dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5d90023934e416fa9241ef7aa4c808a | CC(C)(C)OC(=O)NC(C)(C)C(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1>>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | Cl.CN(CCCN=C=NCC)C.C(C1=CC=CC=C1)OC([C@H](N)CC1=CNC2=CC=CC=C12)=O.O.ON1N=NC2=C1C=CC=C2.C(C)(C)(C)OC(=O)NC(C)(C(=O)O)C>>C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC1=CC=CC=C1)CC1=CNC2=CC=CC=C12)(C)C | O[C:12]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH3:10])[CH3:11])=[O:13].[NH2:14][C@H:15]([CH2:16][c:17]1[cH:18][nH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12)[C:26](=[O:27])[O:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](... | CC(C)(C)OC(=O)NC(C)(C)C(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | null | null | C(Cl)(Cl)Cl.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1c[nH]c2ccccc12)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C:20]>>[C:14]-[C:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:... | null | [] | null | null | 4 | HOUR | Crude D-tryptophan benzyl ester (1.0 g, 3.40 mmol), 1-hydroxybenztriazole hydrate (0.63 g, 4.1 mmol) and t-butoxycarbonyl-α-methylalanine (0.84 g, 4.11 mmol) were stirred together at room temperature in chloroform (20 mL). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (980 mg, 5.11 mmol) was added to this... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | C(Cl)(Cl)Cl.O | null | 4 | CC(C)(C)OC(=O)NC(C)(C)C(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1>C(Cl)(Cl)Cl.O>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80904ffecdf74601af3321b00e801887 | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1>>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O | C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC1=CC=CC=C1)CC1=CNC2=CC=CC=C12)(C)C>>C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)O)CC1=CNC2=CC=CC=C12)(C)C | c1ccc(C[O:28][C:26]([C@H:15]([NH:14][C:12]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH3:10])[CH3:11])=[O:13])[CH2:16][c:17]2[cH:18][nH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]23)=[O:27])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]([CH3:10])([CH3:11])[C:12](=[O:13])[NH:14][C... | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O | null | [Pd] | C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ccc2c1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 102.1 | [{"value": 102.0, "product": "C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)O)CC1=CNC2=CC=CC=C12)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.1, "product": "C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)O)CC1=CNC2=CC=CC=C12)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The benzyl ester (0.82 g, 1.71 mmol) obtained in Step C and 10% palladium on carbon (150 mg) were stirred together in ethyl acetate (5 mL). The solution was degassed and a hydrogen atmosphere introduced over the reactants using a balloon for 32 hours. The reaction products were isolated by filtering the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2[nH]ccc2c1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1>[Pd].C(C)(=O)OCC>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb2559d3fc404f17a5ecee988d37d685 | Cc1ccc(B(O)O)cc1.O=[N+]([O-])c1ccccc1Br>>Cc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | O.CC(C)O.C1(=CC=C(C=C1)B(O)O)C.BrC1=C(C=CC=C1)[N+](=O)[O-]>>CC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-] | OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:16][cH:15]1.Br[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[N+:12](=[O:13])[O-:14])[cH:15][cH:16]1 | Cc1ccc(B(O)O)cc1.O=[N+]([O-])c1ccccc1Br | Cc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | null | null | [OH-].[Na+].C1=CC=CC=C1 | 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](-[#7;+:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | 77.4 | [{"value": 77.4, "product": "CC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A vigorously stirred mixture of 34 g (0.25 mol) of 4-tolylboronic acid and 34 g (0.17 mol) of 2-bromo-1-nitrobenzene in a mixture of 170 mL of 5N sodium hydroxide, 57 mL of water, 215 mL of 2-propanol and 1080 mL of benzene was treated with 11.9 g of (tetrakis)triphenylphosphine palladium(0). The two-phase mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | [OH-].[Na+].C1=CC=CC=C1 | null | null | Cc1ccc(B(O)O)cc1.O=[N+]([O-])c1ccccc1Br>[OH-].[Na+].C1=CC=CC=C1>Cc1ccc(-c2ccccc2[N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-27a0a2a0c29c44ca8129b0684f542de9 | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.NCc1ccc(-c2ccccc2[N+](=O)[O-])cc1>>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)NCc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)O)CC1=CNC2=CC=CC=C12)(C)C.NCC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-].C(C)N(CC)CC>>C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)NCC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])CC1=CNC2=CC=CC=C12)(C)C | O[C:26]([C@H:15]([NH:14][C:12]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH3:10])[CH3:11])=[O:13])[CH2:16][c:17]1[cH:18][nH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12)=[O:27].[NH2:28][CH2:29][c:30]1[cH:31][cH:32][c:33](-[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]2[N+:40](=[O:41])[O-:42])[cH:43][c... | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.NCc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)NCc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1c[nH]c2ccccc12)NCc1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]-[c:10] | 56.9 | [{"value": 50.0, "product": "C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)NCC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])CC1=CNC2=CC=CC=C12)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.9, "product": "C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)NCC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])CC1=CNC2=CC=CC=C12)(C)C", "detai... | null | null | null | null | The acid (338 mg, 0.87 mmol) from Step D and 4-aminomethyl-2'-nitro-1,1'-biphenyl (200 mg, 0.87 mmol) and triethylamine (0.245 mL, 1.76 mmol) were dissolved in methylene chloride (8 mL) and stirred at room temperature. Benzotriazolyl-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (388 mg, 0.87 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.NCc1ccc(-c2ccccc2[N+](=O)[O-])cc1>C(Cl)Cl>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)NCc1ccc(-c2ccccc2[N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-30601e26cfe949648c03f18ace9a74dc | CC(C)(C)OC(=O)NC(C)(C)C(=O)O.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1>>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C1=CC=CC=C1)OC([C@H](N)CCC1=CC=CC=C1)=O.C(C)N(CC)CC.C(C)(C)(C)OC(=O)NC(C)(C(=O)O)C>>C(C1=CC=CC=C1)OC([C@@H](CCC1=CC=CC=C1)NC(C(C)(C)NC(=O)OC(C)(C)C)=O)=O | O[C:12]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH3:10])[CH3:11])=[O:13].[NH2:14][C@H:15]([CH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[C:24](=[O:25])[O:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]([CH3:10])([CH... | CC(C)(C)OC(=O)NC(C)(C)C(=O)O.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1 | CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCCc1ccccc1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C:20]>>[C:14]-[C:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:... | null | [] | null | null | 10 | MINUTE | D-Homophenylalanine benzyl ester (0.87 g; 3.23 mmol), triethylamine (900 ml) and N-(t-butoxycarbonyl)-α-methylalanine (656 mg; 3.23 mmol) were dissolved in dry methylene chloride (6.5 ml) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP-reagent) (1.43 g; 3.23 mmol) was added with stirring... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 0.166667 | CC(C)(C)OC(=O)NC(C)(C)C(=O)O.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1>C(Cl)Cl>CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a50f7cac2645481a8747ad859fb15edc | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1>>CC(C)(CC(=O)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C1=CC=CC=C1)OC([C@H](N)CCC1=CC=CC=C1)=O.C(C)N(CC)CC.C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C>>C(C1=CC=CC=C1)OC([C@@H](CCC1=CC=CC=C1)NC(CC(C)(C)NC(=O)OC(C)(C)C)=O)=O | O[C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:6].[NH2:7][C@H:8]([CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[NH:7][C@H:8]([CH2:9][C... | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1 | CC(C)(CC(=O)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCCc1ccccc1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH2;D1;+0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | D-Homophenylalanine benzyl ester (725 mg; 3.23 mmol) whose preparation was described in Example 7 Step B, triethylamine (750 ml; 5,38 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (585 mg; 2.69 mmol) were dissolved in dry methylene chloride (10 ml) and BOP (1.19 g, 2.69 mmol) was added with stirring in small ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1>C(Cl)Cl>CC(C)(CC(=O)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dbb9dc3e9fc84d65b7962d36a9ed7bea | C=CCO.CC(C)(C)OC(=O)N[C@H](CCc1ccccc1)C(=O)O>>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@H](CCC1=CC=CC=C1)C(=O)O.C(C=C)O.C(CCl)Cl>>C(C=C)OC([C@H](NC(=O)OC(C)(C)C)CCC1=CC=CC=C1)=O | [CH2:1]=[CH:2][CH2:3][OH:4].O[C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:2... | C=CCO.CC(C)(C)OC(=O)N[C@H](CCc1ccccc1)C(=O)O | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)OC(C)(C)C | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H2:13]=[C:14]-[C:15]-[OH;D1;+0:16]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:16]-[C:15]-[... | null | [] | null | null | null | null | N-(t-Butoxycarbonyl)-D-homophenylalanine (2.0 g; 7.16 mmol), allyl alcohol (500 ml; 7.35 mmol) and 4-dimethylaminopyridine (88 mg; 0.72 mmol) were dissolved in dry methylene chloride and stirred at room temperature. EDC (1.4 g; 7.30 mmol) was added to the solution in small batches over 15 minutes and the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | null | C=CCO.CC(C)(C)OC(=O)N[C@H](CCc1ccccc1)C(=O)O>CN(C1=CC=NC=C1)C.C(Cl)Cl>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-65e718a8f3934e1487660a0d4b652d2f | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)OC(C)(C)C>>C=CCOC(=O)[C@H](N)CCc1ccccc1 | C(C=C)OC([C@H](NC(=O)OC(C)(C)C)CCC1=CC=CC=C1)=O.C([O-])(O)=O.[Na+].C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>C(C=C)OC([C@H](N)CCC1=CC=CC=C1)=O | CC(C)(C)OC(=O)[NH:8][C@@H:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@H:7]([NH2:8])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)OC(C)(C)C | C=CCOC(=O)[C@H](N)CCc1ccccc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]-[C:8]=[C;D1;H2:9]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]-[C:8]=[C;D1;H2:9] | null | [] | null | null | null | null | The allyl ester from Step A of this Example (1.96 g; 6.136 mmol) was dissolved in dry methylene chloride (10 ml) and anisole (5 ml) was added. The mixture was stirred at room temperature and trifluoroacetic acid was added drop by drop to the ester over 5 minutes. The reaction mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | null | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)OC(C)(C)C>C(Cl)Cl>C=CCOC(=O)[C@H](N)CCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2788899244b0487da69285b0cbf52602 | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(NC(=O)OCc1ccccc1)C(=O)O>>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)C(C)(C)NC(=O)OCc1ccccc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C=C)OC([C@H](N)CCC1=CC=CC=C1)=O.C(C)N(CC)CC.C(=O)(OCC1=CC=CC=C1)NC(C)(C(=O)O)C>>C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(C(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH2:16].O[C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[NH:22][C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:10]1[cH:11][cH:12... | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(NC(=O)OCc1ccccc1)C(=O)O | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)C(C)(C)NC(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)OCc1ccccc1)NCCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]-[C:16]=[C;D1;H2:17]>>[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8])-[C:12](=[O;D1;H0:13])-[#8... | 69.7 | [{"value": 69.7, "product": "C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(C(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The amine obtained in Step B of this Example (300 mg; 1.37 mmol) triethylamine (380 ml; 2.73 mmol) and N-carbobenzyloxy-2-methylalanine (278 mg; 1.37 mmol) were dissolved in dry methylene chloride (3 ml) and BOP (605 mg; 1.37 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and the resultan... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(NC(=O)OCc1ccccc1)C(=O)O>C(Cl)Cl>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)C(C)(C)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f14a773ff3c34c0780dd20f31d997bc1 | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.CCN(CC)CC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C>>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)CC(C)(C)NC(=O)OCc1ccccc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C=C)OC([C@H](N)CCC1=CC=CC=C1)=O.C(C)N(CC)CC.C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C>>C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(CC(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:10]1[cH:15][cH:14][cH:13][cH:12][cH:29]1)[NH2:16].C[C:27]([CH3:11])([O:26][C:24]([NH:23][C:20]([CH2:19][C:17](O)=[O:18])([CH3:21])[CH3:22])=[O:25])[CH3:28].CCN(CC)[CH2:33][CH3:32].CN(C)[P+](On1nnc2ccc[cH:30][c:31]21)(N(C)C)N(C)C>>[CH2:1]=[CH:2][CH2:3][O:4... | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.CCN(CC)CC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)CC(C)(C)NC(=O)OCc1ccccc1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | OtherReaction | e4ae9f4bd64d994c4bf6cf3491c65a63d610338daa37edabdc3519564d0e669e | 7e47d41c0b43d83b0d84b675f0592f9db7d4836f9998b833a5561e73434c6363 | O=C(CCNC(=O)OCc1ccccc1)NCCCc1ccccc1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-N(-C)-[P+](-O-n1:n:n:c2:c:c:c:[cH;D2;+0:3]:[c;H0;D3;+0:4]:2:1)(-N(-C)-C)-N(-C)-C.C-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-[C:13]-[C;H0;D3;+0:14](-O)=[O;D1;H0:15].[C;D1;H2:16]=[C:17]-[C:18]-[#8:19]-[C:20](=[O;D1;H0:21])-[C:22](-... | 59.7 | [{"value": 59.7, "product": "C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(CC(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | D-Homophenylalanine allyl ester (350 mg; 1.60 mmol), triethylamine (445 μl; 3.19 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (412.8 mg; 1.64 mmol) were dissolved in dry methylene chloride (3 ml) and stirred at room temperature to give a homogeneous solution. BOP was added to the solution over 5 minutes and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Boc | Ether.Secondary amide | c1ccccc1.c1ccc2[nH]nnc2c1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C(C)(=O)OCC | null | null | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.CCN(CC)CC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C>C(Cl)Cl.C(C)(=O)OCC>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)CC(C)(C)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-82c7b29aec314de1861faac34ed15227 | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(CCC(=O)O)NC(=O)OCc1ccccc1>>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)CCC(C)(C)NC(=O)OCc1ccccc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C=C)OC([C@H](N)CCC1=CC=CC=C1)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)OC(=O)NC(CCC(=O)O)(C)C>>C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(CCC(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH2:16].O[C:17](=[O:18])[CH2:19][CH2:20][C:21]([CH3:22])([CH3:23])[NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][c:1... | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(CCC(=O)O)NC(=O)OCc1ccccc1 | C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)CCC(C)(C)NC(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCCNC(=O)OCc1ccccc1)NCCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]-[C:12]=[C;D1;H2:13]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]-[C:12]=[C;D1;H2:13] | null | [] | null | null | null | null | D-Homophenylalanine allyl ester (175 mg; 0.80 mmol) (see Example 9, Step B), triethylamine (222 μl; 1.59 mmol) were dissolved in dry methylene chloride (2 ml) and 4-(benzyloxycarbonylamino)-4-methyl-pentanoic acid (211 mg; 0.80 mmol) added. The solution was stirred at room temperature and BOP (353 mg; 0.80 mmol) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | C=CCOC(=O)[C@H](N)CCc1ccccc1.CC(C)(CCC(=O)O)NC(=O)OCc1ccccc1>C(Cl)Cl>C=CCOC(=O)[C@@H](CCc1ccccc1)NC(=O)CCC(C)(C)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76eb407e00c64615a297c82a5b981a5c | C=CCBr.CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>C=CCOC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@H](CC1=CNC2=CC=CC=C12)C(=O)O.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)OC([C@H](NC(=O)OC(C)(C)C)CC1=CNC2=CC=CC=C12)=O | Br[CH2:3][CH:2]=[CH2:1].[OH:4][C:5](=[O:6])[C@@H:7]([CH2:8][c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12)[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12)[NH:18][C:19](... | C=CCBr.CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O | C=CCOC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)OC(C)(C)C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | 56 | [{"value": 56.0, "product": "C(C=C)OC([C@H](NC(=O)OC(C)(C)C)CC1=CNC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | N-(t-Butoxycarbonyl)-D-tryptophan (3 g; 9.868 mmol) was dissolved in acetone and an aqueous solution of potassium carbonate (2.84 g; 20.58 mmol) added followed by allyl bromide (1.55 g; 12.81 mmol). The reaction mixture was stirred for 18 h and then the acetone was substantially removed by evaporation under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccc2[nH]ccc2c1 | HBr | CC(=O)C | null | 18 | C=CCBr.CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>CC(=O)C>C=CCOC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-275c3bd4a2eb43f196b2a4707e52cd1b | C=CCOC(=O)[C@H](N)Cc1c[nH]c2ccccc12.CC(C)(NC(=O)OCc1ccccc1)C(=O)O>>C=CCOC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)C(C)(C)NC(=O)OCc1ccccc1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C=C)OC([C@H](N)CC1=CNC2=CC=CC=C12)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)OC(=O)NC(C)(C(=O)O)C>>C(C1=CC=CC=C1)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC=C)CC1=CNC2=CC=CC=C12)(C)C | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12)[NH2:18].O[C:19](=[O:20])[C:21]([CH3:22])([CH3:23])[NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][c:9]1[cH:10][... | C=CCOC(=O)[C@H](N)Cc1c[nH]c2ccccc12.CC(C)(NC(=O)OCc1ccccc1)C(=O)O | C=CCOC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)C(C)(C)NC(=O)OCc1ccccc1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)OCc1ccccc1)NCCc1c[nH]c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]-[C:16]=[C;D1;H2:17]>>[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8])-[C:12](=[O;D1;H0:13])-[#8... | 84.5 | [{"value": 84.5, "product": "C(C1=CC=CC=C1)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC=C)CC1=CNC2=CC=CC=C12)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "C(C1=CC=CC=C1)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC=C)CC1=CNC2=CC=CC=C12)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | C(Cl)Cl.C(C)(=O)OCC | null | 16 | C=CCOC(=O)[C@H](N)Cc1c[nH]c2ccccc12.CC(C)(NC(=O)OCc1ccccc1)C(=O)O>C(Cl)Cl.C(C)(=O)OCC>C=CCOC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)C(C)(C)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e392efa1dd0c43839d8e3026d6f4b2ee | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1>>CC(C)(CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | C(C1=CC=CC=C1)OC([C@H](N)CC1=CNC2=CC=CC=C12)=O.C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C>>C(C1=CC=CC=C1)OC([C@@H](CC1=CNC2=CC=CC=C12)NC(CC(C)(C)NC(=O)OC(C)(C)C)=O)=O | O[C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:29][C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:6].