1)=C | Cl[CH2:5][C:2](=[CH2:1])[CH2:3][Cl:4].[OH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH3:14])[cH:15][c:16]1[CH2:17][S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH2:1]=[C:2]([CH2:3][Cl:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][c:16]1[CH2:17][S:18](=[O:19])(=[O... | C=C(CCl)CCl.CC(=O)c1ccc(O)c(CS(=O)(=O)c2ccccc2)c1 | C=C(CCl)COc1ccc(C(=O)OC)cc1CS(=O)(=O)c1ccccc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.CCOCC | Acylation | OtherReaction | 77178c9f76d901cb1fe6c7e159adafad906b7ae05c375169b03230411ae03429 | 4c394635b02fb0de5299b7d137e911f21c9ebfc0eec1816ad013f170ce0f9fe0 | O=S(=O)(Cc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]:[c:14]:1>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[c:11]1:[c:10]:[c:9]:[c:8](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:15]-[CH3;D1;+0:5]):[c:14]:[c:13]:1 | 50 | [{"value": 50.0, "product": "ClCC(COC1=C(C=C(C(=O)OC)C=C1)CS(=O)(=O)C1=CC=CC=C1)=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 3 g (8.62 mmol) of tetrabutylammonium iodide, 3.02 g (20.4 mmol) of potassium carbonate and then 2.36 ml (20.4 mmol) of 2-chloromethyl-3-chloro-1-propene are successively introduced into a solution of 2.5 g (8.16 mmol) of readily accessible 1-{4-hydroxy-3-[(phenylsulfonyl)methyl]phenyl}ethanone in 150 ml of N,N-dimethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.CCOCC | null | 20 | C=C(CCl)CCl.CC(=O)c1ccc(O)c(CS(=O)(=O)c2ccccc2)c1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.CCOCC>C=C(CCl)COc1ccc(C(=O)OC)cc1CS(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1d71153d7a647bc86d1440342c2fac6 | C=C(CCl)COc1ccc(C(=O)OC)cc1CS(=O)(=O)c1ccccc1>>C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1 | O.Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].ClCC(COC1=C(C=C(C(=O)OC)C=C1)CS(=O)(=O)C1=CC=CC=C1)=C>>C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC | Cl[CH2:25][C:2](=[CH2:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]1[CH2:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]2[CH:15]([S:16](=[O:17])(=[O:18])[c:19]2[cH:20]... | C=C(CCl)COc1ccc(C(=O)OC)cc1CS(=O)(=O)c1ccccc1 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1 | null | null | ClCCl.O1CCCC1 | Functional Group Interconversion | OtherReaction | 6b8c466c96c7381d3c662d12cbde5fb716a993369c63e8a3d9a4d09da309a087 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | C=C1COc2ccccc2C(S(=O)(=O)c2ccccc2)C1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[O;D1;H0:5]=[#16:6](=[O;D1;H0:7])(-[c:8])-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[CH;D3;+0:9](-[#16:6](=[O;D1;H0:5])(=[O;D1;H0:7])-[c:8])-[c:10](:[c:11]):[c:12] | 60 | [{"value": 60.0, "product": "C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.7, "product": "C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 1.33 ml of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added to 478 mg (1.21 mmol) of methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-[(phenylsulfonyl)methyl]benzoate dissolved in 39 ml of tetrahydrofuran. The solution is stirred for 5 minutes and then water, 1N hydrochloric acid and dichloromethane are... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2.c1ccccc1 | HCl | ClCCl.O1CCCC1 | null | 0.083333 | C=C(CCl)COc1ccc(C(=O)OC)cc1CS(=O)(=O)c1ccccc1>ClCCl.O1CCCC1>C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0688c3ac6a054939b48bf4505142ac19 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1>>C=C1CCc2cc(C(=O)OC)ccc2OC1 | C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC.O.P(=O)(O)([O-])[O-].[Na+].[Na+].CO.O1CCCC1>>C=C1COC2=C(CC1)C=C(C=C2)C(=O)OC | O=S(=O)(c1ccccc1)[CH:4]1[CH2:3][C:2](=[CH2:1])[CH2:16][O:15][c:14]2[c:5]1[cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12][cH:13]2>>[CH2:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12][cH:13][c:14]2[O:15][CH2:16]1 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1 | C=C1CCc2cc(C(=O)OC)ccc2OC1 | null | [Na].[Hg] | ClCCl | Reduction | OtherReaction | 1403cc7e5a2a911fded57203a36f53d3d03026d3cf24a05d673aa2af9b974752 | d840e89f7e5c2afbebc71c3968f0da9c2e720c3c085dce57700b061c879e763d | C=C1CCc2ccccc2OC1 | O=S(=O)(-[CH;D3;+0:1]1-[C:2]-[C:3](=[C;D1;H2:4])-[C:5]-[#8:6]-[c:7]:[c:8]-1:[c:9])-c1:c:c:c:c:c:1>>[C;D1;H2:4]=[C:3]1-[C:5]-[#8:6]-[c:7]:[c:8](:[c:9])-[CH2;D2;+0:1]-[C:2]-1 | null | [] | null | null | 4 | HOUR | 728 mg (0.95 mmol) of 3% sodium amalgam are added portionwise at 0° C. to a suspension of 85 mg (0.23 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 1, and of 116 mg (0.95 mmol) of sodium hydrogenphosphate in 10 ml of a 1/1 methanol/tetrahydro... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | null | c1ccccc1.c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | HO- | [Na].[Hg].ClCCl | null | 4 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1>[Na].[Hg].ClCCl>C=C1CCc2cc(C(=O)OC)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d43c41bede90405fa3fc743006c413f3 | COC(=O)c1ccc2c(c1)CCC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COC(=O)c1ccc2c(c1)CCC(=CCl)CO2 | O=C1COC2=C(CC1)C=C(C=C2)C(=O)OC.C(CCC)[Li].[Cl-].ClC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O>>ClC=C1COC2=C(CC1)C=C(C=C2)C(=O)OC | O=[C:13]1[CH2:12][CH2:11][c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:17][CH2:16]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:14][Cl:15])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][C:13](=[CH:14][Cl:15])[CH2:16][O:17]2 | COC(=O)c1ccc2c(c1)CCC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)c1ccc2c(c1)CCC(=CCl)CO2 | null | null | O1CCCC1.CCCCCC | C-C Coupling | Wittig with Phosphonium | 33f4b01bff17bc186870f174aa1415cc072a6904bf349e20bef59f70b19d9e13 | 4ccc953afa1928fe5ef55f22a0c593e017875730e9bc8868efb0bd3550ea5ba6 | [CH]=C1CCc2ccccc2OC1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[#8:5]-[c:6].[Cl;D1;H0:7]-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[CH;D2;+0:8]-[Cl;D1;H0:7])-[C:4]-[#8:5]-[c:6] | 24.2 | [{"value": 24.0, "product": "ClC=C1COC2=C(CC1)C=C(C=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.2, "product": "ClC=C1COC2=C(CC1)C=C(C=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 0.08 ml (0.2 mmol) of a 1.9M solution of n-butyllithium in hexane is added dropwise to a suspension of 76 mg (0.22 mmol) of chloromethyltriphenylphosphonium chloride in 1.7 ml of tetrahydrofuran cooled to 0° C. The solution is stirred for one hour and then 40 mg (0.18 mmol) of methyl 3-oxo-2,3,4,5-tetrahydro-1-benzoxep... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | c1ccc2c(c1)CCCCO2.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | HO- | O1CCCC1.CCCCCC | 0 | 1 | COC(=O)c1ccc2c(c1)CCC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>O1CCCC1.CCCCCC>COC(=O)c1ccc2c(c1)CCC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e1a81dcc4f34c74882563a072dc0774 | BrCc1ccccc1.C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1>>C=C1COc2ccc(C(=O)OC)cc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 | C(C1=CC=CC=C1)Br.Cl.CN1C(N(CCC1)C)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC>>C(C1=CC=CC=C1)C1(CC(COC2=C1C=C(C=C2)C(=O)OC)=C)S(=O)(=O)C2=CC=CC=C2 | Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]2[CH:15]([S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32]1>>[CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13]... | BrCc1ccccc1.C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1 | C=C1COc2ccc(C(=O)OC)cc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 | null | null | O1CCCC1.O.ClCCl | C-C Coupling | OtherReaction | 0a2d11efff7a4620e79514433af23ac3b11c4e0755c270119fc4a9c5add176d9 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C=C1COc2ccccc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H2:5]=[C:6]1-[C:7]-[CH;D3;+0:8](-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[c:13](:[c:14]):[c:15]-[#8:16]-[C:17]-1>>[C;D1;H2:5]=[C:6]1-[C:7]-[C;H0;D4;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[c:13](:[c:14]):[c:15]-[#8:16]-[C:... | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)C1(CC(COC2=C1C=C(C=C2)C(=O)OC)=C)S(=O)(=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 0.072 ml (1.1 equivalents) of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and then 0.6 ml (1.1 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 195 mg (0.55 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.O.ClCCl | null | 0.25 | BrCc1ccccc1.C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1>O1CCCC1.O.ClCCl>C=C1COc2ccc(C(=O)OC)cc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab5491429d1d407e8b0a4e35322d8bac | COC(=O)c1ccc2c(c1)C(Cc1ccccc1)CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COC(=O)c1ccc2c(c1)C(Cc1ccccc1)CC(=CCl)CO2 | Cl.C(CCC)[Li].