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-0387783899c642a8b7eb4ba379bcdf5d | ord-192ecfe2801b42658ad839c2a4bd0c17 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>C[C@H](O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.B.CSC>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)[C@H](C)O | OC[CH2:1][O:3][CH2:2][c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[CH3:24]>>[CH3:1][C@H:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])(... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | C[C@H](O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 0e30c71e1bdbca9c9d9f8adcc11efa66570bbf25c7e63fc19f9289f48c7fc2d7 | dc9833ca806fbf3c675d4f98ab6994b9c5e0c271d230efda7590a70ec76216cb | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-[CH2;D2;+0:1]-[O;H0;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7]-[#7:8]>>[#7:8]-[c:7]:[#7;a:6]:[c:4](-[C@H;D3;+0:3](-[CH3;D1;+0:1])-[OH;D1;+0:2]):[c:5] | null | [] | null | null | 5 | MINUTE | To a stirred solution of (R)-Me-CBS-oxazaborolidine (770 μl, 1M in toluene) in THF (3 ml) was added borane-dimethylsulfide (770 μl, 2M in THF) at 0° C. under nitrogen. A solution was stirred for 5 mins, then 6-acetyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 34, ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Secondary alcohol | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | C1CCOC1 | null | 0.083333 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>C1CCOC1>C[C@H](O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f7d458084d742abb56d69e5108bda68 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21.C[C@H](O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>>CO[C@@H](C)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)[C@H](C)O>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)[C@H](C)OC | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc([CH2:1]OCCO)nc3N21.[OH:2][C@@H:3]([CH3:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C@H:12]([CH2:13]2)[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@H:24]1[CH3:25]>>[CH3:1][O:2][C@@H:3]([CH3:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[N:11]1[C... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21.C[C@H](O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | CO[C@@H](C)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | Heteroatom Alkylation and Arylation | O-methylation | 7e870483852ffb352aca9f590b85ef2d650a1641c48aeb57c049af3dab951250 | 8a75cabf1e3e505e5eb3d283576fc2757e90925e89ea99a676b5e5a01a38880f | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-[C@H]1-C-N(-C(=O)-O-C(-C)(-C)-C)-C-[C@@H]2-C-c3:c:c:c(-[CH2;D2;+0:1]-O-C-C-O):n:c:3-N-2-1.[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])-[OH;D1;+0:6]>>[#7;a:2]:[c:3]-[C:4](-[C;D1;H3:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 41 intermediate b), from (4R,9aR)-6-(1-(S)-hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H--2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Primary alcohol.Secondary alcohol.Tertiary amine.Boc | Ether | c1cnc2c(c1)C[C@@H]1CNCCN21 | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21.C[C@H](O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C>>CO[C@@H](C)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e32ff7f058cb4325997af10b7ac9c6ab | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21.O=CCC(F)(F)F>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(O)CC(F)(F)F)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)[Li].FC(CC=O)(F)F>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(CC(F)(F)F)O | OCCOC[c:18]1[cH:17][cH:16][c:15]2[c:27]([n:26]1)[N:28]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2.[CH:19](=[O:20])[CH2:21][C:22]([F:23])([F:24])[F:25]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21.O=CCC(F)(F)F | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(O)CC(F)(F)F)nc3N21 | null | null | null | C-C Coupling | OtherReaction | d6960b4f69fa1f7ae40fcd9b94d83aaa924f18352bb9a377fe700d0b76346333 | aa42d6045b9f6a2a3ed976a451ebf1a94d2c461b8a3304e588eb7e3ad2561159 | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-C-O-C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C:11]-[CH;D2;+0:12]=[O;H0;D1;+0:13]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:11]-[C:8](-[F;D1;H0:7])(-[F;D1;H0:9])-[F;D1;H0:10]):[c:5]:[c:6] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 38 intermediate, from (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b), tert-butyllithium and 3,3,3-trifluoropropanal.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary alcohol | Secondary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21.O=CCC(F)(F)F>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(O)CC(F)(F)F)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d4242cceed147e9bf35f669990436be | CC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(C)(C)O)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(CCC)[Li].CC(=O)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(C)(C)O | [C:19]([CH3:20])([CH3:21])=[O:22].Br[c:18]1[cH:17][cH:16][c:15]2[c:24]([n:23]1)[N:25]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:14][c:15]3[cH:16][cH:17]... | CC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(C)(C)O)nc3N21 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | 955dc987e5dbbc347813811df4e239f955ea858311f269c0e048ea610bf78f4c | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[C;D1;H3:7]-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;H0;D1;+0:10]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[OH;D1;+0:10]):[c:5]:[c:6] | 24.4 | [{"value": 24.4, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(C)(C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 0.30 g (0.81 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 5 ml tetrahydrofuran was cooled to −78 deg C. and treated with 0.61 ml (0.98 mmol) n-butyllithium solution (1.6 M in n-hexane). After 30 min, 80 μL (71 mg, 1.22 mmol) acetone wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Br- | O1CCCC1 | null | 0.5 | CC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>O1CCCC1>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(C)(C)O)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b6e5e145c19478197b39aa10504cac1 | CC(=O)C(C)C.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>CC(C)C(C)(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(CCC)[Li].CC(C(C)=O)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(C(C)C)(C)O | [CH3:1][CH:2]([CH3:3])[C:4]([CH3:5])=[O:6].OCCOC[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[N:13]1[C@H:14]([CH2:15]2)[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH3:27]>>[CH3:1][CH:2]([CH3:3])[C:4]([CH3:5])([OH:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[N:13]1[C@H:14]([CH2:15]... | CC(=O)C(C)C.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | CC(C)C(C)(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | C-C Coupling | OtherReaction | 30d2cf37345e3f539be6ed0ec2e63c1bd0364405453bf9e2f889010eaf034018 | 643fa8c91c1f609d3454f9d66a1e45c6fc2c296d3284c2c6da40bb96c9cecbf0 | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-C-O-C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[C;H0;D3;+0:10](-[C;D1;H3:11])=[O;H0;D1;+0:12]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10](-[C;D1;H3:11])(-[OH;D1;+0:12])-[C:8](-[C;D1;H3:7])-[C;D1;H3:9]):[c:5]:[c:6] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 51 intermediate, from (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b), n-butyllithium and 3-methyl-2-butanone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Primary alcohol | Tertiary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | null | null | null | CC(=O)C(C)C.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>CC(C)C(C)(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3aeb048e68654783bf2fca302fc4dc25 | COCC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>COCC(C)(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(CCC)[Li].COCC(C)=O>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(COC)(C)O | [CH3:1][O:2][CH2:3][C:4]([CH3:5])=[O:6].OCCOC[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[N:13]1[C@H:14]([CH2:15]2)[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH3:27]>>[CH3:1][O:2][CH2:3][C:4]([CH3:5])([OH:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[N:13]1[C@H:14]([CH2:15]2)[CH2... | COCC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | COCC(C)(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | C-C Coupling | OtherReaction | 30d2cf37345e3f539be6ed0ec2e63c1bd0364405453bf9e2f889010eaf034018 | 643fa8c91c1f609d3454f9d66a1e45c6fc2c296d3284c2c6da40bb96c9cecbf0 | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-C-O-C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[#8:7]-[C:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[OH;D1;+0:11])-[C:8]-[#8:7]):[c:5]:[c:6] | null | [] | null | null | null | null | This compound was prepared in analogy to Example 51, intermediate, from (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b), n-butyllithium and methoxy-2-propanone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Primary alcohol | Tertiary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | null | null | null | COCC(C)=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>COCC(C)(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17b941eede84488b9e92575473d7bd1b | CC(=O)CCCCl.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(C)(O)CCCCl)nc3N21 | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)Br.C(C)(C)(C)[Li].ClCCCC(C)=O>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(CCCCl)(C)O | [C:19]([CH3:20])(=[O:21])[CH2:22][CH2:23][CH2:24][Cl:25].Br[c:18]1[cH:17][cH:16][c:15]2[c:27]([n:26]1)[N:28]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]1[CH2:14]2>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][C@H:13]2[CH2:1... | CC(=O)CCCCl.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21 | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(C)(O)CCCCl)nc3N21 | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | 955dc987e5dbbc347813811df4e239f955ea858311f269c0e048ea610bf78f4c | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cnc2c(c1)C[C@@H]1CNCCN21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[C:7]-[C:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[OH;D1;+0:11])-[C:8]-[C:7]):[c:5]:[c:6] | 50.9 | [{"value": 50.9, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(CCCCl)(C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 0.30 g (0.81 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 20 ml diethyl ether was cooled to −100 deg C. and treated dropwise with 65 μl (0.97 mmol) tert-butyllithium (1.5 M solution in n-pentane). After 15 min, 0.12 g (0.11 ml, 0.98 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Br- | C(C)OCC | null | 0.25 | CC(=O)CCCCl.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21>C(C)OCC>C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(C(C)(O)CCCCl)nc3N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6cae64ff2dc4f43a91424aa999563f4 | CC=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(CCC)[Li].C(C)=O>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)C(C)O | [CH3:1][CH:2]=[O:3].OCCOC[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[CH3:24]>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19... | CC=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | d6960b4f69fa1f7ae40fcd9b94d83aaa924f18352bb9a377fe700d0b76346333 | aa42d6045b9f6a2a3ed976a451ebf1a94d2c461b8a3304e588eb7e3ad2561159 | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-C-O-C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].[C;D1;H3:7]-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH;D3;+0:8](-[C;D1;H3:7])-[OH;D1;+0:9]):[c:5]:[c:6] | null | [] | -78 | CELSIUS | 45 | MINUTE | To a stirred solution of (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) (2 g) in THF (24 ml) at −78° C. was added n-butyllithium (2.72 ml, 2.5 M in hexanes) dropwise. The solution was stirred at −78° C. for 45 mins and acetaldehyde ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary alcohol | Secondary alcohol | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | C1CCOC1 | -78 | 0.75 | CC=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>C1CCOC1>CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b693e70e23a741d6b2c133e26b82a717 | CCSSCC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>CCSc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)SSCC.C(C)(=O)[O-].[NH4+].C(CCC)[Li].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)SCC | CCS[S:3][CH2:2][CH3:1].OCCOC[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[CH3:24]>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]1[C@H:11]([CH2:12]2)[CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:1... | CCSSCC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | CCSc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | CO.O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d3ed315001871b61444081f5dd079f1ac421307c1ca1749163246fb25fe059cb | fd975403d3e0b238fc8c0836032f03160a2da70c68f55729be770ea53a5793a7 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C-C-S-[S;H0;D2;+0:1]-[C:2]-[C;D1;H3:3].O-C-C-O-C-[c;H0;D3;+0:4](:[#7;a:5]:[c:6]-[#7:7]):[c:8]:[c:9]>>[#7:7]-[c:6]:[#7;a:5]:[c;H0;D3;+0:4](-[S;H0;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:8]:[c:9] | 53 | [{"value": 53.0, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)SCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.6, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)SCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | THF (5 mL) was cooled to −78° C. under an argon atmosphere. n-Butyl lithium (1.6 M in hexanes, 0.5 mL, 0.8 mmol) was added and the mixture was stirred at −78° C. for 5 min. A mixture of (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Disulfide | Monosulfide | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | Other | CO.O.C1CCOC1 | -78 | 0.083333 | CCSSCC.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>CO.O.C1CCOC1>CCSc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57da838f35c74f14a87b06442b53cb79 | BrCC1CC1.CCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2>>CCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 | C(C)(C)(C)OC(=O)N1CC2CC3=CC=C(N=C3N2C(C1)C)C(CC)O.C1(CC1)CBr>>C1(CC1)COC(CC)C=1N=C2N3[C@@H](CNC[C@H]3CC2=CC1)C | Br[CH2:5][CH:6]1[CH2:7][CH2:8]1.CC(C)(C)OC(=O)[N:18]1[CH2:17][CH:16]2[N:15]([c:13]3[c:12]([cH:11][cH:10][c:9]([CH:3]([CH2:2][CH3:1])[OH:4])[n:14]3)[CH2:22]2)[CH:20]([CH3:21])[CH2:19]1>>[CH3:1][CH2:2][CH:3]([O:4][CH2:5][CH:6]1[CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][c:12]2[c:13]([n:14]1)[N:15]1[C@@H:16]([CH2:17][NH:18][CH2:... | BrCC1CC1.CCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2 | CCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 953ce34e2124c5e9f37c00907ba4e233e8be81988bfc0dfab1c50cfc9607eb39 | bf3875a42a0ef49ed4f1c6f5d01eef95ed4cfbe9178315ffa6628818fc56c6a4 | c1cc2c(nc1COCC1CC1)N1CCNC[C@H]1C2 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1.