[NH2:7][C@H:8]([CH2:9][c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[C:19](=[O:20])[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[NH:7][C@H... | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | CC(C)(CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1c[nH]c2ccccc12)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH2;D1;+0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | Prepared from D-tryptophan benzyl ester (1 g; 3.40 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (0.91 g; 4.19 mmol) by the procedure described in Example 6, Step C. The yield was 0.981 g (58%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1>>CC(C)(CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-31a415ff907141efa27a3abe2528614f | CC(C)(C)OC(=O)NCc1ccccc1-c1ccc(CO)cc1.CCN>>CCNCc1ccc(-c2ccccc2CNC(=O)OC(C)(C)C)cc1 | CS(=O)(=O)Cl.C(C)N(CC)CC.C(C)N.OCC1=CC=C(C=C1)C1=C(C=CC=C1)CNC(=O)OC(C)(C)C>>C(C)NCC1=CC=C(C=C1)C1=C(C=CC=C1)CNC(=O)OC(C)(C)C | O[CH2:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]1.[CH3:1][CH2:2][NH2:3]>>[CH3:1][CH2:2][NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15][NH:16][C:17](=[O:18])[O:19][C:20](... | CC(C)(C)OC(=O)NCc1ccccc1-c1ccc(CO)cc1.CCN | CCNCc1ccc(-c2ccccc2CNC(=O)OC(C)(C)C)cc1 | null | null | CO.C(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccc(-c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6]-[NH2;D1;+0:7]>>[C;D1;H3:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 68.2 | [{"value": 68.0, "product": "C(C)NCC1=CC=C(C=C1)C1=C(C=CC=C1)CNC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "C(C)NCC1=CC=C(C=C1)C1=C(C=CC=C1)CNC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 4-Hydroxymethyl-2'(t-butoxycarbonylaminomethyl)-1,1'-biphenyl (70 mg; 0.224 mmol) was dissolved in dry methylene chloride and stirred at 0° C. in an iced water bath and methanesulfonyl chloride (22 μl; 0.285 mmol) and triethylamine (39 μl; 0.280 mmol) added. The reaction mixture was stirred for 3 h at 0° C. and then 70... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HO- | CO.C(Cl)Cl.C(C)(=O)OCC | 0 | null | CC(C)(C)OC(=O)NCc1ccccc1-c1ccc(CO)cc1.CCN>CO.C(Cl)Cl.C(C)(=O)OCC>CCNCc1ccc(-c2ccccc2CNC(=O)OC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36f08b8e5c0c4222ab2cf761a8e66449 | C=CCO.CC(C)(C)OC(=O)N[C@H](COCc1ccccc1)C(=O)O>>C=CCOC(=O)[C@@H](COCc1ccccc1)NC(=O)OC(C)(C)C | C(C)(=O)OCC.C(C=C)O.C(C)(C)(C)OC(=O)N[C@H](COCC1=CC=CC=C1)C(=O)O.C(CCl)Cl>>C(C=C)OC([C@H](NC(=O)OC(C)(C)C)COCC1=CC=CC=C1)=O | O[CH2:3][CH:2]=[CH2:1].[OH:4][C:5](=[O:6])[C@@H:7]([CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C@@H:7]([CH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][... | C=CCO.CC(C)(C)OC(=O)N[C@H](COCc1ccccc1)C(=O)O | C=CCOC(=O)[C@@H](COCc1ccccc1)NC(=O)OC(C)(C)C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | null | [] | null | null | 2.5 | HOUR | N-(t-Butoxycarbonyl)-O-benzyl-D-serine (600 mg; 2.03 mmol) was dissolved in dry methylene chloride (5 ml), allyl alcohol (152 μl; 2.23 mmol) and DMAP (25 mg; 0.20 mmol) added and finally EDC (428.5 mg; 2.24 mmol) added to the acid. The reaction mixture was stirred at room temperature for 2.5 h and the resulting homogen... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 2.5 | C=CCO.CC(C)(C)OC(=O)N[C@H](COCc1ccccc1)C(=O)O>CN(C)C=1C=CN=CC1.C(Cl)Cl>C=CCOC(=O)[C@@H](COCc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4973b5510ea745408780d7b531a293b6 | CN(C(=O)[C@@H](CCc1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21)c1ccc(-c2ccccc2[N+](=O)[O-])cc1>>CN(C(=O)[C@H](N)CCc1ccccc1)c1ccc(-c2ccccc2[N+](=O)[O-])cc1 | C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H](C(=O)N(C1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])C)CCC1=CC=CC=C1.NCC1CCNCC1>>N[C@@H](C(=O)N(C1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])C)CCC1=CC=CC=C1 | O=C(OCC1c2ccccc2-c2ccccc21)[NH:6][C@@H:5]([C:3]([N:2]([CH3:1])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[N+:25](=[O:26])[O-:27])[cH:28][cH:29]1)=[O:4])[CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][N:2]([C:3](=[O:4])[C@H:5]([NH2:6])[CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12... | CN(C(=O)[C@@H](CCc1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21)c1ccc(-c2ccccc2[N+](=O)[O-])cc1 | CN(C(=O)[C@H](N)CCc1ccccc1)c1ccc(-c2ccccc2[N+](=O)[O-])cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(CCCc1ccccc1)Nc1ccc(-c2ccccc2)cc1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C;D1;H3:7])-[c:8]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6](-[C;D1;H3:7])-[c:8] | null | [] | null | null | null | null | The FMOC amide from Step F (1.15 g; 1.88 mmol) was dissolved in methylene chloride (10 ml) and 4-(aminomethyl)piperidine (1 ml) added. The reaction mixture was stirred at room temperature. The reaction mixture was stirred for 15 minutes and then quenched by adding water. The methylene chloride phase was separated, drie... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CN(C(=O)[C@@H](CCc1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21)c1ccc(-c2ccccc2[N+](=O)[O-])cc1>C(Cl)Cl>CN(C(=O)[C@H](N)CCc1ccccc1)c1ccc(-c2ccccc2[N+](=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f701c8034cd64527bb66e1cb9184c5a6 | CNc1ccc(-c2ccccc2C#N)cc1.O=C(N[C@H](CCc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21>>CN(C(=O)[C@H](N)CCc1ccccc1)c1ccc(-c2ccccc2C#N)cc1 | C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H](C(=O)O)CCC1=CC=CC=C1.CNC1=CC=C(C=C1)C1=C(C=CC=C1)C#N.C(C(=O)Cl)(=O)Cl.C(C)N(CC)CC>>N[C@@H](C(=O)N(C1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C)CCC1=CC=CC=C1 | [CH3:1][NH:2][c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]#[N:26])[cH:27][cH:28]1.O=C(OCC1c2ccccc2-c2ccccc21)[NH:6][C@@H:5]([C:3](O)=[O:4])[CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][N:2]([C:3](=[O:4])[C@H:5]([NH2:6])[CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][... | CNc1ccc(-c2ccccc2C#N)cc1.O=C(N[C@H](CCc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21 | CN(C(=O)[C@H](N)CCc1ccccc1)c1ccc(-c2ccccc2C#N)cc1 | null | CN(C)C=O | C(Cl)Cl | Acylation | OtherReaction | 1f3e78c052292d501d7437edb4bf22606988b28adaa781f40f6d3c5a3d2dcd8c | 77a668978e69174334be4f36a3c7053272639f750105af3c4ac3ba22ece7f87c | O=C(CCCc1ccccc1)Nc1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[NH;D2;+0:5]-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:3](-[NH2;D1;+0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C;D1;H3:6])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 2 | HOUR | (R)-α-[N-(9-Fluorenylmethoxycarbonyl)amino]-benzenebutanoic acid (500 mg; 1.25 mmol), was converted into its corresponding acid chloride according to the procedure descibed in Example 33, Step F using 1 drop of DMF, oxalyl chloride (136 μl) in methylene chloride (2.5 ml). A yellow solid which was the acid chloride (525... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine | Tertiary amide.Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.C(Cl)Cl | null | 2 | CNc1ccc(-c2ccccc2C#N)cc1.O=C(N[C@H](CCc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21>CN(C)C=O.C(Cl)Cl>CN(C(=O)[C@H](N)CCc1ccccc1)c1ccc(-c2ccccc2C#N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-51173d9d709c45cdbf8cf8891134c0bf | OCC(O)C(O)C(O)CO.OC[C@@H](O)[C@H](O)[C@@H](O)CO>>O=C(CO)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | C([C@H](O)[C@@H](O)[C@H](O)CO)O.C(C(C(C(CO)O)O)O)O.C([C@H](C([C@@H](CO)O)O)O)O>>O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C([C@H](C([C@@H](CO)O)O)O)O.OCC(=O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO | [OH:1][CH:2]([CH2:3][OH:4])[CH:5]([OH:6])[CH:7]([OH:8])[CH2:9][OH:10].[OH:11][CH2:12][C@@H:13]([OH:14])[C@H:27]([OH:28])[C@@H:29]([OH:30])[CH2:31][OH:32]>>[O:1]=[C:2]([CH2:3][OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[CH2:9][OH:10].[O:11]=[CH:12][C@H:13]([OH:14])[C@@H:15]([OH:16])[C@H:17]([OH:18])[CH2:19][OH:20].[O:21]=[CH:... | OCC(O)C(O)C(O)CO.OC[C@@H](O)[C@H](O)[C@@H](O)CO | O=C(CO)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | null | null | null | Functional Group Addition | OtherReaction | cbb5e53a24f408b885543123031dd6b6da1e3b619b55409aacf6ea79017bf12e | a05ca77da51178ec59bb2b865241409ac5fa304d04a7a6acaf4ba97f90da5172 | null | [C:1]-[C:2](-[O;D1;H1:3])-[C@H;D3;+0:4](-[O;D1;H1:5])-[C@@H;D3;+0:6](-[O;D1;H1:7])-[CH2;D2;+0:8]-[OH;D1;+0:9].[O;D1;H1:10]-[C:11]-[CH;D3;+0:12](-[O;D1;H1:13])-[CH;D3;+0:14](-[O;D1;H1:15])-[CH;D3;+0:16](-[OH;D1;+0:17])-[C:18]-[O;D1;H1:19]>>[C:20]-[C:21](-[O;D1;H1:22])-[C@@H;D3;+0:6](-[O;D1;H1:7])-[CH;D2;+0:8]=[O;H0;D1;+... | null | [] | null | null | null | null | It is known from European Patent No. 421,882, of which the Applicant is proprietor, to obtain xylitol syrups having a xylitol content of 80% to 90%, the remainder being essentially composed of D-arabitol, pentitol of the natural D series of sugars. These syrups, which are not very viscous and which are particularly wel... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Aldehyde.Aldehyde.Ketone.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | null | Other | null | null | null | OCC(O)C(O)C(O)CO.OC[C@@H](O)[C@H](O)[C@@H](O)CO>>O=C(CO)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9ba26a120c504949aabeae933256e0ed | O=P([O-])([O-])[O-].[NH4+].[NH4+]>>O=P([O-])([O-])O.O=P([O-])([O-])O.[NH4+].[NH4+].[NH4+] | P(=O)([O-])([O-])[O-].[NH4+].[NH4+].[NH4+].[Cl-].[Na+]>>P(=O)([O-])([O-])O.[NH4+].[Na+].[Cl-].[NH4+].P(=O)([O-])([O-])O.[NH4+].[NH4+] | [O-:1][P:2]([O-:3])(=[O:6])[O-:10].[NH4+:12].[NH4+:13]>>[O:1]=[P:2]([O-:3])([O-:4])[OH:5].[O:6]=[P:7]([O-:8])([O-:9])[OH:10].[NH4+:12].[NH4+:13].[NH4+:14] | O=P([O-])([O-])[O-].[NH4+].[NH4+] | O=P([O-])([O-])O.O=P([O-])([O-])O.[NH4+].[NH4+].[NH4+] | null | null | O | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | [O-;H0;D1:1]-[P;H0;D4;+0:2](-[O-;H0;D1:3])(-[O;-;D1;H0:4])=[O;H0;D1;+0:5]>>[O;-;D1;H0:6]-[#15:7](-[O;-;D1;H0:8])(=[O;H0;D1;+0:5])-[OH;D1;+0:1].[O;-;D1;H0:4]-[P;H0;D4;+0:2](-[O;-;D1;H0:9])(-[O;D1;H1:10])=[O;H0;D1;+0:3] | null | [] | null | null | null | null | Sodium ammonium phosphate and ammonium chloride are prepared from an ammonium phosphate (e.g., diammonium phosphate) and sodium chloride in water. The crystallization of sodium ammonium phosphate may take place between -10° C. to 40° C. Using the present invention, technical grade sodium ammonium phosphate and ammonium... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | O=P([O-])([O-])[O-].[NH4+].[NH4+]>O>O=P([O-])([O-])O.O=P([O-])([O-])O.[NH4+].[NH4+].[NH4+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-985d1723ff4d4b1298aaa363af9134e8 | [Cl-].[Na+]>>[Cl-].[NH4+].[Na+] | [Cl-].[NH4+].S(=O)(=O)([O-])[O-].[Na+].[Na+]>>S(=O)(=O)([O-])[O-].[NH4+].[NH4+].[Na+].[Cl-] | [Cl-:6].[Na+:9]>>[Cl-:6].[NH4+:8].[Na+:9] | [Cl-].[Na+] | [Cl-].[NH4+].[Na+] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | It is also known that ammonium chloride and sodium sulphate can be produced from ammonium sulphate and salt (NaCl). According to this reaction, one would expect to produce disodium phosphate and ammonium chloride from sodium chloride and diammonium phosphate if the Na/P molar ratio is 2.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | null | null | null | [Cl-].[Na+]>>[Cl-].[NH4+].[Na+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0cd0c63904c42eabebf3989bb71e6b3 | O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1>>O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1 | C1=CC=C(C=C1)C2=COC3(C2=O)C4=CC=CC=C4C(=O)O3.C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+].Cl.Cl.C(CN)N>>C(CN)N.C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+] | [O:5]=[C:6]([O:7][N:8]1[C:9](=[O:10])[CH2:11][CH:12]([S:13](=[O:14])(=[O:15])[O-:16])[C:17]1=[O:18])[CH:19]1[CH2:20][CH2:21][CH:22]([CH2:23][N:24]2[C:25](=[O:26])[CH:27]=[CH:28][C:29]2=[O:30])[CH2:31][CH2:32]1>>[O:5]=[C:6]([O:7][N:8]1[C:9](=[O:10])[CH2:11][CH:12]([S:13](=[O:14])(=[O:15])[O-:16])[C:17]1=[O:18])[CH:19]1[... | O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1 | O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1 | null | null | C(C)(=O)[O-].[Na+] | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1 | null | null | [] | null | null | null | null | Sulfo-SMCC (1 eq.)(Pierce Chemical Co., Rockford, Ill.) is dissolved in sodium acetate buffer (pH 7) and ethylenediamine dihydrochloride (5 eq.) is added. The reaction is monitored by TLC visualized with fluorescamine. When reaction is complete the reaction mixture is applied directly to a C18 reverse-phase HPLC column... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1.C1CCCCC1.C1=CC[NH]C1 | null | C(C)(=O)[O-].[Na+] | null | null | O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1>C(C)(=O)[O-].[Na+]>O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32657578f2084976872d2cf3b47b25b7 | CC(=O)SCC[N+](C)(C)C.N[C@@H](CS)C(=O)O>>CC(=O)N[C@@H](CS)C(=O)O.C[N+](C)(C)CCS | N[C@@H](CS)C(=O)O.C(C)(=O)SCC[N+](C)(C)C>>SCC[N+](C)(C)C.C(C)(=O)N[C@@H](CS)C(=O)O | [CH3:1][C:2](=[O:3])[S:17][CH2:16][CH2:15][N+:12]([CH3:11])([CH3:13])[CH3:14].[NH2:4][C@@H:5]([CH2:6][SH:7])[C:8](=[O:9])[OH:10]>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]([CH2:6][SH:7])[C:8](=[O:9])[OH:10].[CH3:11][N+:12]([CH3:13])([CH3:14])[CH2:15][CH2:16][SH:17] | CC(=O)SCC[N+](C)(C)C.N[C@@H](CS)C(=O)O | CC(=O)N[C@@H](CS)C(=O)O.C[N+](C)(C)CCS | null | null | null | Acylation | OtherReaction | eadd48a08a1f1a35cc40325d486fb291670e6a7642c6207686313b68b53a9670 | 6543d3ccfa2e7364577832d8ac025f88ec72a87da9e0dea588fa48510f2b1d42 | null | [C:1]-[C:2](-[NH2;D1;+0:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[C:7]-[C:8]-[S;H0;D2;+0:9]-[C;H0;D3;+0:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:10](-[C;D1;H3:11])=[O;D1;H0:12])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[C:7]-[C:8]-[SH;D1;+0:9] | null | [] | null | null | null | null | reacting the cysteine with the acetylthiocholine to form thiocholine and N-acetylcysteine, each in a concentration of about 0.2 molar to about 3.0 molar and in a molar ratio of thiocholine to N-acetylcysteine of 1:1.2 to 1.2:1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Carbo-thioester | Secondary amide.Aliphatic thiol | null | null | null | null | null | null | null | CC(=O)SCC[N+](C)(C)C.N[C@@H](CS)C(=O)O>>CC(=O)N[C@@H](CS)C(=O)O.C[N+](C)(C)CCS |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-987cbce73ecd44fa89c19bbd9f39470c | O=S([O-])[O-].[Na+]>>O=S(=O)([O-])CCS(=O)(=O)[O-].[Na+] | BrCCBr.S(=O)([O-])[O-].[Na+].[Na+]>>C(CS(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+] | [O-:1][S:2]([O-:4])=[O:9].[Na+:12]>>[O:1]=[S:2](=[O:3])([O-:4])[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[O-:10].[Na+:12] | O=S([O-])[O-].[Na+] | O=S(=O)([O-])CCS(=O)(=O)[O-].[Na+] | null | null | O | Oxidation | OtherReaction | b34b58941ad31acdf479ae5ca981fe52f3be011f815cd9cc7ba4ddcb65f38c10 | 1eb7bb476006d502a02416eb81e7f131b3c53487adcd281911e6272706cdec95 | null | [O-;H0;D1:1]-[S;H0;D3;+0:2](-[O;-;D1;H0:3])=[O;H0;D1;+0:4]>>[O;-;D1;H0:5]-[#16:6](=[O;D1;H0:7])(=[O;H0;D1;+0:4])-[C:8]-[C:9]-[S;H0;D4;+0:2](-[O;-;D1;H0:3])(=[O;D1;H0:10])=[O;H0;D1;+0:1] | 65.1 | [{"value": 65.1, "product": "C(CS(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-dibromoethane (37.6 g, 0.20 mol) and sodium sulfite (63.0 g, 0.5 mol) in water (225 mL) was heated at reflux temperature for 20 h. After the mixture was cooled in the refrigerator, crystals were collected. The crude product was repeatedly recrystallized from water-ethanol. The trace amount of inorganic... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonic acid.Sulfonic acid | null | null | null | null | O | null | null | O=S([O-])[O-].[Na+]>O>O=S(=O)([O-])CCS(=O)(=O)[O-].[Na+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b57c36d4bcc2495f859a14c585711e9b | BrCCCBr.O=S([O-])[O-].[Na+]>>O=S(=O)([O-])CCCS(=O)(=O)[O-].[Na+] | BrCCCBr.S(=O)([O-])[O-].[Na+].[Na+].C>>C(CCS(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+] | Br[CH2:5][CH2:7][CH2:6]Br.[O-:1][S:2]([O-:4])=[O:10].[Na+:13]>>[O:1]=[S:2](=[O:3])([O-:4])[CH2:5][CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[O-:11].[Na+:13] | BrCCCBr.O=S([O-])[O-].[Na+] | O=S(=O)([O-])CCCS(=O)(=O)[O-].[Na+] | null | null | O | Oxidation | OtherReaction | dfafa97ac1db18ed9885a8c9ddbde026679d862dea7cad49633322bc494b39ac | 7c941e1ecba24481eaa2d98576388722e2302c88fba0b24ad34fbecf569e3576 | null | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-Br.[O-;H0;D1:4]-[S;H0;D3;+0:5](-[O;-;D1;H0:6])=[O;H0;D1;+0:7]>>[O;-;D1;H0:8]-[#16:9](=[O;D1;H0:10])(=[O;H0;D1;+0:7])-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:1]-[S;H0;D4;+0:5](-[O;-;D1;H0:6])(=[O;D1;H0:11])=[O;H0;D1;+0:4] | 85.6 | [{"value": 85.6, "product": "C(CCS(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared by a modification of the method described in Stone, G. C. H. (1936) J. Am. Chem. Soc., 58:488. 1,3-Dibromopropane (40.4 g, 0.20 mol) was treated with sodium sulfite (60.3 g, 0.50 mol) in water at reflux temperature for 48 h. Inorganic salts (sodium bromide and sodium sulfite) were removed by ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | Sulfonic acid.Sulfonic acid | null | null | null | Br- | O | null | null | BrCCCBr.O=S([O-])[O-].[Na+]>O>O=S(=O)([O-])CCCS(=O)(=O)[O-].[Na+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ab0050d28734f3bbd40feed3cadae32 | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O>>O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O>>C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O.O | OC[C@H]1O[C@@](C[OH:1])([O:7][C@H:6]2[O:5][C@H:4]([CH2:3][OH:2])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]2[OH:9])[C@@H](O)[C@@H]1O>>[OH2:1].[OH:2][CH2:3][C@H:4]1[O:5][CH:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([OH:11])[C@@H:12]1[OH:13] | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O | O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O | null | null | O | Reduction | OtherReaction | 4bdb706d436485c857e245c05b537da9c9d30893ed64af96235ac43136bb801d | 3214caef4749dbf6b36c0350acd3bc28c8a03e3af74b1ea21fbc7730a8d65008 | C1CCOCC1 | null | null | [] | null | null | null | null | 29 parts of liquid saccharose and 49 parts of water were mixed at 60° C. 0.2 parts of stabiliser formed by carrageenans and xanthan gum and 3.5 parts of glucose syrup were then added. 15.5 parts of apple puree, colouring agent and finally 2.1 parts of citric acid were then added thereto. After pasteurisation of the mix... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol | Secondary alcohol | C1CCOC1 | null | C1CCOCC1 | HO- | O | null | null | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O>O>O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-426a2c8a98564f41bccd59759d726727 | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O>>O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O>>C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O.O | OC[C@H]1O[C@@](C[OH:1])([O:7][C@H:6]2[O:5][C@H:4]([CH2:3][OH:2])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]2[OH:9])[C@@H](O)[C@@H]1O>>[OH2:1].