[Cl-].ClC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)C1CC(COC2=C1C=C(C=C2)C(=O)OC)=O>>C(C1=CC=CC=C1)C1CC(COC2=C1C=C(C=C2)C(=O)OC)=CCl | O=[C:20]1[CH2:19][CH:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:24][CH2:23]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:21][Cl:22])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]([CH2:12][c:13]1[cH:14][cH:15][cH:16][cH... | COC(=O)c1ccc2c(c1)C(Cc1ccccc1)CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)c1ccc2c(c1)C(Cc1ccccc1)CC(=CCl)CO2 | null | null | ClCCl.O.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 33f4b01bff17bc186870f174aa1415cc072a6904bf349e20bef59f70b19d9e13 | 4ccc953afa1928fe5ef55f22a0c593e017875730e9bc8868efb0bd3550ea5ba6 | [CH]=C1COc2ccccc2C(Cc2ccccc2)C1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[#8:5]-[c:6].[Cl;D1;H0:7]-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[CH;D2;+0:8]-[Cl;D1;H0:7])-[C:4]-[#8:5]-[c:6] | 53 | [{"value": 53.0, "product": "C(C1=CC=CC=C1)C1CC(COC2=C1C=C(C=C2)C(=O)OC)=CCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.5, "product": "C(C1=CC=CC=C1)C1CC(COC2=C1C=C(C=C2)C(=O)OC)=CCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 1.1 equivalents of n-butyllithium are added to a suspension of 40 mg (0.12 mmol) of chloromethyltriphenylphosphonium chloride in 3 ml of tetrahydrofuran cooled to 0° C. After stirring for one hour, the ylide is added at 0° C. via a hollow tube to 30 mg (0.1 mmol) of methyl 5-benzyl-3-oxo-2,3,4,5-tetrahydro-1-benzoxepin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | c1ccc2c(c1)CCCCO2.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCCO2 | c1ccccc1.c1ccc2c(c1)CCCCO2 | HO- | ClCCl.O.O1CCCC1 | 0 | 1 | COC(=O)c1ccc2c(c1)C(Cc1ccccc1)CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>ClCCl.O.O1CCCC1>COC(=O)c1ccc2c(c1)C(Cc1ccccc1)CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc1f3eb907b64e0188308cae0d70581a | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1.C=CCBr>>C=CCC1(S(=O)(=O)c2ccccc2)CC(=C)COc2ccc(C(=O)OC)cc21 | C(C=C)Br.Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC>>C(C=C)C1(CC(COC2=C1C=C(C=C2)C(=O)OC)=C)S(=O)(=O)C2=CC=CC=C2 | [CH:4]1([S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][C:15](=[CH2:16])[CH2:17][O:18][c:19]2[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27][c:28]21.Br[CH2:3][CH:2]=[CH2:1]>>[CH2:1]=[CH:2][CH2:3][C:4]1([S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][C:15](=[CH2... | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1.C=CCBr | C=CCC1(S(=O)(=O)c2ccccc2)CC(=C)COc2ccc(C(=O)OC)cc21 | null | null | O1CCCC1.O.ClCCl | C-C Coupling | OtherReaction | 79bc13f8b5f05882a3c6a2617dc6381d15033acc40f5dc6619c3addba8aef4fa | 4e1ce4e19860a9931e6216ba313479e4494dc60a286d9f70a4527814b3cbb3e2 | C=C1COc2ccccc2C(S(=O)(=O)c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H2:4]=[C:5]1-[C:6]-[CH;D3;+0:7](-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[c:12](:[c:13]):[c:14]-[#8:15]-[C:16]-1>>[C;D1;H2:4]=[C:5]1-[C:6]-[C;H0;D4;+0:7](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])(-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[c:12](:[c:13]):[c:14]-[#8:15]-[C:16]-1 | 67 | [{"value": 67.0, "product": "C(C=C)C1(CC(COC2=C1C=C(C=C2)C(=O)OC)=C)S(=O)(=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 0.023 ml (1.1 equivalents) of 1,3-dimethylpropyleneurea and then 0.189 ml (1.1 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 61 mg (0.17 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to exa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccccc1.c1ccc2c(c1)CCCCO2 | HBr | O1CCCC1.O.ClCCl | null | 0.25 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1.C=CCBr>O1CCCC1.O.ClCCl>C=CCC1(S(=O)(=O)c2ccccc2)CC(=C)COc2ccc(C(=O)OC)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c49d4299a4bd4422926a75399ae58a44 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1.CCBr>>C=C1COc2ccc(C(=O)OC)cc2C(CC)(S(=O)(=O)c2ccccc2)C1 | C(C)Br.Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC>>C(C)C1(CC(COC2=C1C=C(C=C2)C(=O)OC)=C)S(=O)(=O)C2=CC=CC=C2 | [CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]2[CH:15]([S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1.Br[CH2:16][CH3:17]>>[CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][c:14]2[C:15]([CH2:16][CH3:17])([S:... | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1.CCBr | C=C1COc2ccc(C(=O)OC)cc2C(CC)(S(=O)(=O)c2ccccc2)C1 | null | null | O1CCCC1.O.ClCCl | C-C Coupling | OtherReaction | 0a2d11efff7a4620e79514433af23ac3b11c4e0755c270119fc4a9c5add176d9 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C=C1COc2ccccc2C(S(=O)(=O)c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H2:3]=[C:4]1-[C:5]-[CH;D3;+0:6](-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10])-[c:11](:[c:12]):[c:13]-[#8:14]-[C:15]-1>>[C;D1;H2:3]=[C:4]1-[C:5]-[C;H0;D4;+0:6](-[CH2;D2;+0:1]-[C;D1;H3:2])(-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10])-[c:11](:[c:12]):[c:13]-[#8:14]-[C:15]-1 | 58 | [{"value": 58.0, "product": "C(C)C1(CC(COC2=C1C=C(C=C2)C(=O)OC)=C)S(=O)(=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 0.030 ml (1.1 equivalents) of 1,3-dimethylpropyleneurea and then 0.246 ml (1.1 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 80 mg (0.22 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to exa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2.c1ccccc1 | HBr | O1CCCC1.O.ClCCl | null | 0.25 | C=C1COc2ccc(C(=O)OC)cc2C(S(=O)(=O)c2ccccc2)C1.CCBr>O1CCCC1.O.ClCCl>C=C1COc2ccc(C(=O)OC)cc2C(CC)(S(=O)(=O)c2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55d0fc010eec4baeac9b7ff4dcfea9bf | C=C1COc2ccc(C(C)=O)cc2C(S(=O)(=O)c2ccccc2)C1>>C=C1CCc2cc(C(C)O)ccc2OC1 | C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(C)=O.P(=O)(O)([O-])[O-].[Na+].[Na+].CO.O1CCCC1>>C=C1COC2=C(CC1)C=C(C=C2)C(C)O | O=S(=O)(c1ccccc1)[CH:4]1[CH2:3][C:2](=[CH2:1])[CH2:15][O:14][c:13]2[c:5]1[cH:6][c:7]([C:8]([CH3:9])=[O:10])[cH:11][cH:12]2>>[CH2:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([CH:8]([CH3:9])[OH:10])[cH:11][cH:12][c:13]2[O:14][CH2:15]1 | C=C1COc2ccc(C(C)=O)cc2C(S(=O)(=O)c2ccccc2)C1 | C=C1CCc2cc(C(C)O)ccc2OC1 | null | [Na].[Hg] | O | Reduction | OtherReaction | b53dfd26be6f0f5eafd870670e29785cbeae7e717b7a9db55d5f4c113ab987de | dc5dda88765c78b9cbf727939414381436804136403d7c71b44b3f1693ec9903 | C=C1CCc2ccccc2OC1 | O=S(=O)(-[CH;D3;+0:1]1-[C:2]-[C:3](=[C;D1;H2:4])-[C:5]-[#8:6]-[c:7]:[c:8]-1:[c:9]:[c:10](-[C;H0;D3;+0:11](-[C;D1;H3:12])=[O;H0;D1;+0:13]):[c:14])-c1:c:c:c:c:c:1>>[C;D1;H2:4]=[C:3]1-[C:5]-[#8:6]-[c:7]:[c:8](:[c:9]:[c:10](-[CH;D3;+0:11](-[C;D1;H3:12])-[OH;D1;+0:13]):[c:14])-[CH2;D2;+0:1]-[C:2]-1 | 80.7 | [{"value": 80.7, "product": "C=C1COC2=C(CC1)C=C(C=C2)C(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 3.14 mg (6.82 mmol) of 5% sodium amalgam are added portionwise at 0° C. to 389 mg (1.14 mmol) of 1-[3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone, prepared according to example 13, and 648 mg (4.55 mmol) of sodium hydrogenphosphate in suspension in 50 ml of a 1/1 methanol/tetrahydrofuran ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Sulfone | Secondary alcohol | c1ccccc1.c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | HO- | [Na].[Hg].O | null | 4 | C=C1COc2ccc(C(C)=O)cc2C(S(=O)(=O)c2ccccc2)C1>[Na].[Hg].O>C=C1CCc2cc(C(C)O)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f249fafa738e4090a7c960870da6049d | C=C1CCc2cc(C(C)O)ccc2OC1.O>>CC(=O)c1ccc2c(c1)CCC(=O)CO2 | C(Cl)(Cl)(Cl)Cl.C(C)#N.O.C=C1COC2=C(CC1)C=C(C=C2)C(C)O.OC(C)(C)C(C)(C)O.S(=S)(=O)([O-])[O-].[Na+].[Na+].I(=O)(=O)(=O)[O-].[Na+]>>C(C)(=O)C=1C=CC2=C(CCC(CO2)=O)C1 | C=[C:12]1[CH2:11][CH2:10][c:8]2[c:7]([cH:6][cH:5][c:4]([CH:2]([CH3:1])[OH:3])[cH:9]2)[O:15][CH2:14]1.[OH2:13]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][C:12](=[O:13])[CH2:14][O:15]2 | C=C1CCc2cc(C(C)O)ccc2OC1.O | CC(=O)c1ccc2c(c1)CCC(=O)CO2 | null | O.O.O.[Ru](Cl)(Cl)Cl | ClCCl | Acylation | OtherReaction | 181e308f47a6cb823ec8efc486f7eabe7c93f9ba13abfed4b36c8cd5e336f8fc | 32fe5d39ad0dd0a3e3ab68a0d9671c9a9e2e108ed9bea7d5de812b68045bda7b | O=C1CCc2ccccc2OC1 | C=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[#8:5]-[c:6].[C;D1;H3:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[c:10](:[c:11]):[c:12].[OH2;D0;+0:13]>>[C;D1;H3:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12].[C:3]-[C:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:13])-[C:4]-[#8:5]-[c:6] | 55 | [{"value": 55.0, "product": "C(C)(=O)C=1C=CC2=C(CCC(CO2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 4.7 mg (0.023 mmol) of ruthenium chloride trihydrate are added at 0° C. to 188 mg of 1-(3-methylene-2,3,4,5-tetrahydro-1-benzoxepin-7-yl)ethanol as a mixture with its pinacol dimer, prepared according to example 15, and 1.28 g (5.99 mmol) of sodium periodate in solution in a carbon tetrachloride/acetonitrile/water (2/2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | Other | O.O.O.[Ru](Cl)(Cl)Cl.ClCCl | null | 24 | C=C1CCc2cc(C(C)O)ccc2OC1.O>O.O.O.[Ru](Cl)(Cl)Cl.ClCCl>CC(=O)c1ccc2c(c1)CCC(=O)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e746e8ecaa2442ba976ac2c8f3d8b065 | BrCc1ccccc1.C=C1COc2ccc(C(C)=O)cc2C(S(=O)(=O)c2ccccc2)C1>>C=C1COc2ccc(C(C)=O)cc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 | C(C1=CC=CC=C1)Br.Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(C)=O>>C(C1=CC=CC=C1)C1(CC(COC2=C1C=C(C=C2)C(C)=O)=C)S(=O)(=O)C2=CC=CC=C2 | Br[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][c:13]2[CH:14]([S:22](=[O:23])(=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31]1>>[CH2:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][c:13]2[C:14... | BrCc1ccccc1.C=C1COc2ccc(C(C)=O)cc2C(S(=O)(=O)c2ccccc2)C1 | C=C1COc2ccc(C(C)=O)cc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 | null | null | O1CCCC1.O.ClCCl | C-C Coupling | OtherReaction | 0a2d11efff7a4620e79514433af23ac3b11c4e0755c270119fc4a9c5add176d9 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C=C1COc2ccccc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H2:5]=[C:6]1-[C:7]-[CH;D3;+0:8](-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[c:13](:[c:14]):[c:15]-[#8:16]-[C:17]-1>>[C;D1;H2:5]=[C:6]1-[C:7]-[C;H0;D4;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[c:13](:[c:14]):[c:15]-[#8:16]-[C:... | 97 | [{"value": 97.0, "product": "C(C1=CC=CC=C1)C1(CC(COC2=C1C=C(C=C2)C(C)=O)=C)S(=O)(=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 0.152 ml (2.2 equivalents) of 1,3-dimethylpropyleneurea and then 1.286 ml (2.2 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 200 mg (0.58 mmol) of 1-[3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone, prepared according to exampl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2 | c1ccc2c(c1)CCCCO2.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.O.ClCCl | null | 0.25 | BrCc1ccccc1.C=C1COc2ccc(C(C)=O)cc2C(S(=O)(=O)c2ccccc2)C1>O1CCCC1.O.ClCCl>C=C1COc2ccc(C(C)=O)cc2C(Cc2ccccc2)(S(=O)(=O)c2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-141dcc1cc5a140088ea5e68d2399c500 | C=C(CCl)CCl.O=Cc1ccccc1O>>C=C(CCl)COc1ccccc1C=O | [I-].[Na+].C([O-])([O-])=O.[K+].[K+].ClCC(=C)CCl.OC1=C(C=O)C=CC=C1>>ClCC(COC1=C(C=O)C=CC=C1)=C | Cl[CH2:5][C:2](=[CH2:1])[CH2:3][Cl:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH:13]=[O:14]>>[CH2:1]=[C:2]([CH2:3][Cl:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH:13]=[O:14] | C=C(CCl)CCl.O=Cc1ccccc1O | C=C(CCl)COc1ccccc1C=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:6]=[O;D1;H0:5] | 100.2 | [{"value": 70.0, "product": "ClCC(COC1=C(C=O)C=CC=C1)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "ClCC(COC1=C(C=O)C=CC=C1)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 45 g (0.3 mol) of sodium iodide, 16.5 (0.12 mol) of potassium carbonate and 17.36 ml (0.15 mol) of 3-chloro-2-chloromethyl-1-propene are added to 10.4 ml (0.1 mol) of 2-hydroxybenzaldehyde in solution in acetone. The mixture is left at reflux of the solvent for 12 hours and then the solvent is evaporated. The medium is... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CC(=O)C | null | null | C=C(CCl)CCl.O=Cc1ccccc1O>CC(=O)C>C=C(CCl)COc1ccccc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-927e297db59546fc924cca8ee753e324 | C=C1C=Cc2ccccc2OC1.CS(N)(=O)=O>>OCC1(O)C=Cc2ccccc2OC1 | O.C(C)(C)(C)O.C=C1COC2=C(C=C1)C=CC=C2.CS(=O)(=O)N.S([O-])(O)=O.[Na+]>>OCC1(COC2=C(C=C1)C=CC=C2)O | [CH2:2]=[C:3]1[CH:5]=[CH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[O:13][CH2:14]1.CS(N)(=O)=[O:1]>>[OH:1][CH2:2][C:3]1([OH:4])[CH:5]=[CH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[O:13][CH2:14]1 | C=C1C=Cc2ccccc2OC1.CS(N)(=O)=O | OCC1(O)C=Cc2ccccc2OC1 | null | [Os](=O)(=O)(=O)=O | null | Heteroatom Alkylation and Arylation | OtherReaction | 1dd0175b5e5897c05eeacfea9e93da402a49ee0808c6f9f1e145b9bcb566a8d7 | 3f275d2f23fbd953aef198569e4b9740a8771e7cfb7bc68348b3c74eeaea8c37 | C1=Cc2ccccc2OCC1 | C-S(-N)(=O)=[O;H0;D1;+0:1].[CH2;D1;+0:2]=[C;H0;D3;+0:3]1-[C:4]-[#8:5]-[c:6]:[c:7]-[C:8]=[C:9]-1>>[O;D1;H1:10]-[C;H0;D4;+0:3]1(-[CH2;D2;+0:2]-[OH;D1;+0:1])-[C:4]-[#8:5]-[c:6]:[c:7]-[C:8]=[C:9]-1 | 95 | [{"value": 95.0, "product": "OCC1(COC2=C(C=C1)C=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 160 mg (1 mmol) of 3-methylene-2,3-dihydro-1-benzoxepin, prepared according to example 23, are added to a mixture of 250 mg (1 mmol) of osmium tetroxide and 95 mg (1 mmol) of methanesulfonamide dissolved in 10 ml of a 1/1 water/tert-butanol mixture. After 12 hours at ambient temperature, 1.5 g of sodium bisulfite are i... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Vinyl | Primary alcohol.Tertiary alcohol | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | [Os](=O)(=O)(=O)=O | null | 12 | C=C1C=Cc2ccccc2OC1.CS(N)(=O)=O>[Os](=O)(=O)(=O)=O>OCC1(O)C=Cc2ccccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4aac08ded32d4d21886abfba29f677cd | OCC1(O)C=Cc2ccccc2OC1>>O=C1C=Cc2ccccc2OC1 | I(=O)(=O)(=O)[O-].[Na+].OCC1(COC2=C(C=C1)C=CC=C2)O>>O1CC(C=CC2=C1C=CC=C2)=O | OC[C:2]1([OH:1])[CH:3]=[CH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[O:11][CH2:12]1>>[O:1]=[C:2]1[CH:3]=[CH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[O:11][CH2:12]1 | OCC1(O)C=Cc2ccccc2OC1 | O=C1C=Cc2ccccc2OC1 | null | null | O1CCOCC1.O | Miscellaneous | OtherReaction | 4c323face09bd7ca7c812bd2d273a27bf3fc8629abb540a58cadbb80a381e3cc | d8333db1a8553533b9f31a51fd46ac10421b6606be90ce648ca3b16dc0428896 | O=C1C=Cc2ccccc2OC1 | O-C-[C;H0;D4;+0:1]1(-[OH;D1;+0:2])-[C:3]-[#8:4]-[c:5]:[c:6]-[C:7]=[C:8]-1>>[O;H0;D1;+0:2]=[C;H0;D3;+0:1]1-[C:3]-[#8:4]-[c:5]:[c:6]-[C:7]=[C:8]-1 | 70 | [{"value": 70.0, "product": "O1CC(C=CC2=C1C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "O1CC(C=CC2=C1C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4×28.5 mg (0.55 mmol) of sodium periodate are added in four equal portions over 30 minutes to 106 mg (0.55 mmol) of 3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-3-ol, prepared according to example 24, in solution in 3 ml of a 3/7 dioxane/water mixture. After stirring at ambient temperature for 2 hours, the medium is filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ketone | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | O1CCOCC1.O | null | 2 | OCC1(O)C=Cc2ccccc2OC1>O1CCOCC1.O>O=C1C=Cc2ccccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-acfe2cd6cd61488092e8115fdd52e651 | ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1C=Cc2ccccc2OC1>>ClC=C1C=Cc2ccccc2OC1 | C(CCC)[Li].[Cl-].ClC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CC(C=CC2=C1C=CC=C2)=O>>ClC=C1COC2=C(C=C1)C=CC=C2 | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:2][Cl:1])cc1.O=[C:3]1[CH:4]=[CH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[O:12][CH2:13]1>>[Cl:1][CH:2]=[C:3]1[CH:4]=[CH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[O:12][CH2:13]1 | ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1C=Cc2ccccc2OC1 | ClC=C1C=Cc2ccccc2OC1 | null | null | O1CCCC1.CCCCC | C-C Coupling | Wittig with Phosphonium | 539d98d0a68c79c0ce64fb9b77faf88c2e8998170a817390f2eb321da849bd7d | 4ccc953afa1928fe5ef55f22a0c593e017875730e9bc8868efb0bd3550ea5ba6 | [CH]=C1C=Cc2ccccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5]-[C:6]=[C:7]-1.[Cl;D1;H0:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[Cl;D1;H0:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5]-[C:6]=[C:7]-1 | 52 | [{"value": 52.0, "product": "ClC=C1COC2=C(C=C1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "ClC=C1COC2=C(C=C1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 1.1 eq. of n-butyllithium are added to 104 mg (0.3 mmol) of chloromethyltriphenylphosphonium chloride in solution in tetrahydrofuran cooled to 0° C. After stirring for one hour, 40 mg (0.25 mmol) of 1-benzoxepin-3(2H)-one, prepared according to example 25, are added at ambient temperature and the mixture is left for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | O1CCCC1.CCCCC | 0 | 1 | ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1C=Cc2ccccc2OC1>O1CCCC1.CCCCC>ClC=C1C=Cc2ccccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b1e0f16b5354988b0a789b4e223685d | CC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)CC(=O)CO2>>CC(=O)c1ccc2c(c1)C=CC(=O)CO2 | N12CCCCCC2=NCCC1.C(C)(=O)C=1C=CC2=C(C(CC(CO2)=O)S(=O)(=O)C2=CC=CC=C2)C1.O.Cl>>C(C)(=O)C=1C=CC2=C(C=CC(CO2)=O)C1 | O=S(=O)(c1ccccc1)[CH:10]1[c:8]2[c:7]([cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:9]2)[O:15][CH2:14][C:12](=[O:13])[CH2:11]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]=[CH:11][C:12](=[O:13])[CH2:14][O:15]2 | CC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)CC(=O)CO2 | CC(=O)c1ccc2c(c1)C=CC(=O)CO2 | null | null | ClCCl | Functional Group Interconversion | Cleavage of sulfons and sulfoxides | 0f56729427ccdf9758e239f6d9c2624c4c21e1338166c34e8aac92b936db11eb | 048fee841aa83d6ccd159043413f753eba30ed171e5ec6a25efdb332fddc5ab3 | O=C1C=Cc2ccccc2OC1 | O=S(=O)(-[CH;D3;+0:1]1-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#8:6]-[c:7]:[c:8]-1:[c:9])-c1:c:c:c:c:c:1>>[O;D1;H0:4]=[C:3]1-[C:5]-[#8:6]-[c:7]:[c:8](:[c:9])-[CH;D2;+0:1]=[CH;D2;+0:2]-1 | null | [] | null | null | null | null | 0.084 ml (1.05 equivalents) of 1,8-diazabicyclo[5.4.0]undec-7-ene is added at ambient temperature, under nitrogen, to 184 mg (0.53 mmol) of 7-acetyl-5-(phenylsulfonyl)-4,5-dihydro-1-benzoxepin-3(2H)-one, prepared according to example 14, in suspension in 20 ml of dichloromethane. From the addition of the base, the medi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Sulfone | Ketone | c1ccccc1.c1ccc2c(c1)CCCCO2 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | ClCCl | null | null | CC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)CC(=O)CO2>ClCCl>CC(=O)c1ccc2c(c1)C=CC(=O)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb8285bcd2b84ff3b1be95b859facf7a | COC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)CC(=O)CO2>>COC(=O)c1ccc2c(c1)C=CC(=O)CO2 | N12CCCCCC2=NCCC1.O=C1COC2=C(C(C1)S(=O)(=O)C1=CC=CC=C1)C=C(C=C2)C(=O)OC.O.Cl>>O=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC | O=S(=O)(c1ccccc1)[CH:11]1[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:16][CH2:15][C:13](=[O:14])[CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[O:14])[CH2:15][O:16]2 | COC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)CC(=O)CO2 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2 | null | null | ClCCl | Functional Group Interconversion | Cleavage of sulfons and sulfoxides | 0f56729427ccdf9758e239f6d9c2624c4c21e1338166c34e8aac92b936db11eb | 048fee841aa83d6ccd159043413f753eba30ed171e5ec6a25efdb332fddc5ab3 | O=C1C=Cc2ccccc2OC1 | O=S(=O)(-[CH;D3;+0:1]1-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#8:6]-[c:7]:[c:8]-1:[c:9])-c1:c:c:c:c:c:1>>[O;D1;H0:4]=[C:3]1-[C:5]-[#8:6]-[c:7]:[c:8](:[c:9])-[CH;D2;+0:1]=[CH;D2;+0:2]-1 | null | [] | null | null | null | null | 0.084 ml (1.05 equivalents) of 1,8-diazabicyclo[5.4.0]undec-7-ene is added at ambient temperature to 217 mg (0.6 mmol) of methyl 3-oxo-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 2, in suspension in 20 ml of dichloromethane. From the addition of the base, the medium b... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Sulfone | Ketone | c1ccccc1.c1ccc2c(c1)CCCCO2 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | ClCCl | null | null | COC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)CC(=O)CO2>ClCCl>COC(=O)c1ccc2c(c1)C=CC(=O)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b9fffa4797c49fc8b9d7d7c2063b12c | COC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 | Cl.C(CCC)[Li].[Cl-].ClC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC>>ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC | O=[C:13]1[CH:12]=[CH:11][c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:17][CH2:16]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:14][Cl:15])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[CH:14][Cl:15])[CH2:16][O:17]2 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 | null | null | ClCCl.O.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 539d98d0a68c79c0ce64fb9b77faf88c2e8998170a817390f2eb321da849bd7d | 4ccc953afa1928fe5ef55f22a0c593e017875730e9bc8868efb0bd3550ea5ba6 | [CH]=C1C=Cc2ccccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]=[C:3]-[c:4]:[c:5]-[#8:6]-[C:7]-1.[Cl;D1;H0:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[Cl;D1;H0:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1]1-[C:2]=[C:3]-[c:4]:[c:5]-[#8:6]-[C:7]-1 | 97.3 | [{"value": 96.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 1.3 equivalents of n-butyllithium are added to a suspension of 122 mg (0.35 mmol) of chloromethyltriphenylphosphonium chloride in tetrahydrofuran cooled to 0° C. After stirring for one hour, the ylide is added at 0° C., via a hollow tube, to 55 mg (0.25 mmol) of methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate, prep... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | C1=Cc2ccccc2OCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | ClCCl.O.O1CCCC1 | 0 | 1 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>ClCCl.O.O1CCCC1>COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da6893c26e3d4b92944c5b272507bc23 | COC(=O)C1(O)C=CC=CC1.O=C(O)C(F)(F)F>>COC(=O)c1ccc(O)c(C=O)c1 | O.FC(C(=O)O)(F)F.OC1(C(=O)OC)CC=CC=C1.C1N2CN3CN1CN(C2)C3>>C(=O)C=1C=C(C(=O)OC)C=CC1O | [CH3:1][O:2][C:3](=[O:4])[C:5]1([OH:9])[CH:6]=[CH:7][CH:8]=[CH:10][CH2:13]1.O[C:11](C(F)(F)F)=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([CH:11]=[O:12])[cH:13]1 | COC(=O)C1(O)C=CC=CC1.O=C(O)C(F)(F)F | COC(=O)c1ccc(O)c(C=O)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5da8c048780f74aedff48c41c78ed48a1f83f77fbd8859abf216996356091e23 | 74cae3b1f515707702b22095223480fe6c095d2957b7b866e70054945e4d6312 | c1ccccc1 | F-C(-F)(-F)-[C;H0;D3;+0:1](-O)=[O;D1;H0:2].[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C;H0;D4;+0:7]1(-[OH;D1;+0:8])-[CH2;D2;+0:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-[CH;D2;+0:12]=[CH;D2;+0:13]-1>>[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[CH;D2;+0:1]=[O;D1;H0:2]):[c;H0;D3;+0:11](-[OH;D1... | 37 | [{"value": 37.0, "product": "C(=O)C=1C=C(C(=O)OC)C=CC1O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 24 ml of trifluoroacetic acid are added at 0° C. to a mixture of 4.56 g (30 mmol) of methyl 1-hydroxybenzoate and 8.64 g (60 mmol) of hexamethylenetetramine. The solution is brought to reflux and is stirred for 2 hours. After cooling, the solution is diluted with water to 50 ml. The solution is stirred overnight at amb... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Ester.Tertiary alcohol.Conjugated diene | Aldehyde.Ester.Aromatic alcohol | C1=CCCC=C1 | c1ccccc1 | c1ccccc1 | HF | null | null | 2 | COC(=O)C1(O)C=CC=CC1.O=C(O)C(F)(F)F>>COC(=O)c1ccc(O)c(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0276606162d6416e9332d1d0a1662348 | C=C(CCl)CCl.COC(=O)c1ccc(O)c(C=O)c1>>C=C(CCl)COc1ccc(C(=O)OC)cc1C=O | Cl.CN(C=O)C.ClCC(=C)CCl.C(=O)C=1C=C(C(=O)OC)C=CC1O>>ClCC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C | Cl[CH2:5][C:2](=[CH2:1])[CH2:3][Cl:4].[OH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][c:16]1[CH:17]=[O:18]>>[CH2:1]=[C:2]([CH2:3][Cl:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][c:16]1[CH:17]=[O:18] | C=C(CCl)CCl.COC(=O)c1ccc(O)c(C=O)c1 | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:6]=[O;D1;H0:5] | 52.4 | [{"value": 52.0, "product": "ClCC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.4, "product": "ClCC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 26 | HOUR | 45 ml of dimethylformamide and then 1.15 ml (9.95 mmol) of 2-chloromethyl-3-chloro-1-propene are added under argon to 717 mg (3.98 mmol) of methyl 3-formyl-4-hydroxybenzoate as a mixture with 1.055 g (9.95 mmol) and 440 mg (1.195 mmol) of tetrabutylammonium iodide. The solution is stirred for 26 hours and then water is... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | 26 | C=C(CCl)CCl.COC(=O)c1ccc(O)c(C=O)c1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>C=C(CCl)COc1ccc(C(=O)OC)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4013f461401d4a6c8b6775ee63a3fbac | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O.[I-]>>C=C(CI)COc1ccc(C(=O)OC)cc1C=O | [I-].[Na+].ClCC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C>>ICC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C | Cl[CH2:3][C:2](=[CH2:1])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][c:16]1[CH:17]=[O:18].[I-:4]>>[CH2:1]=[C:2]([CH2:3][I:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][c:16]1[CH:17]=[O:18] | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O.[I-] | C=C(CI)COc1ccc(C(=O)OC)cc1C=O | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[I-;H0;D0:5]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[I;H0;D1;+0:5] | 91 | [{"value": 91.0, "product": "ICC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "ICC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 375 mg (2.5 mmol) of sodium iodide are added to 560 mg (2.08 mmol) of methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-formylbenzoate in solution in 20 ml of acetone. The solution is brought to reflux and is stirred for 5 hours with the exclusion of light. After the usual treatments, 680 mg (91%) of methyl 4-{[2-(iodometh... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C | null | 5 | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O.[I-]>CC(=O)C>C=C(CI)COc1ccc(C(=O)OC)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5df823ed3eb434a8e25c7760acc0ac2 | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O>>C=C1C=Cc2cc(C(=O)OC)ccc2OC1 | ClCC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ICC(COC1=C(C=C(C(=O)OC)C=C1)C=O)=C.C[O-].