[#7;a:11]:[c:12]-[C:13](-[C:14])-[OH;D1;+0:15]>>[#7;a:11]:[c:12]-[C:13](-[C:14])-[O;H0;D2;+0:15]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#7:8]1-[C:7]-[C:6]-[NH;D2;+0:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | (4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-propyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene di-trifluoroacetate (32 mg) was made from 6-(1-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (52 mg), using cyclopropylmethyl bromide (29 μl) in place of methy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary alcohol.Boc | Ether.Secondary amine | c1cnc2c(c1)CC1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C1CC1.c1cnc2c(c1)C[C@@H]1CNCCN21 | HBr | null | null | null | BrCC1CC1.CCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2>>CCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-764f9b0f47cd41078ba8f211eade6ec3 | BrCC1CC1.CCCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2>>CCCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 | C(C)(C)(C)OC(=O)N1CC2CC3=CC=C(N=C3N2C(C1)C)C(CCC)O.C1(CC1)CBr>>C1(CC1)COC(CCC)C=1N=C2N3[C@@H](CNC[C@H]3CC2=CC1)C | Br[CH2:6][CH:7]1[CH2:8][CH2:9]1.CC(C)(C)OC(=O)[N:19]1[CH2:18][CH:17]2[N:16]([c:14]3[c:13]([cH:12][cH:11][c:10]([CH:4]([CH2:3][CH2:2][CH3:1])[OH:5])[n:15]3)[CH2:23]2)[CH:21]([CH3:22])[CH2:20]1>>[CH3:1][CH2:2][CH2:3][CH:4]([O:5][CH2:6][CH:7]1[CH2:8][CH2:9]1)[c:10]1[cH:11][cH:12][c:13]2[c:14]([n:15]1)[N:16]1[C@@H:17]([CH2... | BrCC1CC1.CCCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2 | CCCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 953ce34e2124c5e9f37c00907ba4e233e8be81988bfc0dfab1c50cfc9607eb39 | bf3875a42a0ef49ed4f1c6f5d01eef95ed4cfbe9178315ffa6628818fc56c6a4 | c1cc2c(nc1COCC1CC1)N1CCNC[C@H]1C2 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1.[#7;a:11]:[c:12]-[C:13](-[C:14])-[OH;D1;+0:15]>>[#7;a:11]:[c:12]-[C:13](-[C:14])-[O;H0;D2;+0:15]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#7:8]1-[C:7]-[C:6]-[NH;D2;+0:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | (4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-butyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene di-trifluoroacetate (53 mg) was made from 6-(1-hydroxy-butyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (54 mg), using cyclopropylmethyl bromide (29 μl) in place of methyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary alcohol.Boc | Ether.Secondary amine | c1cnc2c(c1)CC1C[NH]CCN21 | c1cnc2c(c1)C[C@@H]1CNCCN21 | C1CC1.c1cnc2c(c1)C[C@@H]1CNCCN21 | HBr | null | null | null | BrCC1CC1.CCCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2>>CCCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b4c88b2cc3ea496f835922b173f14063 | CC(C)N=C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>CC(C)NC(=O)OCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C)(C)N=C=O.C(C(CO)(CO)N)O.C(C)(=O)[O-].[NH4+].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.CCN(CC)P1(=NC(C)(C)C)N(CCCN1C)C>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NC(C)C)=O | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].OCC[O:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([n:14]1)[N:15]1[C@H:16]([CH2:17]2)[CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][C@H:28]1[CH3:29]>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([n:14]1)[N:1... | CC(C)N=C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | CC(C)NC(=O)OCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | CO.O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | bfdcef94d603610bc023397c9fd8c543489cb4ec55ca1b959b7b6a3585b1518f | c0a505c59b2d824173bac2f315081935a7143c00412035f86581a05b1057abd0 | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-C-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#7;a:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]>>[#7;a:4]:[c:3]-[C:2]-[O;H0;D2;+0:1]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:8]-[C:6](-[C;D1;H3:5])-[C;D1;H3:7] | 436.7 | [{"value": 44.0, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 436.7, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 15, intermediate b) (0.01 g, 0.03 mmol) and DCM (1 mL) was added to PS-BEMP (2.2 mmol/g, 0.03 g, 0.06 mmol). The mixture was shaken at room temperature for 5 min, isopropyl isocyanat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Isocyanate.Primary alcohol | Carbamic ester | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | CO.O.C(Cl)Cl | null | 0.083333 | CC(C)N=C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>CO.O.C(Cl)Cl>CC(C)NC(=O)OCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89a1ffbd0a1940589eb615ed420e2337 | CCN=C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>>CCNC(=O)OCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | C(C(CO)(CO)N)O.C(C)(=O)[O-].[NH4+].C(C)N=C=O.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COCCO>>C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NCC)=O | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].OCC[O:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([n:13]1)[N:14]1[C@H:15]([CH2:16]2)[CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][C@H:27]1[CH3:28]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([n:13]1)[N:14]1[C@H:15]([CH2:1... | CCN=C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21 | CCNC(=O)OCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | CO.O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | bfdcef94d603610bc023397c9fd8c543489cb4ec55ca1b959b7b6a3585b1518f | c0a505c59b2d824173bac2f315081935a7143c00412035f86581a05b1057abd0 | c1cnc2c(c1)C[C@@H]1CNCCN21 | O-C-C-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#7;a:4].[C;D1;H3:5]-[C:6]-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[#7;a:4]:[c:3]-[C:2]-[O;H0;D2;+0:1]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:6]-[C;D1;H3:5] | 215.4 | [{"value": 22.0, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 215.4, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | Ethyl isocyanate (22 mL, 0.31 mmol) was added to a mixture of DMAP (0.008 g, 0.063 mmol) (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 15, intermediate b) (0.02 g, 0.063 mmol), 4 Å molecular sieves (0.02 g, crushed) and DCM (2 mL). The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Isocyanate.Primary alcohol | Carbamic ester | null | null | c1cnc2c(c1)C[C@@H]1C[NH]CCN21 | HO- | CO.O.C(Cl)Cl | 140 | null | CCN=C=O.C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COCCO)nc3N21>CO.O.C(Cl)Cl>CCNC(=O)OCc1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fff4071b81fb4b7f95c5b75670c0f940 | C1CCNC1.CC1CN(C(=O)OC(C)(C)C)CC2Cc3ccc(CO)nc3N12.O=C(c1ncc[nH]1)c1ncc[nH]1>>CC(=O)[O-].C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COC(=O)N4CCCC4)nc3N21.[NH4+] | C(=O)(C=1NC=CN1)C=1NC=CN1.C(C)(C)(C)OC(=O)N1CC2CC3=CC=C(N=C3N2C(C1)C)CO.C(Cl)Cl.N1CCCC1.C(Cl)Cl>>C(C)(=O)[O-].[NH4+].C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(=O)N1CCCC1 | [NH:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1.[CH3:5][CH:6]1[CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH:17]2[CH2:18][c:19]3[cH:20][cH:21][c:22]([CH2:23][OH:24])[n:32][c:33]3[N:34]12.c1c[nH:35][c:1]([C:2](=[O:3])[c:25]2ncc[nH]2)n1>>[CH3:1][C:2](=[O:3])[O-:4].[CH3:5][C@@H:6]1[CH2:7][N:8]([... | C1CCNC1.CC1CN(C(=O)OC(C)(C)C)CC2Cc3ccc(CO)nc3N12.O=C(c1ncc[nH]1)c1ncc[nH]1 | CC(=O)[O-].C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COC(=O)N4CCCC4)nc3N21.[NH4+] | null | null | CO.O | Protection | OtherReaction | 4b9786d005ac83a8256df69fee24e67a3bf05a937ee77762a81abc2a6b78e32c | 2e2a90374c4f14765ccd4c71cec8fc348ec8f0bb11d16cad03ab5d209812ff15 | O=C(OCc1ccc2c(n1)N1CCNC[C@H]1C2)N1CCCC1 | [#7;a:1]:[c:2]-[C:3]-[OH;D1;+0:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1.[O;D1;H0:10]=[C;H0;D3;+0:11](-[c;H0;D3;+0:12]1:[nH;D2;+0:13]:c:c:n:1)-[c;H0;D3;+0:14]1:[nH]:c:c:n:1>>[#7;a:1]:[c:2]-[C:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1.[CH3;D1;+0:12]-[C;H0;D3;+0:11](-[O;-... | 61 | [{"value": 61.0, "product": "C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(=O)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A mixture of 6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (0.02 g, 0.063 mmol) and DCM (1 mL) was cooled to 0° C. and carbonyl diimidazole (0.010 g, 0.063 mmol) was added, the mixture was stirred at 0° C. for 2 h and stirred at room temperature for 3 h. A mix... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Secondary amine | Carbamic ester.Ether | C1CCNC1.c1c[nH]cn1.c1c[nH]cn1 | C1CC[NH]C1 | c1cnc2c(c1)C[C@@H]1C[NH]CCN21.C1CC[NH]C1 | Other | CO.O | 0 | 2 | C1CCNC1.CC1CN(C(=O)OC(C)(C)C)CC2Cc3ccc(CO)nc3N12.O=C(c1ncc[nH]1)c1ncc[nH]1>CO.O>CC(=O)[O-].C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(COC(=O)N4CCCC4)nc3N21.[NH4+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c7e89d4d4514972a067ddc65a248326 | O[C@@H]1c2ccccc2C[C@H]1Br>>BrC1=Cc2ccccc2C1 | Br[C@H]1[C@@H](C2=CC=CC=C2C1)O.C=1(C(=CC=CC1)S(=O)(=O)O)C>>BrC=1CC2=CC=CC=C2C1 | O[C@H:3]1[C@H:2]([Br:1])[CH2:10][c:9]2[c:4]1[cH:5][cH:6][cH:7][cH:8]2>>[Br:1][C:2]1=[CH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1 | O[C@@H]1c2ccccc2C[C@H]1Br | BrC1=Cc2ccccc2C1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | b53354a3faf4f34a55f10532f0c327dcd6f579a8673df09bdf2c1681103d2bc7 | 088a46b222085022f3939658104f3e01a2c0792362ccf400349fe1b7a8942f8f | C1=Cc2ccccc2C1 | O-[C@H;D3;+0:1]1-[C@H;D3;+0:2](-[Br;D1;H0:3])-[C:4]-[c:5]:[c:6]-1:[c:7]>>[Br;D1;H0:3]-[C;H0;D3;+0:2]1=[CH;D2;+0:1]-[c:6](:[c:7]):[c:5]-[C:4]-1 | 96.1 | [{"value": 96.0, "product": "BrC=1CC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "BrC=1CC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500 mL flask was charged with 25.5 g (120 mmol) of trans-2-bromo-1-indanol, 1 g of toluenesulfonic acid and 350 mL of toluene. This was capped with a Dean-Stark trap and heated to reflux for two hours at which time the system was cooled to room temperature and the volatiles removed in vacuo to leave a dark oil. The r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary alcohol | Alkenyl halide | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | HO- | C1(=CC=CC=C1)C | null | null | O[C@@H]1c2ccccc2C[C@H]1Br>C1(=CC=CC=C1)C>BrC1=Cc2ccccc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b447cd02024a491a92ae1236be790cec | BrC1=Cc2ccccc2C1.[Cl][Mg][CH2]c1ccccc1>>C1=C(Cc2ccccc2)Cc2ccccc21 | C(C1=CC=CC=C1)[Mg]Cl.BrC=1CC2=CC=CC=C2C1>>C(C1=CC=CC=C1)C=1CC2=CC=CC=C2C1 | Br[C:2]1=[CH:1][c:16]2[c:11]([cH:12][cH:13][cH:14][cH:15]2)[CH2:10]1.[Cl][Mg][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH:1]1=[C:2]([CH2:3][c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | BrC1=Cc2ccccc2C1.[Cl][Mg][CH2]c1ccccc1 | C1=C(Cc2ccccc2)Cc2ccccc21 | null | null | C(C)OCC.CCOCC | C-C Coupling | OtherReaction | 9b60b4b506726736c91a6847ed3dc2d70713b63564d3909fc0d8737b2370db3d | 25890778c2a34dbd8a57fb42f469f5e416c2ea4b1399554507deb7ca9b3263b7 | C1=C(Cc2ccccc2)Cc2ccccc21 | Br-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1.[Cl]-[Mg]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[CH2;D2;+0:6]-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1):[c:9] | null | [] | 0 | CELSIUS | null | null | A 500 mL 3 neck flask was charged with 2.5 g (13 mmol) of 2-bromo-indene, 50 mg of NiCl2(1,3-bis(diphenylphosphino)propane) (0.06 mmol) and 150 mL of diethyl ether. To this mixture was added dropwise 12.8 mL of 1.0 M benzyl magnesium chloride in ether (12.8 mmol). The reaction was heated to reflux overnight and then qu... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Alkenyl halide | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | c1ccccc1.C1=Cc2ccccc2C1 | Br-.Mg | C(C)OCC.CCOCC | 0 | null | BrC1=Cc2ccccc2C1.[Cl][Mg][CH2]c1ccccc1>C(C)OCC.CCOCC>C1=C(Cc2ccccc2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0aff5b67a1741c1bd8e8bebd2cdd783 | BrC1=Cc2ccccc2C1.CC1(Br)CCCCC1>>C1=C(CC2CCCCC2)Cc2ccccc21 | BrC1(CCCCC1)C.[Mg].BrC=1CC2=CC=CC=C2C1.BrC1(CCCCC1)C>>C1(CCCCC1)CC=1CC2=CC=CC=C2C1 | Br[C:2]1=[CH:1][c:16]2[c:11]([cH:12][cH:13][cH:14][cH:15]2)[CH2:10]1.Br[C:4]1([CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[CH:1]1=[C:2]([CH2:3][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | BrC1=Cc2ccccc2C1.CC1(Br)CCCCC1 | C1=C(CC2CCCCC2)Cc2ccccc21 | null | Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl | CCOCC | C-C Coupling | OtherReaction | 3aeeb34f81a3fe5bd436aeb1f308dec7c234234486fc0965553f3cf269bf41b0 | 38df9c684b90f440feb825a02ee72908fb013d707f38fb430faaa9c092f714b9 | C1=C(CC2CCCCC2)Cc2ccccc21 | Br-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1.Br-[C;H0;D4;+0:6](-[CH3;D1;+0:7])(-[C:8]-[C:9])-[C:10]-[C:11]>>[C:9]-[C:8]-[CH;D3;+0:6](-[CH2;D2;+0:7]-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1)-[C:10]-[C:11] | null | [] | null | null | 1 | HOUR | To a suspension of freshly ground magnesium turnings (0.40 g, 16 mmol) in 100 mL of ether was added about 20 percent of a 100 ml ether solution containing 2.5 g (14 mmol) of bromo-methyl-cyclohexane. The reaction was heated to reflux and the remaining bromo-methyl-cyclohexane solution added over one hour. After 1 hour,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Alkenyl halide | null | C1=Cc2ccccc2C1.C1CCCCC1 | C1CCCCC1.C1=Cc2ccccc2C1 | C1CCCCC1.C1=Cc2ccccc2C1 | Br- | Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl.CCOCC | null | 1 | BrC1=Cc2ccccc2C1.CC1(Br)CCCCC1>Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl.CCOCC>C1=C(CC2CCCCC2)Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b33d4d2bf1e84ea0a51401b9184d99de | C1=C(CC2CCCCC2)Cc2ccccc21.C[SiH](C)NC(C)(C)C>>CC(C)(C)N[Si](C)(C)C1C(CC2CCCCC2)=Cc2ccccc21 | C1(CCCCC1)CC=1CC2=CC=CC=C2C1.C(CCC)[Li].[Cl-].CC(C)(C)N[SiH](C)C>>C1(CCCCC1)CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C | [CH:9]1=[C:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21.[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][SiH:6]([CH3:7])[CH3:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][Si:6]([CH3:7])([CH3:8])[CH:9]1[C:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[... | C1=C(CC2CCCCC2)Cc2ccccc21.C[SiH](C)NC(C)(C)C | CC(C)(C)N[Si](C)(C)C1C(CC2CCCCC2)=Cc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | b92c7d378038ba4f9ce174a25c52d711c0709af473d2ab89a1be629c9476c0f1 | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1=C(CC2CCCCC2)Cc2ccccc21 | [C:1]-[#7:2]-[SiH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[C;H0;D3;+0:8]1=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12](:[c:13])-[CH2;D2;+0:14]-1>>[C:6]-[C:7]-[C;H0;D3;+0:8]1=[CH;D2;+0:14]-[c:12](:[c:13]):[c:10](:[c:11])-[CH;D3;+0:9]-1-[Si;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:2]-[C:1] | 90 | [{"value": 90.0, "product": "C1(CCCCC1)CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C1(CCCCC1)CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 2-(cyclohexylmethyl)indene (2.0 g, 9.4 mmol) in 40 mL of hexanes were added 6.0 mL of butyl lithium (1.6 M hexane; 9.6 mmol). The mixture was stirred overnight, the mother liquor decanted and the solid dissolved in THF. To this was added N-(1,1-dimethylethyl)dimethylsilanamine chloride (1.64 g, 9.9 mmol... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1CCCCC1.C1=Cc2ccccc2C1 | null | null | null | 8 | C1=C(CC2CCCCC2)Cc2ccccc21.C[SiH](C)NC(C)(C)C>>CC(C)(C)N[Si](C)(C)C1C(CC2CCCCC2)=Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c95ea336c63e4d4ea8961bed6584d030 | BrC1=Cc2ccccc2C1.Fc1ccc(CCl)cc1>>Fc1ccc(CC2=Cc3ccccc3C2)cc1 | FC1=CC=C(C=C1)CCl.[Mg].BrC=1CC2=CC=CC=C2C1.[Cl-]>>FC1=CC=C(C=C1)CC=1CC2=CC=CC=C2C1 | Br[C:7]1=[CH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15]1.Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7]2=[CH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH2:15]2)[cH:16][cH:17]1 | BrC1=Cc2ccccc2C1.Fc1ccc(CCl)cc1 | Fc1ccc(CC2=Cc3ccccc3C2)cc1 | null | Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl | CCOCC | C-C Coupling | Negishi | bfc31c4a887fe8d3db2b682735c59a2473fed133129be365487650a8e577dc3e | 97d429fd7dfe7bd125491aacdabeedbb7197c26fd24df3f01f59d01a7ffdb3bf | C1=C(Cc2ccccc2)Cc2ccccc21 | Br-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1.Cl-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[CH2;D2;+0:6]-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1):[c:9] | null | [] | null | null | null | null | To a suspension of freshly ground magnesium (0.58 g, 23 mmol) in 100 mL of ether was added about 3 mL of a 15 mL ether solution containing 3.0 g (21 mmol) of 4-fluorophenylmethyl chloride. The system was carefully heated and after initiation of the reaction, the remaining chloride solution added over 30 minutes while m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Alkenyl halide | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | c1ccccc1.C1=Cc2ccccc2C1 | Br- | Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl.CCOCC | null | null | BrC1=Cc2ccccc2C1.Fc1ccc(CCl)cc1>Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl.CCOCC>Fc1ccc(CC2=Cc3ccccc3C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db7769977e0f437eb6e215240a68b5d9 | C[SiH](C)NC(C)(C)C.Fc1ccc(CC2=Cc3ccccc3C2)cc1>>CC(C)(C)N[Si](C)(C)C1C(Cc2ccc(F)cc2)=Cc2ccccc21 | FC1=CC=C(C=C1)CC=1CC2=CC=CC=C2C1.C(CCC)[Li].[Cl-].CC(C)(C)N[SiH](C)C>>FC1=CC=C(C=C1)CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][SiH:6]([CH3:7])[CH3:8].[CH2:9]1[C:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)=[CH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][Si:6]([CH3:7])([CH3:8])[CH:9]1[C:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)... | C[SiH](C)NC(C)(C)C.Fc1ccc(CC2=Cc3ccccc3C2)cc1 | CC(C)(C)N[Si](C)(C)C1C(Cc2ccc(F)cc2)=Cc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | b92c7d378038ba4f9ce174a25c52d711c0709af473d2ab89a1be629c9476c0f1 | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1=C(Cc2ccccc2)Cc2ccccc21 | [C:1]-[#7:2]-[SiH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]1=[C:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[C:6]-[C:7]1=[C:8]-[c:9]:[c:10](:[c:11])-[CH;D3;+0:12]-1-[Si;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:2]-[C:1] | 97 | [{"value": 97.0, "product": "FC1=CC=C(C=C1)CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "FC1=CC=C(C=C1)CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 2-(4-fluorophenylmethyl)indene (2.21 g, 9.9 mmol) in 45 mL of hexanes were added 6.5 mL of butyl lithium (1.6 M hexane; 10.4 mmol). The mixture was stirred overnight, the mother liquor decanted and the solid dissolved in THF. To this was added N-(1,1-dimethylethyl)dimethylsilanamine chloride (1.80 g, 10... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | c1ccccc1.C1=Cc2ccccc2C1 | null | null | null | 8 | C[SiH](C)NC(C)(C)C.Fc1ccc(CC2=Cc3ccccc3C2)cc1>>CC(C)(C)N[Si](C)(C)C1C(Cc2ccc(F)cc2)=Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c2bcfdbb95d43638ee0afb3e5f26173 | BrC1=Cc2ccccc2C1.CC(C)([CH2][Mg][Cl])c1ccccc1>>CC(C)(CC1=Cc2ccccc2C1)c1ccccc1 | Cl.BrC=1CC2=CC=CC=C2C1.CC(C[Mg]Cl)(C)C1=CC=CC=C1>>CC(CC=1CC2=CC=CC=C2C1)(C)C1=CC=CC=C1 | Br[C:5]1=[CH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1.[Cl][Mg][CH2:4][C:2]([CH3:1])([CH3:3])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5]1=[CH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrC1=Cc2ccccc2C1.CC(C)([CH2][Mg][Cl])c1ccccc1 | CC(C)(CC1=Cc2ccccc2C1)c1ccccc1 | null | null | CCOCC | C-C Coupling | OtherReaction | 9b60b4b506726736c91a6847ed3dc2d70713b63564d3909fc0d8737b2370db3d | 25890778c2a34dbd8a57fb42f469f5e416c2ea4b1399554507deb7ca9b3263b7 | C1=C(CCc2ccccc2)Cc2ccccc21 | Br-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[c:9])-[CH2;D2;+0:10]-[Mg]-[Cl]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[c:9])-[CH2;D2;+0:10]-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1 | null | [] | null | null | null | null | A mixture of 2-bromoindene (2.0 g, 10.2 mmol) and 460 mg of Pd(AcO)2 in 60 mL of ether was treated with 21 mL of 2-methyl-2-phenyl-propanyl magnesium chloride (0.5 M in ether; 10.2 mmol). The mixture was refluxed for one hour, cooled to room temperature and treated with 30 mL of aqueous hydrochloric acid (5 percent). T... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Alkenyl halide | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.c1ccccc1 | Br-.Mg | CCOCC | null | null | BrC1=Cc2ccccc2C1.CC(C)([CH2][Mg][Cl])c1ccccc1>CCOCC>CC(C)(CC1=Cc2ccccc2C1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c251bc11a61b4cf1998e83b17ad6b3cf | CC(C)(CC1=Cc2ccccc2C1)c1ccccc1.C[SiH](C)NC(C)(C)C>>CC(C)(C)N[Si](C)(C)C1C(CC(C)(C)c2ccccc2)=Cc2ccccc21 | [Cl-].CC(C)(C)N[SiH](C)C.CC(CC=1CC2=CC=CC=C2C1)(C)C1=CC=CC=C1.C(CCC)[Li]>>CC(CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C)(C)C1=CC=CC=C1 | [CH2:9]1[C:10]([CH2:11][C:12]([CH3:13])([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)=[CH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21.[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][SiH:6]([CH3:7])[CH3:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][Si:6]([CH3:7])([CH3:8])[CH:9]1[C:10]([CH2:11][C:12]([CH3:13])([CH3:14])[c:15]... | CC(C)(CC1=Cc2ccccc2C1)c1ccccc1.C[SiH](C)NC(C)(C)C | CC(C)(C)N[Si](C)(C)C1C(CC(C)(C)c2ccccc2)=Cc2ccccc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | b92c7d378038ba4f9ce174a25c52d711c0709af473d2ab89a1be629c9476c0f1 | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1=C(CCc2ccccc2)Cc2ccccc21 | [C:1]-[#7:2]-[SiH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]1=[C:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[C:6]-[C:7]1=[C:8]-[c:9]:[c:10](:[c:11])-[CH;D3;+0:12]-1-[Si;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:2]-[C:1] | 96 | [{"value": 96.0, "product": "CC(CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C)(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "CC(CC=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C)(C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 2-(2-methyl-2-phenyl propan-1-yl)indene (1.55 g, 6.2 mmol) in 50 mL of hexanes were added 4.0 mL of butyl lithium (1.6 M hexane; 1.02 equiv.). The mixture was stirred overnight, filtered, the solid was washed with hexanes and dried, recovering 1.05g (66 percent of indenyl lithium salt) of very pale yell... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | c1ccccc1.C1=Cc2ccccc2C1 | null | C1CCOC1 | null | 8 | CC(C)(CC1=Cc2ccccc2C1)c1ccccc1.C[SiH](C)NC(C)(C)C>C1CCOC1>CC(C)(C)N[Si](C)(C)C1C(CC(C)(C)c2ccccc2)=Cc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d016d5953a644d638a4f6edb144b58b4 | BrC1=Cc2ccccc2C1.CC(C)(C)[CH2][Mg][Cl]>>CC(C)(C)CC1=Cc2ccccc2C1 | BrC=1CC2=CC=CC=C2C1.C(C(C)(C)C)[Mg]Cl>>C(C(C)(C)C)C=1CC2=CC=CC=C2C1 | Br[C:6]1=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1.[Cl][Mg][CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6]1=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1 | BrC1=Cc2ccccc2C1.CC(C)(C)[CH2][Mg][Cl] | CC(C)(C)CC1=Cc2ccccc2C1 | null | Cl[Ni]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C1CCOC1 | C-C Coupling | OtherReaction | 9b60b4b506726736c91a6847ed3dc2d70713b63564d3909fc0d8737b2370db3d | 25890778c2a34dbd8a57fb42f469f5e416c2ea4b1399554507deb7ca9b3263b7 | C1=Cc2ccccc2C1 | Br-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[CH2;D2;+0:10]-[Mg]-[Cl]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[CH2;D2;+0:10]-[C;H0;D3;+0:1]1=[C:2]-[c:3]:[c:4]-[C:5]-1 | null | [] | null | null | 8 | HOUR | To a mixture of 2-bromoindene (7.5 g, 39 mmol) and 2.5 g of NiCl2(PPh3)2 in 150 mL of THF was added over 1 hour 50 mL of neopentyl magnesium chloride (1.0 M in THF; 50 mmol). The mixture was stirred overnight and then quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (h... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Alkenyl halide | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | Br-.Mg | Cl[Ni]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1 | null | 8 | BrC1=Cc2ccccc2C1.CC(C)(C)[CH2][Mg][Cl]>Cl[Ni]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1CCOC1>CC(C)(C)CC1=Cc2ccccc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ded912e93ad40fc8c34118387fd0250 | CC(C)(C)CC1=Cc2ccccc2C1.C[SiH](C)NC(C)(C)C>>CC(C)(C)CC1=Cc2ccccc2C1[Si](C)(C)NC(C)(C)C | C(C(C)(C)C)C=1CC2=CC=CC=C2C1.C(CCC)[Li].[Cl-].CC(C)(C)N[SiH](C)C>>C(C(C)(C)C)C=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6]1=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1.[SiH:15]([CH3:16])([CH3:17])[NH:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C:6]1=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[Si:15]([CH3:16])([CH3:17])[NH:18][C:19]([CH3:20])(... | CC(C)(C)CC1=Cc2ccccc2C1.C[SiH](C)NC(C)(C)C | CC(C)(C)CC1=Cc2ccccc2C1[Si](C)(C)NC(C)(C)C | null | null | C1CCOC1 | Miscellaneous | OtherReaction | b92c7d378038ba4f9ce174a25c52d711c0709af473d2ab89a1be629c9476c0f1 | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1=Cc2ccccc2C1 | [C:1]-[#7:2]-[SiH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]1=[C:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[C:1]-[#7:2]-[Si;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH;D3;+0:12]1-[C:7](-[C:6])=[C:8]-[c:9]:[c:10]-1:[c:11] | 103.2 | [{"value": 102.0, "product": "C(C(C)(C)C)C=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.2, "product": "C(C(C)(C)C)C=1C(C2=CC=CC=C2C1)[Si](NC(C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 2-neopentylindene (0.81 g, 4.3 mmol) in 30 mL of hexanes were added 2.9 mL of butyl lithium (1.6 M hexane; 4.7 mmol). The mixture was stirred for one hour, diluted with 20 mL of THF and to this added N-(1,1-dimethylethyl)dimethylsilanamine chloride (1.84 g, 11.2 mmol) in 10 mL of THF. After stirring ove... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | null | C1CCOC1 | null | 1 | CC(C)(C)CC1=Cc2ccccc2C1.C[SiH](C)NC(C)(C)C>C1CCOC1>CC(C)(C)CC1=Cc2ccccc2C1[Si](C)(C)NC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fedfeb7246d14800a6bb242376675b00 | C=Cc1ccc(CCl)cc1.[C-]#N>>C=Cc1ccc(CC#N)cc1 | C(=C)C1=CC=C(CCl)C=C1.CS(=O)C.[C-]#N.[K+]>>C(=C)C1=CC=C(CC#N)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:11][cH:10]1.[C-:8]#[N:9]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]#[N:9])[cH:10][cH:11]1 | C=Cc1ccc(CCl)cc1.[C-]#N | C=Cc1ccc(CC#N)cc1 | null | null | O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 17 | HOUR | A mixture of 22.2 g 4-vinyl benzylchloride (0.131 mol), 60 mL dimethylsulfoxide, and 12.8 g potassium cyanide (0.196 mol) was stirred at room temperature for 17 hours. The mixture was poured into 500 mL water and extracted several times with ethyl acetate. The combined organic layers were washed with brine and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Other | O | null | 17 | C=Cc1ccc(CCl)cc1.[C-]#N>O>C=Cc1ccc(CC#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca7f67dfd1304f62a578fc6a4b55c45f | C=Cc1ccc(CCl)cc1.CC(O)(C#N)CC#N>>C=Cc1ccc(CC(C)(C#N)C#N)cc1 | C(C)N(CC)CC.C(=C)C1=CC=C(CCl)C=C1.CC(C#N)(O)CC#N.CS(=O)C>>C(#N)C(CC1=CC=C(C=C)C=C1)(C)C#N | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:15][cH:14]1.O[C:8](C[C:10]#[N:11])([CH3:9])[C:12]#[N:13]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])([C:10]#[N:11])[C:12]#[N:13])[cH:14][cH:15]1 | C=Cc1ccc(CCl)cc1.CC(O)(C#N)CC#N | C=Cc1ccc(CC(C)(C#N)C#N)cc1 | null | null | O | C-C Coupling | OtherReaction | 02d515828f04406e18b8ef8840bd7a72060eb69cf0ce22dadcd9c5ce6d0782a3 | b98ee86cf4cd317d95f71daa3ee0f57fb69df6eb03a25136110c1b1f6cdcbf35 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O-[C;H0;D4;+0:5](-[C;D1;H3:6])(-C-[C;H0;D2;+0:7]#[N;D1;H0:8])-[C:9]#[N;D1;H0:10]>>[C;D1;H3:6]-[C;H0;D4;+0:5](-[C:9]#[N;D1;H0:10])(-[C;H0;D2;+0:7]#[N;D1;H0:8])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 64 | [{"value": 64.0, "product": "C(#N)C(CC1=CC=C(C=C)C=C1)(C)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A sample (2.53 g) of triethylamine (25 mmol) was added dropwise to a mixture of 4.01 g 4-vinylbenzyl chloride (25 mmol), 2.00 g monomethyl malonitrile (25 mmol), and 15 mL DMSO at room temperature. The mixture was stirred at room temperature for 17 hours then poured into 100 mL water. A pink solid precipitated and was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile.Tertiary alcohol | Nitrile | null | null | c1ccccc1 | HCl | O | null | 17 | C=Cc1ccc(CCl)cc1.CC(O)(C#N)CC#N>O>C=Cc1ccc(CC(C)(C#N)C#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-889b54b10bbf459ba06308db43df6aa0 | C=Cc1ccc(C=C(C#N)C#N)cc1.[C-]#N>>C=Cc1ccc(C(C#N)C(C#N)C#N)cc1 | Cl.[C-]#N.[K+].C(#N)C(=CC1=CC=C(C=C)C=C1)C#N.C(C)O>>C(#N)C(C(C#N)C#N)C1=CC=C(C=C)C=C1 | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:10]([C:11]#[N:12])[C:13]#[N:14])[cH:15][cH:16]1.[C-:8]#[N:9]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([C:8]#[N:9])[CH:10]([C:11]#[N:12])[C:13]#[N:14])[cH:15][cH:16]1 | C=Cc1ccc(C=C(C#N)C#N)cc1.[C-]#N | C=Cc1ccc(C(C#N)C(C#N)C#N)cc1 | null | null | O | C-C Coupling | OtherReaction | e60c5c43322dfc46d7f6c74a9700db994e17c940f4ba384de70b2fce04697817 | b8bacb90390718f4555f6dee24489036b4f724075b0543a5a9bf8e9abad9b32c | c1ccccc1 | [C-;H0;D1:1]#[N;D1;H0:2].[N;D1;H0:3]#[C:4]-[C;H0;D3;+0:5](-[C:6]#[N;D1;H0:7])=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:3]#[C:4]-[CH;D3;+0:5](-[C:6]#[N;D1;H0:7])-[CH;D3;+0:8](-[C;H0;D2;+0:1]#[N;D1;H0:2])-[c:9](:[c:10]):[c:11] | null | [] | null | null | 17 | HOUR | To a mixture of 2.00 g 4-(2,2′-dicyanoethenyl)styrene (11 mmol) and 30 mL ethanol was added a solution of 1.45 g potassium cyanide (22 mmol) in 3 mL water. The mixture was stirred at room temperature for 17 hours. 1.8 mL concentrated HCl (22 mmol) was then added and the mixture was concentrated under vacuum. Ten millil... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitrile | null | null | c1ccccc1 | null | O | null | 17 | C=Cc1ccc(C=C(C#N)C#N)cc1.[C-]#N>O>C=Cc1ccc(C(C#N)C(C#N)C#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5458c1810da14b22b17018798e405eb9 | CCO[Si](OCC)(OCC)OCC.FC(F)=C(F)Cl>>CCO[Si](OCC)(OCC)C(F)=C(F)F | C(F)(F)=C(F)Cl.[Li]C(C)CC.[Si](OCC)(OCC)(OCC)OCC>>C(F)(F)=C(F)[Si](OCC)(OCC)OCC | CCO[Si:4]([O:3][CH2:2][CH3:1])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10].Cl[C:13](=[C:11]([F:12])[F:15])[F:14]>>[CH3:1][CH2:2][O:3][Si:4]([O:5][CH2:6][CH3:7])([O:8][CH2:9][CH3:10])[C:11]([F:12])=[C:13]([F:14])[F:15] | CCO[Si](OCC)(OCC)OCC.FC(F)=C(F)Cl | CCO[Si](OCC)(OCC)C(F)=C(F)F | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 53eff72092e8f5ade8d4bfad8013dfa23341e8393ad668703cc0fb3ccf4c8a08 | 3cf8d90bfee56183340da505f9fa64e7a905e2b3b9d09d04cd0c1a0af0f1667c | null | C-C-O-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[C;D1;H3:4])(-[#8:5]-[C:6]-[C;D1;H3:7])-[#8:8]-[C:9]-[C;D1;H3:10].Cl-[C;H0;D3;+0:11](-[F;D1;H0:12])=[C;H0;D3;+0:13](-[F;D1;H0:14])-[F;H0;D1;+0:15]>>[C;D1;H3:10]-[C:9]-[#8:8]-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[C;D1;H3:4])(-[#8:5]-[C:6]-[C;D1;H3:7])-[C;H0;D3;+0:13](-[F;D1;H0:14])=[C;H0;D3;... | null | [] | -80 | CELSIUS | 15 | MINUTE | 200 ml of freshly distilled dry Et2O is added to a 500 ml vessel (under an argon atmosphere). The vessel is cooled down to −80° C. and 15 g (0.129 mol) of CF2═CFCl gas is bubbled to Et2O. 100 ml (0.13 mol) of sec-BuLi is added dropwise during three hours. The temperature of the solution is kept below −60° C. all the ti... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Silyl protective group | Alkenyl halide.Alkenyl halide.Alkenyl halide.Silyl protective group | null | null | null | HCl | CCOCC | -80 | 0.25 | CCO[Si](OCC)(OCC)OCC.FC(F)=C(F)Cl>CCOCC>CCO[Si](OCC)(OCC)C(F)=C(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a93a27bfb7fd4c638aa74d18829c69e1 | CCO[Si](OCC)(OCC)OCC.Fc1c(F)c(F)c(Br)c(F)c1F>>CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F | BrC1=C(C(=C(C(=C1F)F)F)F)F.[Mg].C(C)O[Si](OCC)(OCC)OCC>>FC1=C(C(=C(C(=C1[Si](OCC)(OCC)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F | O([Si:4](O[CH2:13][CH3:11])([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])[CH2:9][CH3:8].Br[c:19]1[c:20]([F:10])[c:22]([F:23])[c:24]([F:25])[c:26]([F:27])[c:28]1[F:29]>>[CH3:1][CH2:2][O:3][Si:4]([O:5][CH2:6][CH3:7])([c:8]1[c:9]([F:10])[c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1[F:18])[c:19]1[c:20]([F:21])[c:22]([F:23])... | CCO[Si](OCC)(OCC)OCC.Fc1c(F)c(F)c(Br)c(F)c1F | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F | null | null | C(C)OCC.CCOCC | Miscellaneous | OtherReaction | 3a5bc17cbe6b64db6ff084181a0df36349852160422e4b26fdeda194c32be759 | 45e321aaf249152f99e6a64045778e46382bef35c7fac5be0808cd39c17e250d | c1ccc([SiH2]c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:8]:1-[F;H0;D1;+0:9].[C;D1;H3:10]-[C:11]-[#8:12]-[Si;H0;D4;+0:13](-O-[CH2;D2;+0:14]-[CH3;D1;+0:15])(-O-[CH2;D2;+0:16]-[CH3;D1;+0:17])-[#8:18]-[C:19]-[C;D1;H3:20]>>[C;D1;H3:10]-[C:11]-[#8:12]-[Si;H0;D4;+0:13](-[#8:18]-[C:19]-[C;D1;H3:20])(... | null | [] | 35 | CELSIUS | 16 | HOUR | 265.2 mL (1.95 mol, 525.353 g) bromopentafluorobenzene, 52.11 g (2.144 mol) magnesium powder and 216 mL (0.975 mol, 203.025 g) tetraethoxysilane are mixed together at room temperature and diethylether is added dropwise to the vigorously stirred solution until an exothermic reaction is observed (˜240 ML). The solution i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Silyl protective group | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Silyl protective group | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(C)OCC.CCOCC | 35 | 16 | CCO[Si](OCC)(OCC)OCC.Fc1c(F)c(F)c(Br)c(F)c1F>C(C)OCC.CCOCC>CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6cdff6ad7efb463eb5fc594fb3ae829b | CCO[Si](Cl)(OCC)c1c(F)c(F)c(F)c(F)c1F.Fc1c(F)c(F)c(Cl)c(F)c1F>>CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F | ClC1=C(C(=C(C(=C1F)F)F)F)F.C(C)O[Si](C1=C(C(=C(C(=C1F)F)F)F)F)(Cl)OCC.[Li]C(C)CC>>FC1=C(C(=C(C(=C1[Si](OCC)(OCC)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F | Cl[Si:4]([O:3][CH2:2][CH3:1])([O:5][CH2:6][CH3:7])[c:8]1[c:9]([F:10])[c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1[F:18].Cl[c:24]1[c:22]([F:23])[c:20]([F:21])[c:19]([F:25])[c:28]([F:29])[c:26]1[F:27]>>[CH3:1][CH2:2][O:3][Si:4]([O:5][CH2:6][CH3:7])([c:8]1[c:9]([F:10])[c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1... | CCO[Si](Cl)(OCC)c1c(F)c(F)c(F)c(F)c1F.Fc1c(F)c(F)c(Cl)c(F)c1F | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 7fa36a0b3b7c89304f5e806314959b69f226a4708c349302d6d29b6538498212 | 1d1d4847f7abeb99a221f7e78fd6132bf0c95686547b23fb7c10af6932b9a978 | c1ccc([SiH2]c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[#8:2]-[C:3])(-[#8:4]-[C:5])-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[c:10](-[F;D1;H0:11]):[c:12](-[F;D1;H0:13]):[c;H0;D3;+0:14](-[F;H0;D1;+0:15]):[c:16](-[F;D1;H0:17]):[c:18]:1-[F;D1;H0:19]>>[C:3]-[#8:2]-[Si;H0;D4;+0:1](-[#8:4]-[C:5])(-[c:6](:[c:7]):[c:8])-[c;H0;D3;+0:14]1:[c:12](-[F;D1;H0:13]):[c:1... | null | [] | -70 | CELSIUS | 30 | MINUTE | 39.52 g (0.195 mol) chloropentafluorobenzene is weighed to a 1000 mL vessel and 250 mL Et2O is added. The vessel is cooled down to −70° C. and 150 mL (0.195 mol) of sec-BuLi (1.3 M) is added dropwise during one hour. The temperature of the solution is kept below −50° C. all the time. The solution is stirred for 30 minu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Silyl protective group | Aromatic halide.Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CCOCC | -70 | 0.5 | CCO[Si](Cl)(OCC)c1c(F)c(F)c(F)c(F)c1F.Fc1c(F)c(F)c(Cl)c(F)c1F>CCOCC>CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8219d298c4747048523409ec4685924 | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Cl.O=S(Cl)Cl>>Fc1c(F)c(F)c([Si](Cl)(Cl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F | FC1=C(C(=C(C(=C1[Si](OCC)(OCC)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.S(=O)(Cl)Cl.Cl.[NH+]1=CC=CC=C1>>FC1=C(C(=C(C(=C1[Si](Cl)(Cl)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F | CCO[Si:8](OCC)([c:7]1[c:5]([F:6])[c:3]([F:4])[c:2]([F:1])[c:24]([F:25])[c:22]1[F:23])[c:11]1[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[c:20]1[F:21].[ClH:10].O=S(Cl)[Cl:9]>>[F:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([Si:8]([Cl:9])([Cl:10])[c:11]2[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[c:20]2... | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Cl.O=S(Cl)Cl | Fc1c(F)c(F)c([Si](Cl)(Cl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F | null | null | null | Miscellaneous | OtherReaction | 21162c04e8137d28e9d221e45dc51c67e95ecd1576369705955677df8e291fde | 15a3722c8646b9f58173a79826214bfa9831ab4bb7562e4577146137df6a8592 | c1ccc([SiH2]c2ccccc2)cc1 | C-C-O-[Si;H0;D4;+0:1](-O-C-C)(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].Cl-S(=O)-[Cl;H0;D1;+0:8].[ClH;D0;+0:9]>>[Cl;H0;D1;+0:9]-[Si;H0;D4;+0:1](-[Cl;H0;D1;+0:8])(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 16 | HOUR | 180.93 g (0.400 mol) di(pentafluorophenyl)diethoxysilane, 146 mL (2.00 mol, 237.9 g) thionylchloride and 4.92 g (0.0426 mol) pyridinium hydrochloride are refluxed and stirred for 16 h. Excess of SOCl2 is evaporated and di(pentafluorophenyl)dichlorosilane isolated by vacuum-distillation.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | 16 | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Cl.O=S(Cl)Cl>>Fc1c(F)c(F)c([Si](Cl)(Cl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebe86df30b2441388fb356c07f9e4914 | C=CC(=O)[O-].CCO[Si](Cl)(OCC)OCC>>C=CC(=O)[Si](OCC)(OCC)OCC | C(C=C)(=O)[O-].[Na+].Cl[Si](OCC)(OCC)OCC>>C(=O)(C=C)[Si](OCC)(OCC)OCC | [O-][C:3]([CH:2]=[CH2:1])=[O:4].Cl[Si:5]([O:6][CH2:7][CH3:8])([O:9][CH2:10][CH3:11])[O:12][CH2:13][CH3:14]>>[CH2:1]=[CH:2][C:3](=[O:4])[Si:5]([O:6][CH2:7][CH3:8])([O:9][CH2:10][CH3:11])[O:12][CH2:13][CH3:14] | C=CC(=O)[O-].CCO[Si](Cl)(OCC)OCC | C=CC(=O)[Si](OCC)(OCC)OCC | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 2a094323228e6c897bc4d3422b60e2e1f170cc555516918c0a4ca831bb19d92a | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | null | Cl-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[C;D1;H3:4])(-[#8:5]-[C:6]-[C;D1;H3:7])-[#8:8]-[C:9]-[C;D1;H3:10].[C;D1;H2:11]=[C:12]-[C;H0;D3;+0:13](-[O-])=[O;D1;H0:14]>>[C;D1;H2:11]=[C:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[C;D1;H3:4])(-[#8:5]-[C:6]-[C;D1;H3:7])-[#8:8]-[C:9]-[C;D1;H3:10] | null | [] | -70 | CELSIUS | null | null | 6.123 g (0.0651 mol) sodium acrylate is dissolved to 25 mL THF and cooled to −70° C. 12.8 mL (0.0651 mol, 12.938 g) chlorotriethoxysilane in THF (15 mL) is added dropwise to reaction solution. The solution is stirred for over night allowing it to warm up to room temperature. NaCl is removed by filtration and solution e... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | null | null | null | Other | C1CCOC1 | -70 | null | C=CC(=O)[O-].CCO[Si](Cl)(OCC)OCC>C1CCOC1>C=CC(=O)[Si](OCC)(OCC)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa42970fa3e14feb959cd2441453e5ef | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Cl>>Fc1c(F)c(F)c([SiH](OCCCl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F | FC1=C(C(=C(C(=C1[Si](OCC)(OCC)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.S(=O)(Cl)Cl.Cl.[NH+]1=CC=CC=C1>>FC1=C(C(=C(C(=C1[SiH](OCCCl)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F | CCO[Si:8]([c:7]1[c:5]([F:6])[c:3]([F:4])[c:2]([F:1])[c:26]([F:27])[c:24]1[F:25])([O:9][CH2:10][CH3:11])[c:13]1[c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[c:20]([F:21])[c:22]1[F:23].[ClH:12]>>[F:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([SiH:8]([O:9][CH2:10][CH2:11][Cl:12])[c:13]2[c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[c:... | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Cl | Fc1c(F)c(F)c([SiH](OCCCl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F | null | null | null | Miscellaneous | OtherReaction | 2219208717f9e23e17a51bfe75f2f117a7f4f4ef80249b50815b30742d172858 | b405e373bae3187bd461d31e25bc2965a72639024a3b72ce52be33225bda14bf | c1ccc([SiH2]c2ccccc2)cc1 | C-C-O-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[CH3;D1;+0:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[ClH;D0;+0:11]>>[Cl;H0;D1;+0:11]-[CH2;D2;+0:4]-[C:3]-[#8:2]-[SiH;D3;+0:1](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 16 | HOUR | 180.93 g (0.400 mol) di(pentafluorophenyl)diethoxysilane, 29 mL (0.400 mol, 47.6 g) thionylchloride and 4.92 g (0.0426 mol) pyridinium hydrochloride are refluxed and stirred for 16 h. Unreacted SOCl2 is evaporated and di(pentafluorophenyl)chloroethoxysilane isolated by vacuum distillation.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary halide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | 16 | CCO[Si](OCC)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Cl>>Fc1c(F)c(F)c([SiH](OCCCl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e16df46a787347caa7ae242d3f98f8b9 | Fc1c(F)c(F)c([SiH](OCCCl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F.[Li][c]1c(F)c(F)c(F)c(F)c1F>>CCO[Si](c1c(F)c(F)c(F)c(F)c1F)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Fc1c(F)c(F)c(C(CO[SiH3])(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F | FC1=C(C(=C(C(=C1[SiH](OCCCl)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.C1(=C(F)C(F)=C(F)C(F)=C1F)[Li]>>FC1=C(C(=C(C(=C1C(CO[SiH3])(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.[Si](C1=C(F)C(F)=C(F)C(F)=C1F)(C1=C(F)C(F)=C(F)C(F)=C1F)(C1=C(F)C(F)=C(F)C(F)=C1F)OCC | Cl[CH2:1][CH2:2][O:3][SiH:4]([c:16]1[c:17]([F:18])[c:19]([F:20])[c:21]([F:22])[c:23]([F:24])[c:25]1[F:26])[c:27]1[c:28]([F:29])[c:30]([F:31])[c:32]([F:33])[c:34]([F:35])[c:36]1[F:37].[Li][c:45]1[c:49]([F:59])[c:5]([F:7])[c:54]([F:55])[c:52]([F:53])[c:50]1[F:51]>>[CH3:1][CH2:2][O:3][Si:4]([c:5]1[c:6]([F:7])[c:8]([F:9])[... | Fc1c(F)c(F)c([SiH](OCCCl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F.[Li][c]1c(F)c(F)c(F)c(F)c1F | CCO[Si](c1c(F)c(F)c(F)c(F)c1F)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Fc1c(F)c(F)c(C(CO[SiH3])(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F | null | null | CCOCC | Aromatic Heterocycle Formation | OtherReaction | fbcfb43aa425b3810eae3fce63d6281ccdde6bea3ba45005bb1cb113813beb68 | f9b8cf4f79e4217081b25b3e99d4367edc00ef512a7b92db85d1918008539fe3 | c1ccc(C(c2ccccc2)c2ccccc2)cc1.c1ccc([SiH](c2ccccc2)c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[SiH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[F;D1;H0:11]-[c;H0;D3;+0:12]1:[c:13](-[F;D1;H0:14]):[c;H0;D3;+0:15](-[F;D1;H0:16]):[c;H0;D3;+0:17](-[F;H0;D1;+0:18]):[c;H0;D3;+0:19](-[F;H0;D1;+0:20]):[c;H0;D3;+0:21]:1-[Li]>>[#8:22]-[C:23]-[C;H0;D4;+0:21](-[c:24](:[c:25]):[c:26])(-[... | null | [] | null | null | null | null | 88.54 g (0.200 mol) of di(pentafluorophenyl)chloroethoxysilane in Et2O is slowly added to solution of C6F5—Li (0.200 mol, 34.80 g, prepared in situ) in Et2O at −78° C. The solution is stirred for over night allowing it to warm up to room temperature. Formed clear solution is filtered and evaporated to dryness to result... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Primary halide.Aryl lithium | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Silyl protective... | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Li | CCOCC | null | null | Fc1c(F)c(F)c([SiH](OCCCl)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F.[Li][c]1c(F)c(F)c(F)c(F)c1F>CCOCC>CCO[Si](c1c(F)c(F)c(F)c(F)c1F)(c1c(F)c(F)c(F)c(F)c1F)c1c(F)c(F)c(F)c(F)c1F.Fc1c(F)c(F)c(C(CO[SiH3])(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f1b5569857ad4bc69f007d641c3d1aae | CCO[Si](Cl)(OCC)OCC.O=C([O-])C(F)(F)Cl>>CCO[Si](OCC)(OCC)OC(=O)C(F)(F)Cl | ClC(C(=O)[O-])(F)F.[Na+].Cl[Si](OCC)(OCC)OCC>>ClC(C(=O)O[Si](OCC)(OCC)OCC)(F)F | Cl[Si:4]([O:3][CH2:2][CH3:1])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10].[O-:11][C:12](=[O:13])[C:14]([F:15])([F:16])[Cl:17]>>[CH3:1][CH2:2][O:3][Si:4]([O:5][CH2:6][CH3:7])([O:8][CH2:9][CH3:10])[O:11][C:12](=[O:13])[C:14]([F:15])([F:16])[Cl:17] | CCO[Si](Cl)(OCC)OCC.O=C([O-])C(F)(F)Cl | CCO[Si](OCC)(OCC)OC(=O)C(F)(F)Cl | null | null | CCOCC | Protection | OtherReaction | 8fcc4c3cc9b76ad7a25dadc60c2bf40d0808fa925288f755ee2252a082747b94 | f0dce65f75d702dc7e016c0abdb24b26134ae5c509e2d0da4a21967fb59ed09d | null | Cl-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[C;D1;H3:4])(-[#8:5]-[C:6]-[C;D1;H3:7])-[#8:8]-[C:9]-[C;D1;H3:10].[C:11]-[C:12](-[O-;H0;D1:13])=[O;D1;H0:14]>>[C:11]-[C:12](=[O;D1;H0:14])-[O;H0;D2;+0:13]-[Si;H0;D4;+0:1](-[#8:2]-[C:3]-[C;D1;H3:4])(-[#8:5]-[C:6]-[C;D1;H3:7])-[#8:8]-[C:9]-[C;D1;H3:10] | null | [] | -70 | CELSIUS | null | null | 15.246 g (0.10 mol) sodium chlorodifluoroacetate, is dissolved to 100 mL Et2O and cooled to −70° C. 19.7 mL (0.10 mol, 19.872 g) chlorotriethoxysilane in Et2O (50 mL) was added dropwise to reaction solution. The solution was stirred for over night allowing it to warm up to room temperature. NaCl is removed by filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | null | null | null | Other | CCOCC | -70 | null | CCO[Si](Cl)(OCC)OCC.O=C([O-])C(F)(F)Cl>CCOCC>CCO[Si](OCC)(OCC)OC(=O)C(F)(F)Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d73a86df4d0d4a32a23007aeff1a94e4 | COc1cccc(I)c1N.O=C(O)CC1=CCC2(CC1)OCCO2>>COc1cccc(I)c1NC(=O)CC1=CCC2(CC1)OCCO2 | [I-].ClC1=[N+](C=CC=C1)C.O1CCOC12CC=C(CC2)CC(=O)O.C(C)N(CC)CC.IC1=C(N)C(=CC=C1)OC>>O1CCOC12CC=C(CC2)CC(=O)NC2=C(C=CC=C2OC)I | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([I:8])[c:9]1[NH2:10].O[C:11](=[O:12])[CH2:13][C:14]1=[CH:15][CH2:16][C:17]2([CH2:18][CH2:19]1)[O:20][CH2:21][CH2:22][O:23]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([I:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]1=[CH:15][CH2:16][C:17]2([CH2:18][CH2:19]1)[O:20][CH2:21][CH2:2... | COc1cccc(I)c1N.O=C(O)CC1=CCC2(CC1)OCCO2 | COc1cccc(I)c1NC(=O)CC1=CCC2(CC1)OCCO2 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC1=CCC2(CC1)OCCO2)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](=[C:5]-[C:6])-[C:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:6]-[C:5]=[C:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:7] | 90 | [{"value": 89.6, "product": "O1CCOC12CC=C(CC2)CC(=O)NC2=C(C=CC=C2OC)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1=CCC2(CC1)OCCO2 | HO- | ClCCl | null | null | COc1cccc(I)c1N.O=C(O)CC1=CCC2(CC1)OCCO2>ClCCl>COc1cccc(I)c1NC(=O)CC1=CCC2(CC1)OCCO2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6ecb22d1266e4ad1878d98cb3b30a37b | BrCCSSCCBr.CCC#N.Cc1nc2ccccc2n1C>>Cc1n(C)c2ccccc2[n+]1CCSSCC[n+]1c(C)n(C)c2ccccc21.[Br-].[Br-] | CN1C(=NC2=C1C=CC=C2)C.BrCCSSCCBr.C(CC)#N>>[Br-].[Br-].S(SCC[N+]1=C(N(C2=C1C=CC=C2)C)C)CC[N+]2=C(N(C1=C2C=CC=C1)C)C | [CH2:4]([CH2:12][S:15][S:14][CH2:10][CH2:9][Br:29])[Br:30].[CH2:1]([C:2]#[N:3])[CH3:27].