[OH:2][CH2:3][C@H:4]1[O:5][CH:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([OH:11])[C@@H:12]1[OH:13] | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O | O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O | null | null | O | Reduction | OtherReaction | 4bdb706d436485c857e245c05b537da9c9d30893ed64af96235ac43136bb801d | 3214caef4749dbf6b36c0350acd3bc28c8a03e3af74b1ea21fbc7730a8d65008 | C1CCOCC1 | null | null | [] | null | null | null | null | For this purpose, a composition was prepared by mixing 18.5 parts of liquid saccharose and 68 parts of water at 60° C. 0.2 parts of stabiliser formed by carrageenans and xanthan gum and 3.5 parts of glucose syrup were then added. 10 parts of apple puree and colouring agent were added and the mixture was pasteurised at ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol | Secondary alcohol | C1CCOC1 | null | C1CCOCC1 | HO- | O | null | null | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O>O>O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a341d33ac8ca4d4dbeafbd8b5790110d | CC(C)=O.Cc1ccccc1.N#C[S-]>>C=Cc1ccc(CSC#N)cc1.C=Cc1ccccc1 | [S-]C#N.[K+].CC(=O)C.C1(=CC=CC=C1)C>>C=CC1=CC=CC=C1.S(C#N)CC1=CC=C(C=C)C=C1 | O=[C:12]([CH3:1])[CH3:14].[c:6]1([CH3:7])[cH:16][cH:17][cH:18][cH:19][cH:20]1.[S-:8][C:9]#[N:10]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C:9]#[N:10])[cH:11][cH:12]1.[CH2:13]=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | CC(C)=O.Cc1ccccc1.N#C[S-] | C=Cc1ccc(CSC#N)cc1.C=Cc1ccccc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 95f6b80107a2e3e1ea403a4587cde35cb6c99d517b7d5ad83528721b2e3acaa8 | 57a7b0b4cda119dfd964beeceb47d950936660c56ce34b88855dbb58b35e9241 | c1ccccc1.c1ccccc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[CH3;D1;+0:3].[CH3;D1;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1.[N;D1;H0:11]#[C:12]-[S-;H0;D1:13]>>[C;D1;H2:14]=[CH;D2;+0:2]-[c:15]1:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1.[CH2;D1;+0:3]=[C:16]-[c:17]1:[c:18]:[c:19]:[c;H0;D3;+0:5](-[CH2;D2;+0:4]-[S;H0;D... | null | [] | null | null | null | null | The desired terpolymer of styrene, 4-thiocyanatomethylstyrene, and vinyl benzyl polyethylene glycol was synthesized from the terpolymer of Step II as follows: 1.5 g of the terpolymer formed in Step II was mixed with 350 mL of toluene taken in a 500 mL flask and the contents stirred. To this mixture was added 1.2 g of p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Monosulfide.Thiocyanate.Vinyl.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | null | CC(C)=O.Cc1ccccc1.N#C[S-]>CN(C)C=O>C=Cc1ccc(CSC#N)cc1.C=Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-da3a70b3badd4e8da28a4299f8a4a21a | C#CCCOC1CCCCO1>>C#CCCCOC1CCCCO1 | O.NN.[Li+].[AlH4-].C(CC#C)OC1OCCCC1.BrBr.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OO.O1CCCC=C1.C(CCC)[Li].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>O1C(CCCC1)OCCCC#C | [CH:2]#[C:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C#CCCOC1CCCCO1 | C#CCCCOC1CCCCO1 | null | [N+](=O)([O-])[O-].[Ag+].[N+](=O)([O-])[O-].[Ag+] | null | Functional Group Interconversion | OtherReaction | 717941f395a910361dbd079f0406c8739db3d600df9659ab84f995c3dd1e77a5 | f5163dfbf670ee9f38d1be788eef0e0a983df5868f48fe01d48741d6a3f98157 | C1CCOCC1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[CH;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[C;H0;D2;+0:4]#[C;D1;H1:5] | null | [] | null | null | null | null | Hydrazine hydrate and hydrogen peroxide (30 wt. % solution in water) were purchased from Mallinckrodt (Chesterfield, Mo.) and Fisher Chemical Co. (Fair Lawn, N.J.), respectively. Butyllithium (1.6M and 2.5M solutions in hexane), 2-(3-butynyloxy)tetrahydro-2H-pyran (1-(tetrahydopyran-2-yloxy)-3-butyne), lithium tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | C1CCOCC1 | Other | [N+](=O)([O-])[O-].[Ag+].[N+](=O)([O-])[O-].[Ag+] | null | null | C#CCCOC1CCCCO1>[N+](=O)([O-])[O-].[Ag+].[N+](=O)([O-])[O-].[Ag+]>C#CCCCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6cc52ce6268b484891e547260b4cddbc | CCC#CCO.Cc1ccc(S(=O)(=O)Cl)cc1>>CCC#CCOS(=O)(=O)c1ccc(C)cc1 | [OH-].[K+].C(C#CCC)O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)OCC#CCC)C | [CH3:1][CH2:2][C:3]#[C:4][CH2:5][OH:6].Cl[S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][O:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1 | CCC#CCO.Cc1ccc(S(=O)(=O)Cl)cc1 | CCC#CCOS(=O)(=O)c1ccc(C)cc1 | null | null | [Cl-].[Na+].O.C1CCOC1 | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | 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]#[C:9]-[C:10]-[OH;D1;+0:11]>>[C:7]-[C:8]#[C:9]-[C:10]-[O;H0;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 76.4 | [{"value": 76.4, "product": "C1(=CC=C(C=C1)S(=O)(=O)OCC#CCC)C", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1.5 | HOUR | A solution of 2-pentyn-1-ol (8.40 g, 100 mmol) in THF (60 mL) was treated with p-toluenesulfonyl chloride (23.9 g, 125 mmol) at -10° C., followed by pulverized KOH (11.3 g, 200 mmol) without allowing the temperature to exceed -5° C. After 1.5 hours of stirring at -10° C., 50 mL of saturated brine was added and the prod... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | [Cl-].[Na+].O.C1CCOC1 | -10 | 1.5 | CCC#CCO.Cc1ccc(S(=O)(=O)Cl)cc1>[Cl-].[Na+].O.C1CCOC1>CCC#CCOS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20e7740b40a84d63aa989b9ae2ca2acc | BrBr.CCC=CCC=CCCCO>>CC/C=C\C/C=C\CCCBr | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrBr.C(CCC=CCC=CCC)O.C(=O)(O)[O-].[Na+]>>BrCCC\C=C/C\C=C/CC | Br[Br:11].O[CH2:10][CH2:9][CH2:8][CH:7]=[CH:6][CH2:5][CH:4]=[CH:3][CH2:2][CH3:1]>>[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][Br:11] | BrBr.CCC=CCC=CCCCO | CC/C=C\C/C=C\CCCBr | null | null | C(Cl)Cl.O | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | null | Br-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]-[C:5]=[C:6]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]/[C:5]=[C:6] | 32 | [{"value": 32.0, "product": "BrCCC\\C=C/C\\C=C/CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of triphenylphosphine (20.9 g, 80 mmol) in CH2Cl2 (100 ml) was treated with Br2 (7.8 g, 49 mmol) in CH2Cl2 (15 mL, 0° C.) and the mixture was stirred at room temperature for 20 min. Into the slightly yellow suspension that formed, the crude mixture of 4 and 4Z,7Z)-4,7-decadien-1-ol (12.4 g) in CH2Cl2 (15 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | null | HBr | C(Cl)Cl.O | null | 0.333333 | BrBr.CCC=CCC=CCCCO>C(Cl)Cl.O>CC/C=C\C/C=C\CCCBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1bd848ddd0dc4cfa834fa8dfc6a62227 | C#CCCOC1CCCCO1.CC/C=C\C/C=C\CCCBr>>CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1 | BrCCC\C=C/C\C=C/CC.O1C(CCCC1)OCCC#C.CCCCCC.C(CCC)[Li]>>O1C(CCCC1)OCCC#CCCC\C=C/C\C=C/CC | [CH:11]#[C:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1.Br[CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH3:1]>>[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1 | C#CCCOC1CCCCO1.CC/C=C\C/C=C\CCCBr | CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | a2902088eeffba8af7cde0e465024f8c5b6cd6239687cb7ab88d93a01519cd51 | 65c5c213019f4e08c3c32f7e1ced539ac3ff1efc4a39855e6d21bd16502eefc5 | C1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5] | 55 | [{"value": 55.0, "product": "O1C(CCCC1)OCCC#CCCC\\C=C/C\\C=C/CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1-(tetrahydropyran-2-yloxy)-3-butyne (2.25 g, 14 mmol) in dry THF (15 ml) was treated at -50° C. with n-butyllithium hexane solution (11 ml, 17.5 mmol). After 15 min at -30° C., the mixture was kept at room temperature for 30 min. The mixture was then treated at 0° C. with 5 (3.0 g, 13.8 mmol) dissolved i... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Alkyne | Alkyne | null | null | C1CCOCC1 | HBr | C1CCOC1 | null | 0.25 | C#CCCOC1CCCCO1.CC/C=C\C/C=C\CCCBr>C1CCOC1>CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ab5f2747c1246a3b5a9230c3b5b5892 | CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1>>CC/C=C\C/C=C\CCCC#CCCO | O1C(CCCC1)OCCC#CCCC\C=C/C\C=C/CC>>C(CC#CCCC\C=C/C\C=C/CC)O | C1CCC([O:15][CH2:14][CH2:13][C:12]#[C:11][CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH3:1])OC1>>[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][OH:15] | CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1 | CC/C=C\C/C=C\CCCC#CCCO | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | null | [C:1]#[C:2]-[C:3]-[C:4]-[O;H0;D2;+0:5]-C1-C-C-C-C-O-1>>[C:1]#[C:2]-[C:3]-[C:4]-[OH;D1;+0:5] | 83 | [{"value": 83.0, "product": "C(CC#CCCC\\C=C/C\\C=C/CC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6 (2.2 g, 7.5 mmol) in methanol (50 mL) was stirred with DOWEX™ 50W-X8 (Dow Chemical, Midland, Mich.) ion exchange resin (2 g) and the formation of 7 was monitored by TLC. The resin was removed by filtration and washed with methanol (3×20 mL). The alcohol 7 was purified by flash chromatography (1.3 g, 83%... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | null | HO- | CO | null | null | CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1>CO>CC/C=C\C/C=C\CCCC#CCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b18349f92ab4ab2a31939346351aab8 | CC/C=C\C/C=C\CCCBr.CC/C=C\C/C=C\CCCCCCCOC(C)=O>>CCCCC/C=C\CCC/C=C/CCOC(C)=O | BrCCC\C=C/C\C=C/CC.C(C)(=O)OCCCCCCC\C=C/C\C=C/CC.O1C(CCCC1)OCCC\C=C/C\C=C/CC>>C(C)(=O)OCC\C=C\CCC\C=C/CCCCC | Br[CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH3:1].CC/C=C\C/C=C\CCC[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]([CH3:17])=[O:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][C:16]([CH3:17])=[O:18] | CC/C=C\C/C=C\CCCBr.CC/C=C\C/C=C\CCCCCCCOC(C)=O | CCCCC/C=C\CCC/C=C/CCOC(C)=O | null | null | null | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5]\[C:6]/[CH;D2;+0:7]=[CH;D2;+0:8]\[C:9]-[C;D1;H3:10].C-C/C=C\C/C=C\C-C-C-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[C:13]-[C:14]>>[C:14]-[C:13]/[CH;D2;+0:12]=[CH;D2;+0:11]/[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5]\[C:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[C:9]-[C;D1;H3:10] | null | [] | null | null | null | null | Dry THF (3 ml) was treated with trimethylsilyl iodide (260 mg, 185 μl, 1.30 mmol) at room temperature and stirred for 15 min to form 4-trimethylsiloxybutyl iodide (11). A solution of CuCN. (LiCl)2 in THF (1M, 100 μl) was added, and the mixture was cooled to -40° C. The above prepared solution of Grignard reagent 10, wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | null | HBr | null | null | null | CC/C=C\C/C=C\CCCBr.CC/C=C\C/C=C\CCCCCCCOC(C)=O>>CCCCC/C=C\CCC/C=C/CCOC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a6b921b6b9d454fb8489fe840ddec57 | C#CCCCOC1CCCCO1.CCCCCBr>>CCCCCC#CCCCOC1CCCCO1 | O1C(CCCC1)OCCCC#C.C(CCC)[Li].C(CCCC)Br.CCCCCC>>O1C(CCCC1)OCCCC#CCCCCC | [CH:6]#[C:7][CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17]1.Br[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17]1 | C#CCCCOC1CCCCO1.CCCCCBr | CCCCCC#CCCCOC1CCCCO1 | null | null | CN1CCCN(C1=O)C | C-C Coupling | OtherReaction | a2902088eeffba8af7cde0e465024f8c5b6cd6239687cb7ab88d93a01519cd51 | 65c5c213019f4e08c3c32f7e1ced539ac3ff1efc4a39855e6d21bd16502eefc5 | C1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]#[CH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:6]#[C:5]-[C:4] | 58 | [{"value": 58.0, "product": "O1C(CCCC1)OCCCC#CCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Tetrahydopyran-2-yloxy)-4-pentyne (1) (0.66 g, 3.90 mmol) was metallated with n-butyllithium solution (2.5M) in hexane (1.87 ml, 1.2 eq.). Addition of a solution of n-pentyl bromide (0.725 ml, 1.5 eq.) in DMPU (2 ml) produced 0.54 g (58% yield) of the title compound (15). 1H NMR (200 MHz) δ: 4.60 (m, 1H, CH-2'), 3.6... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Alkyne | Alkyne | null | null | C1CCOCC1 | HBr | CN1CCCN(C1=O)C | null | null | C#CCCCOC1CCCCO1.CCCCCBr>CN1CCCN(C1=O)C>CCCCCC#CCCCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e5f31ed3fd4346d9967feec4d8f3e24d | CCCCCC#CCCCOC1CCCCO1.[Ni]>>CC(=O)[O-].CC(=O)[O-].[Ni+2] | O1C(CCCC1)OCCCC#CCCCCC.[Ni]>>C(C)(=O)[O-].[Ni+2].C(C)(=O)[O-] | CCCC[CH2:5][C:6]#CCCC[O:3][CH:2]1[CH2:1]CCC[O:4]1.[Ni:9]>>[CH3:1][C:2](=[O:3])[O-:4].[CH3:5][C:6](=[O:7])[O-:8].[Ni+2:9] | CCCCCC#CCCCOC1CCCCO1.[Ni] | CC(=O)[O-].CC(=O)[O-].[Ni+2] | null | null | C(C)O | Acylation | OtherReaction | 2f340fbc5a4e453cff3d58cdbcd5df3c66d4c0ce7bc0561d47c0b4557350e1ce | cccf3c7b77140e050567e7c3d51d59570cf8b57c0909b466cc70b1284353b3a3 | null | C-C-C-C-[CH2;D2;+0:1]-[C;H0;D2;+0:2]#C-C-C-C-[O;H0;D2;+0:3]-[CH;D3;+0:4]1-[CH2;D2;+0:5]-C-C-C-[O;H0;D2;+0:6]-1.[Ni;H0;D0;+0:7]>>[CH3;D1;+0:5]-[C;H0;D3;+0:4](-[O-;H0;D1:6])=[O;H0;D1;+0:3].[CH3;D1;+0:1]-[C;H0;D3;+0:2](-[O;-;D1;H0:8])=[O;D1;H0:9].[Ni+2;H0;D0:7] | null | [] | null | null | null | null | 1-(Tetrahydropyran-2-yloxy)-4-decyne (15) (0.5 g, 2.1 mmol), prepared according to Example 13, was hydrogenated in ethanol (20 ml) over P2-Ni, formed from nickel acetate (75 mg) deactivated with ethylenediamine (0.2 ml) for 4 hr. After chromatography on silica gel, the product (16) (0.43 g) was obtained in 85% yield. G... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Alkyne | null | C1CCOCC1 | null | null | Other | C(C)O | null | null | CCCCCC#CCCCOC1CCCCO1.[Ni]>C(C)O>CC(=O)[O-].CC(=O)[O-].[Ni+2] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-486cc915e99745379d961e1fc7268a73 | BrBr.CCCCC/C=C\CCCOC1CCCCO1>>CCCCC/C=C\CCCBr | O1C(CCCC1)OCCC\C=C/CCCCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrBr>>BrCCC\C=C/CCCCC | Br[Br:11].C1CCC(O[CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])OC1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][Br:11] | BrBr.CCCCC/C=C\CCCOC1CCCCO1 | CCCCC/C=C\CCCBr | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 729729201dd51d0c8d3a04a278bc2364265bfb40acfeab8bf38c8b1c7b990e75 | 584f78421401c9ef21e71fadcbb76af4243eed60702b564d34493db8cfc1becb | null | Br-[Br;H0;D1;+0:1].[C:2]=[C:3]\[C:4]-[C:5]-[CH2;D2;+0:6]-O-C1-C-C-C-C-O-1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:6]-[C:5]-[C:4]/[C:3]=[C:2] | 90 | [{"value": 90.0, "product": "BrCCC\\C=C/CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice-cool solution of triphenylphosphine (0.72 g, 2.74 mmol) and bromine (0.41 g, 2.6 mmol) in CH2Cl2, a solution of (4Z)-1-(tetrahydropyran-2-yloxy)-4-decene (16) (0.41 g, 1.71 mmol), prepared according to Example 16, in methylene chloride was added dropwise. Isolation and purification by conventional means affor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary halide | C1CCOCC1 | null | null | HBr | C(Cl)Cl | null | null | BrBr.CCCCC/C=C\CCCOC1CCCCO1>C(Cl)Cl>CCCCC/C=C\CCCBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f15776952b34a539da4eb150087740b | CC/C=C\C/C=C\CCC/C=C/CCOC(C)=O.CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1.CC/C=C\C/C=C\CCCCCCCO[Si](C)(C)C>>CC/C=C\CCCCCC/C=C/CCOC(C)=O | C#CCC.O1C(CCCC1)OCCC\C=C/CCCCC.O1C(CCCC1)OCCC#CCCC\C=C/C\C=C/CC.BrCCCCCCOC1OCCCC1.BrCCCCCCOC1OCCCC1.O1C(CCCC1)OCCC\C=C/CCCCC.C(C)(=O)OCC\C=C\CCC\C=C/CCCCC.C(C)(=O)OCC\C=C\CCC\C=C/C\C=C/CC.C[Si](OCCCCCCC\C=C/C\C=C/CC)(C)C>>C(C)(=O)OCC\C=C\CCCCCC\C=C/CC | CC/C=C\C/C=C\[CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][C:16]([CH3:17])=[O:18].C(#CCCOC1CCCCO1)CCC/C=[CH:6]\[CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH3:1].CC/C=C\C/C=C\CC[CH2:7]CCCCO[Si](C)(C)C>>[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][C:16... | CC/C=C\C/C=C\CCC/C=C/CCOC(C)=O.CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1.CC/C=C\C/C=C\CCCCCCCO[Si](C)(C)C | CC/C=C\CCCCCC/C=C/CCOC(C)=O | null | null | C(Cl)(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 110620469c9a1e347c8d5ae50f053bbfcd31236258cd6d2ed454593db79b15b6 | 9d9ee273c9321f51502caf23b61abf935b514d598fbf4ae5f4928d0a887c11ab | null | C-C/C=C\C/C=C\C-C-[CH2;D2;+0:1]-C-C-C-C-O-[Si](-C)(-C)-C.C-C/C=C\C/C=C\[CH2;D2;+0:2]-[C:3]-[C:4]/[C:5]=[C:6].[C:7]/[C:8]=[C:9]\[C:10]/[CH;D2;+0:11]=C\C-C-C-C#C-C-C-O-C1-C-C-C-C-O-1>>[C:6]=[C:5]/[C:4]-[C:3]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:11]-[C:10]/[C:9]=[C:8]\[C:7] | 15 | [{"value": 15.0, "product": "C(C)(=O)OCC\\C=C\\CCCCCC\\C=C/CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Starting from 1-butyne and 1-bromo-6-(tetrahydropyran-2-yloxy)-hexane (22), the (3E,11Z)-3,11-tetradecadien-1-yl acetate (30) was prepared by a synthetic route similar to that used for the preparation of (3E,8Z)-3,8-tetradecadien-1-yl acetate (21), as depicted in the following scheme. ##STR18## The yield was 15% [17 mg... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Alkyne.Silyl protective group | null | C1CCOCC1 | null | null | HO- | C(Cl)(Cl)(Cl)Cl | null | null | CC/C=C\C/C=C\CCC/C=C/CCOC(C)=O.CC/C=C\C/C=C\CCCC#CCCOC1CCCCO1.CC/C=C\C/C=C\CCCCCCCO[Si](C)(C)C>C(Cl)(Cl)(Cl)Cl>CC/C=C\CCCCCC/C=C/CCOC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48e5492592614940b5cbab975adec0bb | O=P([O-])([O-])OP(=O)([O-])[O-].[Ca]>>O.O.O=P([O-])([O-])OP(=O)([O-])[O-].[Ca+2] | [Cl-].[Ca+2].[Cl-].[O-]P([O-])(=O)OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Ca].[P]>>O.O.[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ca+2].[Ca+2] | [O:1]=[P:4]([O-:5])([O-:6])[O:7][P:8](=[O:9])([O-:10])[O-:11].[Ca:12]>>[OH2:1].[OH2:2].[O:3]=[P:4]([O-:5])([O-:6])[O:7][P:8](=[O:9])([O-:10])[O-:11].[Ca+2:12] | O=P([O-])([O-])OP(=O)([O-])[O-].[Ca] | O.O.O=P([O-])([O-])OP(=O)([O-])[O-].[Ca+2] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [#15:1]-[#8:2]-[P;H0;D4;+0:3](-[O;-;D1;H0:4])(-[O;-;D1;H0:5])=[O;H0;D1;+0:6].[Ca;H0;D0;+0:7]>>[#15:1]-[#8:2]-[P;H0;D4;+0:3](-[O;-;D1;H0:4])(-[O;-;D1;H0:5])=[O;D1;H0:8].[Ca+2;H0;D0:7].[OH2;D0;+0:6] | null | [] | null | null | null | null | An aqueous calcium chloride solution and an aqueous sodium pyrophosphate solution were mixed together so that the calcium/phosphorus atomic ratio became 1:1, and the mixture was allowed to stand for a whole day to form calcium diphosphate dihydrate (Ca2P2O7.2H2O) crystals, which were then filtered off. The thus prepare... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | null | null | null | O=P([O-])([O-])OP(=O)([O-])[O-].[Ca]>>O.O.O=P([O-])([O-])OP(=O)([O-])[O-].[Ca+2] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a28675e5d044056be5059476c8f3ce9 | CS(=O)(=O)Cl>>CS(=O)(=O)O | C(C)N(CC)CC.C1(CCCCC1)C=1C(=CC(=C(C1)C(C1=CC(=C(C=C1)O)O)C1=C(C=C(C(=C1)C1CCCCC1)O)C)C)O.CS(=O)(=O)Cl>>C1(CCCCC1)C=1C(=CC(=C(C1)C(C1=CC(=C(C=C1)O)O)C1=C(C=C(C(=C1)C1CCCCC1)O)C)C)O.CS(=O)(=O)O | Cl[S:2]([CH3:1])(=[O:3])=[O:5]>>[CH3:1][S:2](=[O:3])(=[O:4])[OH:5] | CS(=O)(=O)Cl | CS(=O)(=O)O | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | 6c113db978119dd30ec9ac70e3a1ccab457b8adfa2d854ef650cc9d0d938808f | 5664dc87dc3eea7f40384c1c98932c2b6f77a01ae2083f96843fa9d662971745 | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;H0;D1;+0:4]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:5])-[OH;D1;+0:4] | null | [] | null | null | null | null | Bis(5 -cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane(1.0 mole), naphthoquinone-1,2-diazido-5-sulfonyl chloride (2.0 moles) and methanesulfonyl chloride(0.5 moles) were dissolved in dioxane (4,000 g). To the resulting solution, dioxane (1,500 g) having triethylamine (500 g) dissolved therein was added ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | null | null | O1CCOCC1 | null | null | CS(=O)(=O)Cl>O1CCOCC1>CS(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf4091059f4c4259bc4581b2905f26f6 | CS(=O)(=O)Cl>>CS(=O)(=O)O | OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C(C)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O.CS(=O)(=O)Cl.C(C)N(CC)CC>>OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C(C)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O.CS(=O)(=O)O | Cl[S:34]([CH3:33])(=[O:35])=[O:37]>>[CH3:33][S:34](=[O:35])(=[O:36])[OH:37] | CS(=O)(=O)Cl | CS(=O)(=O)O | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | 6c113db978119dd30ec9ac70e3a1ccab457b8adfa2d854ef650cc9d0d938808f | 5664dc87dc3eea7f40384c1c98932c2b6f77a01ae2083f96843fa9d662971745 | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;H0;D1;+0:4]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:5])-[OH;D1;+0:4] | null | [] | null | null | null | null | One (1.0) mole of 1-[1-(4-hydroxyphenyl)isopropyl]-4-[1,1-bis(4-hydroxyphenyl)ethyl]benzene, naphthoquinone-1,2-diazido-5-sulfonyl chloride (2.0 moles) and methanesulfonyl chloride (0.5 moles) were dissolved in dioxane (4,000 g). To the resulting solution, dioxane (2,000 g) having triethylamine (500 g) dissolved therei... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | null | null | O1CCOCC1 | null | null | CS(=O)(=O)Cl>O1CCOCC1>CS(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-34a870e6034145a8adf96361ff614be2 | Ic1ccccc1.c1ccc(Nc2ccc3c4c(cccc24)CC3)cc1>>c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | NC1=CC=C2CCC=3C=CC=C1C32.IC1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=CC=CC=C1.C1(=CC=CC=C1)NC1=CC=C2CCC=3C=CC=C1C32>>C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32 | I[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:12]2[cH:13][cH:14][c:15]3[c:16]4[c:17]([cH:18][cH:19][cH:20][c:21]24)[CH2:22][CH2:23]3)[cH:24][cH:25]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][c:15]3[c:16]4[c:17]([cH:18][cH:19][cH:20][c:21]2... | Ic1ccccc1.c1ccc(Nc2ccc3c4c(cccc24)CC3)cc1 | c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | null | [Cu] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]:[c:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:12]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:8](-[c:7](:[c:6]):[c:12])-[c:9](:[c:10]):[c:11]):[c:4]:[c:5] | 75.7 | [{"value": 75.7, "product": "C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32", "details": "PERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 26 | HOUR | 33.85 g (0.2 mol) of 5-aminoacenaphtthene was mixed with 102.1 g (0.5 mol) of iodo benzene, 1.3 g (0.02 mol) of copper powder, 34.5 g (0.25 mol) of anhydrous potassium carbonate and 100 ml of nitrobenzene, and the mixture was stirred at 200° C. for 26 hours. The reaction was determined to be finished when disappearance... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cc2c3c(cccc3c1)CC2 | HI | [Cu].C1(=CC=CC=C1)C | 200 | 26 | Ic1ccccc1.c1ccc(Nc2ccc3c4c(cccc24)CC3)cc1>[Cu].C1(=CC=CC=C1)C>c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c9df1b4f59204cf6ba44f7f63a8372d9 | CN(C)C=O.c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1>>O=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32.C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32.[OH-].[Na+].CN(C=O)C.P(=O)(Cl)(Cl)Cl>>C(=O)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32 | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][cH:5][c:6]([N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17]3[c:18]4[c:19]([cH:20][cH:21][cH:22][c:23]24)[CH2:24][CH2:25]3)[cH:26][cH:27]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17]3[c:18]4[c:... | CN(C)C=O.c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | O=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | null | null | O | C-C Coupling | OtherReaction | aae5f0134f66d7b9e3ae1bdd9b3a75c7cb29a8908ff53e1c4658205cbcae8547 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7] | 86.6 | [{"value": 86.6, "product": "C(=O)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | 32.14 g (0.1 mol) of the above prepared 5-(N,N-diphenylamino)acenaphthene was dissolved in 300 ml of N,N-dimethylformamide, and 22.73 g (0.15 mol) of phosphorus oxychloride was dropwise added thereto at room temperature for 30 minutes. After raising the temperature to 50° C., the reaction mixture was stirred for 14 hou... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cc2c3c(cccc3c1)CC2 | Other | O | 50 | 0.5 | CN(C)C=O.c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1>O>O=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b58f8f3df4214a82901f48cbd358ba6b | CC(C)(C)[O-].CO.O=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1>>Cc1ccc(C=Cc2ccc(N(c3ccccc3)c3ccc4c5c(cccc35)CC4)cc2)cc1 | CC(C)([O-])C.[K+].CO.O.C(=O)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32>>CC1=CC=C(C=CC2=CC=C(C=C2)N(C2=CC=CC=C2)C2=CC=C3CCC=4C=CC=C2C43)C=C1 | [O-][C:2]([CH3:1])([CH3:3])[CH3:34].O[CH3:6].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([N:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][c:22]3[c:23]4[c:24]([cH:25][cH:26][cH:27][c:28]24)[CH2:29][CH2:30]3)[cH:31][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([N:12]([c:13]... | CC(C)(C)[O-].CO.O=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | Cc1ccc(C=Cc2ccc(N(c3ccccc3)c3ccc4c5c(cccc35)CC4)cc2)cc1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | f0a0592b1a1e7c5334fb06381d02732361ab23bcea2e7f9781480ab4da02338a | 916508af6de7b69ef7f25dc9a08aafad6db32342143032e3e6d5dcfab38f0b04 | C(=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1)c1ccccc1 | O-[CH3;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[CH3;D1;+0:9])-[O-]>>[C;D1;H3:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c:10]:[c:11](-[CH;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]):[c:12]:[cH;D2;+0:9]:1 | 85 | [{"value": 85.0, "product": "CC1=CC=C(C=CC2=CC=C(C=C2)N(C2=CC=CC=C2)C2=CC=C3CCC=4C=CC=C2C43)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 20.96 g (0.06 mol) of 5-[N-(4-formylphenyl)-N-phenylamino]acenaphthene prepared in Preparation Example 1 and 17.44 g (0.072 mol) of diethyl 4-methylbenzyl phosphonate were dissolved in 300 ml of N,N-dimethylformamide, and 10.1 g (0.09 mol) of potassium-tert-butoxide was added thereto at room temperature for 20 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Methanol | null | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1cc2c3c(cccc3c1)CC2 | null | CN(C=O)C | null | 0.333333 | CC(C)(C)[O-].CO.O=Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1>CN(C=O)C>Cc1ccc(C=Cc2ccc(N(c3ccccc3)c3ccc4c5c(cccc35)CC4)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f7732a0ba48b458e9add51628a8da0ea | CC(=O)OC(C)=O.Nc1ccc2c3c(cccc13)CC2>>CC(=O)Nc1ccc2c3c(cccc13)CC2 | NC1=CC=C2CCC=3C=CC=C1C32.C(C)(=O)OC(C)=O.NC1=CC=C2CCC=3C=CC=C1C32>>C(C)(=O)NC1=CC=C2CCC=3C=CC=C1C32 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]3[c:10]([cH:11][cH:12][cH:13][c:14]13)[CH2:15][CH2:16]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]3[c:10]([cH:11][cH:12][cH:13][c:14]13)[CH2:15][CH2:16]2 | CC(=O)OC(C)=O.Nc1ccc2c3c(cccc13)CC2 | CC(=O)Nc1ccc2c3c(cccc13)CC2 | null | null | C(C)(=O)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1cc2c3c(cccc3c1)CC2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 96.4 | [{"value": 96.4, "product": "C(C)(=O)NC1=CC=C2CCC=3C=CC=C1C32", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.4, "product": "C(C)(=O)NC1=CC=C2CCC=3C=CC=C1C32", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 15 | MINUTE | 50 ml of glacial acetic acid was added to 6.77 g (0.04 mol) of 5-aminoacenaphthene and the mixture was stirred at 60° C. to dissolve, and 8.16 g (0.08 mol) acetic anhydride was dropwise added thereto for 15 minutes. After finishing the dropwise addition, the mixture was stirred at the same temperature for 2 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1cc2c3c(cccc3c1)CC2 | HO- | C(C)(=O)O | 60 | 0.25 | CC(=O)OC(C)=O.Nc1ccc2c3c(cccc13)CC2>C(C)(=O)O>CC(=O)Nc1ccc2c3c(cccc13)CC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b70ac3636d7b43a287feb3a7f751e2d4 | CC(=O)Nc1ccc2c3c(cccc13)CC2.Cc1ccc(I)cc1>>Cc1ccc(Nc2ccc3c4c(cccc24)CC3)cc1 | C(C)(=O)NC1=CC=C2CCC=3C=CC=C1C32.C(C)(=O)NC1=CC=C2CCC=3C=CC=C1C32.[OH-].[K+].IC1=CC=C(C=C1)C.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=CC=CC=C1>>C1(=CC=C(C=C1)NC1=CC=C2CCC=3C=CC=C1C32)C | CC(=O)[NH:6][c:7]1[cH:8][cH:9][c:10]2[c:11]3[c:12]([cH:13][cH:14][cH:15][c:16]13)[CH2:17][CH2:18]2.I[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]4[c:12]([cH:13][cH:14][cH:15][c:16]24)[CH2:17][CH2:18]3)[cH:19][cH:20]1 | CC(=O)Nc1ccc2c3c(cccc13)CC2.Cc1ccc(I)cc1 | Cc1ccc(Nc2ccc3c4c(cccc24)CC3)cc1 | null | [Cu] | C(CC(C)C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 4763e31bea43ae027a9f6a9b2dfaf0a863c582414461eb226c3255e1383821c8 | 1114ab2898bd0ea809755408ff9536c46f0d2f5958471cb24361706255b159ef | c1ccc(Nc2ccc3c4c(cccc24)CC3)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].I-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]>>[c:3]:[c:2](-[NH;D2;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[c:4] | 72.3 | [{"value": 72.3, "product": "C1(=CC=C(C=C1)NC1=CC=C2CCC=3C=CC=C1C32)C", "details": "PERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 6 | HOUR | 7.39 g (0.035 mol) of the above prepared 5-(N-acetylamino)acenaphthene was mixed with 10.91 g (0.05 mol) of p-iodo toluene, 0.32 g (0.005 mol) of copper powder, 5.52 g (0.04 mol) of anhydrous potassium carbonate and 10 ml of nitrobenzene, and the mixture was stirred at 200° C. for 6 hours. The reaction was determined t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cc2c3c(cccc3c1)CC2 | HI | [Cu].C(CC(C)C)O.O | 200 | 6 | CC(=O)Nc1ccc2c3c(cccc13)CC2.Cc1ccc(I)cc1>[Cu].C(CC(C)C)O.O>Cc1ccc(Nc2ccc3c4c(cccc24)CC3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a22b523213134b988e3fb268968dfa76 | Cc1ccc(Nc2ccc3c4c(cccc24)CC3)cc1.Ic1ccccc1>>Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | C1(=CC=C(C=C1)NC1=CC=C2CCC=3C=CC=C1C32)C.C1(=CC=C(C=C1)NC1=CC=C2CCC=3C=CC=C1C32)C.IC1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=CC=CC=C1>>C1(=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:13]2[cH:14][cH:15][c:16]3[c:17]4[c:18]([cH:19][cH:20][cH:21][c:22]24)[CH2:23][CH2:24]3)[cH:25][cH:26]1.I[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][c:16]3[c:17]4[c:18]([cH:19][cH:20]... | Cc1ccc(Nc2ccc3c4c(cccc24)CC3)cc1.Ic1ccccc1 | Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | null | [Cu] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]:[c:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:12]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:8](-[c:7](:[c:6]):[c:12])-[c:9](:[c:10]):[c:11]):[c:4]:[c:5] | 83.8 | [{"value": 83.8, "product": "C1(=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.66 g (0.018 mol) of the above prepared 5-[N-(4-tolyl)amino]acenaphthene was mixed with 4.99 g (0.022 mol) of iodo benzene, 0.13 g (0.002 mol) of copper powder, 2.76 g (0.02 mol) of anhydrous potassium carbonate and 5 ml of nitrobenzene, and the resultant mixture was stirred at 200° C. for 25 hours. The reaction was d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cc2c3c(cccc3c1)CC2 | HI | [Cu].C1(=CC=CC=C1)C | null | null | Cc1ccc(Nc2ccc3c4c(cccc24)CC3)cc1.Ic1ccccc1>[Cu].C1(=CC=CC=C1)C>Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20078ac392344345839361b7b292e056 | Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1.O=P(Cl)(Cl)Cl>>Cc1ccc(N(c2ccc(C=O)cc2)c2ccc3c4c(cccc24)CC3)cc1 | C1(=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32)C.C1(=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32)C.[OH-].[Na+].CN(C=O)C.P(=O)(Cl)(Cl)Cl>>C(=O)C1=CC=C(C=C1)N(C1=CC=C(C=C1)C)C1=CC=C2CCC=3C=CC=C1C32 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][cH:10][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][c:18]3[c:19]4[c:20]([cH:21][cH:22][cH:23][c:24]24)[CH2:25][CH2:26]3)[cH:27][cH:28]1.ClP(Cl)(Cl)=[O:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13][cH:14]2)[c:15]2[cH:16][cH:17][c... | Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1.O=P(Cl)(Cl)Cl | Cc1ccc(N(c2ccc(C=O)cc2)c2ccc3c4c(cccc24)CC3)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | e3eb3563143a436a1b6dd1eadac83913d5a87e712b8ad652ab28367873285db5 | be117abed4a0a0378ea43d3a5c1ccf903b86823ade7e92fcb09d68743e45d19a | c1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1 | Cl-P(-Cl)(-Cl)=[O;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[O;H0;D1;+0:1]=[C:7]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 97.1 | [{"value": 97.1, "product": "C(=O)C1=CC=C(C=C1)N(C1=CC=C(C=C1)C)C1=CC=C2CCC=3C=CC=C1C32", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 10 | MINUTE | 4.7 g (0.014 mol) of the above prepared 5-[N-(4-tolyl)-N-phenylamino]acenaphthene was dissolved in 30 ml of N,N-dimethylformamide, and 3.22 g (0.021 mol) of phosphorus oxychloride was dropwise added thereto at room temperature for 10 minutes. After the temperature was raised to 50° C., and the mixture was stirred for 1... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cc2c3c(cccc3c1)CC2 | Other | O | 50 | 0.166667 | Cc1ccc(N(c2ccccc2)c2ccc3c4c(cccc24)CC3)cc1.O=P(Cl)(Cl)Cl>O>Cc1ccc(N(c2ccc(C=O)cc2)c2ccc3c4c(cccc24)CC3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a9ed02b548945d8a2465cef6a9abb9e | N#CCCCCC#N.O=P([O-])([O-])OP(=O)([O-])[O-]>>N#CCCCCC(N)=O | C(CCCCC#N)#N.[O-]P([O-])(=O)OP(=O)([O-])[O-]>>C(#N)CCCCC(=O)N | [N:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].O=P([O-])([O-])OP([O-])([O-])=[O:9]>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH2:8])=[O:9] | N#CCCCCC#N.O=P([O-])([O-])OP(=O)([O-])[O-] | N#CCCCCC(N)=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | null | O=P(-[O-])(-[O-])-O-P(-[O-])(-[O-])=[O;H0;D1;+0:1].[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[C:2]-[C:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[O;H0;D1;+0:1] | null | [] | 5 | CELSIUS | 24 | HOUR | Various Pseudomonas strains were grown on 10 mM adipontrile in PR Basal medium for 24 h and harvested by centrifugation. Wet cell pastes were frozen for storage. To test for biocatalyst reaction, 50 mg of frozen cell paste was resuspended in 1 mL of 50 mM pyrophosphate buffer, pH 7.5. Adiponitrile substrate was added t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | null | Other | null | 5 | 24 | N#CCCCCC#N.O=P([O-])([O-])OP(=O)([O-])[O-]>>N#CCCCCC(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-62c80c03f0274ea6842044f298f2f2f0 | N#CCCCCC#N.O=P([O-])([O-])OP(=O)([O-])[O-]>>N#CCCCCC(N)=O | C(CCCCC#N)#N.[O-]P([O-])(=O)OP(=O)([O-])[O-]>>C(#N)CCCCC(=O)N | [N:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].O=P([O-])([O-])OP([O-])([O-])=[O:9]>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH2:8])=[O:9] | N#CCCCCC#N.O=P([O-])([O-])OP(=O)([O-])[O-] | N#CCCCCC(N)=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | null | O=P(-[O-])(-[O-])-O-P(-[O-])(-[O-])=[O;H0;D1;+0:1].[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[C:2]-[C:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[O;H0;D1;+0:1] | null | [] | 30 | CELSIUS | 4 | HOUR | In a 20 mL glass vial, 50 mg wet cell paste of 20-5-SBN-1b (ATCC 55735) was resuspended in 1 mL of 50 mM pyrophosphate buffer, pH 7.5. Adiponitrile was added to a final concentration of 400 mM and the reaction mixture was shaken at 200 rpm at 30° C. for 4 h on a rotary shaker. Cells were removed by centrifugation and t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | null | Other | null | 30 | 4 | N#CCCCCC#N.O=P([O-])([O-])OP(=O)([O-])[O-]>>N#CCCCCC(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5b62ce49ffab4c1db9e358eac8f40d5a | C[C@@H](N)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O.O=C([O-])C(=O)Cc1ccccc1>>N[C@@H](Cc1ccccc1)C(=O)O.N[C@H](Cc1ccccc1)C(=O)O | N[C@@H](C)C(=O)O.N[C@@H](CC1=CC=CC=C1)C(=O)O.N[C@H](C)C(=O)O.C1(=CC=CC=C1)CC(C(=O)[O-])=O>>N[C@H](CC1=CC=CC=C1)C(=O)O.N[C@@H](CC1=CC=CC=C1)C(=O)O | C[C@@H:2]([NH2:1])[C:10](=[O:11])[OH:12].[NH2:13][C@@H:14]([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=[O:23])[OH:24].O=C([O-])C(=O)[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[NH2:1][C@@H:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12].[NH2:13][C@H:14]([CH2:15][c:16]1[cH:17][cH... | C[C@@H](N)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O.O=C([O-])C(=O)Cc1ccccc1 | N[C@@H](Cc1ccccc1)C(=O)O.N[C@H](Cc1ccccc1)C(=O)O | null | null | null | C-C Coupling | OtherReaction | b47050f08d82e3e68de9d69580af9026f89fe179af05d47a7df8437aa12924dc | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | c1ccccc1.c1ccccc1 | C-[C@@H;D3;+0:1](-[N;D1;H2:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].O=C(-[O-])-C(=O)-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[N;D1;H2:2]-[C@@H;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | null | [] | null | null | null | null | Using cultures of recombinant cells of the present invention with the addition of D-, L-alanine and L-phenylalanine as additional sources of D-alanine and phenylpyruvate substrates for the D-aminotransferase gene product resulted in the production of 13.66 g/l of D-phenylalanine and 0.47 g/l of L-phenylalanine, a 94% e... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | C[C@@H](N)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O.O=C([O-])C(=O)Cc1ccccc1>>N[C@@H](Cc1ccccc1)C(=O)O.N[C@H](Cc1ccccc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ca050bcf3e3041878a46906ef366ed6a | C[C@H](N)C(=O)O.C[C@H](N)C(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>N[C@@H](Cc1ccccc1)C(=O)O.N[C@H](Cc1ccccc1)C(=O)O | N[C@@H](C)C(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.N[C@@H](C)C(=O)O>>N[C@H](CC1=CC=CC=C1)C(=O)O.N[C@@H](CC1=CC=CC=C1)C(=O)O | [NH2:1][C@H:2]([C:10](=[O:11])[OH:12])[CH3:17].[C:5]([C@@H:14]([NH2:13])[CH3:15])(=[O:23])[OH:24].O=[CH:3][C@H:4](O)[C@@H:9](O)[C@H:8](O)[C@H:7](O)[CH2:6]O>>[NH2:1][C@@H:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12].[NH2:13][C@H:14]([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=[O... | C[C@H](N)C(=O)O.C[C@H](N)C(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | N[C@@H](Cc1ccccc1)C(=O)O.N[C@H](Cc1ccccc1)C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8788bca7db1c16f497c50d4ecbd4e7b6300043102b0ed8387a00a51db34dc368 | eec4a41bd1d060d27fb2d966a546f07959e09f93c8e37af3aa50924ec628c32c | c1ccccc1.c1ccccc1 | O-[CH2;D2;+0:1]-[C@@H;D3;+0:2](-O)-[C@@H;D3;+0:3](-O)-[C@H;D3;+0:4](-O)-[C@@H;D3;+0:5](-O)-[CH;D2;+0:6]=O.[CH3;D1;+0:7]-[C@H;D3;+0:8](-[N;D1;H2:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[OH;D1;+0:12].[CH3;D1;+0:13]-[C@H;D3;+0:14](-[N;D1;H2:15])-[C:16](=[O;D1;H0:17])-[O;D1;H1:18]>>[N;D1;H2:15]-[C@@H;D3;+0:14](-[CH2;D2;+0:6]... | null | [] | null | null | 12 | HOUR | The amount of glucose fed was 2021 g over 52 hours. The fermentation medium included a D-, L-alanine feed whereby a total of 1400 mls of 167 g/l D-, L-alanine was fed at a rate of 1.9 ml/min starting 12 hrs from the beginning of the fermentation. In addition, L-phenylalanine was fed at the same concentration and rate a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Carboxylic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | 12 | C[C@H](N)C(=O)O.C[C@H](N)C(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>N[C@@H](Cc1ccccc1)C(=O)O.N[C@H](Cc1ccccc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4e4527ef977240138a93b4260c881157 | Nc1nc(=O)c2ncn([C@@H]3O[C@@H]4COP(=O)(O)O[C@H]4[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O>>Nc1nc(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O | C=1N=C(C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)N.C1=NC2=C(N1[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)NC(=NC2=O)N>>C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O.C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)NC(=NC2=O)N | [NH2:1][c:2]1[n:3][c:4](=[O:5])[c:6]2[n:7][cH:8][n:9]([C@@H:10]3[O:11][C@@H:12]4[CH2:13][O:14][P:15](=[O:16])([OH:17])[O:20][C@H:19]4[C@H:21]3[OH:22])[c:23]2[nH:24]1.