[Na+]>>C=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC | O=[CH:4][c:5]1[cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12][cH:13][c:14]1[O:15][CH2:16][C:2](=[CH2:1])[CH2:3]Cl>>[CH2:1]=[C:2]1[CH:3]=[CH:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[cH:12][cH:13][c:14]2[O:15][CH2:16]1 | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O | C=C1C=Cc2cc(C(=O)OC)ccc2OC1 | null | null | C(C)#N.CO | C-C Coupling | OtherReaction | cd8aa2006e08ebd6c5752a804163d33604e551cb274de5cfef9b1f643743b122 | a3dca447376ff0c6fe3968bb1ab0785c8926c417c53ba2b61f8ebdb52a7e5a2a | C=C1C=Cc2ccccc2OC1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 54 | [{"value": 54.0, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 333 mg (1 mmol) of a 60/40 mixture of methyl 4-{[2-(iodomethyl)-2-propenyl]oxy}-3-formylbenzoate and of methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-formylbenzoate and then 297 mg (1.133 mmol) of triphenylphosphine are successively introduced into the 50 ml single-necked flask. The combined mixture is subjected to a s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | null | null | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HCl | C(C)#N.CO | null | 1 | C=C(CCl)COc1ccc(C(=O)OC)cc1C=O>C(C)#N.CO>C=C1C=Cc2cc(C(=O)OC)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ac67eff34a54ca7bf3f8d6b1731f03d | C=C1C=Cc2cc(C(=O)OC)ccc2OC1>>C=C1C=Cc2cc(C(=O)O)ccc2OC1 | [OH-].[K+].C=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC.Cl>>C=C1COC2=C(C=C1)C=C(C=C2)C(=O)O | C[O:10][C:8]([c:7]1[cH:6][c:5]2[c:13]([cH:12][cH:11]1)[O:14][CH2:15][C:2](=[CH2:1])[CH:3]=[CH:4]2)=[O:9]>>[CH2:1]=[C:2]1[CH:3]=[CH:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12][c:13]2[O:14][CH2:15]1 | C=C1C=Cc2cc(C(=O)OC)ccc2OC1 | C=C1C=Cc2cc(C(=O)O)ccc2OC1 | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C=C1C=Cc2ccccc2OC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 88.2 | [{"value": 88.0, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.2 g of potassium hydroxide pellets are added to 4 g (18.5 mmol) of methyl 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 35, in solution in 20 ml of 80% aqueous ethanol. The medium is brought to reflux for 4 hours and then, after cooling, is treated with 1N hydrochloric acid until p... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=Cc2ccccc2OCC1 | Other | C(C)O | null | null | C=C1C=Cc2cc(C(=O)OC)ccc2OC1>C(C)O>C=C1C=Cc2cc(C(=O)O)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d7c1f62e8e2547cea838bf05bb3c09f8 | C=C1C=Cc2cc(C(=O)O)ccc2OC1.Nc1ccccc1>>C=C1C=Cc2cc(C(=O)Nc3ccccc3)ccc2OC1 | [Cl-].COC1=NC(=NC(=N1)OC)[N+]1(CCOCC1)C.NC1=CC=CC=C1.C=C1COC2=C(C=C1)C=C(C=C2)C(=O)O>>C=C1COC2=C(C=C1)C=C(C=C2)C(=O)NC2=CC=CC=C2 | O[C:8]([c:7]1[cH:6][c:5]2[c:19]([cH:18][cH:17]1)[O:20][CH2:21][C:2](=[CH2:1])[CH:3]=[CH:4]2)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH2:1]=[C:2]1[CH:3]=[CH:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]2[O:20][CH2:21]1 | C=C1C=Cc2cc(C(=O)O)ccc2OC1.Nc1ccccc1 | C=C1C=Cc2cc(C(=O)Nc3ccccc3)ccc2OC1 | null | null | CO | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C=C1C=Cc2cc(C(=O)Nc3ccccc3)ccc2OC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 49 | [{"value": 49.0, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(=O)NC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(=O)NC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 1.12 g (4.07 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride and then 0.379 g (4.07 mmol) of aniline are successively added to 0.75 g (3.7 mmol) of 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylic acid, prepared according to example 40, in solution in 25 ml of methanol. The medium is stirre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1=Cc2ccccc2OCC1.c1ccccc1 | HO- | CO | null | 24 | C=C1C=Cc2cc(C(=O)O)ccc2OC1.Nc1ccccc1>CO>C=C1C=Cc2cc(C(=O)Nc3ccccc3)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2bc99a6f11a2488abd035af078d29166 | C=C1C=Cc2cc(C(=O)OC)ccc2OC1.CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@H](Oc1nnc(O[C@H](c2ccnc3ccc(OC)cc23)[C@H]2C[C@@H]3CCN2C[C@@H]3CC)c2ccccc12)c1ccnc2ccc(OC)cc12.CS(N)(=O)=O>>COC(=O)c1ccc2c(c1)C=CC(O)(CO)CO2 | S(=O)([O-])OS(=O)[O-].[Na+].[Na+].C(C)(C)(C)O.O.CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OC)OC5=NN=C(C6=CC=CC=C65)O[C@@H]([C@H]7C[C@@H]8CCN7C[C@@H]8CC)C9=C1C=C(C=CC1=NC=C9)OC.CS(=O)(=O)N.C(C)(C)(C)O.O.C=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC>>OC1(COC2=C(C=C1)C=C(C=C2)C(=O)OC)CO | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[CH2:15])[CH2:17][O:18]2.CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@@H](c1ccnc2ccc(OC)cc12)[O:14]c1nnc(O[C@H](c2ccnc3ccc(OC)cc23)[C@H]2C[C@@H]3CCN2C[C@@H]3CC)c2ccccc12.CS(N)(=O)=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH... | C=C1C=Cc2cc(C(=O)OC)ccc2OC1.CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@H](Oc1nnc(O[C@H](c2ccnc3ccc(OC)cc23)[C@H]2C[C@@H]3CCN2C[C@@H]3CC)c2ccccc12)c1ccnc2ccc(OC)cc12.CS(N)(=O)=O | COC(=O)c1ccc2c(c1)C=CC(O)(CO)CO2 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 6e442f716680a56517ea1ae63548e6febe18422775fb7d10a8f7f59df9256545 | f275e2b911856e91a6e8071aae74404b344120b5a7e2bb0af9b98d866ffebd4b | C1=Cc2ccccc2OCC1 | C-C-[C@H]1-C-N2-C-C-[C@H]-1-C-[C@@H]-2-[C@H](-O-c1:n:n:c(-[O;H0;D2;+0:1]-[C@@H](-[C@H]2-C-[C@H]3-C-C-N-2-C-[C@H]-3-C-C)-c2:c:c:n:c3:c:c:c(-O-C):c:c:2:3):c2:c:c:c:c:c:1:2)-c1:c:c:n:c2:c:c:c(-O-C):c:c:1:2.C-S(-N)(=O)=[O;H0;D1;+0:2].[CH2;D1;+0:3]=[C;H0;D3;+0:4]1-[C:5]=[C:6]-[c:7]:[c:8]-[#8:9]-[C:10]-1>>[OH;D1;+0:1]-[C;H0;... | 100 | [{"value": 100.0, "product": "OC1(COC2=C(C=C1)C=C(C=C2)C(=O)OC)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | 21 g (7 equivalents) of AD-mix-α and 1.31 g (13.8 mmol) of methanesulfonamide dissolved in 75 ml of a 1/1 tert-butyl alcohol/water mixture are added at ambient temperature to 3 g (13.8 mmol) of methyl 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 35, in suspension in 20 ml of a 1/1 t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether.Ether.Ether.Ether.Tertiary amine.Tertiary amine.Vinyl | Primary alcohol.Tertiary alcohol | C1=Cc2ccccc2OCC1.c1ccc2ncccc2c1.c1ccc2ncccc2c1.c1ccc2cnncc2c1.C1CN2CCC1CC2.C1CN2CCC1CC2 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | ClCCl | null | 96 | C=C1C=Cc2cc(C(=O)OC)ccc2OC1.CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@H](Oc1nnc(O[C@H](c2ccnc3ccc(OC)cc23)[C@H]2C[C@@H]3CCN2C[C@@H]3CC)c2ccccc12)c1ccnc2ccc(OC)cc12.CS(N)(=O)=O>ClCCl>COC(=O)c1ccc2c(c1)C=CC(O)(CO)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a795c22745ff44ec960187343b96c62e | COC(=O)c1ccc2c(c1)C=CC(O)(CO)CO2>>COC(=O)c1ccc2c(c1)C=CC(=O)CO2 | I(=O)(=O)(=O)[O-].[Na+].OC1(COC2=C(C=C1)C=C(C=C2)C(=O)OC)CO>>O=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC | OC[C:13]1([OH:14])[CH:12]=[CH:11][c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:16][CH2:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[O:14])[CH2:15][O:16]2 | COC(=O)c1ccc2c(c1)C=CC(O)(CO)CO2 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2 | null | null | O1CCOCC1.O | Miscellaneous | OtherReaction | 4c323face09bd7ca7c812bd2d273a27bf3fc8629abb540a58cadbb80a381e3cc | d8333db1a8553533b9f31a51fd46ac10421b6606be90ce648ca3b16dc0428896 | O=C1C=Cc2ccccc2OC1 | O-C-[C;H0;D4;+0:1]1(-[OH;D1;+0:2])-[C:3]=[C:4]-[c:5]:[c:6]-[#8:7]-[C:8]-1>>[O;H0;D1;+0:2]=[C;H0;D3;+0:1]1-[C:3]=[C:4]-[c:5]:[c:6]-[#8:7]-[C:8]-1 | 45 | [{"value": 45.0, "product": "O=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": "O=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 116 mg (0.54 mmol) of sodium periodate are added at ambient temperature in 4 equal portions, every quarter of an hour, to 135 mg (0.54 mmol) of methyl 3-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 45, in solution in 16 ml of a 3/1 dioxane/water mixture. After the usua... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ketone | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | O1CCOCC1.O | null | null | COC(=O)c1ccc2c(c1)C=CC(O)(CO)CO2>O1CCOCC1.O>COC(=O)c1ccc2c(c1)C=CC(=O)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4bb72300ba5c4c05b76cf13a23b63ef4 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC(Cl)(Cl)Br>>COC(=O)c1ccc2c(c1)C=CC(=C(Cl)Cl)CO2 | BrC(Cl)(Cl)Cl.O=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>ClC(=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC)Cl | O=[C:13]1[CH:12]=[CH:11][c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:18][CH2:17]1.Cl[C:14](Br)([Cl:15])[Cl:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[C:14]([Cl:15])[Cl:16])[CH2:17][O:18]2 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC(Cl)(Cl)Br | COC(=O)c1ccc2c(c1)C=CC(=C(Cl)Cl)CO2 | null | null | C(C)#N | C-C Coupling | OtherReaction | 5910cf971eb6d9d154a60935a0d4cd400795a28843523ac74cc375ae09a50221 | 9b69c6acf5f96bd89ba7feda6794a83098e618a606bbf5124735bee2db81e0ee | C=C1C=Cc2ccccc2OC1 | Br-[C;H0;D4;+0:1](-Cl)(-[Cl;D1;H0:2])-[Cl;D1;H0:3].O=[C;H0;D3;+0:4]1-[C:5]=[C:6]-[c:7]:[c:8]-[#8:9]-[C:10]-1>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](-[Cl;D1;H0:3])=[C;H0;D3;+0:4]1-[C:5]=[C:6]-[c:7]:[c:8]-[#8:9]-[C:10]-1 | 74 | [{"value": 74.0, "product": "ClC(=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 0.046 ml (2 equivalents) of bromotrichloromethane is added to 50 mg (0.23 mmol) of methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 49, and 214 mg (0.92 mmol) of triphenylphosphine in suspension in 0.5 ml of acetonitrile, which is stirred beforehand at 0° C. for 2 hours. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Tertiary halide.Ketone | Alkenyl halide.Alkenyl halide | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | Br- | C(C)#N | 0 | 2 | COC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC(Cl)(Cl)Br>C(C)#N>COC(=O)c1ccc2c(c1)C=CC(=C(Cl)Cl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-954ff43e90644cdc809fe4fa5bee8c9a | CN(C)C(=O)c1ccc2c(c1)C=CC(=O)CO2.CNO>>CON=C1C=Cc2cc(C(=O)N(C)C)ccc2OC1 | CNO.CN(C(=O)C=1C=CC2=C(C=CC(CO2)=O)C1)C.CO>>CON=C1COC2=C(C=C1)C=C(C=C2)C(=O)N(C)C | O=[C:4]1[CH:5]=[CH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[cH:15][cH:16][c:17]2[O:18][CH2:19]1.[CH3:1][NH:3][OH:2]>>[CH3:1][O:2][N:3]=[C:4]1[CH:5]=[CH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[cH:15][cH:16][c:17]2[O:18][CH2:19]1 | CN(C)C(=O)c1ccc2c(c1)C=CC(=O)CO2.CNO | CON=C1C=Cc2cc(C(=O)N(C)C)ccc2OC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5384bfed642291592577e388f462fbe7a47ca7db661aa0250e0927c6c04a2b41 | 8c052f9ef549b4f361c78f993cdc42cacbd253a7d96709e648aa4ade80c3417e | N=C1C=Cc2ccccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5]-[C:6]=[C:7]-1.[CH3;D1;+0:8]-[NH;D2;+0:9]-[OH;D1;+0:10]>>[CH3;D1;+0:8]-[O;H0;D2;+0:10]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5]-[C:6]=[C:7]-1 | 38 | [{"value": 38.0, "product": "CON=C1COC2=C(C=C1)C=C(C=C2)C(=O)N(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 37 mg of N-methylhydroxylamine are added to 150 mg (0.65 mmol) of N,N-dimethyl-3-oxo-2,3-dihydro-1-benzoxepin-7-carboxamide, prepared according to example 53, in solution in 1 ml of methanol, and the medium is stirred at ambient temperature for 2 hours. After evaporating the methanol, followed by the conventional treat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | null | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | null | null | 2 | CN(C)C(=O)c1ccc2c(c1)C=CC(=O)CO2.CNO>>CON=C1C=Cc2cc(C(=O)N(C)C)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec588e9c9ad0476aa2ef0f51fdd2c601 | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2>>O=C(O)c1ccc2c(c1)C=CC(=CCl)CO2 | [OH-].[K+].ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC.Cl>>ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]=[CH:11][C:12](=[CH:13][Cl:14])[CH2:15][O:16]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]=[CH:11][C:12](=[CH:13][Cl:14])[CH2:15][O:16]2 | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 | O=C(O)c1ccc2c(c1)C=CC(=CCl)CO2 | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | [CH]=C1C=Cc2ccccc2OC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 63.4 | [{"value": 63.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 145 mg (2.6 mmol) of potassium hydroxide pellets are added to 0.5 g (2 mmol) of methyl 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 32, in solution in 8 ml of 80% aqueous ethanol, and the medium is brought to reflux for 3 hours. After cooling, the medium is brought to acidit... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=Cc2ccccc2OCC1 | Other | C(C)O | null | null | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2>C(C)O>O=C(O)c1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0cccb0dc3ef4d53b68c107a8f87a28f | Nc1ccccc1.O=C(O)c1ccc2c(c1)C=CC(=CCl)CO2>>O=C(Nc1ccccc1)c1ccc2c(c1)C=CC(=CCl)CO2 | [Cl-].COC1=NC(=NC(=N1)OC)[N+]1(CCOCC1)C.NC1=CC=CC=C1.ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)O>>ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)NC2=CC=CC=C2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.O[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[CH:16]=[CH:17][C:18](=[CH:19][Cl:20])[CH2:21][O:22]2>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[CH:16]=[CH:17][C:18](=[CH:19][Cl:20])[CH2:21][O:22]2 | Nc1ccccc1.O=C(O)c1ccc2c(c1)C=CC(=CCl)CO2 | O=C(Nc1ccccc1)c1ccc2c(c1)C=CC(=CCl)CO2 | null | null | CO | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | [CH]=C1C=Cc2cc(C(=O)Nc3ccccc3)ccc2OC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 15.3 | [{"value": 15.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)NC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)NC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 127 mg (0.46 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride and then 39 mg (0.42 mmol) of aniline are added to 100 mg (0.42 mmol) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylic acid, prepared according to example 63, in solution in 4 ml of methanol, and the medium is stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1=Cc2ccccc2OCC1 | HO- | CO | null | 3 | Nc1ccccc1.O=C(O)c1ccc2c(c1)C=CC(=CCl)CO2>CO>O=C(Nc1ccccc1)c1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aafb996dd83d4cf1a59f6366ed0cb2bc | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2>>OCc1ccc2c(c1)C=CC(=CCl)CO2 | [H-].C(C(C)C)[Al+]CC(C)C.[Li+].[H-].ClC=C1COC2=C(C=C1)C=C(C=C2)C(=O)OC>>ClC=C1COC2=C(C=C1)C=C(C=C2)CO | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]=[CH:10][C:11](=[CH:12][Cl:13])[CH2:14][O:15]2>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]=[CH:10][C:11](=[CH:12][Cl:13])[CH2:14][O:15]2 | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 | OCc1ccc2c(c1)C=CC(=CCl)CO2 | null | null | ClCCl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | [CH]=C1C=Cc2ccccc2OC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 108.9 | [{"value": 100.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.9, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2.72 ml (2.72 mmol) of a lithium diisobutylaluminum hydride solution are added at a temperature of −78° C. to 217 mg (0.87 mmol) of methyl 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 32, in solution in 10 ml of dichloromethane. The solution is stirred at this temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=Cc2ccccc2OCC1 | Other | ClCCl | null | 1 | COC(=O)c1ccc2c(c1)C=CC(=CCl)CO2>ClCCl>OCc1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0b09ff6b9044664bc9097945bc3719f | OCc1ccc2c(c1)C=CC(=CCl)CO2>>O=Cc1ccc2c(c1)C=CC(=CCl)CO2 | O.C[N+]1(CCOCC1)[O-].ClC=C1COC2=C(C=C1)C=C(C=C2)CO>>ClC=C1COC2=C(C=C1)C=C(C=C2)C=O | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]=[CH:10][C:11](=[CH:12][Cl:13])[CH2:14][O:15]2>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]=[CH:10][C:11](=[CH:12][Cl:13])[CH2:14][O:15]2 | OCc1ccc2c(c1)C=CC(=CCl)CO2 | O=Cc1ccc2c(c1)C=CC(=CCl)CO2 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | [CH]=C1C=Cc2ccccc2OC1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 76.4 | [{"value": 76.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.4, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 84 mg (0.62 mmol) of 4-methylmorpholine N-oxide monohydrate and 207 mg of 4 Å molecular sieve are added to 92 mg (0.415 mmol) of [3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]methanol, prepared according to example 71, in solution in 1 ml of dichloromethane. 14.6 mg (0.041 mmol) of tetrapropylammonium perruthenate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1=Cc2ccccc2OCC1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.ClCCl | null | 1 | OCc1ccc2c(c1)C=CC(=CCl)CO2>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.ClCCl>O=Cc1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68307f44708f49ae8a56e3c5e7660de9 | NO.O=Cc1ccc2c(c1)C=CC(=CCl)CO2>>CC(=NO)c1ccc2c(c1)C=CC(=CCl)CO2 | C(C)(=O)[O-].[Na+].Cl.NO.ClC=C1COC2=C(C=C1)C=C(C=C2)C=O>>ClC=C1COC2=C(C=C1)C=C(C=C2)C(C)=NO | [NH2:3][OH:4].O=[CH:2][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[CH:14][Cl:15])[CH2:16][O:17]2>>[CH3:1][C:2](=[N:3][OH:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]=[CH:12][C:13](=[CH:14][Cl:15])[CH2:16][O:17]2 | NO.O=Cc1ccc2c(c1)C=CC(=CCl)CO2 | CC(=NO)c1ccc2c(c1)C=CC(=CCl)CO2 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | [CH]=C1C=Cc2ccccc2OC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C;D1;H3:7]-[C;H0;D3;+0:1](=[N;H0;D2;+0:5]-[O;D1;H1:6])-[c:2](:[c:3]):[c:4] | 103.1 | [{"value": 100.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(C)=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.1, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(C)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 12.3 mg (0.15 mmol) of sodium acetate and then 10.4 mg (0.15 mmol) of hydroxylamine hydrochloride are added at ambient temperature to 30 mg (0.136 mmol) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carbaldehyde, prepared according to example 72, in solution in 2 ml of methanol. The solution is stirred for 24 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | C1=Cc2ccccc2OCC1 | null | CO | null | 24 | NO.O=Cc1ccc2c(c1)C=CC(=CCl)CO2>CO>CC(=NO)c1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0e13ba0b93e45088f5ce0a2dc8c4dcf | CC1(CCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)OCCO1.O=Cc1ccc2c(c1)C=CC(=CCl)CO2>>CC1(CCC=Cc2ccc3c(c2)C=CC(=CCl)CO3)OCCO1 | C(CCC)[Li].