[c:5]12[cH:6][cH:7][cH:8][cH:24][c:23]1[n:21]([CH3:22])[c:19]([CH3:20])[n:18]2>>[CH3:1][c:2]1[n:3]([CH3:4])[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n+:11]1[CH2:12][CH2:13][S:14][S:15][CH2:16][CH2:17][n+:18]1[c:19]([CH3:20])[n:21]([CH3:... | BrCCSSCCBr.CCC#N.Cc1nc2ccccc2n1C | Cc1n(C)c2ccccc2[n+]1CCSSCC[n+]1c(C)n(C)c2ccccc21.[Br-].[Br-] | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0447bb3c9e276bec928b0d92099224296e6427cd48f567bb6c9099af288e71d9 | 5316d105e2c472abb39cea36ce6b9381b4038d98ac2d05213d0504c9c1634e70 | c1ccc2c(c1)[nH]c[n+]2CCSSCC[n+]1c[nH]c2ccccc21 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[S;H0;D2;+0:4]-[S;H0;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[Br;H0;D1;+0:8].[C;D1;H3:9]-[c:10]1:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]2:[c:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c;H0;D3;+0:17]:2:[#7;a:18]:1-[C;D1;H3:19].[CH3;D1;+0:20]-[CH2;D2;+0:21]-[C;H0;D2;+0:22]#[N;H0;D1;+0:23]>>[... | null | [] | null | null | null | null | 2.4 g of 1,2-dimethylbenzimidazole, 2.1 g of bis(2-bromoethyl) disulfide and 6 ml of propionitrile were stirred at 100 C in a sealed 20 ml reactor for 8 h. After cooling, filtration, washing with 3 times 10 ml and drying under vacuum, 2.2 g of beige solid were recovered. The analyses showed that the product was in conf... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Nitrile.Disulfide | Disulfide | c1nc2ccccc2[nH]1 | c1[n+]c2ccccc2[nH]1.c1nc2ccccc2[n+]1 | c1[n+]c2ccccc2[nH]1.c1nc2ccccc2[n+]1 | null | null | null | null | BrCCSSCCBr.CCC#N.Cc1nc2ccccc2n1C>>Cc1n(C)c2ccccc2[n+]1CCSSCC[n+]1c(C)n(C)c2ccccc21.[Br-].[Br-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ec8236a187c1419c973899f581646a85 | Cc1nc2ccccc2n1C.O=C(CCl)NCCSSCCNC(=O)CCl>>Cc1n(CC(=O)NCCSSCCNC(=O)Cn2c(C)[n+](C)c3ccccc32)c2ccccc2[n+]1C.[Cl-].[Cl-] | CN1C(=NC2=C1C=CC=C2)C.S(SCCNC(CCl)=O)CCNC(CCl)=O>>[Cl-].S(SCCNC(CN1C(=[N+](C2=C1C=CC=C2)C)C)=O)CCNC(CN2C(=[N+](C1=C2C=CC=C1)C)C)=O.[Cl-] | [CH3:1][c:2]1[n:3][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[n:35]1[CH3:36].[CH2:4]([C:5](=[O:6])[NH:7][CH2:8][CH2:9][S:10][S:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[CH2:17][Cl:38])[Cl:37]>>[CH3:1][c:2]1[n:3]([CH2:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][S:10][S:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[CH2:17][n:18]2[c:1... | Cc1nc2ccccc2n1C.O=C(CCl)NCCSSCCNC(=O)CCl | Cc1n(CC(=O)NCCSSCCNC(=O)Cn2c(C)[n+](C)c3ccccc32)c2ccccc2[n+]1C.[Cl-].[Cl-] | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 28738305309c509d67ffc78db7b9e5208255930f0a6cea2ebff0bef37b8a5b44 | 93c3c3a9d911884e235f2497f5f3854e35b49abbb8cac69cd063aca2ca6dfc07 | O=C(Cn1c[nH+]c2ccccc21)NCCSSCCNC(=O)Cn1c[nH+]c2ccccc21 | [C;D1;H3:1]-[c:2]1:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n;H0;D3;+0:8]:1-[C;D1;H3:9].[C:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[Cl;H0;D1;+0:15].[C:16]-[#7:17]-[C:18](=[O;D1;H0:19])-[CH2;D2;+0:20]-[Cl;H0;D1;+0:21]>>[C:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[#7;a:22](:[c:23]):[c:24].[C:16]-[#7:1... | 129.8 | [{"value": 129.8, "product": "[Cl-].S(SCCNC(CN1C(=[N+](C2=C1C=CC=C2)C)C)=O)CCNC(CN2C(=[N+](C1=C2C=CC=C1)C)C)=O.[Cl-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of compound 1,2-dimethyl-1H-benzimidazole (2.93 g, 20 mmol) and N,N′-(disulfanediyldiethane-2,1-diyl)bis(2-chloroacetamide) (1.53 g, 5 mmol) in 20 ml of acetonitrile was heated to reflux for 24 h. After cooling, the resulting white solids were collected by filtration and washed with ethyl acetate and dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1nc2ccccc2[nH]1 | c1[n+]c2ccccc2[nH]1.c1[n+]c2ccccc2[nH]1 | c1[n+]c2ccccc2[nH]1.c1[n+]c2ccccc2[nH]1 | null | C(C)#N | null | null | Cc1nc2ccccc2n1C.O=C(CCl)NCCSSCCNC(=O)CCl>C(C)#N>Cc1n(CC(=O)NCCSSCCNC(=O)Cn2c(C)[n+](C)c3ccccc32)c2ccccc2[n+]1C.[Cl-].[Cl-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8955fbefec794c7e845c91bc66158cae | Cc1n(CC(=O)NCCSSCCNC(=O)Cn2c(C)[n+](C)c3ccccc32)c2ccccc2[n+]1C.O=Cc1ccc(N(CCO)CCO)cc1.[Cl-]>>C[n+]1c(C=Cc2ccc(N(CCO)CCO)cc2)n(CC(=O)NCCSSCCNC(=O)Cn2c(C=Cc3ccc(N(CCO)CCO)cc3)[n+](C)c3ccccc32)c2ccccc21.[Cl-] | OCCN(C1=CC=C(C=O)C=C1)CCO.[Cl-].S(SCCNC(CN1C(=[N+](C2=C1C=CC=C2)C)C)=O)CCNC(CN2C(=[N+](C1=C2C=CC=C1)C)C)=O.[Cl-]>>[Cl-].S(SCCNC(CN1C(=[N+](C2=C1C=CC=C2)C)C=CC2=CC=C(C=C2)N(CCO)CCO)=O)CCNC(CN2C(=[N+](C1=C2C=CC=C1)C)C=CC1=CC=C(C=C1)N(CCO)CCO)=O.[Cl-] | [CH3:1][n+:2]1[c:3]([CH3:4])[n:19]([CH2:20][C:21](=[O:22])[NH:23][CH2:24][CH2:25][S:26][S:27][CH2:28][CH2:29][NH:30][C:31](=[O:32])[CH2:33][n:34]2[c:35]([CH3:36])[n+:10]([CH3:52])[c:9]3[cH:8][cH:7][cH:56][cH:57][c:58]32)[c:59]2[cH:60][cH:61][cH:62][cH:63][c:64]12.[CH2:5]([CH2:46][N:42]([c:41]1[cH:40][cH:39][c:38]([CH:3... | Cc1n(CC(=O)NCCSSCCNC(=O)Cn2c(C)[n+](C)c3ccccc32)c2ccccc2[n+]1C.O=Cc1ccc(N(CCO)CCO)cc1.[Cl-] | C[n+]1c(C=Cc2ccc(N(CCO)CCO)cc2)n(CC(=O)NCCSSCCNC(=O)Cn2c(C=Cc3ccc(N(CCO)CCO)cc3)[n+](C)c3ccccc32)c2ccccc21.[Cl-] | null | null | N1CCCCC1.C(C)O | Aromatic Heterocycle Formation | OtherReaction | bfac5f5e36cc85d66578a8f74e1a85d129451539b63d5afed5842fe9dec2515b | 51f1fc92ffad047320e99831383058674edb2b0fe946d4b93d597a6093648550 | O=C(Cn1c(C=Cc2ccccc2)[nH+]c2ccccc21)NCCSSCCNC(=O)Cn1c(C=Cc2ccccc2)[nH+]c2ccccc21 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7;a:5]1:[c;H0;D3;+0:6](-[CH3;D1;+0:7]):[n+;H0;D3:8](-[CH3;D1;+0:9]):[c;H0;D3;+0:10]2:[c:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c:14]:[c;H0;D3;+0:15]:1:2.[#7:16]-[C:17](=[O;D1;H0:18])-[C:19]-[#7;a:20]1:[c:21]:[c:22]:[#7;a;+:23](-[C;D1;H3:24]):[c:25]:1-[CH3;D1;+0:26].[C:27]-[#7:28](-[c:29])-[... | 163.3 | [{"value": 163.3, "product": "[Cl-].S(SCCNC(CN1C(=[N+](C2=C1C=CC=C2)C)C=CC2=CC=C(C=C2)N(CCO)CCO)=O)CCNC(CN2C(=[N+](C1=C2C=CC=C1)C)C=CC1=CC=C(C=C1)N(CCO)CCO)=O.[Cl-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirring solution of 4-[bis(2-hydroxyethyl)-amino]benzaldehyde (1.7 g, 8.1 mmol) and 1,1′-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chloride (1.2 g, 2 mmol) in 35 ml of ethanol, 0.5 ml of piperidine was added as a catalyst. The reaction mixture was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol | Primary alcohol.Primary alcohol.Primary alcohol.Tertiary amine | c1[n+]c2ccccc2[nH]1 | c1ccccc1.c1[n+]c2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1[n+]c2ccccc2[nH]1.c1nc2ccccc2[n+]1 | Other | N1CCCCC1.C(C)O | null | null | Cc1n(CC(=O)NCCSSCCNC(=O)Cn2c(C)[n+](C)c3ccccc32)c2ccccc2[n+]1C.O=Cc1ccc(N(CCO)CCO)cc1.[Cl-]>N1CCCCC1.C(C)O>C[n+]1c(C=Cc2ccc(N(CCO)CCO)cc2)n(CC(=O)NCCSSCCNC(=O)Cn2c(C=Cc3ccc(N(CCO)CCO)cc3)[n+](C)c3ccccc32)c2ccccc21.[Cl-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8195caeae8504cdfb40a16fc4ca39ca5 | O=C1CCC(=O)N1Cl.Oc1ccc2cc(Br)ccc2c1>>Oc1ccc2cc(Br)ccc2c1Cl | ClN1C(CCC1=O)=O.BrC=1C=C2C=CC(=CC2=CC1)O>>BrC=1C=C2C=CC(=C(C2=CC1)Cl)O | O=C1CCC(=O)N1[Cl:13].[OH:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[c:12]1[Cl:13] | O=C1CCC(=O)N1Cl.Oc1ccc2cc(Br)ccc2c1 | Oc1ccc2cc(Br)ccc2c1Cl | null | [Cl-].[Zr+4].[Cl-].[Cl-].[Cl-] | ClCCl | Functional Group Interconversion | Chlorination | 81d64bb32d0f6a3be305261e3f08b82dbfacdc440d165afbf6e1007b89d12ba6 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2ccccc2c1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[O;D1;H1:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6](:[c:7]):[c:8]):[c:3](-[O;D1;H1:2]):[c:4] | 95.4 | [{"value": 95.4, "product": "BrC=1C=C2C=CC(=C(C2=CC1)Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | HOUR | The synthesis of (S1-2) was carried out following the method described in Synlett, No. 18, 2837 (2005), wherein 29.9 g of N-chlorosuccinimide and 600 ml of dichloromethane were added to a reactor in nitrogen atmosphere and cooled to 0° C., 2.6 g of zirconium (IV) chloride was added, and then 50 g of 6-bromo-2-naphthol ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HO- | [Cl-].[Zr+4].[Cl-].[Cl-].[Cl-].ClCCl | 0 | 10 | O=C1CCC(=O)N1Cl.Oc1ccc2cc(Br)ccc2c1>[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-].ClCCl>Oc1ccc2cc(Br)ccc2c1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ecfb716693ae4e1b944330ff514b9b38 | CCCCCc1ccc(OB(O)O)cc1.Oc1ccc2cc(Br)ccc2c1Cl>>CCCCCc1ccc(-c2ccc3c(Cl)c(O)ccc3c2)cc1 | BrC=1C=C2C=CC(=C(C2=CC1)Cl)O.C(CCCC)C1=CC=C(C=C1)OB(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C.C(C)O.O>>C(CCCC)C1=CC=C(C=C1)C=1C=C2C=CC(=C(C2=CC1)Cl)O | OB(O)O[c:9]1[cH:8][cH:7][c:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:23][cH:22]1.Br[c:10]1[cH:11][cH:12][c:13]2[c:14]([Cl:15])[c:16]([OH:17])[cH:18][cH:19][c:20]2[cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[c:14]([Cl:15])[c:16]([OH:17])[cH:18][cH:19][c:20]3[cH:21]2... | CCCCCc1ccc(OB(O)O)cc1.Oc1ccc2cc(Br)ccc2c1Cl | CCCCCc1ccc(-c2ccc3c(Cl)c(O)ccc3c2)cc1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 9fc9dff744cc846334d9bc7e7a64db654dd19d3989d30f8148ed6edada90c4b1 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2ccc3ccccc3c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 78.1 | [{"value": 78.1, "product": "C(CCCC)C1=CC=C(C=C1)C=1C=C2C=CC(=C(C2=CC1)Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | At first, 55 g of 6-bromo-1-chloro-2-naphthol (S1-2), 12.3 g of 4-pentyl-phenylboric acid (S1-3), 1.0 g of tetrakis(triphenylphosphine) palladium, 13.6 g of sodium carbonate and 100 ml of a mixed solvent of toluene/ethanol/water=3/3/1 were added to a reactor in nitrogen atmosphere and refluxed for 10 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | CCCCCc1ccc(OB(O)O)cc1.Oc1ccc2cc(Br)ccc2c1Cl>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>CCCCCc1ccc(-c2ccc3c(Cl)c(O)ccc3c2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-36825357a8654c3ebe21c8be8ba058ad | C#CCCCCC.Oc1ccc2cc(Br)ccc2c1Cl>>CCCC#Cc1ccc2c(Cl)c(O)ccc2c1 | ClC1=C(C=CC2=CC(=CC=C12)Br)O.C#CCCCCC>>ClC1=C(C=CC2=CC(=CC=C12)C#CCCC)O | C(C[CH2:3][C:4]#[CH:5])[CH2:2][CH3:1].Br[c:6]1[cH:7][cH:8][c:9]2[c:10]([Cl:11])[c:12]([OH:13])[cH:14][cH:15][c:16]2[cH:17]1>>[CH3:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Cl:11])[c:12]([OH:13])[cH:14][cH:15][c:16]2[cH:17]1 | C#CCCCCC.Oc1ccc2cc(Br)ccc2c1Cl | CCCC#Cc1ccc2c(Cl)c(O)ccc2c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | C(C)N(CC)CC | C-C Coupling | OtherReaction | 427d52803b094b22f8f109b6c17c82e6ccc9792ebeaad9bc5ad19cad543470b3 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2ccccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[CH2;D2;+0:7]-C-C-[CH2;D2;+0:8]-[C:9]#[CH;D1;+0:10]>>[C;D1;H3:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[C:9]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 88.7 | [{"value": 88.7, "product": "ClC1=C(C=CC2=CC(=CC=C12)C#CCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The synthesis of (S7-3) was carried out following the method described in Synthesis, No. 9, 1439 (2004). At first, 38.3 g of 1-chloro-6-bromo-2-naphthol (S1-2), 5.2 g of PdCl2(PPh3)2, 0.71 g of copper iodide and 400 ml of triethylamine were added to a reactor in nitrogen atmosphere, stirred at room temperature, added w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)N(CC)CC | null | null | C#CCCCCC.Oc1ccc2cc(Br)ccc2c1Cl>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)N(CC)CC>CCCC#Cc1ccc2c(Cl)c(O)ccc2c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4ee3e8ab5fd74d1e987263adc9c61aec | CO.Nc1ccc(CCCC(=O)O)cc1>>COC(=O)CCCc1ccc(N)cc1 | NC1=CC=C(C=C1)CCCC(=O)O.CO.Cl>>Cl.NC1=CC=C(C=C1)CCCC(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]1 | CO.Nc1ccc(CCCC(=O)O)cc1 | COC(=O)CCCc1ccc(N)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[C;D1;H3:5] | null | [] | 85 | CELSIUS | 8 | HOUR | 4-(4-Aminophenyl)butyric acid (5 g) was dissolved in 40 ml methanol. The solution was refluxed at 80-90° C. with stirring for 4 h while hydrogen chloride gas was bubbled through the solution. After the reaction mixture was cooled to room temperature, ethyl ether (100 ml.) was added. The mixture, which separated into tw... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | 85 | 8 | CO.Nc1ccc(CCCC(=O)O)cc1>>COC(=O)CCCc1ccc(N)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7ad3c80e6a114559a344dfef4ff5a10f | C=CC(=O)O.CC(CO)(CO)CO>>C=C(C)C(=O)[O-] | C(C=C)(=O)[O-].C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(O)C(C)(CO)CO.C(C=C)(=O)O.C(C=C)(=O)O.C(O)C(CC)(CO)CO>>C(C=C)(=O)[O-].C(C(=C)C)(=O)[O-] | C=C[C:4](=[O:5])[OH:6].OC[C:2](CO)([CH2:1]O)[CH3:3]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O-:6] | C=CC(=O)O.CC(CO)(CO)CO | C=C(C)C(=O)[O-] | null | null | null | C-C Coupling | OtherReaction | 62f73fadabecb1028dc44d47a4aa6deabc8d2947414bdf9221d3464bf4781db4 | 0321122f7e5bc0e71191c2a7ff8ac8dbdb901c1574c2a7fc8617c3d7157b5e18 | null | C=C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:3].O-C-[C;H0;D4;+0:4](-[C;D1;H3:5])(-C-O)-[CH2;D2;+0:6]-O>>[C;D1;H3:5]-[C;H0;D3;+0:4](=[CH2;D1;+0:6])-[C;H0;D3;+0:1](-[O-;H0;D1:3])=[O;D1;H0:2] | null | [] | null | null | null | null | The monomer or oligomer used in the invention is preferably a monomer or oligomer which has two or more ethylenic unsaturated double bonds and which is addition-polymerized by irradiation with light. The monomer or oligomer may be a compound having at least one addition-polymerizable ethylenic unsaturated group therein... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Primary alcohol.Primary alcohol.Vinyl | Vinyl | null | null | null | HO- | null | null | null | C=CC(=O)O.CC(CO)(CO)CO>>C=C(C)C(=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c9764fada08d4935a6780c2b27f8914f | CC(C)CC=O.CCOC(=O)CC#N.[C-]#N>>CC(C)CC(C#N)CC#N | [C-]#N.[K+].C(#N)CC(=O)OCC.C(CC(C)C)=O.CCCCCC.[C-]#N.[K+]>>C(C(C)C)C(C#N)CC#N | O=[CH:5][CH2:4][CH:2]([CH3:1])[CH3:3].CCOC(=O)[CH2:8][C:9]#[N:10].[C-:6]#[N:7]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([C:6]#[N:7])[CH2:8][C:9]#[N:10] | CC(C)CC=O.CCOC(=O)CC#N.[C-]#N | CC(C)CC(C#N)CC#N | null | N1CCCCC1 | O | C-C Coupling | OtherReaction | 6dc05b3a6e876c75c6dbab5781f5480d959c666dfb7ac5ccc518a35ff90a9256 | e26083923a4a9500fd7be37ec20ca2eb2438e97a8c4290618ebb404c7dafc6a3 | null | C-C-O-C(=O)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[CH;D2;+0:4]-[C:5]-[C:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[C:6]-[C:5]-[CH;D3;+0:4](-[C;H0;D2;+0:7]#[N;D1;H0:8])-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3] | 99 | [{"value": 99.0, "product": "C(C(C)C)C(C#N)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of ethyl cyanoacetate (73.3 g, 6.48 mol), isovaleraldehyde (613.9 g, 7.13 mol), piperidine (5.5 g, 0.065 mol), and hexane (0.5 L) was placed under reflux with continuous removal of water. When no additional water was collected, the mixture was cooled and distilled under vacuum to remove solvent. Isopropanol (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Nitrile | null | null | null | HO- | N1CCCCC1.O | null | 4 | CC(C)CC=O.CCOC(=O)CC#N.[C-]#N>N1CCCCC1.O>CC(C)CC(C#N)CC#N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1f983ea140bf4fae817d9268d98150b0 | CC(C)CC(C#N)CC#N.O.[OH-]>>CC(C)C[C@H](C#N)CC(=O)[O-] | C(C(C)C)C(C#N)CC#N.[OH-].[K+].O>>C(#N)[C@H](CC(=O)[O-])CC(C)C.[K+] | N#[C:9][CH2:8][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6]#[N:7].[OH2:10].[OH-:11]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([C:6]#[N:7])[CH2:8][C:9](=[O:10])[O-:11] | CC(C)CC(C#N)CC#N.O.[OH-] | CC(C)C[C@H](C#N)CC(=O)[O-] | null | null | null | Acylation | OtherReaction | cb9a8ea3ed9eeb498b619a6b85570e3b997dc347c183b7d17f284dca9ec775a0 | 008964d7bb90cfbde4bd18c4917d4eb54e22d0dca2eed4eedb8aa20612ca2af7 | null | N#[C;H0;D2;+0:1]-[C:2]-[C:3].[OH-;D0:4].