[OH:18][P:40]1(=[O:41])[O:39][CH2:38][C@H:37]2[O:36][C@@H:35]([n:34]3[c:30]4[n:29][cH:28][n:27][c:26]([NH2:25])[c:31]4[n:32][cH:33]3)[C@H:46]([OH:47])[C@@... | Nc1nc(=O)c2ncn([C@@H]3O[C@@H]4COP(=O)(O)O[C@H]4[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O | Nc1nc(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O | null | null | null | Miscellaneous | OtherReaction | aa17667f8b741130e83d131d323d153ef4079e376eeaacc64ab5d0dd33c5cd61 | 97340401e708c23011c193957a1863de6b8895607cc7ceebe54b6a3b81ea560d | O=c1nc[nH]c2c1ncn2[C@H]1CCCO1.c1ncc2ncn([C@H]3CCCO3)c2n1 | [#8:1]-[C:2]1-[C:3]-[#8:4]-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[O;D1;H1:7])-[O;H0;D2;+0:8]-[C:9]-1-[C:10].[#8:11]-[C:12]1-[C:13]-[#8:14]-[P;H0;D4;+0:15](=[O;D1;H0:16])(-[OH;D1;+0:17])-[O;H0;D2;+0:18]-[C:19]-1-[C:20]>>[#8:11]-[C:12](-[C:13]-[#8:14]-[P;H0;D4;+0:15](=[O;D1;H0:16])(-[O;D1;H1:21])-[O;D1;H1:22])-[C:19](-[OH;D1;+0:... | null | [] | null | null | null | null | The enzyme of the present invention isolated and purified from rat cerebral cortex in Example was acted on [8-3H] cAMP and [8-3H] cGMP as substrates to form [8-3H] 5'-AMP and [8-3H] 5'-GMP, respectively. The products were reacted with 5'-nucleotidase to form [8-3H] adenosine and [8-3H] guanosine, respectively. These pr... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary alcohol.Secondary alcohol.Phosphate ester.Phosphate ester | C1C[C@@H]2O[P]OC[C@H]2O1.C1C[C@@H]2O[P]OC[C@H]2O1 | null | c1ncc2[nH]cnc2n1.C1CCOC1.c1ncnc2nc[nH]c12.C1CCOC1 | Other | null | null | null | Nc1nc(=O)c2ncn([C@@H]3O[C@@H]4COP(=O)(O)O[C@H]4[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O>>Nc1nc(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd6d1a78ee72419a8409d1047d1e9c38 | C1CO1.CCCCCCCCCCCCCCCCCCNC>>CCCCCCCCCCCCCCCCCCN(C)CCO | CNCCCCCCCCCCCCCCCCCC.C1CO1>>OCCN(C)CCCCCCCCCCCCCCCCCC | [CH2:21]1[CH2:22][O:23]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([... | C1CO1.CCCCCCCCCCCCCCCCCCNC | CCCCCCCCCCCCCCCCCCN(C)CCO | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 7de6cb7ffc33700c22d0ce54ea22e03fc1bea9a639db7a130c2c399ea3700642 | 128400f60196a90df2be08c769daa326293f26a6f70a086568a2c266322e372f | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:6]-[C:5]-[OH;D1;+0:7] | 86.6 | [{"value": 86.6, "product": "OCCN(C)CCCCCCCCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | An autoclave provided with a stirrer, a thermometer, a pressure gauge and a pressure dropping funnel was charged with 250 g of N-methyloctadecylamine and heated to 160° C. Then 45 g of ethylene oxide was occasionally added dropwise thereto under a pressure of 0 to 6 kg/cm2G. Three hours were required for completing the... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary alcohol.Tertiary amine | C1CO1 | null | null | null | null | 160 | null | C1CO1.CCCCCCCCCCCCCCCCCCNC>>CCCCCCCCCCCCCCCCCCN(C)CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d450d9a3b4314144865c4274817143d7 | CCCCCCCCCCCCCCCCCC(=O)O.CCCCCCCCCCCCCCCCCCN(C)CCO>>CCCCCCCCCCCCCCCCCCN(C)CCOC(=O)CCCCCCCCCCCCCCCCC | OCCN(C)CCCCCCCCCCCCCCCCCC.C(CCCCCCCCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCCCCCCCC)(=O)OCCN(C)CCCCCCCCCCCCCCCCCC | [OH:23][C:24](=[O:25])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].O[CH2:22][CH2:21][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[... | CCCCCCCCCCCCCCCCCC(=O)O.CCCCCCCCCCCCCCCCCCN(C)CCO | CCCCCCCCCCCCCCCCCCN(C)CCOC(=O)CCCCCCCCCCCCCCCCC | null | null | null | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | null | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[C:5](-[C:4])=[O;D1;H0:6] | 96.5 | [{"value": 96.5, "product": "C(CCCCCCCCCCCCCCCCC)(=O)OCCN(C)CCCCCCCCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A four-neck flask provided with a stirrer, a thermometer and a dehydrating tube was charged with 200 g of the N-(2-hydroxyethyl)-N-methyloctadecylamine and 174 g of octadecanoic acid. The mixture was heated to 180° C. and maintained at this temperature for 12 hours while distilling off the water thus formed. Thus 350 g... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | null | HO- | null | 180 | null | CCCCCCCCCCCCCCCCCC(=O)O.CCCCCCCCCCCCCCCCCCN(C)CCO>>CCCCCCCCCCCCCCCCCCN(C)CCOC(=O)CCCCCCCCCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c4fd97650ffa477c91c1528e59316f4a | C#CCOc1cc(-n2nc(CCC=C)[nH]c2=O)c(Cl)cc1Cl.O=C(OO)c1cccc(Cl)c1>>C#CCOc1cc(-n2nc(CCC3CO3)[nH]c2=O)c(Cl)cc1Cl | ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC=C.C([O-])([O-])=O.[Na+].[Na+].ClC=1C=C(C(=O)OO)C=CC1>>ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC1CO1 | [CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH2:11][CH2:12][CH:13]=[CH2:14])[nH:16][c:17]2=[O:18])[c:19]([Cl:20])[cH:21][c:22]1[Cl:23].O=C(O[OH:15])c1cccc(Cl)c1>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH2:11][CH2:12][CH:13]3[CH2:14][O:15]3)[nH:16][c:17]2=[O:18])[c:19]([Cl:20])[c... | C#CCOc1cc(-n2nc(CCC=C)[nH]c2=O)c(Cl)cc1Cl.O=C(OO)c1cccc(Cl)c1 | C#CCOc1cc(-n2nc(CCC3CO3)[nH]c2=O)c(Cl)cc1Cl | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | fa67e488c6e215faf3f8ba92b55089cf5ac738315c63f0805edf5ac603aa4c40 | 8f36f0953871bb4e46b1272823a9df5d866ec11318b28272136c57016b5bffba | O=c1[nH]c(CCC2CO2)nn1-c1ccccc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[C:3]-[CH;D2;+0:4]=[CH2;D1;+0:5]>>[C:2]-[C:3]-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-1 | 95.4 | [{"value": 95.4, "product": "ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC1CO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 500 mg (1.48 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3-butenyl)-3H- 1,2,4-triazol-3-one in 20 mL of dichloromethane was added 172 mg (1.63 mmol) of sodium carbonate and 970 mg of m-chloroperoxybenzoic acid (50-60%, 2.81 mmol) in an ice bath. The reaction mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Allyl | Ether | c1ccccc1 | C1CO1 | c1ccccc1.c1nc[nH]n1.C1CO1 | HCl | ClCCl | null | 24 | C#CCOc1cc(-n2nc(CCC=C)[nH]c2=O)c(Cl)cc1Cl.O=C(OO)c1cccc(Cl)c1>ClCCl>C#CCOc1cc(-n2nc(CCC3CO3)[nH]c2=O)c(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2736e404c5764e36926699eef871adb6 | C#CCOc1cc(-n2nc(CCC3CO3)[nH]c2=O)c(Cl)cc1Cl>>C#CCOc1cc(-n2nc3n(c2=O)CC(O)CC3)c(Cl)cc1Cl | ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC1CO1.C([O-])([O-])=O.[K+].[K+]>>ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)O)C1=O | [CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH2:18][CH2:17][CH:15]3[CH2:14][O:16]3)[nH:11][c:12]2=[O:13])[c:19]([Cl:20])[cH:21][c:22]1[Cl:23]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]3[n:11]([c:12]2=[O:13])[CH2:14][CH:15]([OH:16])[CH2:17][CH2:18]3)[c:19]([Cl:20])[cH:21][c:22]1[Cl:2... | C#CCOc1cc(-n2nc(CCC3CO3)[nH]c2=O)c(Cl)cc1Cl | C#CCOc1cc(-n2nc3n(c2=O)CC(O)CC3)c(Cl)cc1Cl | null | null | C(C)#N | Miscellaneous | OtherReaction | 8a1e2ba333438ec4bf65f5dde9fc2657ecc85bcbc203e7f6c36e36567619a509 | 816a42e4e92b4becc10e09218671f2e2a7942c9348b22e40d965e6444e589265 | O=c1n(-c2ccccc2)nc2n1CCCC2 | [O;D1;H0:1]=[c:2]1:[nH;D2;+0:3]:[c:4](-[C:5]-[C:6]-[C:7]2-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-2):[#7;a:10]:[#7;a:11]:1-[c:12]>>[O;D1;H0:1]=[c:2]1:[#7;a:11](-[c:12]):[#7;a:10]:[c:4]2:[n;H0;D3;+0:3]:1-[CH2;D2;+0:8]-[C:7](-[OH;D1;+0:9])-[C:6]-[C:5]-2 | 36.8 | [{"value": 36.8, "product": "ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)O)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 500 mg (1.41 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one and 563 mg (4.08 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in v... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | c1nc[nH]n1.C1CO1 | c1nnc2n1CCCC2 | c1ccccc1.c1nnc2n1CCCC2 | null | C(C)#N | null | null | C#CCOc1cc(-n2nc(CCC3CO3)[nH]c2=O)c(Cl)cc1Cl>C(C)#N>C#CCOc1cc(-n2nc3n(c2=O)CC(O)CC3)c(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9634d1d63f934be6bfca6b1b336ece9e | C#CCOc1cc(-n2nc3n(c2=O)CC(O)CC3)c(Cl)cc1Cl.CCN(CC)S(F)(F)F>>C#CCOc1cc(-n2nc3n(c2=O)CC(F)CC3)c(Cl)cc1Cl | ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)O)C1=O.C(C)N(CC)S(F)(F)F>>ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)F)C1=O | O[CH:15]1[CH2:14][n:11]2[c:10]([n:9][n:8](-[c:7]3[cH:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:22]([Cl:23])[cH:21][c:19]3[Cl:20])[c:12]2=[O:13])[CH2:18][CH2:17]1.CCN(CC)S(F)(F)[F:16]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]3[n:11]([c:12]2=[O:13])[CH2:14][CH:15]([F:16])[CH2:17][CH2:18]3)[c:19]([Cl:20])[cH... | C#CCOc1cc(-n2nc3n(c2=O)CC(O)CC3)c(Cl)cc1Cl.CCN(CC)S(F)(F)F | C#CCOc1cc(-n2nc3n(c2=O)CC(F)CC3)c(Cl)cc1Cl | null | null | ClCCl | Functional Group Interconversion | OtherReaction | d8fbab1d02e1efd4596161d3c366fdb64771eeec247c936cd515b9bbca4f09d5 | 2e01f8a2520bb2c01521f4c10ab406a1b29fe14554ff1fda976238a9b96e671b | O=c1n(-c2ccccc2)nc2n1CCCC2 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-[CH;D3;+0:2]1-[C:3]-[#7;a:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2-[C:9]-[C:10]-1>>[F;H0;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[#7;a:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2-[C:9]-[C:10]-1 | 37.7 | [{"value": 37.7, "product": "ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)F)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 169 mg (0.477 mmol) of 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-6-hydroxy-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one in 5 mL of dichloromethane was added 76 μl (0.573 mmol) of diethylaminosulfur trifluoride (DAST) at 0° C. The reaction mixture was stirred at 0° C. for 1h. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary amine | Secondary halide | c1nnc2n1CCCC2 | c1nnc2n1CCCC2 | c1ccccc1.c1nnc2n1CCCC2 | HF | ClCCl | 0 | 1 | C#CCOc1cc(-n2nc3n(c2=O)CC(O)CC3)c(Cl)cc1Cl.CCN(CC)S(F)(F)F>ClCCl>C#CCOc1cc(-n2nc3n(c2=O)CC(F)CC3)c(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64c534178a4a4c3f822722a59b57a089 | C#CCOc1cc(-n2nc(CCC=C)[nH]c2=O)c(Cl)cc1Cl.[O-][I+3]([O-])([O-])[O-]>>C#CCOc1cc(-n2nc(CCC=O)[nH]c2=O)c(Cl)cc1Cl | ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC=C.I(=O)(=O)(=O)[O-].[Na+]>>ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC=O | C=[CH:13][CH2:12][CH2:11][c:10]1[n:9][n:8](-[c:7]2[cH:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:21]([Cl:22])[cH:20][c:18]2[Cl:19])[c:16](=[O:17])[nH:15]1.[O-][I+3]([O-])([O-])[O-:14]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH2:11][CH2:12][CH:13]=[O:14])[nH:15][c:16]2=[O:17])[c:18]([Cl:19])[cH:20][c:21]... | C#CCOc1cc(-n2nc(CCC=C)[nH]c2=O)c(Cl)cc1Cl.[O-][I+3]([O-])([O-])[O-] | C#CCOc1cc(-n2nc(CCC=O)[nH]c2=O)c(Cl)cc1Cl | null | [Os](=O)(=O)(=O)=O | O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | b16cdbf18e0a0961ab3e2390d6e4aee8b329f7136e9bd1c8a4c806ff7a76d090 | c8848c7c3d9cc0904f82fae046e80cc577adb0f636b4d050e73f85888c0c7f1d | O=c1[nH]cnn1-c1ccccc1 | C=[CH;D2;+0:1]-[C:2]-[C:3].[O-;H0;D1:4]-[I+3](-[O-])(-[O-])-[O-]>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 92.2 | [{"value": 92.2, "product": "ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 500 mg (1.48 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-2,4-dihydro-5-(3-butenyl)-3H-1,2,4-triazol-3-one in a mixture of 10 mL of tetrahydrofuran and 10 mL of water was added 696 mg (3.25 mmol) of sodium periodate and 167 mL of 0.18M aqueous solution of osmium tetroxide at room temperature. The ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Aldehyde | null | null | c1ccccc1.c1nc[nH]n1 | HI | [Os](=O)(=O)(=O)=O.O.O1CCCC1 | null | null | C#CCOc1cc(-n2nc(CCC=C)[nH]c2=O)c(Cl)cc1Cl.[O-][I+3]([O-])([O-])[O-]>[Os](=O)(=O)(=O)=O.O.O1CCCC1>C#CCOc1cc(-n2nc(CCC=O)[nH]c2=O)c(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a4b58ae25a9460d8b441c80118dd2e8 | CC(=O)Oc1cc(-n2nc3n(c2=O)CCCC3)c(Cl)cc1Cl.O=C1CCC(=O)N1Br>>CC(=O)Oc1cc(-n2nc3n(c2=O)CCCC3Br)c(Cl)cc1Cl | C(C)(=O)OC=1C(=CC(=C(C1)N1N=C2N(CCCC2)C1=O)Cl)Cl.BrN1C(CCC1=O)=O>>C(C)(=O)OC=1C(=CC(=C(C1)N1N=C2N(CCCC2Br)C1=O)Cl)Cl | [CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]3[n:11]([c:12]2=[O:13])[CH2:14][CH2:15][CH2:16][CH2:17]3)[c:19]([Cl:20])[cH:21][c:22]1[Cl:23].O=C1CCC(=O)N1[Br:18]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]3[n:11]([c:12]2=[O:13])[CH2:14][CH2:15][CH2:16][CH:17]3[Br:18])[c:19]([Cl:20])[cH:... | CC(=O)Oc1cc(-n2nc3n(c2=O)CCCC3)c(Cl)cc1Cl.O=C1CCC(=O)N1Br | CC(=O)Oc1cc(-n2nc3n(c2=O)CCCC3Br)c(Cl)cc1Cl | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl secondary | 865273dafce70d025fe5f37b7c3b9e9a944136dd18628bfe5f064e092d7013a4 | d425bc7fa712969b9477dfeabb5ca2470f442214b30503c51715e13a06c60154 | O=c1n(-c2ccccc2)nc2n1CCCC2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]-[#7;a:3]1:[#7;a:4]:[c:5]2:[#7;a:6](:[c:7]:1)-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-2>>[Br;H0;D1;+0:1]-[CH;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[#7;a:6]2:[c:7]:[#7;a:3](-[c:2]):[#7;a:4]:[c:5]:2-1 | 93.6 | [{"value": 93.6, "product": "C(C)(=O)OC=1C(=CC(=C(C1)N1N=C2N(CCCC2Br)C1=O)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3.55 g (10.4 mmol) of 5,6,7,8-tetrahydro-2-(5-acetyloxy-2,4-dichlorophenyl)-1,2,4-triazolo[4,3-α]pyridin-3(2H)-one in 100 mL of carbon tetrachloride was added 2.03 g (11.4 mmol) of N-bromosuccinimide at room temperature. The mixture was warmed under reflux by irradiating with a sun lamp for 3h. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Secondary halide | c1nnc2n1CCCC2.C1CCNC1 | c1nnc2n1CCCC2 | c1ccccc1.c1nnc2n1CCCC2 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | CC(=O)Oc1cc(-n2nc3n(c2=O)CCCC3)c(Cl)cc1Cl.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CC(=O)Oc1cc(-n2nc3n(c2=O)CCCC3Br)c(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-04601f04a9e04e4b899149b8d86a04b2 | C#CCOc1cc(-n2nc3n(c2=O)CCCC3O)c(Cl)cc1Cl.CCN(CC)S(F)(F)F>>C#CCOc1cc(-n2nc3n(c2=O)CCCC3F)c(Cl)cc1Cl | ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CCCC2O)C1=O.C(C)N(CC)S(F)(F)F>>ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CCCC2F)C1=O | O[CH:17]1[c:10]2[n:9][n:8](-[c:7]3[cH:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:22]([Cl:23])[cH:21][c:19]3[Cl:20])[c:12](=[O:13])[n:11]2[CH2:14][CH2:15][CH2:16]1.CCN(CC)S(F)(F)[F:18]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]3[n:11]([c:12]2=[O:13])[CH2:14][CH2:15][CH2:16][CH:17]3[F:18])[c:19]([Cl:20])[cH:2... | C#CCOc1cc(-n2nc3n(c2=O)CCCC3O)c(Cl)cc1Cl.CCN(CC)S(F)(F)F | C#CCOc1cc(-n2nc3n(c2=O)CCCC3F)c(Cl)cc1Cl | null | null | ClCCl | Functional Group Interconversion | OtherReaction | d8fbab1d02e1efd4596161d3c366fdb64771eeec247c936cd515b9bbca4f09d5 | 2e01f8a2520bb2c01521f4c10ab406a1b29fe14554ff1fda976238a9b96e671b | O=c1n(-c2ccccc2)nc2n1CCCC2 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-[CH;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[#7;a:6]2:[c:7]:[#7;a:8](-[c:9]):[#7;a:10]:[c:11]:2-1>>[F;H0;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[#7;a:6]2:[c:7]:[#7;a:8](-[c:9]):[#7;a:10]:[c:11]:2-1 | 90.2 | [{"value": 90.2, "product": "ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CCCC2F)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 4 | HOUR | To a solution of 300 mg (0.847 mmol) of 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-8-hydroxy-1,2,4-triazolo[4,3-α]pyridin-3(2H)-one in 10 mL of dichloromethane was added 123 mL (0.930 mmol) of diethylaminosulfur trifluoride (DAST) at -78° C. The reaction mixture was stirred at -78° C. for 4h. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary amine | Secondary halide | c1nnc2n1CCCC2 | c1nnc2n1CCCC2 | c1ccccc1.c1nnc2n1CCCC2 | HF | ClCCl | -78 | 4 | C#CCOc1cc(-n2nc3n(c2=O)CCCC3O)c(Cl)cc1Cl.CCN(CC)S(F)(F)F>ClCCl>C#CCOc1cc(-n2nc3n(c2=O)CCCC3F)c(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2169f1be862948a3a9409a68450a60e7 | CCOC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>>CCOP(=O)(OCC)C(CC(=O)O)P(=O)(OCC)OCC | [OH-].[Na+].C(C)OP(=O)(C(CC(=O)OCC)P(=O)(OCC)OCC)OCC>>O(CC)P(=O)(C(CC(=O)O)P(=O)(OCC)OCC)OCC | CC[O:13][C:11]([CH2:10][CH:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])[P:14](=[O:15])([O:16][CH2:17][CH3:18])[O:19][CH2:20][CH3:21])=[O:12]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][C:11](=[O:12])[OH:13])[P:14](=[O:15])([O:16][CH2:17][CH3:18])[O:19][CH2:20][CH3:21] | CCOC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | CCOP(=O)(OCC)C(CC(=O)O)P(=O)(OCC)OCC | null | null | CCO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "O(CC)P(=O)(C(CC(=O)O)P(=O)(OCC)OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "O(CC)P(=O)(C(CC(=O)O)P(=O)(OCC)OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of NaOH (4.00 g, 100 mmol) in water (50 ml) was added to a solution of ethyl 3,3-bis(diethoxyphosphinyl)propionate (32.6 g, 87 mmol) in EtOH (100 ml), and heated at 80° C. for 1 hour. After cooling, the EtOH was evaporated, and the residue was acidified to methyl orange with 12N HCl. The product was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CCO.O | 80 | null | CCOC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>CCO.O>CCOP(=O)(OCC)C(CC(=O)O)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64a7cfe6196c4bb8ae1073b5f5bdac47 | CCCN(CCC)C(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>>CCCN(CCC)CCC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | C(CC)N(C(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O)CCC.B.CSC.Cl>>C(C)OP(OCC)(=O)C(CCN(CCC)CCC)P(OCC)(=O)OCC | O=[C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9][CH:10]([P:11](=[O:12])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[P:19](=[O:20])([O:21][CH2:22][CH3:23])[O:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH2:8][CH2:9][CH:10]([P:11](=[O:12])([O:13][CH2:14][CH3:15])[O:16][CH2:1... | CCCN(CCC)C(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | CCCN(CCC)CCC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | null | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[#7:4](-[C:5])-[C:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[#7:4](-[C:5])-[C:6] | 60 | [{"value": 60.0, "product": "C(C)OP(OCC)(=O)C(CCN(CCC)CCC)P(OCC)(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "C(C)OP(OCC)(=O)C(CCN(CCC)CCC)P(OCC)(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A solution of N,N-dipropyl-3,3-bis(diethoxyphosphinyl)propionamide (1.25 g, 2.9 mmol) in THF (7.1 ml) was cooled to 0° C., and borane-methylsulfide (0.71 ml, 7.1 mmol) was added via syringe. The reaction was stirred at 0° C. for 20 minutes, then warmed at 65 C. for 3 hours. The reaction mixture was cooled to 0° C. and ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | null | Other | C1CCOC1 | 0 | 0.333333 | CCCN(CCC)C(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>C1CCOC1>CCCN(CCC)CCC(P(=O)(OCC)OCC)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-513ee407692540e49f626f2d20b712d3 | CCOP(=O)(OCC)C(CC(=O)N(C)OC)P(=O)(OCC)OCC>>CCOP(=O)(OCC)C(CC(=O)CC)P(=O)(OCC)OCC | CON(C(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O)C.[H-].[Na+].C1CCOC1.C1CCOC1.[H-]>>O=C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC | CON([C:11]([CH2:10][CH:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])[P:15](=[O:16])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22])=[O:12])[CH3:14]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][C:11](=[O:12])[CH2:13][CH3:14])[P:15](=[O:16])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22... | CCOP(=O)(OCC)C(CC(=O)N(C)OC)P(=O)(OCC)OCC | CCOP(=O)(OCC)C(CC(=O)CC)P(=O)(OCC)OCC | null | null | null | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | null | C-O-N(-[CH3;D1;+0:1])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:6]-[CH3;D1;+0:1] | 54 | [{"value": 54.0, "product": "O=C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | A solution of N-methoxy-N-methyl-3,3-bis(diethoxyphosphinyl)propionamide (1.00 g, 2.6 mmol) in THF (5 ml) was slowly added to a slurry of 80% sodium hydride (80 mg, 2.7 mmol) in THF (10 ml) at 0° C. Stirring was continued until all of the hydride was consumed (~20 minutes). The solution was cooled to -78° C. and ethylm... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | null | HO- | null | -78 | null | CCOP(=O)(OCC)C(CC(=O)N(C)OC)P(=O)(OCC)OCC>>CCOP(=O)(OCC)C(CC(=O)CC)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ea7684e9a71040288dbea5e299a3c7d7 | CCOP(=O)(OCC)C(CC(=O)CC)P(=O)(OCC)OCC.NCc1ccccc1>>CCOP(=O)(OCC)C(CC(CC)NCc1ccccc1)P(=O)(OCC)OCC | [BH3-]C#N.[Na+].O=C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC.CC1=C(C(=C(C=C1C2(C3=CC=CC=C3S(=O)(=O)O2)C4=CC(=C(C(=C4C)Br)O)C(C)C)C(C)C)O)Br.C(C1=CC=CC=C1)N.[BH3-]C#N.[Na+]>>C(C1=CC=CC=C1)NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC | O=[C:11]([CH2:10][CH:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])[P:22](=[O:23])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[CH2:12][CH3:13].[NH2:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][CH:11]([CH2:12][CH3:13])[NH:14][C... | CCOP(=O)(OCC)C(CC(=O)CC)P(=O)(OCC)OCC.NCc1ccccc1 | CCOP(=O)(OCC)C(CC(CC)NCc1ccccc1)P(=O)(OCC)OCC | null | null | C(C)(=O)O.CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C;D1;H3:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C:3]-[C:2]-[CH;D3;+0:1](-[C:4]-[C;D1;H3:5])-[NH;D2;+0:6]-[C:7]-[c:8] | null | [] | null | null | 4 | DAY | To a stirred solution of tetraethyl 3-oxopentane-1,1-bisphosphonate (0.50 g, 1.4 mmol) in methanol (5 ml) was added a small amount of bromothymol blue and benzylamine (0.75 g, 7.0 mmol). Acetic acid was added dropwise until the solution turned yellow (pH=6), and NaCNBH3 (57 mg, 0.9 mmol) was added. The resulting yellow... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | C(C)(=O)O.CO | null | 96 | CCOP(=O)(OCC)C(CC(=O)CC)P(=O)(OCC)OCC.NCc1ccccc1>C(C)(=O)O.CO>CCOP(=O)(OCC)C(CC(CC)NCc1ccccc1)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d06fa7cb400433aac9523d5cb4e75c0 | CCCCNC(=O)CCl.CCOP(=O)(CP(=O)(OCC)OCC)OCC>>CCCCNC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | C(CCC)NC(CCl)=O.[I-].[K+].[Cl-].[Na+].C(P(OCC)(OCC)=O)P(OCC)(OCC)=O.[H-].[Na+].[H-]>>C(CCC)NC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O | Cl[CH2:8][C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[CH2:9]([P:10](=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])[P:18](=[O:19])([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[CH2:8][CH:9]([P:10](=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])[P:18](... | CCCCNC(=O)CCl.CCOP(=O)(CP(=O)(OCC)OCC)OCC | CCCCNC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | null | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5].[#8:6]-[#15:7](-[#8:8])(=[O;D1;H0:9])-[CH2;D2;+0:10]-[#15:11](-[#8:12])(-[#8:13])=[O;D1;H0:14]>>[#8:6]-[#15:7](-[#8:8])(=[O;D1;H0:9])-[CH;D3;+0:10](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5])-[#15:11](-[#8:12])(-[#8:13])=[O;D1;H0:14] | 70 | [{"value": 70.0, "product": "C(CCC)NC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "C(CCC)NC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetraethyl methylenebisphosphonate (1.44 g, 5.0 mmol) in THF (1 mL) was added to a slurry of 80% sodium hydride (150 mg, 5.0 mmol) in THF (4 mL) at 0° C. The reaction was warmed to room temperature and stirred until all of the hydride was consumed. A solution of N-butyl-2-chloroacetamide (0.75 g, 5.0 mmol) in THF (1 ml... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | null | HCl | C1CCOC1 | null | null | CCCCNC(=O)CCl.CCOP(=O)(CP(=O)(OCC)OCC)OCC>C1CCOC1>CCCCNC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3f7c12ece3d5427682be4ea183c9152d | CCCCNC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>>CCCCNCCC(P(=O)(O)O)P(=O)(O)O | C(CCC)NC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O.B.CSC.Cl>>C(CCC)NCCC(P(O)(=O)O)P(O)(=O)O | CC[O:11][P:9]([CH:8]([CH2:7][C:6](=O)[NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[P:13](=[O:14])([O:15]CC)[O:16]CC)(=[O:10])[O:12]CC>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH:8]([P:9](=[O:10])([OH:11])[OH:12])[P:13](=[O:14])([OH:15])[OH:16] | CCCCNC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | CCCCNCCC(P(=O)(O)O)P(=O)(O)O | null | null | C1CCOC1 | Reduction | OtherReaction | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | null | C-C-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[O;H0;D2;+0:4]-C-C)-[C:5](-[C:6]-[C;H0;D3;+0:7](=O)-[#7:8]-[C:9])-[#15:10](=[O;D1;H0:11])(-[O;H0;D2;+0:12]-C-C)-[O;H0;D2;+0:13]-C-C>>[C:9]-[#7:8]-[CH2;D2;+0:7]-[C:6]-[C:5](-[#15:10](=[O;D1;H0:11])(-[OH;D1;+0:12])-[OH;D1;+0:13])-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[OH;D1;+0:4] | 109 | [{"value": 109.0, "product": "C(CCC)NCCC(P(O)(=O)O)P(O)(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A solution of N-butyl-3,3-bis(diethoxyphosphinyl)propionamide (1.40 g, 3.5 mmol) in THF (9 mL) was cooled to 0° C., and borane-methyl sulfide (0.90 ml, 9.0 mmol) was added via syringe. The reaction was stirred at 0° C. for 5 minutes, then warmed to 65° C. for 3 hours. The reaction mixture was cooled to 0° C. and 6N HCl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | null | HO- | C1CCOC1 | 0 | 0.083333 | CCCCNC(=O)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>C1CCOC1>CCCCNCCC(P(=O)(O)O)P(=O)(O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18119a89941c4368a7ad288ebe54d59f | CCOP(=O)(OCC)C(CCCCN)P(=O)(OCC)OCC.O=C(Cl)c1ccccc1>>CCOP(=O)(OCC)C(CCCCNC(=O)c1ccccc1)P(=O)(OCC)OCC | C(C1=CC=CC=C1)(=O)Cl.NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC.C(C)N(CC)CC>>C(C1=CC=CC=C1)(=O)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC | [CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[P:23](=[O:24])([O:25][CH2:26][CH3:27])[O:28][CH2:29][CH3:30].Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH... | CCOP(=O)(OCC)C(CCCCN)P(=O)(OCC)OCC.O=C(Cl)c1ccccc1 | CCOP(=O)(OCC)C(CCCCNC(=O)c1ccccc1)P(=O)(OCC)OCC | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 30.7 | [{"value": 30.7, "product": "C(C1=CC=CC=C1)(=O)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzoyl chloride (0.73 g, 5.0 mmol) in dichloromethane was added slowly to a solution of tetraethyl 5-aminopentane-1,1-bisphosphonate (1.50 g, 4.5 mmol) from Example 11, part A, and triethylamine (0.76 mL, 5.5 mmol) in dichloromethane at 0° C. After warming to room temperature for 30 minutes, the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | ClCCl | null | null | CCOP(=O)(OCC)C(CCCCN)P(=O)(OCC)OCC.O=C(Cl)c1ccccc1>ClCCl>CCOP(=O)(OCC)C(CCCCNC(=O)c1ccccc1)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-861d1c5c6eb14e7f813a68ed25b21881 | CCOP(=O)(OCC)C(CCCCNC(=O)c1ccccc1)P(=O)(OCC)OCC>>CCOP(=O)(OCC)C(CCCCNCc1ccccc1)P(=O)(OCC)OCC | C(C1=CC=CC=C1)(=O)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC.CSC.B.Cl>>C(C1=CC=CC=C1)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC | O=[C:15]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])[P:22](=[O:23])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:... | CCOP(=O)(OCC)C(CCCCNC(=O)c1ccccc1)P(=O)(OCC)OCC | CCOP(=O)(OCC)C(CCCCNCc1ccccc1)P(=O)(OCC)OCC | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccccc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[c:4](:[c:5]):[c:6]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[c:4](:[c:5]):[c:6] | 45.8 | [{"value": 45.8, "product": "C(C1=CC=CC=C1)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A solution of tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate (0.63 g, 1.36 mmol) in THF (3.4 mL) was cooled to 0° C., and borane methylsulfide (0.34 ml, 3.4 mmol) was added via syringe. The reaction was stirred at 0° C. for 20 minutes, then warmed to 65° C. for 2.5 hours. The reaction mixture was cooled to 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1 | Other | C1CCOC1 | 0 | 0.333333 | CCOP(=O)(OCC)C(CCCCNC(=O)c1ccccc1)P(=O)(OCC)OCC>C1CCOC1>CCOP(=O)(OCC)C(CCCCNCc1ccccc1)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f9159e7c4774638b827a4db2641898a | CCCCCC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)[N+](=O)[O-]>>CCCCCC(N)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | C(=O)[O-].[NH4+].[N+](=O)([O-])C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC.C(=O)[O-].[NH4+]>>NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC | O=[N+:7]([O-])[CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:8][CH:9]([P:10](=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])[P:18](=[O:19])([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH2:7])[CH2:8][CH:9]([P:10](=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17... | CCCCCC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)[N+](=O)[O-] | CCCCCC(N)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | null | [Pd].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | null | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | 95 | [{"value": 95.0, "product": "NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a stirred solution of tetraethyl 3-nitrooctane-1,1-bisphosphonate (0.70 g, 1.62 mmol) in methanol (4 mL) was added ammonium formate (0.45 g, 6.9 mmol) and 10% palladium on carbon (0.070 g). After 24 hours, more 10% palladium on carbon (0.035 g) and ammonium formate (0.45 g, 6.9 mmol) were added. After stirring for a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | null | Other | [Pd].[Pd].CO | null | 24 | CCCCCC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)[N+](=O)[O-]>[Pd].[Pd].CO>CCCCCC(N)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66715e3038e443c89124069570855fa8 | CCCCCC(N)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>>CCCCCC(N)CC(P(=O)([O-])[O-])P(=O)([O-])O.[NH4+].[NH4+].[NH4+] | NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC.Br[Si](C)(C)C>>[NH4+].[NH4+].[NH4+].NC(CC(P([O-])(=O)[O-])P(O)(=O)[O-])CCCCC | CC[O:12][P:10]([CH:9]([CH2:8][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[NH2:7])[P:14](=[O:15])([O:16]CC)[O:17]CC)(=[O:11])[O:13]CC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH2:7])[CH2:8][CH:9]([P:10](=[O:11])([O-:12])[O-:13])[P:14](=[O:15])([O-:16])[OH:17].[NH4+:18].[NH4+:19].[NH4+:20] | CCCCCC(N)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC | CCCCCC(N)CC(P(=O)([O-])[O-])P(=O)([O-])O.[NH4+].[NH4+].[NH4+] | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | C-C-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[C:4]-[#15:5](=[O;D1;H0:6])(-[O;H0;D2;+0:7]-C-C)-[O;H0;D2;+0:8]-C-C)-[O;H0;D2;+0:9]-C-C>>[O-;H0;D1:1]-[#15:2](-[O-;H0;D1:9])(=[O;D1;H0:3])-[C:4]-[#15:5](-[O-;H0;D1:7])(=[O;D1;H0:6])-[OH;D1;+0:8] | 419.8 | [{"value": 419.8, "product": "[NH4+].[NH4+].[NH4+].NC(CC(P([O-])(=O)[O-])P(O)(=O)[O-])CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of tetraethyl 3-aminooctane-1,1-bisphosphonate (0.45 g, 1.12 mmol) in dry dichloromethane (1.1 mL) was added bromotrimethylsilane (1.05 mL, 7.85 mmol) via syringe. After 18 hours, the mixture was concentrated under vacuum. To the residue was added 3N NH4OH (8 mL) which was stirred for 30 minutes at room t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | ClCCl | null | 18 | CCCCCC(N)CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC>ClCCl>CCCCCC(N)CC(P(=O)([O-])[O-])P(=O)([O-])O.[NH4+].[NH4+].[NH4+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73770e6874334f60888ff4ce1f4e06f1 | CO.Cc1ccc(OCC(=O)O)cc1.O=Cc1ccccc1S(=O)(=O)O.[Na].c1ccc([PH+](c2ccccc2)c2ccccc2)cc1>>COC(=O)c1ccc(/C=C/c2cccc[c]2[Na])c(S(=O)(=O)O)c1 | C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C(=O)(O)COC1=CC=C(C=C1)C.C(=O)C1=C(C=CC=C1)S(=O)(=O)O.[Na].CO.C[O-].[Na+]>>[Na]C1=C(/C=C/C2=C(C=C(C=C2)C(=O)OC)S(=O)(=O)O)C=CC=C1 | O[CH3:1].c1[c:8]([CH3:9])[cH:7][cH:6]c(O[CH2:5][C:3]([OH:2])=[O:4])[cH:23]1.O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:18]1[S:19](=[O:20])(=[O:21])[OH:22].[Na:17].c1ccc([PH+](c2ccccc2)c2cccc[cH:16]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](/[CH:9]=[CH:10]/[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Na:1... | CO.Cc1ccc(OCC(=O)O)cc1.O=Cc1ccccc1S(=O)(=O)O.[Na].c1ccc([PH+](c2ccccc2)c2ccccc2)cc1 | COC(=O)c1ccc(/C=C/c2cccc[c]2[Na])c(S(=O)(=O)O)c1 | null | CS(=O)(=O)O | null | Heteroatom Alkylation and Arylation | OtherReaction | a5892bc718af7fd687d0891e151f9bacf978b68c56679fea314853496fdb59cb | a88642547a8d0b18ebe5827c60bfffb7fd0e6760c9bffb376aaf721018ea99e5 | C(=C/c1ccccc1)\c1ccccc1 | O-[CH3;D1;+0:1].O=[CH;D2;+0:2]-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[O;D1;H1:12].[CH3;D1;+0:13]-[c;H0;D3;+0:14]1:[c:15]:[cH;D2;+0:16]:c(-O-[CH2;D2;+0:17]-[C:18](=[O;D1;H0:19])-[OH;D1;+0:20]):[cH;D2;+0:21]:c:1.[Na;H0;D0;+0:22].[cH;D2;+0:23]1:c:c:c:c:c:1-[P... | null | [] | null | null | null | null | To 146 gm (0.327 mol) of the adduct prepared in Example 10 in a 2 L, three-neck round bottom flask equipped with a magnetic stirring bar, condenser, addition funnel, and thermometer connected to a temperature controlling device (Thermowatch, I2R), is added 2-formylbenzenesulfonic acid, sodium salt, hydrate (Aldrich, 80... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Ether.Methanol | Ester | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CS(=O)(=O)O | null | null | CO.Cc1ccc(OCC(=O)O)cc1.O=Cc1ccccc1S(=O)(=O)O.[Na].c1ccc([PH+](c2ccccc2)c2ccccc2)cc1>CS(=O)(=O)O>COC(=O)c1ccc(/C=C/c2cccc[c]2[Na])c(S(=O)(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a27e3faf3c24930a2eeef0ff4a98ee9 | COC.COc1cccc(-c2oc3ccccc3c2C)c1.COc1cccc(-c2oc3ccccc3c2C)c1.O>>Cc1c(-c2cccc(O)c2)oc2ccccc12.Cc1c(-c2cccc(OCC(O)CO)c2)oc2ccccc12 | O.COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2.COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2.Cl.N1=CC=CC=C1.COC>>OC(COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2)CO.OC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2 | [CH3:28][O:29][CH3:30].C[O:9][c:8]1[cH:7][cH:6][cH:5][c:4](-[c:3]2[c:2]([CH3:1])[c:17]3[c:12]([o:11]2)[cH:13][cH:14][cH:15][cH:16]3)[cH:10]1.[CH3:18][c:19]1[c:20](-[c:21]2[cH:22][cH:23][cH:24][c:25]([O:26][CH3:27])[cH:32]2)[o:33][c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]12.[OH2:31]>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6... | COC.COc1cccc(-c2oc3ccccc3c2C)c1.COc1cccc(-c2oc3ccccc3c2C)c1.O | Cc1c(-c2cccc(O)c2)oc2ccccc12.Cc1c(-c2cccc(OCC(O)CO)c2)oc2ccccc12 | null | [Ti](Cl)(Cl)(Cl)Cl.[Zn] | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 7787e927eda04892d51ea69720338113e3a470222203566827db92b9f1cbe895 | 65ac6f7cf6ec095bf5a4e40cc6a8549e6c1b4a5d53d05b78aaa58078db8ffa96 | c1ccc(-c2cc3ccccc3o2)cc1.c1ccc(-c2cc3ccccc3o2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#8:6]-[c:7].[CH3;D1;+0:8]-[O;H0;D2;+0:9]-[CH3;D1;+0:10].[OH2;D0;+0:11]>>[OH;D1;+0:9]-[CH;D3;+0:8](-[CH2;D2;+0:5]-[#8:6]-[c:7])-[CH2;D2;+0:10]-[OH;D1;+0:11].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The ester which results from the condensation of 2'-hydroxyacetophenone and m-anisic acid is converted to 2-(3-methoxyphenyl)-3-methylbenzofuran by reductive cyclization in dioxane with a titanium tetrachloride/zinc metal catalyst according to the method of Banerji and Nayak, J. Chem. Soc., Chem. Comm., (1990), 150. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Ether.Primary alcohol.Secondary alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2occc2c1.c1ccccc1.c1ccc2occc2c1 | Other | [Ti](Cl)(Cl)(Cl)Cl.[Zn].O1CCOCC1 | null | null | COC.COc1cccc(-c2oc3ccccc3c2C)c1.COc1cccc(-c2oc3ccccc3c2C)c1.O>[Ti](Cl)(Cl)(Cl)Cl.[Zn].O1CCOCC1>Cc1c(-c2cccc(O)c2)oc2ccccc12.Cc1c(-c2cccc(OCC(O)CO)c2)oc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5dd2c77bb7de45af8bd5e3455820ca7e | Cc1c(-c2cccc(O)c2)oc2ccccc12.OCC1CO1>>Cc1c(-c2cccc(OCC(O)CO)c2)oc2ccccc12 | CS(=O)(=O)O.C[O-].[Na+].OC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2.C1C(O1)CO>>OC(COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2)CO | [CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:15]2)[o:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.[CH2:10]1[CH:11]([CH2:13][OH:14])[O:12]1>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]([OH:12])[CH2:13][OH:14])[cH:15]2)[o:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | Cc1c(-c2cccc(O)c2)oc2ccccc12.OCC1CO1 | Cc1c(-c2cccc(OCC(O)CO)c2)oc2ccccc12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c8f37de1487a64e5d0f374942194fdf1fb5ee79a4a7c0eead7f4385797f6a345 | d65f28c52f0777a08a008cfdcfc030aaa24bdbbd95c8114c9f5ad2abd4641bd1 | c1ccc(-c2cc3ccccc3o2)cc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 200 | CELSIUS | null | null | The ester which results from the condensation of 2'-hydroxyacetophenone and m-anisic acid is converted to 2-(3-methoxyphenyl)-3-methylbenzofuran by reductive cyclization in dioxane with a titanium tetrachloride/zinc metal catalyst according to the method of Banerji and Nayak, J. Chem. Soc., Chem. Comm., (1990), 150. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Secondary alcohol | C1CO1 | null | c1ccccc1.c1ccc2occc2c1 | null | CO | 200 | null | Cc1c(-c2cccc(O)c2)oc2ccccc12.OCC1CO1>CO>Cc1c(-c2cccc(OCC(O)CO)c2)oc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-19b4002a336d4a0c990cd5217402dc7e | O=S(=O)(O)CCO.OCC(O)CO.[Na]>>O=S(=O)([O-])CCOCC(O)CO.[Na+] | S(=O)(=O)(O)CCO.[Na].[OH-].[Na+].OCC(O)CO.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>OC(COCCS(=O)(=O)[O-])CO.[Na+] | [O:1]=[S:2](=[O:3])([OH:4])[CH2:5][CH2:6][OH:7].O[CH2:8][CH:9]([OH:10])[CH2:11][OH:12].[Na:13]>>[O:1]=[S:2](=[O:3])([O-:4])[CH2:5][CH2:6][O:7][CH2:8][CH:9]([OH:10])[CH2:11][OH:12].[Na+:13] | O=S(=O)(O)CCO.OCC(O)CO.[Na] | O=S(=O)([O-])CCOCC(O)CO.[Na+] | null | null | O | Functional Group Interconversion | OtherReaction | e8fb1027e56e3c54291c20a3c526ee1e94fc86a9ca345d4e7c58af742e7a29e9 | 72e2e67028b40f6270954d8b22bd8a0c5a3a0929b41d153aa51c47f0d73fd934 | null | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[O;D1;H1:4].[Na;H0;D0;+0:5].[O;D1;H0:6]=[#16:7](=[O;D1;H0:8])(-[OH;D1;+0:9])-[C:10]-[C:11]-[OH;D1;+0:12]>>[C:3]-[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[C:11]-[C:10]-[#16:7](-[O-;H0;D1:9])(=[O;D1;H0:6])=[O;D1;H0:8].[Na+;H0;D0:5] | null | [] | 200 | CELSIUS | null | null | To a 500 mL, three neck, round bottom flask equipped with a magnetic stirring bar, modified Claisen head, condenser (set for distillation), thermometer, and temperature controller (Therm-O-Watch®, I2R) was added isethionic acid, sodium salt (Aldrich, 50.0 gm, 0.338 mol), sodium hydroxide (2.7 g, 0.0675 mol), and glycer... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Ether | null | null | null | HO- | O | 200 | null | O=S(=O)(O)CCO.OCC(O)CO.[Na]>O>O=S(=O)([O-])CCOCC(O)CO.[Na+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-929810e1bbe644d497f54844a1a40378 | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O>>CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1 | C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C.N1=CC=CC=C1.O>>C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O | [OH:4][C@H:5]1[CH2:6][CH2:7][C@@:8]2([CH3:9])[C:10](=[CH:11][CH2:12][C@@H:13]3[C@@H:14]2[CH2:15][CH2:16][C@:17]2([CH3:18])[C:19](=[O:20])[CH2:21][CH2:22][C@@H:23]32)[CH2:24]1.[OH2:3]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C@@:8]2([CH3:9])[C:10](=[CH:11][CH2:12][C@@H:13]3[C@@H:14]2[CH2:15][CH2:16][C@:17]2([CH3... | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1 | null | null | null | Acylation | OtherReaction | 959a87fd7ff99d445b5957c6cdcb595e35c7aeec865dcf9e1912a4cdfcb738f9 | 37f9d0c402085ae7a53dbce85561bce6850cbef4177e39b629509223b5de2bec | O=C1CC[C@@H]2C1CC[C@@H]1C3CCCCC3=CC[C@@H]21 | [C:1]=[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6].[OH2;D0;+0:7]>>[C:1]=[C:2]-[C:3]-[C:4](-[O;H0;D2;+0:5]-[C:8](-[C;D1;H3:9])=[O;H0;D1;+0:7])-[C:6] | null | [] | null | null | 16 | HOUR | Dehydroepiandrosterone (2.88 g, 10 mmol) is dissolved in a mixture (100 ml) of anhydride acetic and pyridine (1:1 v/v) and left at room temperature for 16 h. The mixture is then poured carefully into iced water and after 16 h, crystals are filtered and dried in vacuo.