[I-].CC1(OCCO1)CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.ClC=C1COC2=C(C=C1)C=C(C=C2)C=O>>ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC2(OCCO2)C | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:5][CH2:4][CH2:3][C:2]2([CH3:1])[O:20][CH2:21][CH2:22][O:23]2)cc1.O=[CH:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH:13]=[CH:14][C:15](=[CH:16][Cl:17])[CH2:18][O:19]2>>[CH3:1][C:2]1([CH2:3][CH2:4][CH:5]=[CH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[CH:13]=[CH:14][C:15](=[CH:16][Cl:... | CC1(CCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)OCCO1.O=Cc1ccc2c(c1)C=CC(=CCl)CO2 | CC1(CCC=Cc2ccc3c(c2)C=CC(=CCl)CO3)OCCO1 | null | null | O1CCCC1.ClCCl | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | [CH]=C1C=Cc2cc(C=CCCC3OCCO3)ccc2OC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[C:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 71 | [{"value": 71.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC2(OCCO2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.2, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC2(OCCO2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 0.206 ml (0.41 mmol) of a 1.9M n-butyllithium solution is added dropwise to 207 mg (0.435 mmol) of [3-(2-methyl-1,3-dioxolan-2-yl)propyl](triphenyl)phosphonium iodide in suspension in 3.2 ml of tetrahydrofuran cooled to 0° C. The medium is stirred for one hour and then the ylide is added at 0° C., via a hollow tube, to... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1=Cc2ccccc2OCC1.C1COCO1 | HO- | O1CCCC1.ClCCl | 0 | 1 | CC1(CCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)OCCO1.O=Cc1ccc2c(c1)C=CC(=CCl)CO2>O1CCCC1.ClCCl>CC1(CCC=Cc2ccc3c(c2)C=CC(=CCl)CO3)OCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c3c7961006b41ffb02668b7da8d8836 | CC1(CCC=Cc2ccc3c(c2)C=CC(=CCl)CO3)OCCO1>>CC(=O)CCC=Cc1ccc2c(c1)C=CC(=CCl)CO2 | ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC2(OCCO2)C.CC(=O)C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC(C)=O | C1C[O:3][C:2]([CH3:1])([CH2:4][CH2:5][CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[CH:14]=[CH:15][C:16](=[CH:17][Cl:18])[CH2:19][O:20]3)O1>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH:14]=[CH:15][C:16](=[CH:17][Cl:18])[CH2:19][O:20]2 | CC1(CCC=Cc2ccc3c(c2)C=CC(=CCl)CO3)OCCO1 | CC(=O)CCC=Cc1ccc2c(c1)C=CC(=CCl)CO2 | null | CC#N.CC#N.Cl[Pd]Cl | ClCCl | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | [CH]=C1C=Cc2ccccc2OC1 | [C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D4;+0:5]1(-[C;D1;H3:6])-O-C-C-[O;H0;D2;+0:7]-1>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7] | 80.4 | [{"value": 80.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C=CCCC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 6 mg (0.023 mmol) of bis(acetonitrile)palladium(II) chloride are added to 79 mg (0.237 mmol) of 3-(chloromethylene)-7-[4-(2-methyl-1,3-dioxolan-2-yl)-1-butenyl]-2,3-dihydro-1-benzoxepin, prepared according to example 74, in solution in 1.5 ml of dichloromethane. After stirring at ambient temperature for 3 hours, 0.5 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | C1=Cc2ccccc2OCC1 | HO- | CC#N.CC#N.Cl[Pd]Cl.ClCCl | null | 3 | CC1(CCC=Cc2ccc3c(c2)C=CC(=CCl)CO3)OCCO1>CC#N.CC#N.Cl[Pd]Cl.ClCCl>CC(=O)CCC=Cc1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d42fe0218dfb4682b7e7b0388106e575 | C=C(CCl)CCl.CC(=O)c1ccc(O)c(C=O)c1>>C=C(CCl)COc1ccc(C(C)=O)cc1C=O | Cl.C([O-])([O-])=O.[Na+].[Na+].ClCC(=C)CCl.C(C)(=O)C=1C=CC(=C(C=O)C1)O>>C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CCl | Cl[CH2:5][C:2](=[CH2:1])[CH2:3][Cl:4].[OH:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][c:15]1[CH:16]=[O:17]>>[CH2:1]=[C:2]([CH2:3][Cl:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][c:15]1[CH:16]=[O:17] | C=C(CCl)CCl.CC(=O)c1ccc(O)c(C=O)c1 | C=C(CCl)COc1ccc(C(C)=O)cc1C=O | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:6]=[O;D1;H0:5] | 52.7 | [{"value": 52.0, "product": "C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 21 | HOUR | 6.02 g (16.31 mmol) of tetrabutylammonium iodide, 6.17 g (2.5 equivalents) of sodium carbonate and, finally, 6.7 ml (58.2 mmol) of 2-chloromethyl-3-chloro-1-propene are successively added to 3.82 g (23 mmol) of 5-acetyl-2-hydroxybenzaldehyde, prepared according to Tromelin, A. et al., Synthesis, (1985), 1074–1076, and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.CN(C=O)C | null | 21 | C=C(CCl)CCl.CC(=O)c1ccc(O)c(C=O)c1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.CN(C=O)C>C=C(CCl)COc1ccc(C(C)=O)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-74898563749d45e290e940e012a4e69f | C=C(CCl)COc1ccc(C(C)=O)cc1C=O.[I-]>>C=C(CI)COc1ccc(C(C)=O)cc1C=O | [I-].[Na+].C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CCl.O>>C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CI | Cl[CH2:3][C:2](=[CH2:1])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][c:15]1[CH:16]=[O:17].[I-:4]>>[CH2:1]=[C:2]([CH2:3][I:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][c:15]1[CH:16]=[O:17] | C=C(CCl)COc1ccc(C(C)=O)cc1C=O.[I-] | C=C(CI)COc1ccc(C(C)=O)cc1C=O | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].[I-;H0;D0:5]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH2;D2;+0:1]-[I;H0;D1;+0:5] | 100.1 | [{"value": 100.0, "product": "C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CI", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CI", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 531 mg (3.54 mmol) of sodium iodide are added to 894 mg (3.54 mmol) of 5-acetyl-2-{[2-(chloromethyl)-2-propenyl]oxy}benzaldehyde in solution in 10 ml of distilled acetone. The medium is brought to reflux and is stirred for 5 hours. Water is added and then the solution is concentrated. After the addition of water and di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C | null | 5 | C=C(CCl)COc1ccc(C(C)=O)cc1C=O.[I-]>CC(=O)C>C=C(CI)COc1ccc(C(C)=O)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-790f5a2328ca4e0baebd073feb8f231d | C=C(CI)COc1ccc(C(C)=O)cc1C=O>>C=C1C=Cc2cc(C(C)=O)ccc2OC1 | C[O-].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)C=1C=CC(=C(C=O)C1)OCC(=C)CI.O>>C=C1COC2=C(C=C1)C=C(C=C2)C(C)=O | O=[CH:4][c:5]1[cH:6][c:7]([C:8]([CH3:9])=[O:10])[cH:11][cH:12][c:13]1[O:14][CH2:15][C:2](=[CH2:1])[CH2:3]I>>[CH2:1]=[C:2]1[CH:3]=[CH:4][c:5]2[cH:6][c:7]([C:8]([CH3:9])=[O:10])[cH:11][cH:12][c:13]2[O:14][CH2:15]1 | C=C(CI)COc1ccc(C(C)=O)cc1C=O | C=C1C=Cc2cc(C(C)=O)ccc2OC1 | null | null | C(C)#N.CO | C-C Coupling | OtherReaction | cd8aa2006e08ebd6c5752a804163d33604e551cb274de5cfef9b1f643743b122 | a3dca447376ff0c6fe3968bb1ab0785c8926c417c53ba2b61f8ebdb52a7e5a2a | C=C1C=Cc2ccccc2OC1 | I-[CH2;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](=[C;D1;H2:4])-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 58 | [{"value": 58.0, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.9, "product": "C=C1COC2=C(C=C1)C=C(C=C2)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 973 mg (3.575 mmol) of triphenylphosphine are added under argon to 1.118 g (3.25 mmol) of 5-acetyl-2-{[2-(iodomethyl)-2-propenyl]oxy}benzaldehyde in solution in 30 ml of acetonitrile. The medium is brought to reflux and is stirred for 14 hours. After cooling the solution, 0.743 ml (3.25 mmol) of a 25% solution of sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | null | null | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HI | C(C)#N.CO | null | 14 | C=C(CI)COc1ccc(C(C)=O)cc1C=O>C(C)#N.CO>C=C1C=Cc2cc(C(C)=O)ccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b79389c3e42424d85f643dbd66bbb59 | CC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 | C(CCC)[Li].[Cl-].ClC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)C=1C=CC2=C(C=CC(CO2)=O)C1>>ClC=C1COC2=C(C=C1)C=C(C=C2)C(C)=O | O=[C:12]1[CH:11]=[CH:10][c:8]2[c:7]([cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:9]2)[O:16][CH2:15]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:13][Cl:14])cc1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]=[CH:11][C:12](=[CH:13][Cl:14])[CH2:15][O:16]2 | CC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 | null | null | O1CCCC1.CCCCC | C-C Coupling | Wittig with Phosphonium | 539d98d0a68c79c0ce64fb9b77faf88c2e8998170a817390f2eb321da849bd7d | 4ccc953afa1928fe5ef55f22a0c593e017875730e9bc8868efb0bd3550ea5ba6 | [CH]=C1C=Cc2ccccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]=[C:3]-[c:4]:[c:5]-[#8:6]-[C:7]-1.[Cl;D1;H0:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[Cl;D1;H0:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1]1-[C:2]=[C:3]-[c:4]:[c:5]-[#8:6]-[C:7]-1 | 55 | [{"value": 55.