[OH2;D0;+0:5]>>[C:3]-[C:2]-[C;H0;D3;+0:1](-[O-;H0;D1:4])=[O;H0;D1;+0:5] | 31.3 | [{"value": 31.3, "product": "C(#N)[C@H](CC(=O)[O-])CC(C)C.[K+]", "details": "PERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 24 | HOUR | Two 125 mL jacketed reaction vessels maintained at 30° C. were each charged with 2-isobutyl-succinonitrile (6.81 g), NIT-102 C2 (1.70 g) and 118.2 mL of reaction buffer. After stirring for 24 h, the product mixtures were decanted, leaving the enzyme catalyst in the reaction vessels. Reaction buffer (20 mL) was added to... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | null | null | Other | null | 30 | 24 | CC(C)CC(C#N)CC#N.O.[OH-]>>CC(C)C[C@H](C#N)CC(=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bd8fc4c7ce38441fa4641ac7dc4e14fb | CC(C)C[C@H](C#N)CC(=O)[O-]>>CC(C)C[C@H](CN)CC(=O)O | [H][H].C(#N)[C@H](CC(=O)[O-])CC(C)C.[K+].O.[OH-].[K+]>>NC[C@H](CC(=O)O)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([C:6]#[N:7])[CH2:8][C:9](=[O:10])[O-:11]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([CH2:6][NH2:7])[CH2:8][C:9](=[O:10])[OH:11] | CC(C)C[C@H](C#N)CC(=O)[O-] | CC(C)C[C@H](CN)CC(=O)O | null | [Ni] | C(C)(C)O | Reduction | OtherReaction | d1bed676818ccfba4538548ad5725e14faa0bde929d3b81751cf51bb1324050c | 98da29020170d02a49096f4ff0f65efc1df41f78dba9143e9ca571d3472e4c6a | null | [C:1]-[C:2](-[C:3]-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6])-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]>>[C:1]-[C:2](-[C:3]-[C:4](=[O;D1;H0:6])-[OH;D1;+0:5])-[CH2;D2;+0:7]-[NH2;D1;+0:8] | 26.1 | [{"value": 26.1, "product": "NC[C@H](CC(=O)O)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | A mixture of potassium (S)-3-cyano-5-methylhexanoate (20 g, 103.5 mmol), water (50 mL), 45% KOH (12 g), isopropanol (12 g), and Raney Nickel were shaken overnight in a Parr Shaker under 50 psi of hydrogen. The mixture was filtered, heated to approximately 50° C., treated with acetic acid (6.5 mL) and stirred overnight ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid.Primary amine | null | null | null | null | [Ni].C(C)(C)O | 50 | 8 | CC(C)C[C@H](C#N)CC(=O)[O-]>[Ni].C(C)(C)O>CC(C)C[C@H](CN)CC(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4e9f69e5b34e4ce9a111518c0a0e0d2c | CC(C)C[C@@H](C#N)CC#N>>CC(C)CC(C#N)CC#N | C(C(C)C)[C@@H](C#N)CC#N.C(C(C)C)[C@@H](C#N)CC#N.C1(=CC=CC=C1)C.N12CCCCCC2=NCCC1>>C(C(C)C)C(C#N)CC#N | [CH3:1][CH:2]([CH3:3])[CH2:4][C@@H:5]([C:6]#[N:7])[CH2:8][C:9]#[N:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([C:6]#[N:7])[CH2:8][C:9]#[N:10] | CC(C)C[C@@H](C#N)CC#N | CC(C)CC(C#N)CC#N | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 84 | [{"value": 84.0, "product": "C(C(C)C)C(C#N)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The racemization of (R)-2-isobutyl-succinonitrile was carried out on material recovered from bioconversion of racemic 2-isobutyl-succinonitrile with NIT-102 C2. A mixture of (R)-2-isobutyl-succinonitrile (1.36 g, 10 mmol, 69% ee), toluene (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.076 g, 5 mmol) was refluxed... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | CC(C)C[C@@H](C#N)CC#N>O>CC(C)CC(C#N)CC#N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9e2a7d5ee6154d40b7d62d423320545d | CC(C)(C)C(=O)Cl.Nc1cnc(Br)cn1>>CC(C)(C)C(=O)Nc1cnc(Br)cn1 | CC(C(=O)Cl)(C)C.NC1=NC=C(N=C1)Br.ClCCl.N1=CC=CC=C1>>BrC=1N=CC(=NC1)NC(C(C)(C)C)=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][n:10][c:11]([Br:12])[cH:13][n:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10][c:11]([Br:12])[cH:13][n:14]1 | CC(C)(C)C(=O)Cl.Nc1cnc(Br)cn1 | CC(C)(C)C(=O)Nc1cnc(Br)cn1 | null | null | C(C)O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cnccn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1 | 90.4 | [{"value": 90.4, "product": "BrC=1N=CC(=NC1)NC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "BrC=1N=CC(=NC1)NC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | A 3-necked 1 L round bottomed flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen inlet/outlet was charged with 50.00 g (287.4 mmol) of 2-amino-5-bromopyrazine (1), 218 mL of dichloromethane and 30.50 mL (377.1 mmol) of pyridine. Then, 39.30 mL (319.1 mmol) of trimethylacetyl chloride (PivCl) wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnccn1 | HCl | C(C)O | 40 | 2 | CC(C)(C)C(=O)Cl.Nc1cnc(Br)cn1>C(C)O>CC(C)(C)C(=O)Nc1cnc(Br)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c52e6a4d4f9a43eb8ee7ebb98fc9064c | CC(=O)OC(C)(C)C.COC(=O)c1cnc(NC(=O)C(C)(C)C)cn1>>CC(C)(C)OC(=O)CC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | C(C)(=O)OC(C)(C)C.COC(=O)C1=NC=C(N=C1)NC(C(C)(C)C)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>C(C)(C)(C)OC(CC(=O)C1=NC=C(N=C1)NC(C(C)(C)C)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH3:8].CO[C:9](=[O:10])[c:11]1[cH:12][n:13][c:14]([NH:15][C:16](=[O:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][n:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][n:13][c:14]([NH:15][C:16](=[O:17])[C:18]([CH3:19])([CH3:20])[CH3... | CC(=O)OC(C)(C)C.COC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | CC(C)(C)OC(=O)CC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1cnccn1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:13]-[C:14](-[CH3;D1;+0:15])=[O;D1;H0:16]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:13]-[C:14](=[O;D1;H0:16])-[CH2;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c... | null | [] | -20 | CELSIUS | 40 | MINUTE | A 3-necked 1-L round bottomed flask equipped with a magnetic stirrer, addition funnel, thermocouple probe and nitrogen inlet/outlet was charged with 25.00 mL (185.5 mmol) of tert-butyl acetate, 20.00 g (84.30 mmol) of the compound prepared in step 2 and 20 mL of THF. After cooling to −20° C., a solution of 261.4 mL (26... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1cnccn1 | HO- | C1CCOC1 | -20 | 0.666667 | CC(=O)OC(C)(C)C.COC(=O)c1cnc(NC(=O)C(C)(C)C)cn1>C1CCOC1>CC(C)(C)OC(=O)CC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d44c0ab013454a00a29d89cf16f093fb | CC(C)(C)OC(=O)CC(=O)c1cnc(NC(=O)C(C)(C)C)cn1.O=C1CCC(=O)N1Br>>CC(C)(C)OC(=O)C(Br)C(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | C(C)(C)(C)OC(CC(=O)C1=NC=C(N=C1)NC(C(C)(C)C)=O)=O.C(C)(C)(C)OC(CC(=O)C1=NC=C(N=C1)NC(C(C)(C)C)=O)=O.BrN1C(CCC1=O)=O>>C(C)(C)(C)OC(C(C(=O)C1=NC=C(N=C1)NC(C(C)(C)C)=O)Br)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:10](=[O:11])[c:12]1[cH:13][n:14][c:15]([NH:16][C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][n:24]1.O=C1CCC(=O)N1[Br:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([Br:9])[C:10](=[O:11])[c:12]1[cH:13][n:14][c:15]([NH:16][C:17](=[O:18])[C:1... | CC(C)(C)OC(=O)CC(=O)c1cnc(NC(=O)C(C)(C)C)cn1.O=C1CCC(=O)N1Br | CC(C)(C)OC(=O)C(Br)C(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | null | [Br-].[Li+] | CC(CC)=O | Functional Group Interconversion | Wohl-Ziegler bromination carbonyl secondary | 378bfaa227061b3b87fe41d7f0ed9bc6e32aaccb8a79603355b3ea7208512823 | 3d14e126a2db3a0341a7e40fc42485c00b479abde6df306a6b05aa95fa66fc97 | c1cnccn1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]):[#7;a:15]>>[#7;a:2]:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[Br;H0;D1;+0:1])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[... | null | [] | null | null | 1 | HOUR | A 1-L round bottomed flask equipped with a magnetic stirrer was charged with 73.00 mg (0.841 mmol) of lithium bromide and the butanone solution obtained in step 3 (ca. 100 mL), which theoretically contained 27.09 g (84.30 mmol) of 3-[5-(2,2-dimethyl-propionylamino)-pyrazin-2-yl]-3-oxo-propionic acid-tert-butyl ester an... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Tertiary amide.Tertiary amide | Secondary halide | C1CCNC1 | null | c1cnccn1 | HO- | [Br-].[Li+].CC(CC)=O | null | 1 | CC(C)(C)OC(=O)CC(=O)c1cnc(NC(=O)C(C)(C)C)cn1.O=C1CCC(=O)N1Br>[Br-].[Li+].CC(CC)=O>CC(C)(C)OC(=O)C(Br)C(=O)c1cnc(NC(=O)C(C)(C)C)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-be1165b7684041fa91ec2ef11dffc25a | CC(=O)O.CC(C)(C)C(=O)Nc1cnc(C(=O)CBr)cn1>>CC(=O)OCC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | BrCC(=O)C=1N=CC(=NC1)NC(C(C)(C)C)=O.C(C)(=O)O.CN(C)C=O.C(C)(=O)[O-].[Na+]>>CC(C(=O)NC=1N=CC(=NC1)C(COC(C)=O)=O)(C)C | [CH3:1][C:2](=[O:3])[OH:4].Br[CH2:5][C:6](=[O:7])[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][n:20]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][n:20]1 | CC(=O)O.CC(C)(C)C(=O)Nc1cnc(C(=O)CBr)cn1 | CC(=O)OCC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | null | null | C([O-])(O)=O.[Na+].C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 0a34f89ec364d3fdae2ae7b8ae6d57bca28a6817d300e53d63c96938c9decea2 | 74650eef1e59339f2bab6a723374286cbec450331ae083c312d7e2d35fb28786 | c1cnccn1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7].[C;D1;H3:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[#7;a:7]:[c:6]:[c:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[C:9](-[C;D1;H3:8])=[O;D1;H0:10]):[#7;a:5] | 90.9 | [{"value": 90.0, "product": "CC(C(=O)NC=1N=CC(=NC1)C(COC(C)=O)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "CC(C(=O)NC=1N=CC(=NC1)C(COC(C)=O)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A 500 mL round bottomed flask equipped with a magnetic stirrer, addition funnel, thermocouple probe and nitrogen inlet/outlet was charged with 4.40 mL (76.86 mmol) of acetic acid, 140 mL of DMF and 7.000 g (85.33 mmol) of sodium acetate. Then, 23.30 g (77.62 mmol) of the compound obtained in step 5 was added portionwis... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ketone.Ester | null | null | c1cnccn1 | HBr | C([O-])(O)=O.[Na+].C(C)(=O)OCC | null | 1 | CC(=O)O.CC(C)(C)C(=O)Nc1cnc(C(=O)CBr)cn1>C([O-])(O)=O.[Na+].C(C)(=O)OCC>CC(=O)OCC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a51e3f161c854b78a1d46c42a07deb48 | CC(=O)OCC(=O)c1cnc(NC(=O)C(C)(C)C)cn1>>CC(C)(C)C(=O)Nc1cnc([C@H](O)CO)cn1 | C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C4N=CN=C5N)OP(=O)(O)O)O)O)O)C(=O)N.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC(C(=O)NC=1N=CC(=NC1)C(COC(C)=O)=O)(C)C.[OH-].[Na+]>>O[C@H](CO)C=1N=CC(=NC1)NC(C(C)(C)C)=O | CC(=O)[O:15][CH2:14][C:12]([c:11]1[n:10][cH:9][c:8]([NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[n:17][cH:16]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10][c:11]([C@H:12]([OH:13])[CH2:14][OH:15])[cH:16][n:17]1 | CC(=O)OCC(=O)c1cnc(NC(=O)C(C)(C)C)cn1 | CC(C)(C)C(=O)Nc1cnc([C@H](O)CO)cn1 | null | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | COC(C)(C)C | Reduction | OtherReaction | 67089bd4b5ba61d4201285032d065b7dbb074f27b1058a42daae9f0677a26309 | fb0acaa903b6e5b1d95989a91fad01e909b2ecc65b96c636622bf14cc20a64c2 | c1cnccn1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1>>[OH;D1;+0:4]-[C@H;D3;+0:3](-[C:2]-[OH;D1;+0:1])-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1 | 105.1 | [{"value": 105.1, "product": "O[C@H](CO)C=1N=CC(=NC1)NC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 37 | CELSIUS | 11.2 | HOUR | 50 g of acetic acid 2-[5-(2,2-dimethylpropionylamino)-pyrazin-2-yl]-2-oxo-ethyl ester (178 mmol) was stirred in 150 ml tert-butyl methyl ether (TBME). Subsequently the reaction buffer, 674 mL 20 mM of 2-(4-morpholino)-ethansulfonic acid, and 100.1 g of D-glucose (658 mmol) were added. The temperature was adjusted to 29... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Primary alcohol.Secondary alcohol | null | null | c1cnccn1 | Other | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.COC(C)(C)C | 37 | 11.2 | CC(=O)OCC(=O)c1cnc(NC(=O)C(C)(C)C)cn1>O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.COC(C)(C)C>CC(C)(C)C(=O)Nc1cnc([C@H](O)CO)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9d5a4d4f98314113864f6374baf40375 | CC1(C)OC[C@H](c2cnc(NC(=O)C(C)(C)C)cn2)O1>>CC1(C)OC[C@H](c2cnc(N)cn2)O1 | CC1(OC[C@@H](O1)C=1N=CC(=NC1)NC(C(C)(C)C)=O)C.C([O-])([O-])=O.[K+].[K+]>>CC1(OC[C@@H](O1)C=1N=CC(=NC1)N)C | CC(C)(C)C(=O)[NH:11][c:10]1[n:9][cH:8][c:7]([C@H:6]2[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:14]2)[n:13][cH:12]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([c:7]2[cH:8][n:9][c:10]([NH2:11])[cH:12][n:13]2)[O:14]1 | CC1(C)OC[C@H](c2cnc(NC(=O)C(C)(C)C)cn2)O1 | CC1(C)OC[C@H](c2cnc(N)cn2)O1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1cnc([C@H]2COCO2)cn1 | C-C(-C)(-C)-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 63 | [{"value": 63.0, "product": "CC1(OC[C@@H](O1)C=1N=CC(=NC1)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.7, "product": "CC1(OC[C@@H](O1)C=1N=CC(=NC1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 16.5 | HOUR | A mixture of N-[5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (8.4 g, 30.7 mmol) and potassium carbonate (4.32 g, 31.2 mmol) in methanol (150 mL) was stirred at 25° C. for 16.5 h, at which time, thin layer chromatography suggested partial conversion to a more polar product. In an effor... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1COCO1.c1cnccn1 | HO- | CO | 25 | 16.5 | CC1(C)OC[C@H](c2cnc(NC(=O)C(C)(C)C)cn2)O1>CO>CC1(C)OC[C@H](c2cnc(N)cn2)O1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ee129ff49d444468b0d5f9e3b6d54c78 | CC1(C)OC[C@H](c2cnc(N)cn2)O1.CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)O)cc1Cl>>CC1(C)OC[C@H](c2cnc(NC(=O)[C@H](CC3CCCC3)c3ccc(S(C)(=O)=O)c(Cl)c3)cn2)O1 | CC1(OC[C@@H](O1)C=1N=CC(=NC1)N)C.ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)O)CC1CCCC1.Cl.N1=CC=CC=C1.C(C(=O)Cl)(=O)Cl>>ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H]1OC(OC1)(C)C)CC1CCCC1 | [CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([c:7]2[cH:8][n:9][c:10]([NH2:11])[cH:32][n:33]2)[O:34]1.O[C:12](=[O:13])[C@H:14]([CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1)[c:21]1[cH:22][cH:23][c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[c:29]([Cl:30])[cH:31]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([c:7]2[cH:8][n:9][c... | CC1(C)OC[C@H](c2cnc(N)cn2)O1.CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)O)cc1Cl | CC1(C)OC[C@H](c2cnc(NC(=O)[C@H](CC3CCCC3)c3ccc(S(C)(=O)=O)c(Cl)c3)cn2)O1 | null | CN(C=O)C | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc([C@H]2COCO2)cn1)[C@H](CC1CCCC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[C:4]-[C:3](-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1 | 92.4 | [{"value": 92.0, "product": "ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H]1OC(OC1)(C)C)CC1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H]1OC(OC1)(C)C)CC1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | 25 | CELSIUS | 15 | MINUTE | A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in Example 1, 6.29 g, 19.01 mmol) and N,N-dimethylformamide (2 drops) in methylene chloride (70 mL) was stirred at 2° C. and then treated with oxalyl chloride (4.15 mL, 45.7 mmol). The mixture was stirred at 2° C. for 5 min... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCO1.c1cnccn1.C1CCCC1.c1ccccc1 | HO- | CN(C=O)C.C(Cl)Cl | 25 | 0.25 | CC1(C)OC[C@H](c2cnc(N)cn2)O1.CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)O)cc1Cl>CN(C=O)C.C(Cl)Cl>CC1(C)OC[C@H](c2cnc(NC(=O)[C@H](CC3CCCC3)c3ccc(S(C)(=O)=O)c(Cl)c3)cn2)O1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e0cbd1d1d82348cab77171db0c6c9b71 | CC1(C)OC[C@H](c2cnc(NC(=O)[C@H](CC3CCCC3)c3ccc(S(C)(=O)=O)c(Cl)c3)cn2)O1>>CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)Nc2cnc([C@H](O)CO)cn2)cc1Cl | ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H]1OC(OC1)(C)C)CC1CCCC1.Cl>>ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H](CO)O)CC1CCCC1 | CC1(C)[O:24][C@@H:23]([c:22]2[n:21][cH:20][c:19]([NH:18][C:16]([C@@H:9]([c:8]3[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:30]([Cl:31])[cH:29]3)[CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)=[O:17])[n:28][cH:27]2)[CH2:25][O:26]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C@@H:9]([CH2:10][CH:11]2[CH2... | CC1(C)OC[C@H](c2cnc(NC(=O)[C@H](CC3CCCC3)c3ccc(S(C)(=O)=O)c(Cl)c3)cn2)O1 | CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)Nc2cnc([C@H](O)CO)cn2)cc1Cl | null | null | O1CCCC1 | Deprotection | Acetal hydrolysis to diol | 5f7e1daa6b91d1ca6716348acae46f804565b19cb8bd8a05be2ed6c083743e87 | d0de49ebcb43eafba55a762f6d5237c53d7a87b3a882d6753f793a17a3c3a120 | O=C(Nc1cnccn1)[C@H](CC1CCCC1)c1ccccc1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[c:3](:[#7;a:4]):[c:5]:[#7;a:6])-[C:7]-[O;H0;D2;+0:8]-1>>[#7;a:4]:[c:3](-[C:2](-[OH;D1;+0:1])-[C:7]-[OH;D1;+0:8]):[c:5]:[#7;a:6] | 88 | [{"value": 88.0, "product": "ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H](CO)O)CC1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "ClC=1C=C(C=CC1S(=O)(=O)C)[C@H](C(=O)NC1=NC=C(N=C1)[C@@H](CO)O)CC1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 15 | MINUTE | A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrazin-2-yl]-propionamide (8.85 g, 17.4 mmol) in tetrahydrofuran (50 mL) was treated with a 1N aqueous hydrochloric acid solution (50 mL). The resulting milky reaction mixture was stirred at 25° C., and with... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Secondary alcohol | C1COCO1 | null | c1ccccc1.C1CCCC1.c1cnccn1 | Other | O1CCCC1 | 25 | 0.25 | CC1(C)OC[C@H](c2cnc(NC(=O)[C@H](CC3CCCC3)c3ccc(S(C)(=O)=O)c(Cl)c3)cn2)O1>O1CCCC1>CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)Nc2cnc([C@H](O)CO)cn2)cc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aa18151d93744dfa8c50f3a6124f9344 | CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O.COOC(OOC)c1ccc(OC)cc1>>COc1ccc(C2OCC(C)(C)C(C(=O)NCCC(=O)O)O2)cc1 | [Na+].[Cl-].C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O.COOC(C1=CC=C(C=C1)OC)OOC.C(CCNC([C@H](O)C(C)(C)CO)=O)(=O)O>>COC1=CC=C(C=C1)C1OCC(C(O1)C(=O)NCCC(=O)O)(C)C | [OH:8][CH2:9][C:10]([CH3:11])([CH3:12])[C@H:13]([C:14](=[O:15])[NH:16][CH2:17][CH2:18][C:19](=[O:20])[OH:21])[OH:22].COO[CH:7](OOC)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[O:8][CH2:9][C:10]([CH3:11])([CH3:12])[CH:13]([C:14](=[O:15])[NH:16][CH2:17][CH2:18][C:19](=... | CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O.COOC(OOC)c1ccc(OC)cc1 | COc1ccc(C2OCC(C)(C)C(C(=O)NCCC(=O)O)O2)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1c9ed7e9907a52aa853017401ba192a392555ad3bdef93bc4ebed717b1a6bd37 | 8b2fe1279ea7c0102f8cff4096ea33dc53f0367c0044ecf40a029bb7b576474a | c1ccc(C2OCCCO2)cc1 | C-O-O-[CH;D3;+0:1](-O-O-C)-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C@H;D3;+0:9](-[OH;D1;+0:10])-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C:14]-[OH;D1;+0:15]>>[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[O;H0;D2;+0:10]-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[O;H0;D2;+0:15]-[C:14]-[C:11]-1(-[C;D1;H3:12])-[C;D1;... | 51 | [{"value": 51.0, "product": "COC1=CC=C(C=C1)C1OCC(C(O1)C(=O)NCCC(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Pantothenic acid (7) (4.6 g, 2.24×10−2 mols) was dissolved in dry DCM (30 mL). Camphor sulfonic acid (0.52 g, 2.24×10−3 mols) and p-anisaldehyde-dimethoxy-acetal (3.82 mL, 2.24×10−2 mols) were added to the reaction mixture. The reaction was stirred overnight at room temperature with a drying tube. The crude reaction pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol.Peroxide.Peroxide | Ether.Ether | null | C1COCOC1 | c1ccccc1.C1COCOC1 | HO- | C(Cl)Cl | null | 8 | CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O.COOC(OOC)c1ccc(OC)cc1>C(Cl)Cl>COc1ccc(C2OCC(C)(C)C(C(=O)NCCC(=O)O)O2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-71ffcbba883a4093b8e3933b35c16e12 | C#CCO.CC(C)(C)OC(=O)NCCC(=O)O>>C#CCOC(=O)CCNC(=O)OC(C)(C)C | C(=O)(OC(C)(C)C)NCCC(=O)O.C(C#C)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C#C)OC(CCNC(=O)OC(C)(C)C)=O | [CH:1]#[C:2][CH2:3][OH:4].O[C:5](=[O:6])[CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH:1]#[C:2][CH2:3][O:4][C:5](=[O:6])[CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | C#CCO.CC(C)(C)OC(=O)NCCC(=O)O | C#CCOC(=O)CCNC(=O)OC(C)(C)C | null | null | CCOC(=O)C | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H1:5]#[C:6]-[C:7]-[OH;D1;+0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:7]-[C:6]#[C;D1;H1:5] | null | [] | null | null | null | null | N-Boc-β-alanine (1.91 g, 10.1 mmol) and propargyl alcohol (0.675 g, 12 mmol) were dissolved in EtOAc (25 mL). Dicyclohexyl-carbodiimide (DCC, 2.06 g, 10 mmol) was added to the solution and after 16 h of stirring at room temperature, the reaction mixture was filtered and evaporated to dryness under vacuum. Crude product... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | null | HO- | CCOC(=O)C | null | null | C#CCO.CC(C)(C)OC(=O)NCCC(=O)O>CCOC(=O)C>C#CCOC(=O)CCNC(=O)OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-81c8b3c0439348328e900f92313d677b | C#CCN.O>>C#CC(N)=O | O.C(C)(C)(C)OC(=O)NCCC(=O)O.C(C#C)N.C(C)(C)N=C=NC(C)C>>C(C#C)(=O)N.C(=O)(OC(C)(C)C)NCCC(=O)O | [CH:1]#[C:2][CH2:3][NH2:4].[OH2:5]>>[CH:1]#[C:2][C:3]([NH2:4])=[O:5] | C#CCN.O | C#CC(N)=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | eab691698070c5dee83e588a0e8bed5d626b2f9511ddcfdefa508073baf7bdbd | beeeedd85cd19caa5cbb31250c77bce1d6f3aa4d0aa1624d5dbe675657f87894 | null | [C;D1;H1:1]#[C:2]-[CH2;D2;+0:3]-[N;D1;H2:4].[OH2;D0;+0:5]>>[C;D1;H1:1]#[C:2]-[C;H0;D3;+0:3](-[N;D1;H2:4])=[O;H0;D1;+0:5] | null | [] | null | null | 16 | HOUR | N-Boc-β-alanine (1a) (1.05 g, 5.5 mmol) and propargyl amine (0.90 g, 16.5 mmol) were dissolved in THF (10 mL). Diisopropyl-carbodiimide (DIC, 695 g, 5.5 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. Water was added (20 mL) and the product was extracted into EtOAc (3×30 mL). The comb... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amide | null | null | null | null | C1CCOC1 | null | 16 | C#CCN.O>C1CCOC1>C#CC(N)=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8e758045aae44395ac6c2925d1fafcd3 | CC(=O)OC(C)=O.NCCC(=O)O>>CC(=O)NCCC(=O)O | C(C)(=O)OC(C)=O.NCCC(=O)O.C(C)#N.C(C)(=O)OC(C)=O>>C(C)(=O)NCCC(=O)O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][CH2:6][C:7](=[O:8])[OH:9]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][C:7](=[O:8])[OH:9] | CC(=O)OC(C)=O.NCCC(=O)O | CC(=O)NCCC(=O)O | null | null | C(=O)(O)[O-].[Na+] | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | null | 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](=[O;D1;H0:8])-[O;D1;H1:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | 3 | HOUR | To a solution of β-alanine (2.25 g, 25 mmol) in aq. NaHCO3 (15 mL) was added acetonitrile (15 mL) and acetic anhydride (2.55 g, 25 mmol). The reaction mixture was stirred at room temperature for 3 h. Acetic anhydride (2.55 g, 25 mmol) was added and after 2 h and pH was adjusted to 4-5 by addition of NaH2PO4.
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | null | HO- | C(=O)(O)[O-].[Na+] | null | 3 | CC(=O)OC(C)=O.NCCC(=O)O>C(=O)(O)[O-].[Na+]>CC(=O)NCCC(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-128be03e30fc479198b6496eaff8785b | C#CCCC(=O)O.CCOC(=O)CON>>C#CCCC(=O)NOCC(=O)OCC | C(C)OC(CON)=O.C(CCC#C)(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)OC(CONC(CCC#C)=O)=O | O[C:5]([CH2:4][CH2:3][C:2]#[CH:1])=[O:6].[NH2:7][O:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH3:14]>>[CH:1]#[C:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][O:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH3:14] | C#CCCC(=O)O.CCOC(=O)CON | C#CCCC(=O)NOCC(=O)OCC | null | null | CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]#[C;D1;H1:6].[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#8:11]-[NH2;D1;+0:12]>>[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#8:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]#[C;D1;H1:6] | null | [] | null | null | 16 | HOUR | To a solution of 2-Aminoxy-acetic acid ethyl ester (573 mg, 4.8 mmol) and 4-Pentynoic acid (441 mg, 4.5 mmol) in 15 mL EtOAc were added dicyclohexylcarbodiimide (928 mg, 4.5 mmol) and the resulting mixture was stirred at room temperature for 16 h.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | null | HO- | CCOC(=O)C | null | 16 | C#CCCC(=O)O.CCOC(=O)CON>CCOC(=O)C>C#CCCC(=O)NOCC(=O)OCC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c1a6f8c1a01b4e9980cd4e74051819a9 | CCC#CC(=O)O.O=c1c2ccccc2nnn1O>>C#CCCC(=O)On1nnc2ccccc2c1=O | ON1N=NC2=C(C1=O)C=CC=C2.C(C#CCC)(=O)O.C1(CCCCC1)N=C=NC1CCCCC1.ON1N=NC2=C(C1=O)C=CC=C2>>O=C1C2=C(N=NN1OC(CCC#C)=O)C=CC=C2 | [CH3:1][CH2:2][C:3]#[C:4][C:5](=[O:6])[OH:7].O[n:8]1[n:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[c:17]1=[O:18]>>[CH:1]#[C:2][CH2:3][CH2:4][C:5](=[O:6])[O:7][n:8]1[n:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[c:17]1=[O:18] | CCC#CC(=O)O.O=c1c2ccccc2nnn1O | C#CCCC(=O)On1nnc2ccccc2c1=O | null | null | C1CCOC1 | Miscellaneous | OtherReaction | bd14a890de40c7ed26a72e8a276f93f802dee3bbe6254be0cf17a6250bae9629 | 3852eb70cbd566b052744f0db10a95c07f319296b2eb91e70d93390855a9724a | O=c1[nH]nnc2ccccc12 | O-[n;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1=[O;D1;H0:7].[CH3;D1;+0:8]-[CH2;D2;+0:9]-[C;H0;D2;+0:10]#[C;H0;D2;+0:11]-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14]>>[CH;D1;+0:8]#[C;H0;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-[n;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1=[O;D1... | null | [] | -10 | CELSIUS | 1 | HOUR | Pentynoic acid (200 mg, 2.04 mmol) was dissolved in THF (4 mL). The solution was cooled in a brine-icewater bath. A solution of dicyclohexylcarbodiimide (421 mg, 2.04 mmol) in THF (2 mL) was added. 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one (333 mg, 2.04 mmol) was added after 5 minutes. The reaction mixture was stirred 1 h... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Alkyne | Alkyne | c1ccc2nnncc2c1 | c1ccc2nnncc2c1 | c1ccc2nnncc2c1 | HO- | C1CCOC1 | -10 | 1 | CCC#CC(=O)O.O=c1c2ccccc2nnn1O>C1CCOC1>C#CCCC(=O)On1nnc2ccccc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-befd86f60b4344fb96ef09d3a9c92e0e | CC(C)[Si](Cl)(Cl)C(C)C.OCc1ccccc1.[C-]#[C-]>>C#C[Si](OCc1ccccc1)(C(C)C)C(C)C | [C-]#[C-].[Li+].[Li+].C(CN)N.C(C)(C)N(CC)C(C)C.Cl[Si](C(C)C)(C(C)C)Cl.C(C1=CC=CC=C1)O>>C(C1=CC=CC=C1)O[Si](C(C)C)(C(C)C)C#C | Cl[Si:3](Cl)([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:16])[CH3:17].[OH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[C-:1]#[C-:2]>>[CH:1]#[C:2][Si:3]([O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:16])[CH3:17] | CC(C)[Si](Cl)(Cl)C(C)C.OCc1ccccc1.[C-]#[C-] | C#C[Si](OCc1ccccc1)(C(C)C)C(C)C | null | null | C1CCOC1.O | Protection | OtherReaction | 4e267470195ee554796de69a875c2224d0cafa09fde9745e8f938819d37fcf2f | 2f001953e2d851b35367430b8d2e3f8e4ef39fad53493d06d9dfc03208d1b42a | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-Cl)(-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7].[C-;H0;D1:8]#[C-;H0;D1:9].[OH;D1;+0:10]-[C:11]-[c:12]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[Si;H0;D4;+0:1](-[C;H0;D2;+0:9]#[CH;D1;+0:8])(-[O;H0;D2;+0:10]-[C:11]-[c:12])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7] | 41 | [{"value": 41.0, "product": "C(C1=CC=CC=C1)O[Si](C(C)C)(C(C)C)C#C", "details": "PERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 3 | HOUR | A solution of benzyl alcohol (0.1 mL, 1.0 mmol) in THF (0.5 mL) was added dropwise to a cooled (−78° C.) solution of diisopropylethylamine (1 mL), dichlorodiisopropylsilane (0.3 mL, 1.62 mmol) in THF (4 mL). The solution was stirred for 3 h (−78→−20° C.). The mixture was cooled down to −78° C. and lithiumacetylid-ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Alkyne.Silyl protective group | null | null | c1ccccc1 | Other | C1CCOC1.O | -20 | 3 | CC(C)[Si](Cl)(Cl)C(C)C.OCc1ccccc1.[C-]#[C-]>C1CCOC1.O>C#C[Si](OCc1ccccc1)(C(C)C)C(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-db1ef5c66d4a4683bca61b52ee2978bf | CC(N)CC(=O)O.COc1cc(COC(=O)Cl)c([N+](=O)[O-])cc1OC>>COc1cc(COC(=O)NC(C)CC(=O)O)c([N+](=O)[O-])cc1OC | COC1=C(C=C(C(=C1)COC(=O)Cl)[N+](=O)[O-])OC.[OH-].[Na+].NC(CC(=O)O)C.O.[OH-].[Na+]>>COC1=CC(=C(COC(=O)NC(CC(=O)O)C)C=C1OC)[N+](=O)[O-] | [NH2:10][CH:11]([CH3:12])[CH2:13][C:14](=[O:15])[OH:16].Cl[C:8]([O:7][CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21][c:17]1[N+:18](=[O:19])[O-:20])=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][O:7][C:8](=[O:9])[NH:10][CH:11]([CH3:12])[CH2:13][C:14](=[O:15])[OH:16])[c:17]([N+:18](=[O:19])[O-:20])[cH:... | CC(N)CC(=O)O.COc1cc(COC(=O)Cl)c([N+](=O)[O-])cc1OC | COc1cc(COC(=O)NC(C)CC(=O)O)c([N+](=O)[O-])cc1OC | null | null | O1CCOCC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[C:6](-[NH2;D1;+0:7])-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C;D1;H3:5])-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | 36 | [{"value": 36.0, "product": "COC1=CC(=C(COC(=O)NC(CC(=O)O)C)C=C1OC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.0, "product": "COC1=CC(=C(COC(=O)NC(CC(=O)O)C)C=C1OC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 3-Amino-butyric acid (147 mg, 1.43 mmol) was mixed with water (10 mL), dioxane (10 mL) and 2 M NaOH (10 mL). The mixture was cooled to 0° C. and treated with Nvoc-Cl (1.58 mmol). 2 M NaOH was added in small portions (8×1.25 mL) during 75 minutes. The cooling bath was removed and the reaction mixture was left at room te... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | O1CCOCC1 | 0 | null | CC(N)CC(=O)O.COc1cc(COC(=O)Cl)c([N+](=O)[O-])cc1OC>O1CCOCC1>COc1cc(COC(=O)NC(C)CC(=O)O)c([N+](=O)[O-])cc1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ef4d96badb8b48f0bcb90ff68efff15e | COc1cc(COC(=O)NC(C)CC(=O)O)c([N+](=O)[O-])cc1OC.O=C1C=CC(=O)N1c1ccc(O)cc1>>COc1cc(COC(=O)NC(C)CC(=O)Oc2ccc(N3C(=O)C=CC3=O)cc2)c([N+](=O)[O-])cc1OC | OC1=CC=C(C=C1)N1C(C=CC1=O)=O.COC1=CC(=C(COC(=O)NC(CC(=O)O)C)C=C1OC)[N+](=O)[O-].CC(N=C=NC(C)C)C>>O=C1N(C(C=C1)=O)C1=CC=C(C=C1)OC(CC(C)NC(=O)OCC1=C(C=C(C(=C1)OC)OC)[N+](=O)[O-])=O | O[C:14]([CH2:13][CH:11]([NH:10][C:8]([O:7][CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:35]([O:36][CH3:37])[cH:34][c:30]1[N+:31](=[O:32])[O-:33])=[O:9])[CH3:12])=[O:15].