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ester | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | Other | null | null | 16 | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O>>CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1079585e7a194106a0429ed7ca89727f | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(Cl)OCc1ccccc1>>C[C@]12CC[C@H](OC(=O)OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C.C(C1=CC=CC=C1)OC(=O)Cl>>C(C1=CC=CC=C1)OC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O | [CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:17][C:18]1=[CH:19][CH2:20][C@@H:21]1[C@@H:22]2[CH2:23][CH2:24][C@:25]2([CH3:26])[C:27](=[O:28])[CH2:29][CH2:30][C@@H:31]12.Cl[C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([O:6][C:7](=[O:8])[O:9][CH2:10][c:11]3... | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(Cl)OCc1ccccc1 | C[C@]12CC[C@H](OC(=O)OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 16a18aa130cea39a3a662ee8b6057b54f71a5546be78b0c40ff9ad2c1213d664 | 75f277925c316017cfa5d00758bde92cc568ffecb2651aae6fab24b6daa74c11 | O=C(OCc1ccccc1)O[C@H]1CCC2C(=CC[C@H]3[C@@H]4CCC(=O)C4CC[C@H]23)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]=[C:6]-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8](-[C:10])-[C:7]-[C:6]=[C:5] | null | [] | null | null | 30 | MINUTE | To a stirred solution of dehydroepiandrosterone (2.88 % 10 mmol) in methylene chloride (100 mL) is added dropwise benzylchloroformate, over a period of 30 min following the known procedure (F. Reber and T. Reichstein, Helv. Chim. Acta, 28, 1164, 1945). After stirring for 3 h, the mixture is washed with water and evapor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol | Carbonic Ester | null | null | c1ccccc1.C1=C2CCCC[C@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | HCl | C(Cl)Cl | null | 0.5 | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(Cl)OCc1ccccc1>C(Cl)Cl>C[C@]12CC[C@H](OC(=O)OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6642d755fcb048beb2e3a7e3e3b838c6 | C=O.CC(=O)OCCl.C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12>>CC(=O)O.C[C@]12CC[C@H](OCO)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | C(C)(=O)OCCl.C(C)(=O)Cl.C=O.C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C.[H-].[Na+].[H-].[Na+]>>C(C)(=O)O.OCO[C@@H]1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O | [CH2:11]=[O:12].ClC[O:4][C:2]([CH3:1])=[O:3].[CH3:5][C@:6]12[CH2:7][CH2:8][C@H:9]([OH:10])[CH2:13][C:14]1=[CH:15][CH2:16][C@@H:17]1[C@@H:18]2[CH2:19][CH2:20][C@:21]2([CH3:22])[C:23](=[O:24])[CH2:25][CH2:26][C@@H:27]12>>[CH3:1][C:2](=[O:3])[OH:4].[CH3:5][C@:6]12[CH2:7][CH2:8][C@H:9]([O:10][CH2:11][OH:12])[CH2:13][C:14]1... | C=O.CC(=O)OCCl.C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | CC(=O)O.C[C@]12CC[C@H](OCO)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | [Cl-].[Cl-].[Zn+2] | C1CCOC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 1a9395c10ca76090517f98be345a719f76251743a8a92b7bc57bfb61a8b1655b | 7e58f7e56164cfb063118065627b0f677475303dc2b8ba84dacb11f878913aed | O=C1CC[C@@H]2C1CC[C@@H]1C3CCCCC3=CC[C@@H]21 | Cl-C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[CH2;D1;+0:5]=[O;H0;D1;+0:6].[C:7]=[C:8]-[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]=[C:8]-[C:9]-[C:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:5]-[OH;D1;+0:6])-[C:12] | null | [] | null | null | null | null | To a solution of dehydroepiandrosterone (2.88 g, 10 mmol) in THF (100 mL) is added sodium hydride (11 mmol, 60% in oil) at room temperature under an argon atmosphere. When all the sodium hydride has reacted, chloromethyl acetate (prepared from acetyl chloride and formaldehyde (or derivative) using ZnCl2 as catalyst) is... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Formaldehyde.Ester.Secondary alcohol | Carboxylic acid.Ether.Primary alcohol | null | null | C1=C2CCCC[C@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | HCl | [Cl-].[Cl-].[Zn+2].C1CCOC1.O | null | null | C=O.CC(=O)OCCl.C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12>[Cl-].[Cl-].[Zn+2].C1CCOC1.O>CC(=O)O.C[C@]12CC[C@H](OCO)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-126b62e8f9c14b19bd96ee46b744d0b7 | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(C)c(=O)n2C)OCC | CN1C(=O)N(C=2N=CNC2C1=O)C.ClCCCCP(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>CN1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:23][CH2:24][CH3:25].[nH:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH3:18])[c:19](=[O:20])[n:21]2[CH3:22]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH3:18])[c:19](=[... | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)c2[nH]cnc2n(C)c1=O | CCOP(=O)(CCCCn1cnc2c1c(=O)n(C)c(=O)n2C)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:[c:14]:1=[O;D1;H0:15]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9]2:[#7;a:7](-[C;D1;H3:8]):[c:6]:[#7;a:5](-[C;D1;H3:4]):[c:14](=[O;D1;H0:15]):[c:13]:2:1 | null | [] | 70 | CELSIUS | null | null | 10.9 g (0.05 mol) of 1,3-dimethylxanthine were suspended in 150 ml of DMF, treated with 13.7 g (0.06 mol) of diethyl 4-chlorobutanephosphonate and 7.0 g (0.05 mol) of activated potassium carbonate and heated at 70° C. for approximately 4 hours. The solid was then filtered off, the filtrate was concentrated under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | CN(C)C=O | 70 | null | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)c2[nH]cnc2n(C)c1=O>CN(C)C=O>CCOP(=O)(CCCCn1cnc2c1c(=O)n(C)c(=O)n2C)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0e2048f259f14c369c409d485f3d1e95 | BrCCCBr.CCBr.CCOP(OCC)OCC>>CCOP(=O)(CCCBr)OCC | BrCCCBr.P(OCC)(OCC)OCC.BrCC>>BrCCCP(OCC)(=O)OCC | Br[CH2:6][CH2:7][CH2:8][Br:9].Br[CH2:2][CH3:1].CC[O:3][P:4]([O:5]CC)[O:10][CH2:11][CH3:12]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][Br:9])[O:10][CH2:11][CH3:12] | BrCCCBr.CCBr.CCOP(OCC)OCC | CCOP(=O)(CCCBr)OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e746a4bbdeb1bd93cf6f9b604439d9c6c63bcf906752fdb4eb1d1aaca7f7c595 | 1bf8450aa85de8176950624f95531e53b97b1bac759bf7a1510546cbfef8b9d1 | null | Br-[CH2;D2;+0:1]-[C;D1;H3:2].Br-[CH2;D2;+0:3]-[C:4]-[C:5].C-C-[O;H0;D2;+0:6]-[P;H0;D3;+0:7](-[#8:8]-[C:9])-[O;H0;D2;+0:10]-C-C>>[C:9]-[#8:8]-[P;H0;D4;+0:7](=[O;H0;D1;+0:10])(-[CH2;D2;+0:3]-[C:4]-[C:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | 130 | CELSIUS | null | null | A mixture of 605 g (3.0 mol) of 1,3-dibromopropane and 250 g (1.5 mol) of triethyl phosphite was heated at an oil bath temperature of 130° C., while stirring and passing in nitrogen, for approximately 5 hours until approximately 154 g (1.5 mol) of bromoethane distilled over into a strongly ice-cooled receiver. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | null | null | HBr | null | 130 | null | BrCCCBr.CCBr.CCOP(OCC)OCC>>CCOP(=O)(CCCBr)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7d7141538f0422c85b05b45f2b6979e | CCOCOCC.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>CCOCn1cnc2c1c(=O)[nH]c(=O)n2C | CN1C(NC(C=2NC=NC12)=O)=O.C(C)OCOCC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)(=O)[O-].[Na+]>>C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)C | CCO[CH2:4][O:3][CH2:2][CH3:1].[nH:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH3:16]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH3:16] | CCOCOCC.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 82589f00df7347b300983ffcf7e3ab490c8226c85728ef746198e8f397b81806 | ccc058ecd89f692c39a92bd6db91fb86578428d38b5955a659e0a2343eccf0fd | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | C-C-O-[CH2;D2;+0:1]-[#8:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[nH;D2;+0:11]:[c:12]:[#7;a:13]:[c:14]:1:2>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:12]:[#7;a:13]:[c:14]2:[#7;a:5](-[C;D1;H3:4]):[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]:2:1 | null | [] | 90 | CELSIUS | null | null | 52.5 g (0.28 mol) of p-toluenesulfonyl chloride were initially introduced into 50 ml of dimethylformamide and 22.6 g (0.29 mol) of sodium acetate were introduced with stirring and ice-cooling. The mixture was subsequently stirred for one hour, treated with 39.1 g of formaldehyde diethyl acetal and again subsequently st... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ether | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | CN(C=O)C | 90 | null | CCOCOCC.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>CN(C=O)C>CCOCn1cnc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7603175462343e28fe8ca12d8b33976 | BrCc1ccccc1.CCOCn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C | C(C1=CC=CC=C1)Br.C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)C.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C(=O)N(C=2N=CN(C2C1=O)COCC)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:20](=[O:21])[n:22]2[CH3:23]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20](=[O:21])[n:22]2[CH3:2... | BrCc1ccccc1.CCOCn1cnc2c1c(=O)[nH]c(=O)n2C | CCOCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2nc[nH]c2c(=O)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]2:[#7;a:10](-[C;D1;H3:11]):[c:12](=[O;D1;H0:13]):[nH;D2;+0:14]:[c:15](=[O;D1;H0:16]):[c:17]:1:2>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]2:[#7;a:10](-[C;D1;H3:11]):[c:12](=[O;D1;H0:13]):[n;H0;D3;+0:14](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:15](=[O;D1... | null | [] | 90 | CELSIUS | 8 | HOUR | 205 g (1.2 mol) of benzyl bromide were added to a suspension of 224 g (1 mol) of 7-ethoxymethyl-3-methylxanthine and 165 g of potassium carbonate in 1000 ml of dimethylformamide and the mixture was then stirred overnight at 90° C. The reaction solution was filtered hot, the filtrate was concentrated under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.c1ccccc1 | HBr | CN(C=O)C | 90 | 8 | BrCc1ccccc1.CCOCn1cnc2c1c(=O)[nH]c(=O)n2C>CN(C=O)C>CCOCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a7e91768d4c487cad45cb6ac939a6f7 | CCOCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C>>Cn1c(=O)n(Cc2ccccc2)c(=O)c2[nH]cnc21 | C(C1=CC=CC=C1)N1C(=O)N(C=2N=CN(C2C1=O)COCC)C.Cl>>Cl.C(C1=CC=CC=C1)N1C(=O)N(C=2N=CNC2C1=O)C | CCOC[n:17]1[c:16]2[c:14](=[O:15])[n:6]([CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[c:4](=[O:5])[n:3]([CH3:2])[c:20]2[n:19][cH:18]1>>[CH3:2][n:3]1[c:4](=[O:5])[n:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14](=[O:15])[c:16]2[nH:17][cH:18][n:19][c:20]12 | CCOCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C | Cn1c(=O)n(Cc2ccccc2)c(=O)c2[nH]cnc21 | null | null | null | Reduction | OtherReaction | 8d95695d3b7944b0963f4887dc50bd8cf245d5b3d94bbee056f9862d4eeae931 | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=c1[nH]c2nc[nH]c2c(=O)n1Cc1ccccc1 | C-C-O-C-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]2:[#7;a:5](-[C;D1;H3:6]):[c:7]:[#7;a:8](-[C:9]):[c:10](=[O;D1;H0:11]):[c:12]:2:1>>[C:9]-[#7;a:8]1:[c:7]:[#7;a:5](-[C;D1;H3:6]):[c:4]2:[#7;a:3]:[c:2]:[nH;D2;+0:1]:[c:12]:2:[c:10]:1=[O;D1;H0:11] | null | [] | 60 | CELSIUS | 6 | HOUR | The unpurified 1-benzyl-7-ethoxymethyl-3-methylxanthine was treated with 1000 ml of 5N hydrochloric acid and stirred at 60° C. for 6 hours. The precipitated solid was filtered off with suction, washed with ethanol and dried under reduced pressure (164 g). It was possible from the mother liquor, after concentrating to a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | null | 60 | 6 | CCOCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C>>Cn1c(=O)n(Cc2ccccc2)c(=O)c2[nH]cnc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b88eb8cb6094a9a8d87846b4529cb21 | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)n(Cc2ccccc2)c(=O)c2[nH]cnc21>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C)OCC | Cl.C(C1=CC=CC=C1)N1C(=O)N(C=2N=CNC2C1=O)C.ClCCCCP(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:29][CH2:30][CH3:31].[nH:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25](=[O:26])[n:27]2[CH3:28]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:1... | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)n(Cc2ccccc2)c(=O)c2[nH]cnc21 | CCOP(=O)(CCCCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2nc[nH]c2c(=O)n1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:[c:14]:1=[O;D1;H0:15]>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:13]:2:[c:14]:1=[O;D1;H0:15] | null | [] | 70 | CELSIUS | 6 | HOUR | 20 g (0.078 mol) of 1-benzyl-3-methylxanthine hydrochloride, 21.4 g (0.094 mol) of diethyl 4-chlorobutanephosphonate and 26 g (0.2 mol) of potassium carbonate were suspended in 400 ml of dimethylformamide and stirred at 70° C. for 6 hours. The solution was filtered hot and the dimethylformamide was evaporated under red... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.c1ccccc1 | HCl | CN(C=O)C | 70 | 6 | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)n(Cc2ccccc2)c(=O)c2[nH]cnc21>CN(C=O)C>CCOP(=O)(CCCCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7770e21bea004978a0779f7b92547672 | CCOP(=O)(CCCCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C)OCC>>CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC | C(C1=CC=CC=C1)N1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C.N>>CN1C(NC(C=2N(C=NC12)CCCCP(OCC)(OCC)=O)=O)=O | c1ccc(C[n:17]2[c:15](=[O:16])[c:14]3[n:10]([CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:22][CH2:23][CH3:24])[cH:11][n:12][c:13]3[n:20]([CH3:21])[c:18]2=[O:19])cc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[nH:17][c:18](=[O:19])[n:2... | CCOP(=O)(CCCCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C)OCC | CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC | null | [Pd] | C(C)O | Deprotection | OtherReaction | 3d9a5ab3644944bc89314c4573926012058c142eafe4129eb62ce309eab26216 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[C;D1;H3:7]):[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10](-C-c3:c:c:c:c:c:3):[c:11](=[O;D1;H0:12]):[c:13]:1:2>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[C;D1;H3:7]):[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]:[c:11](=[O;D1;H0:12]):[c:13]:1:2 | null | [] | null | null | 48 | HOUR | 13 g (0.03 mol) of diethyl [4-(1-benzyl-3-methylxanthin-7-yl)-butyl]phosphonate were suspended in 150 ml of ethanol with 2 g of palladium on activated carbon (10%) and, after addition of 3 ml of concentrated ammonia solution, hydrogenated with shaking at 1.5 bar in the course of 48 hours. The catalyst was filtered off,... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | [Pd].C(C)O | null | 48 | CCOP(=O)(CCCCn1cnc2c1c(=O)n(Cc1ccccc1)c(=O)n2C)OCC>[Pd].C(C)O>CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-841b9089cd1f4520ba61b48f730e5eeb | CCI.CCOCn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOCn1cnc2c1c(=O)n(CC)c(=O)n2C | C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)C.C(C)I.C([O-])([O-])=O.[K+].[K+]>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CC)=O)C | I[CH2:13][CH3:14].[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:15](=[O:16])[n:17]2[CH3:18]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH3:14])[c:15](=[O:16])[n:17]2[CH3:18] | CCI.CCOCn1cnc2c1c(=O)[nH]c(=O)n2C | CCOCn1cnc2c1c(=O)n(CC)c(=O)n2C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]2:[#7;a:8](-[C;D1;H3:9]):[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]:[c:13](=[O;D1;H0:14]):[c:15]:1:2>>[C:3]-[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]2:[#7;a:8](-[C;D1;H3:9]):[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:13](=[O;D1;H0:14]):[c:15]:1:2 | null | [] | 70 | CELSIUS | 5 | HOUR | 30 g (0.134 mol) of 7-ethoxymethyl-3-methylxanthine were suspended in 500 ml of absolute DMF with 25 g (0.161 mol) of ethyl iodide and 22.2 g (0.161 mol) of potassium carbonate and the mixture was stirred at 70° C. for 5 hours. The solution was filtered and the residue which remained was crystallized in diisopropyl eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HI | CN(C)C=O | 70 | 5 | CCI.CCOCn1cnc2c1c(=O)[nH]c(=O)n2C>CN(C)C=O>CCOCn1cnc2c1c(=O)n(CC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e4a1fe78dd64b49acf4eb3616e08f35 | CCOCn1cnc2c1c(=O)n(CC)c(=O)n2C>>CCn1c(=O)c2[nH]cnc2n(C)c1=O | C(C)OCN1C=NC=2N(C(N(C(C12)=O)CC)=O)C.Cl>>C(C)N1C(=O)N(C=2N=CNC2C1=O)C | CCOC[n:7]1[c:6]2[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:13](=[O:14])[n:11]([CH3:12])[c:10]2[n:9][cH:8]1>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[nH:7][cH:8][n:9][c:10]2[n:11]([CH3:12])[c:13]1=[O:14] | CCOCn1cnc2c1c(=O)n(CC)c(=O)n2C | CCn1c(=O)c2[nH]cnc2n(C)c1=O | null | null | C(C)O | Reduction | OtherReaction | 8d95695d3b7944b0963f4887dc50bd8cf245d5b3d94bbee056f9862d4eeae931 | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | C-C-O-C-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]2:[#7;a:5](-[C;D1;H3:6]):[c:7]:[#7;a:8](-[C:9]):[c:10](=[O;D1;H0:11]):[c:12]:2:1>>[C:9]-[#7;a:8]1:[c:7]:[#7;a:5](-[C;D1;H3:6]):[c:4]2:[#7;a:3]:[c:2]:[nH;D2;+0:1]:[c:12]:2:[c:10]:1=[O;D1;H0:11] | null | [] | null | null | null | null | 28.7 g (0.11 mol) of 7-ethoxymethyl-1-ethyl-3-methylxanthine were stirred at 60° C. for 60 hours in a solution of 200 ml of 5N hydrochloric acid and 200 ml of ethanol. The reaction mixture was concentrated to dryness and the residue which remained was crystallized in ethyl acetate/diisopropyl ether.