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.0, "product": "ClC=C1COC2=C(C=C1)C=C(C=C2)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 1.1 equivalents of n-butyllithium are added to 309 mg (0.89 mmol) of chloromethyltriphenylphosphonium chloride in 5 ml of tetrahydrofuran cooled to 0° C. After stirring for one hour, 150 mg (0.74 mmol) of 7-acetyl-1-benzoxepin-3(2H)-one, prepared according to example 79, are added at ambient temperature. The medium is ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | C1=Cc2ccccc2OCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1=Cc2ccccc2OCC1 | C1=Cc2ccccc2OCC1 | HO- | O1CCCC1.CCCCC | 0 | 1 | CC(=O)c1ccc2c(c1)C=CC(=O)CO2.ClC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>O1CCCC1.CCCCC>CC(=O)c1ccc2c(c1)C=CC(=CCl)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc7c84b695ff493b9d788642c9763ea0 | Cc1ccc(O)cc1.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>>Cc1ccc(OS(=O)(=O)c2cccc(N)c2)cc1 | [Sn](Cl)Cl.C1=CC(=CC=C1O)C.N1=CC=CC=C1.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl>>NC=1C=C(C=CC1)S(=O)(=O)OC1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:17][cH:18]1.O=[N+:15]([O-])[c:14]1[cH:13][cH:12][cH:11][c:10]([S:7](Cl)(=[O:8])=[O:9])[cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:16]2)[cH:17][cH:18]1 | Cc1ccc(O)cc1.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | Cc1ccc(OS(=O)(=O)c2cccc(N)c2)cc1 | null | null | Cl.C(Cl)(Cl)Cl | Acylation | OtherReaction | 0f17f52386aa31153b43ba6292c0360cf635a875b254cd05f4597231d283adc0 | 5452d749a309ee3a24f18a5d8d8ac3d612b02da20bfd045c9772626370a17052 | O=S(=O)(Oc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[c:7](-[N+;H0;D3:8](=O)-[O-]):[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:8]-[c:7](:[c:9]):[c:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:5] | 71.4 | [{"value": 71.4, "product": "NC=1C=C(C=CC1)S(=O)(=O)OC1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 50 g (0.463 mole) of p-cresol (4-methylphenol) and 37 mL (0.458 mole) of pyridine dissolved in 250 mL of chloroform was added 50 g (0.226 mole) of 3-nitrobenzenesulfonyl chloride. The reaction was allowed to stir at ambient temperature. After 2 hours, the reaction was judged complete by TLC and the volatiles were re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonyl halide | Primary amine.Sulfonate | null | null | c1ccccc1.c1ccccc1 | Other | Cl.C(Cl)(Cl)Cl | null | 2 | Cc1ccc(O)cc1.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>Cl.C(Cl)(Cl)Cl>Cc1ccc(OS(=O)(=O)c2cccc(N)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfbc990807b743f29b14ef279f7a239c | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)O)cc6c5)cc4c3)c2)cc1.[OH-]>>O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.[Na+] | CC1=CC=C(C=C1)OS(=O)(=O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)O.[OH-].[Na+].Cl>>[Na+].[Na+].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)[O-].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=... | [O:1]=[S:68](=[O:37])([c:67]1[cH:66][cH:65][c:64]2[cH:63][cH:62][c:61]([NH:60][C:44]([NH:3][c:2]3[cH:20][cH:21][c:22]4[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[OH:14])[cH:15][c:41]4[cH:40]3)=[O:43])[cH:84][c:83]2[cH:82]1)[NH:71][c:72]1[cH:73][cH:74][cH:75][c:76]([S:77]([O:56][c:46]2[cH:4][cH:51][c:52]([CH3:57])[cH:58... | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)O)cc6c5)cc4c3)c2)cc1.[OH-] | O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.[Na+] | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2dd1ba3fff9c92dc787cca5101038606519bf17e25df652cde93905c3989c0e0 | 2ed33179e64b4d883ef533a708ed0330b53fffe689f52713ef507e3428d8d94b | O=C(Nc1ccc2ccccc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1.O=C(Nc1ccc2ccccc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]:[c:13]-[#7:14]-[S;H0;D4;+0:15](=[O;H0;D1;+0:16])(=[O;H0;D1;+0:17])-[c:18](:[c:19]):[c:20]):[c:21]:[cH;D2;+0:22]:1.[O;D1;H0:23]=[#16:24](=[O;D1;H0:25])(-[OH;D1;+0:26... | null | [] | null | null | 6 | HOUR | To 8 mg (0.011 mmol) of compound 8 was added 2 mL of 5 N NaOH. The reaction was allowed to stir at ambient temperature for 6 hours. The reaction was acidified with 6 N HCl and the solution was added to a small reverse-phase (C18) solid phase extraction column. The column was washed with H2O followed by 50:50 (v:v) CH3C... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Urea.Sulfonate | Sulfonamide.Sulfonamide.Urea.Urea.Sulfonic acid.Sulfonic acid.Sulfonic acid | c1ccc2ccccc2c1.c1ccccc1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | null | null | null | 6 | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)O)cc6c5)cc4c3)c2)cc1.[OH-]>>O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.[Na+] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d8f8941d558d487dac6430f9c8d0c26d | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1.[OH-]>>O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)... | CC1=CC=C(C=C1)OS(=O)(=O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)OC1=CC=C(C=C1)C.[OH-].[Na+].Cl>>[Na+].[Na+].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)[O-].S(=O)(=O)(O)C=1C=C(C=CC1)NS... | [O:1]=[C:2]([NH:3][c:81]1[cH:82][cH:83][c:84]2[cH:85][cH:86][c:87]([S:88](=[O:89])(=[O:90])[NH:91][c:92]3[cH:93][cH:94][cH:95][c:96]([S:36](=[O:37])(=[O:38])[O:75][c:67]4[cH:68][cH:34][c:35]([CH3:50])[cH:71][cH:76]4)[cH:101]3)[cH:102][c:103]2[cH:104]1)[NH:55][c:56]1[cH:57][cH:58][c:59]2[cH:8][cH:9][c:10]([S:11](=[O:12]... | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1.[OH-] | O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.[Na+] | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ec5c62283bf6a54bc73e468b3adbdbc87f44856eea1662142f34da2be77d6851 | 4cd607b55decb7cd9e62b5940d4bb0492ea6857d4bf00321865fbff3b89163be | O=C(Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:15]:[cH;D2;+0:16]:1.[CH3;D1;+0:17]-[c;H0;D3;+0:18]1:[c:19]:[cH;D2;+0:20]:[c;H0;D3;+0:21](-[O;H0;D2;+0:22]-[#16:23](=[O;D1;H0:24])(=[O;D1;H0:... | null | [] | null | null | 6 | HOUR | To 35 mg (0.036 mmol) of compound 9 was added 2 mL of 5 N NaOH. The reaction was allowed to stir at ambient temperature for 6 hours. The reaction was acidified with 6 N HCl and the solution was added to a small reverse-phase (C18) solid phase extraction column. The column was washed with H2O followed by 50:50 (v:v) CH3... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Urea.Sulfonate | Sulfonamide.Sulfonamide.Sulfonamide.Urea.Urea.Sulfonic acid.Sulfonic acid.Sulfonic acid | c1ccc2ccccc2c1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | null | null | null | 6 | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1.[OH-]>>O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9e74391cbf14242bd3b427717f72d39 | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3cc(O)c4ccc(NC(=O)Nc5ccc6c(O)cc(S(=O)(=O)O)cc6c5)cc4c3)c2)cc1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1>>O=C(Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1)Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1 | OC1=CC(=CC2=CC(=CC=C12)NC(=O)NC1=CC2=CC(=CC(=C2C=C1)O)S(=O)(=O)NC1=CC(=CC=C1)S(=O)(=O)OC1=CC=C(C=C1)C)S(=O)(=O)O.[Na+].[Na+].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)[O-].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)[O-]... | Cc1ccc(O[S:37]([c:36]2[cH:35][cH:34][cH:33][c:32]([NH:31][S:28]([c:27]3[cH:26][c:24]([OH:25])[c:23]4[cH:22][cH:21][c:20]([NH:19][C:2](=[O:1])[NH:3][c:4]5[cH:5][cH:6][c:7]6[c:8]([OH:9])[cH:10][c:11]([S:12](=[O:13])(=[O:14])[OH:15])[cH:16][c:17]6[cH:18]5)[cH:44][c:43]4[cH:42]3)(=[O:29])=[O:30])[cH:41]2)(=[O:38])=[O:39])c... | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3cc(O)c4ccc(NC(=O)Nc5ccc6c(O)cc(S(=O)(=O)O)cc6c5)cc4c3)c2)cc1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1 | O=C(Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1)Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1 | null | null | null | Miscellaneous | OtherReaction | 5651ad236e30fc5e1fb136f94e6b47964049343b023233af6edbbb99ad9da079 | c29fbd699f0e9548504fd648142985b754dd32ed818b292df8b8b9a4b9bc07ea | O=C(Nc1ccc2ccccc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1 | C-c1:c:c:c(-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):c:c:1.O=C(-N-c1:c:c:c2:c:c:c(-S(=O)(=O)-[O-]):c:c:2:c:1)-N-c1:c:c:c2:c:c:c(-S(=O)(=O)-N-c3:c:c:c:c(-S(=O)(=O)-[OH;D1;+0:7]):c:3):c:c:2:c:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[OH;D1;+0:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared from compound 10 according to the procedure described for the synthesis of compound 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Urea.Sulfonic acid.Sulfonic acid.Sulfonate | Sulfonic acid | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | null | c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | HO- | null | null | null | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3cc(O)c4ccc(NC(=O)Nc5ccc6c(O)cc(S(=O)(=O)O)cc6c5)cc4c3)c2)cc1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1>>O=C(Nc1ccc2c(O)cc(S(=O)(=O)O)cc2c1)Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1 |
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