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | C(C)O | null | null | CCOCn1cnc2c1c(=O)n(CC)c(=O)n2C>C(C)O>CCn1c(=O)c2[nH]cnc2n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66898f10be454898bdbc10dabbccc95a | CCCC(Cl)P(=O)(OCC)OCC.CCn1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(CC)c(=O)n2C)OCC | C(C)N1C(=O)N(C=2N=CNC2C1=O)C.ClC(CCC)P(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)N1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C | Cl[CH:6]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:24][CH2:25][CH3:26])[CH2:7][CH2:8][CH3:9].[nH:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH2:18][CH3:19])[c:20](=[O:21])[n:22]2[CH3:23]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH2:18][... | CCCC(Cl)P(=O)(OCC)OCC.CCn1c(=O)c2[nH]cnc2n(C)c1=O | CCOP(=O)(CCCCn1cnc2c1c(=O)n(CC)c(=O)n2C)OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d2d10e0bf3282dbee093e452ce5b563e0a690db4b22dcbf64e79bd3aa60743f8 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH;D3;+0:1](-[C:2]-[C:3]-[CH3;D1;+0:4])-[#15:5](-[#8:6])(-[#8:7])=[O;D1;H0:8].[C:9]-[#7;a:10]1:[c:11]:[#7;a:12](-[C;D1;H3:13]):[c:14]2:[#7;a:15]:[c:16]:[nH;D2;+0:17]:[c:18]:2:[c:19]:1=[O;D1;H0:20]>>[#8:6]-[#15:5](-[#8:7])(=[O;D1;H0:8])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[n;H0;D3;+0:17]1:[c:16]:[#7;a:15]:[c:14]... | null | [] | null | null | null | null | 9.7 g (0.05 mol) of 1-ethyl-3-methylxanthine were stirred at 70° C. for 6 hours with 12.7 g (0.06 mol) of diethyl chlorobutanephosphonate and 8.3 g of potassium carbonate. The solution was filtered, the solvent was evaporated, and the residue which remained was chromatographed (eluent: ethyl acetate/methanol 10: 1) and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCCC(Cl)P(=O)(OCC)OCC.CCn1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(CC)c(=O)n2C)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b41b35df72e44c4adc18e6e041d2837 | ClCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | C(C1=CC=CC=C1)Cl.[H-].[Na+].CN1C(NC(C=2NC=NC12)=O)=O.[H][H]>>C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C | Cl[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][cH:11][nH:12]2>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][cH:11][n:12]2[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | ClCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[c:15]:1:[#7;a:14]:[c:13]:[n;H0;D3;+0:12]:2-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 100 | CELSIUS | 1 | HOUR | 16.8 g (0.7 mol) of sodium hydride were introduced in portions with stirring into a suspension of 99.6 g (0.6 mol) of 3-methylxanthine in 1.5 l of dimethylformamide. After evolution of hydrogen had ended, the mixture was heated to 100° C., treated dropwise with 76 g (0.6 mol) of benzyl chloride and heated at 120° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | CN(C=O)C.O | 100 | 1 | ClCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>CN(C=O)C.O>Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eadaded2a68a4a4683c2b0691e2f1aa0 | CCOCCl.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C.C(C)OCCl.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)COCC)=O)C | Cl[CH2:4][O:3][CH2:2][CH3:1].[nH:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][n:12]2[CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]([CH3:21])[c:22]1=[O:23]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][n:12]2[CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]([CH3:21])[c:22]1=[O... | CCOCCl.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CCOCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f1a41fa8f82aa77600cb200025b462ea732d1b9362867647d4b1c004bfdafb56 | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[#8:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:... | null | [] | null | null | null | null | 20 g (0.078 mol) of 7-benzyl-3-methylxanthine were stirred at 80° C. for 6 hours with 8.8 g (0.094 mol) of ethoxymethyl chloride and 13 g of potassium carbonate in 500 ml of absolute dimethylformamide, the mixture was filtered and concentrated, and the residue which remained was chromatographed (eluent: dichloromethane... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOCCl.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>CN(C=O)C>CCOCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8274ed2fb34e4d4d9f44b77cbe179a49 | CCOCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O>>CCOCn1c(=O)c2[nH]cnc2n(C)c1=O | C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)COCC)=O)C>>C(C)OCN1C(=O)N(C=2N=CNC2C1=O)C | c1ccc(C[n:9]2[c:8]3[c:6](=[O:7])[n:5]([CH2:4][O:3][CH2:2][CH3:1])[c:15](=[O:16])[n:13]([CH3:14])[c:12]3[n:11][cH:10]2)cc1>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[nH:9][cH:10][n:11][c:12]2[n:13]([CH3:14])[c:15]1=[O:16] | CCOCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O | CCOCn1c(=O)c2[nH]cnc2n(C)c1=O | null | [Pd] | C(C)O | Deprotection | OtherReaction | 3d9a5ab3644944bc89314c4573926012058c142eafe4129eb62ce309eab26216 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[n;H0;D3;+0:9](-C-c3:c:c:c:c:c:3):[c:10]:2:[c:11]:1=[O;D1;H0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:2:[c:11]:1=[O;D1;H0:12] | null | [] | null | null | null | null | 17.5 g (0.056 mol) of 7-benzyl-1-ethoxymethyl-3-methylxanthine were hydrogenated over 1.8 g of palladium (10%) on activated carbon at room temperature for 8 hours in 500 ml of ethanol. The catalyst was filtered off and the filtrate was concentrated to dryness and crystallized from dimethylformamide/diisopropyl ether.
C... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | [Pd].C(C)O | null | null | CCOCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O>[Pd].C(C)O>CCOCn1c(=O)c2[nH]cnc2n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8750cc7ad61a432da65104ddaeebb4b3 | CCCC(Cl)P(=O)(OCC)OCC.CCOCn1c(=O)[nH]c2nc[nH]c2c1=O>>CCOCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(C)c1=O | C(C)OCN1C(=O)NC=2N=CNC2C1=O.C([O-])([O-])=O.[K+].[K+].ClC(CCC)P(OCC)(=O)OCC>>C(C)OCN1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C | Cl[CH:16]([CH2:15][CH2:14][CH3:13])[P:17](=[O:18])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24].[CH3:1][CH2:2][O:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][nH:12]2)[nH:25][c:27]1=[O:28]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][n:12]2[CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:1... | CCCC(Cl)P(=O)(OCC)OCC.CCOCn1c(=O)[nH]c2nc[nH]c2c1=O | CCOCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 945badfe62d08793a7a77e1f7911213401b8f39f60cb6469278838440322098e | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH;D3;+0:1](-[C:2]-[C:3]-[CH3;D1;+0:4])-[#15:5](-[#8:6])(-[#8:7])=[O;D1;H0:8].[C:9]-[#7;a:10]1:[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14]2:[#7;a:15]:[c:16]:[nH;D2;+0:17]:[c:18]:2:[c:19]:1=[O;D1;H0:20]>>[#8:6]-[#15:5](-[#8:7])(=[O;D1;H0:8])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[n;H0;D3;+0:17]1:[c:16]:[#7;a:15]:[c... | null | [] | null | null | null | null | 4 g (0.018 mol) of 1-ethoxymethylxanthine were stirred at 70° C. for 6 hours with 3 g of potassium carbonate and 4.9 g (0.0214 mol) of diethyl chlorobutanephosphonate. The solution was filtered and concentrated, and the residue which remained was chromatographed (eluent: dichloromethane/methanol 20:1).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | null | null | null | null | CCCC(Cl)P(=O)(OCC)OCC.CCOCn1c(=O)[nH]c2nc[nH]c2c1=O>>CCOCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c12104568b5442eda2e049aa7fbffb8a | CCOP(=O)(CCCCCl)OCC.CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(C)c1=O)OCC | C(C)OP(=O)(OCC)CCCCN1C=NC=2N(C(NC(C12)=O)=O)C.ClCCCCP(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OP(=O)(OCC)CCCCN1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)C | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:34][CH2:35][CH3:36].[nH:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH2:18][CH2:19][CH2:20][CH2:21][P:22](=[O:23])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[n:30]([CH3:31])[c:32]1=[O:33]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH... | CCOP(=O)(CCCCCl)OCC.CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC | CCOP(=O)(CCCCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(C)c1=O)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:... | null | [] | 70 | CELSIUS | null | null | 8 g (0.022 mol) of 7-(4-diethylphosphonobutyl)-3-methylxanthine (according to Example 24) were suspended in 100 ml of DMF, treated with 6.13 g (0.027 mol) of diethyl 4-chlorobutanephosphonate and 3.7 g (0.028 mol) of activated potassium carbonate and heated at 70° C. for 4 hours. The product was then filtered, the filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | CN(C)C=O | 70 | null | CCOP(=O)(CCCCCl)OCC.CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC>CN(C)C=O>CCOP(=O)(CCCCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a8fa17d9b69648f1b64d1468e8fdce34 | CCOP(=O)(CCCBr)OCC.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCn1cnc2c1c(=O)n(C)c(=O)n2C)OCC | CN1C(=O)N(C=2N=CNC2C1=O)C.BrCCCP(OCC)(=O)OCC>>CN1C(=O)N(C=2N=CN(C2C1=O)CCCP(OCC)(OCC)=O)C | Br[CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:22][CH2:23][CH3:24].[nH:9]1[cH:10][n:11][c:12]2[c:13]1[c:14](=[O:15])[n:16]([CH3:17])[c:18](=[O:19])[n:20]2[CH3:21]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][n:9]1[cH:10][n:11][c:12]2[c:13]1[c:14](=[O:15])[n:16]([CH3:17])[c:18](=[O:19])[n:20]2[CH... | CCOP(=O)(CCCBr)OCC.Cn1c(=O)c2[nH]cnc2n(C)c1=O | CCOP(=O)(CCCn1cnc2c1c(=O)n(C)c(=O)n2C)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:[c:14]:1=[O;D1;H0:15]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9]2:[#7;a:7](-[C;D1;H3:8]):[c:6]:[#7;a:5](-[C;D1;H3:4]):[c:14](=[O;D1;H0:15]):[c:13]:2:1 | null | [] | null | null | null | null | The title substance was prepared from 1,3-dimethylxanthine and diethyl 3-bromopropanephosphonate analogously to Example 1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCOP(=O)(CCCBr)OCC.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCn1cnc2c1c(=O)n(C)c(=O)n2C)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37d510efe3de46df8fb8264294561f22 | CCCn1c(=O)c2[nH]cnc2n(CCC)c1=O.CCOP(=O)(CCCBr)OCC>>CCCn1c(=O)c2c(ncn2CCCP(=O)(OCC)OCC)n(CCC)c1=O | C(CC)N1C(=O)N(C=2N=CNC2C1=O)CCC.BrCCCP(OCC)(=O)OCC>>C(CC)N1C(=O)N(C=2N=CN(C2C1=O)CCCP(OCC)(OCC)=O)CCC | [CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[c:8]([n:9][cH:10][nH:11]2)[n:23]([CH2:24][CH2:25][CH3:26])[c:27]1=[O:28].Br[CH2:12][CH2:13][CH2:14][P:15](=[O:16])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[c:8]([n:9][cH:10][n:11]2[CH2:12][CH2:13][CH2:14][P:15](=[O:16])(... | CCCn1c(=O)c2[nH]cnc2n(CCC)c1=O.CCOP(=O)(CCCBr)OCC | CCCn1c(=O)c2c(ncn2CCCP(=O)(OCC)OCC)n(CCC)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]2:[#7;a:5](-[C:4]):[c:6]:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[c:11]:2:1 | null | [] | null | null | null | null | The title substance was prepared from 1,3-dipropylxanthine and diethyl 3-bromopropanephosphonate analogously to Example 1 and chromatographed on silica gel (eluent: ethyl acetate/methanol 20:1).
Conditions: See reaction.notes.procedure_details.
Workup: chromatographed on silica gel (eluent: ethyl acetate/methanol 20:1) | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HBr | null | null | null | CCCn1c(=O)c2[nH]cnc2n(CCC)c1=O.CCOP(=O)(CCCBr)OCC>>CCCn1c(=O)c2c(ncn2CCCP(=O)(OCC)OCC)n(CCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d917ed641af4aa08c8cf5aa6c47bd70 | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCCCBr)OCC>>CCCCn1c(=O)c2c(ncn2CCCCCP(=O)(OCC)OCC)n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=CNC2C1=O)CCCC.BrCCCCCP(OCC)(=O)OCC>>C(CCC)N1C(=O)N(C=2N=CN(C2C1=O)CCCCCP(OCC)(OCC)=O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][nH:12]2)[n:26]([CH2:27][CH2:28][CH2:29][CH3:30])[c:31]1=[O:32].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][P:18](=[O:19])([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][n:12]2... | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCCCBr)OCC | CCCCn1c(=O)c2c(ncn2CCCCCP(=O)(OCC)OCC)n(CCCC)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]2:[#7;a:5](-[C:4]):[c:6]:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[c:11]:2:1 | null | [] | null | null | null | null | The title substance was prepared from 1,3-dibutylxanthine and diethyl 5-bromopentanephosphonate analogously to Example 9.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HBr | null | null | null | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCCCBr)OCC>>CCCCn1c(=O)c2c(ncn2CCCCCP(=O)(OCC)OCC)n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-02d09630ce874394bc3b749bf3745493 | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCCCl)OCC>>CCCCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=CNC2C1=O)CCCC.ClCCCCP(OCC)(=O)OCC>>C(CCC)N1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][nH:12]2)[n:25]([CH2:26][CH2:27][CH2:28][CH3:29])[c:30]1=[O:31].Cl[CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:18])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][n:12]2[CH2:13]... | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCCCl)OCC | CCCCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(CCCC)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]2:[#7;a:5](-[C:4]):[c:6]:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[c:11]:2:1 | null | [] | null | null | null | null | The title substance was prepared from 1,3-dibutylxanthine and diethyl 4-chlorobutanephosphonate analogously to Example 9.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCCCl)OCC>>CCCCn1c(=O)c2c(ncn2CCCCP(=O)(OCC)OCC)n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa87420356fe4ddca1dff1d5942c9cf8 | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCBr)OCC>>CCCn1c(=O)c2c(ncn2CCCP(=O)(OCC)OCC)n(CCC)c1=O | C(CCC)N1C(=O)N(C=2N=CNC2C1=O)CCCC.BrCCCP(OCC)(=O)OCC>>C(CC)N1C(=O)N(C=2N=CN(C2C1=O)CCCP(OCC)(OCC)=O)CCC | C[CH2:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[c:8]([n:9][cH:10][nH:11]2)[n:23]([CH2:24][CH2:25][CH2:26]C)[c:27]1=[O:28].Br[CH2:12][CH2:13][CH2:14][P:15](=[O:16])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[c:8]([n:9][cH:10][n:11]2[CH2:12][CH2:13][CH2:14][P:15](=[O:16]... | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCBr)OCC | CCCn1c(=O)c2c(ncn2CCCP(=O)(OCC)OCC)n(CCC)c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-[CH2;D2;+0:4]-[C:5]-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]-[C:11]-[CH2;D2;+0:12]-C):[c:13]2:[#7;a:14]:[c:15]:[nH;D2;+0:16]:[c:17]:2:[c:18]:1=[O;D1;H0:19]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:16]1:[c:15]:[#7;a:14]:[c:13]2:[#7;a:9](-[C:10]-[C:11]-[CH3;D1;+0:12]):[c:8]:[#7;a:7](-[C:6]-[C:5... | null | [] | null | null | null | null | The title substance was prepared from 1,3-dibutylxanthine and diethyl 3-bromopropanephosphonate analogously to Example 9.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HBr | null | null | null | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CCOP(=O)(CCCBr)OCC>>CCCn1c(=O)c2c(ncn2CCCP(=O)(OCC)OCC)n(CCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7fae1dd89d25493ea4ac31663986c9df | CCOP(=O)(CCCCCl)OCC.COC(C)n1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(C(C)OC)c(=O)n2C)OCC | COC(C)N1C(=O)N(C=2N=CNC2C1=O)C.ClCCCCP(OCC)(=O)OCC>>COC(C)N1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:26][CH2:27][CH3:28].[nH:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH:18]([CH3:19])[O:20][CH3:21])[c:22](=[O:23])[n:24]2[CH3:25]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[n... | CCOP(=O)(CCCCCl)OCC.COC(C)n1c(=O)c2[nH]cnc2n(C)c1=O | CCOP(=O)(CCCCn1cnc2c1c(=O)n(C(C)OC)c(=O)n2C)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:[c:14]:1=[O;D1;H0:15]>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:13]:2:[c:14]:1=[O;D1;H0:15] | null | [] | null | null | null | null | The title substance was prepared from 1-methoxyethyl-3-methylxanthine and diethyl 4-chlorobutanephosphonate analogously to Example 4 and crystallized from diisopropyl ether.
Conditions: See reaction.notes.procedure_details.
Workup: crystallized from diisopropyl ether | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCOP(=O)(CCCCCl)OCC.COC(C)n1c(=O)c2[nH]cnc2n(C)c1=O>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(C(C)OC)c(=O)n2C)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54829741e0d340c6aeb01d34861de329 | CCC(C)CCl.CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(CCC(C)C)c(=O)n2C)OCC | CN1C(NC(C=2N(C=NC12)CCCCP(OCC)(OCC)=O)=O)=O.CC(CCl)CC>>CC(CCN1C(=O)N(C=2N=CN(C2C1=O)CCCCP(OCC)(OCC)=O)C)C | Cl[CH2:19][CH:20]([CH2:21][CH3:18])[CH3:22].[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[O:16])[nH:17][c:23](=[O:24])[n:25]2[CH3:26])[O:27][CH2:28][CH3:29]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][n:12][c:13]2[c:14]1[c:15](=[... | CCC(C)CCl.CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC | CCOP(=O)(CCCCn1cnc2c1c(=O)n(CCC(C)C)c(=O)n2C)OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[CH3;D1;+0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15](-[CH2;D2;+0:5]-[CH2... | null | [] | null | null | null | null | The title substance was prepared from diethyl [4-(3-methylxanthin-7-yl)-butyl]phosphonate and 2-methylbutyl chloride analogously to Example 1 and chromatographed on silica gel (eluent: dichloromethane/methanol 10:1)
Conditions: See reaction.notes.procedure_details.
Workup: chromatographed on silica gel (eluent: dichlor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCC(C)CCl.CCOP(=O)(CCCCn1cnc2c1c(=O)[nH]c(=O)n2C)OCC>>CCOP(=O)(CCCCn1cnc2c1c(=O)n(CCC(C)C)c(=O)n2C)OCC |
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