[OH:16][c:17]1[cH:18][cH:19][c:20]([N:21]2[C:22](=[O:23])[CH:24]=[CH:25][C:26]2=[O:27])[cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][O:7][C:8](=[O:... | COc1cc(COC(=O)NC(C)CC(=O)O)c([N+](=O)[O-])cc1OC.O=C1C=CC(=O)N1c1ccc(O)cc1 | COc1cc(COC(=O)NC(C)CC(=O)Oc2ccc(N3C(=O)C=CC3=O)cc2)c([N+](=O)[O-])cc1OC | null | null | C1CCOC1 | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(CCNC(=O)OCc1ccccc1)Oc1ccc(N2C(=O)C=CC2=O)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 0 | CELSIUS | null | null | 1-(4-Hydroxy-phenyl)-pyrrole-2,5-dione (1 mmol), NHS (1.0 mmol) and 3-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-butyric acid (1 mmol) is dissolved in THF (3 mL). The solution is cooled to 0° C. and treated dropwise with DIC (1.2 mmol). The cooling bath is removed after 1 hour and the reaction mixture is left at ro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1.C1=CC[NH]C1 | HO- | C1CCOC1 | 0 | null | COc1cc(COC(=O)NC(C)CC(=O)O)c([N+](=O)[O-])cc1OC.O=C1C=CC(=O)N1c1ccc(O)cc1>C1CCOC1>COc1cc(COC(=O)NC(C)CC(=O)Oc2ccc(N3C(=O)C=CC3=O)cc2)c([N+](=O)[O-])cc1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-331c9182a33848c096ac46b0d1e7327c | CCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C>>C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O | CNC1(CCCCC1=O)C=2C=CC=CC2Cl.CC=1C=CC=C(C1NC2=NCCCS2)C.CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C>>C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@]34C | CCCCCCC(=O)[O:21][C@@H:20]1[C@@:2]2([CH3:1])[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C:9]4=[CH:10][C:11](=[O:12])[CH2:13][CH2:14][C@:15]34[CH3:16])[C@@H:17]2[CH2:18][CH2:19]1>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C:9]4=[CH:10][C:11](=[O:12])[CH2:13][CH2:14][C@:15]34[CH3:16])[C@@H:17]1[CH2:1... | CCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O | null | null | null | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | O=C1C=C2CC[C@H]3[C@@H]4CCCC4CC[C@@H]3C2CC1 | C-C-C-C-C-C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4] | null | [] | null | null | null | null | Male AR-97Q mice and their normal littermates were castrated or sham-operated via the abdominal route under ketamine-xylazine anesthesia (50 mg/kg ketamine and 10 mg/kg xylazine, i.p.) at 4 weeks of age. Female AR-97Q mice and their littermates were subcutaneously injected 20 μg of testosterone enanthate dissolved in 2... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1=C2CC[C@H]3[C@@H]4CCC[C@@H]4CC[C@@H]3[C@H]2CCC1 | HO- | null | null | null | CCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C>>C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6acfba33d3264d7893baed6626e51411 | CC(C)(C)c1ccc(S)cc1.NCCCl>>CC(C)(C)c1ccc(SCCN)cc1 | Cl.ClCCN.C(=O)([O-])[O-].[K+].[K+].C(C)(C)(C)C1=CC=C(C=C1)S>>C(C)(C)(C)C1=CC=C(C=C1)SCCN | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([SH:9])[cH:13][cH:14]1.Cl[CH2:10][CH2:11][NH2:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S:9][CH2:10][CH2:11][NH2:12])[cH:13][cH:14]1 | CC(C)(C)c1ccc(S)cc1.NCCCl | CC(C)(C)c1ccc(SCCN)cc1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[N;D1;H2:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H2:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 74.1 | [{"value": 74.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)SCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "C(C)(C)(C)C1=CC=C(C=C1)SCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | To a stirring mixture of 4.36 g (38.0 mmol) of 2-chloroethylamine hydrochloride and 12.00 g (87.0 mmol) of K2CO3 in 30 mL of CHCl3 was added 4.82 g (29.0 mmol) of 4-t-butylbenzenethiol. The mixture was stirred at 50° C. in a sealed vial overnight. The mixture was washed three times with distilled water, dried with MgSO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1 | HCl | C(Cl)(Cl)Cl | 50 | 8 | CC(C)(C)c1ccc(S)cc1.NCCCl>C(Cl)(Cl)Cl>CC(C)(C)c1ccc(SCCN)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3ae22f97cb3a4f52b62b49ef8cde42a7 | Cc1cc(C(C)(C)C)cc(C)c1[N+](=O)[O-]>>Cc1cc(C(C)(C)C)cc(C)c1N | [N+](=O)([O-])C1=C(C=C(C=C1C)C(C)(C)C)C.[N+](=O)([O-])C1=C(C=C(C=C1C)C(C)(C)C)C.[Cl-].[Cl-].[Ca+2]>>CC1=C(N)C(=CC(=C1)C(C)(C)C)C | O=[N+:13]([O-])[c:12]1[c:2]([CH3:1])[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]1[CH3:11]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([CH3:11])[c:12]1[NH2:13] | Cc1cc(C(C)(C)C)cc(C)c1[N+](=O)[O-] | Cc1cc(C(C)(C)C)cc(C)c1N | null | [Zn] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93.2 | [{"value": 93.0, "product": "CC1=C(N)C(=CC(=C1)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "CC1=C(N)C(=CC(=C1)C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | Water, 20 mL, was added to a mixture of 12.0 g (58.0 mmol) of 1-nitro-4-tert-butyl-2,6-dimethylbenzene dissolved in 160 mL of ethanol. To the stirring solution of 1-nitro-4-tert-butyl-2,6-dimethylbenzene was added CaCl2, 4.8 g (43.2 mmol), dissolved in 20 mL of water, followed by the addition of zinc powder, 50.0 g (76... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Zn].O.C(C)O | 65 | 8 | Cc1cc(C(C)(C)C)cc(C)c1[N+](=O)[O-]>[Zn].O.C(C)O>Cc1cc(C(C)(C)C)cc(C)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-973258b32ab84a219a5fabe31279058c | CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O>>COC(=O)[C@@H](N)C[Si](C)(C)C.Cl | C(C)(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O.C[Si](C)(C)Cl>>Cl.COC([C@@H](N)C[Si](C)(C)C)=O | CC(C)(C)OC(=O)[NH:6][C@H:5]([C:3]([OH:2])=[O:4])[CH2:7][Si:8]([CH3:9])([CH3:10])[CH3:11]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][Si:8]([CH3:9])([CH3:10])[CH3:11].[ClH:12] | CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O | COC(=O)[C@@H](N)C[Si](C)(C)C.Cl | null | null | CO | Miscellaneous | OtherReaction | 7808bb99be630acdad65a861102ab89d3cfe5057444293e2c0619a45c7cac95d | a982aaac60b2789e2bafd29803ed2303422f9e2a84dbea210fa11abe5a6bb059 | null | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[C;D1;H3:7] | null | [] | 0 | CELSIUS | null | null | The compound of Example 6A (300 mg) is dissolved in methanol (3 ml) and cooled to 0° C. Trimethylsilyl chloride (590 mg, 4.7 eq.) is added dropwise in the course of 30 min. and the mixture is warmed to RT overnight. The volatile components are removed on a Rotavapor and subsequently under high vacuum. The target compou... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Ester.Primary amine | null | null | null | HO- | CO | 0 | null | CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O>CO>COC(=O)[C@@H](N)C[Si](C)(C)C.Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9eb46e7b49624619b17b506a64b86825 | C[C@@H](O)[C@H](CC(C)(C)C)NC(=O)OCc1ccccc1>>CC(=O)[C@H](CC(C)(C)C)NC(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](C)O)CC(C)(C)C.C(C)(C)N(C(C)C)CC>>C(C1=CC=CC=C1)OC(=O)N[C@H](C(C)=O)CC(C)(C)C | [CH3:1][C@@H:2]([OH:3])[C@H:4]([CH2:5][C:6]([CH3:7])([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][C:2](=[O:3])[C@H:4]([CH2:5][C:6]([CH3:7])([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[C@@H](O)[C@H](CC(C)(C)C)NC(=O)OCc1ccccc1 | CC(=O)[C@H](CC(C)(C)C)NC(=O)OCc1ccccc1 | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccccc1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C@@H;D3;+0:6](-[C;D1;H3:7])-[OH;D1;+0:8]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8] | null | [] | null | null | 2 | HOUR | Pyridine-SO3 complex (285 mg, 1.79 mmol) is added to a solution of the compound of Example 68A (50 mg, 0.18 mmol) and N,N-diisopropylethylamine (310 μl, 1.79 mmol) in 2 ml of DMSO at 10° C. with and the mixture is slowly warmed to RT. After 2 h, 50 ml of ice/water are added to the reaction mixture. The mixture is extra... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1 | null | CS(=O)C | null | 2 | C[C@@H](O)[C@H](CC(C)(C)C)NC(=O)OCc1ccccc1>CS(=O)C>CC(=O)[C@H](CC(C)(C)C)NC(=O)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9498df38666541029593c0303df2705b | CC(C)C1CCC(=O)C(Br)C1.NC(=S)N=C(N)N>>CC(C)C1CCc2nc(NC(=N)N)sc2C1 | C(=NC(=S)N)(N)N.BrC1C(CCC(C1)C(C)C)=O.C(C)(=O)OCC>>C(C)(C)C1CC2=C(N=C(S2)NC(=N)N)CC1 | O=[C:7]1[CH2:6][CH2:5][CH:4]([CH:2]([CH3:1])[CH3:3])[CH2:16][CH:15]1Br.[NH2:8][C:9]([N:10]=[C:11]([NH2:12])[NH2:13])=[S:14]>>[CH3:1][CH:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][c:7]2[n:8][c:9]([NH:10][C:11](=[NH:12])[NH2:13])[s:14][c:15]2[CH2:16]1 | CC(C)C1CCC(=O)C(Br)C1.NC(=S)N=C(N)N | CC(C)C1CCc2nc(NC(=N)N)sc2C1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 373f7dad3b93db51a4eb7c72e5b9d2383177f968f1532a60649d983079a4e4eb | b2acdbda34ff0f9c191e84f29366b133b5877f45419e401e78a1fee07acd5878 | c1nc2c(s1)CCCC2 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=O.[N;D1;H2:7]-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[N;H0;D2;+0:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[S;H0;D1;+0:13]>>[N;D1;H2:7]-[C;H0;D3;+0:8](=[NH;D1;+0:9])-[NH;D2;+0:10]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:6]2:[c;H0;D3;+0:1](:[s;H0;D2;+0:13]:1)-[C:2]-[C:3]... | null | [] | null | null | null | null | 2-imino-4-thiobiuret (5 mmol) is added accompanied by stirring to a solution of 2-bromo-4-isopropyl-cyclohexanone (5 mmol) in ethanol (10 ml) and the reaction mixture is then refluxed for 16 hours. After evaporating-off of the solvent ethyl acetate is added to the residue and the precipitated-out product is isolated by... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Thioamide.Primary amine | Secondary amine | C1CCCCC1 | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | HBr | C(C)O | null | null | CC(C)C1CCC(=O)C(Br)C1.NC(=S)N=C(N)N>C(C)O>CC(C)C1CCc2nc(NC(=N)N)sc2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0ecac82cc1a2459c8015004b4a9a5d94 | O=C1C=CCCC1.[Li][CH2]CCC>>CCCCC1CCCC(=O)C1 | C(CCC)[Li].C1(C=CCCC1)=O>>C(CCC)C1CC(CCC1)=O | [CH:5]1=[CH:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6]1.[Li][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][C:9](=[O:10])[CH2:11]1 | O=C1C=CCCC1.[Li][CH2]CCC | CCCCC1CCCC(=O)C1 | null | [Cu](I)I | CSC.CCCCCC | C-C Coupling | OtherReaction | 28b1be6c7514f9985f2105225361336afce605846319fbf3be0c9a27d2a65663 | 8ac73d846ffa810afad7791249e0c3da217153f89750c2cecfde1a2d6cfa87fe | O=C1CCCCC1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Li].[O;D1;H0:4]=[C:5]1-[C:6]-[C:7]-[C:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-1>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:9]1-[C:8]-[C:7]-[C:6]-[C:5](=[O;D1;H0:4])-[CH2;D2;+0:10]-1 | null | [] | -78 | CELSIUS | null | null | A solution of copper iodide (6.3 mmol) in dimethyl sulphide (12 ml) is cooled to 50° C. A solution of butyl lithium (6.2 mmol) is added dropwise accompanied by stirring and stirred for a further 5 to 15 mins. The reaction mixture is cooled to −78° C. and then a solution precooled to −78° C. of cyclohex-2-enone (6 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyl lithium | Ketone | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1 | Li | [Cu](I)I.CSC.CCCCCC | -78 | null | O=C1C=CCCC1.[Li][CH2]CCC>[Cu](I)I.CSC.CCCCCC>CCCCC1CCCC(=O)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f651fb4d2f9b40ec9126eb165fce1524 | CC(C)C1CCC(=O)C(Br)C1.CCCCC1CCCC(=O)C1>>CCCCC1CCC(Br)C(=O)C1 | C(CCC)C1CC(CCC1)=O.BrC1C(CCC(C1)C(C)C)=O>>BrC1C(CC(CC1)CCCC)=O | CC(C)C1CC[C:10](=[O:11])[CH:8]([Br:9])C1.O=C1C[CH2:7][CH2:6][CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([Br:9])[C:10](=[O:11])[CH2:12]1 | CC(C)C1CCC(=O)C(Br)C1.CCCCC1CCCC(=O)C1 | CCCCC1CCC(Br)C(=O)C1 | null | null | null | C-C Coupling | Bromination | b51efa558fa8fcc06d635bb9582af5d9535e70b2d77b877bfb91954c1bd42275 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCCCC1 | C-C(-C)-C1-C-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[Br;D1;H0:4])-C-1.O=C1-C-[CH2;D2;+0:5]-[C:6]-[C:7](-[C:8])-[CH2;D2;+0:9]-1>>[Br;D1;H0:4]-[CH;D3;+0:3]1-[CH2;D2;+0:5]-[C:6]-[C:7](-[C:8])-[CH2;D2;+0:9]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | The bromination of 3-butylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CCCCC1CCCC(=O)C1>>CCCCC1CCC(Br)C(=O)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2490bc6217a344258faf2fe00e97dd10 | CC(C)(C)C1CCCCC1=O.Cc1ccc(S(=O)(=O)Cl)cc1>>CC(C)(C)C1CCCC(Cl)C1=O | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)(C)(C)C1C(CCCC1)=O.C(C)(C)NC(C)C>>C(C)(C)(C)C1C(C(CCC1)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:11]1=[O:12].Cc1ccc(S(=O)(=O)[Cl:10])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([Cl:10])[C:11]1=[O:12] | CC(C)(C)C1CCCCC1=O.Cc1ccc(S(=O)(=O)Cl)cc1 | CC(C)(C)C1CCCC(Cl)C1=O | null | null | O1CCCC1 | Functional Group Interconversion | Chlorination | 20e8a4d3681173dc9e9da88575f9fe7a348e67fe4c318c792871e04df36eb34a | 9c97ac441354a7b254fc871ecfc0ffa12484c2b9851b481c82aee8aaf40dc185 | O=C1CCCCC1 | C-c1:c:c:c(-S(=O)(=O)-[Cl;H0;D1;+0:1]):c:c:1.[C:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[Cl;H0;D1;+0:1])-[C:6]-[C:7] | 81 | [{"value": 81.0, "product": "C(C)(C)(C)C1C(C(CCC1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | N-butyl lithium is added dropwise to a solution, cooled to 0° C., of diisopropylamine (5.5 mmol) in dry tetrahydrofuran. After the addition is complete the mixture is cooled to −78° C., and a solution of 2-tert-butylcyclohexanone (5 mmol) in dry tetrahydrofuran (50 ml) is introduced, followed by the addition of p-tolue... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Sulfonyl halide | Secondary halide | C1CCCCC1.c1ccccc1 | C1CCCCC1 | C1CCCCC1 | TsOH.HO- | O1CCCC1 | -78 | 0.5 | CC(C)(C)C1CCCCC1=O.Cc1ccc(S(=O)(=O)Cl)cc1>O1CCCC1>CC(C)(C)C1CCCC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4a9b7976539f4e5b878d784e3b817458 | CC1(C)C=CC(=O)CC1>>CC1(C)CCC(=O)CC1 | CC1(C=CC(CC1)=O)C.[H][H]>>CC1(CCC(CC1)=O)C | [CH3:1][C:2]1([CH3:3])[CH:4]=[CH:5][C:6](=[O:7])[CH2:8][CH2:9]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[CH2:8][CH2:9]1 | CC1(C)C=CC(=O)CC1 | CC1(C)CCC(=O)CC1 | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 36c089d27e46ae7bb4df3563f4ed1e4684984208b1f092ae42b91f9c5627fd64 | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1CCCCC1 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-1>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1 | 94 | [{"value": 94.0, "product": "CC1(CCC(CC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.8, "product": "CC1(CCC(CC1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4,4-dimethyl-cyclohex-2-enone (3 mmol) in ethyl acetate is hydrogenated overnight at room temperature using Pd/C (0.05 mmol) with hydrogen under normal pressure. Filtration over celite and then concentration by evaporation produces 4,4-dimethyl-cyclohexanone (355 mg) in a yield of 94% (J. Org. Chem. 2001,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1 | null | [Pd].C(C)(=O)OCC | null | null | CC1(C)C=CC(=O)CC1>[Pd].C(C)(=O)OCC>CC1(C)CCC(=O)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-312792e97e6b409eab8f4e81fba9f738 | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CCC(=O)CC1>>CC1(C)CCC(=O)C(Br)C1 | CC1(CCC(CC1)=O)C.BrC1C(CCC(C1)C(C)C)=O>>BrC1C(CCC(C1)(C)C)=O | CC(C)[CH:2]1[CH2:4][CH2:5][C:6](=[O:7])[CH:8]([Br:9])[CH2:10]1.O=C1CCC([CH3:1])([CH3:3])CC1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[CH:8]([Br:9])[CH2:10]1 | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CCC(=O)CC1 | CC1(C)CCC(=O)C(Br)C1 | null | null | null | C-C Coupling | Bromination | fdb4152cf05f04104a2af982aa2e8a2a18303e8ab46a5cbbbf7525222000aebb | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=C1CCCCC1 | C-C(-C)-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1.O=C1-C-C-C(-[CH3;D1;+0:8])(-[CH3;D1;+0:9])-C-C-1>>[CH3;D1;+0:8]-[C;H0;D4;+0:1]1(-[CH3;D1;+0:9])-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1 | null | [] | null | null | null | null | The bromination of 4,4-dimethylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CCC(=O)CC1>>CC1(C)CCC(=O)C(Br)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-be64916b5b9544259c2628d6994ce129 | CC(C)(C)C1CCCC(Cl)C1=O.CCC(C)C1CCCCC1=O>>CCC(C)C1CCCC(Cl)C1=O | C(C)(CC)C1C(CCCC1)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>C(C)(CC)C1C(C(CCC1)Cl)=O | CC(C)(C)[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([Cl:10])[C:11]1=[O:12].O=C1CCCCC1[CH:3]([CH2:2][CH3:1])[CH3:4]>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([Cl:10])[C:11]1=[O:12] | CC(C)(C)C1CCCC(Cl)C1=O.CCC(C)C1CCCCC1=O | CCC(C)C1CCCC(Cl)C1=O | null | null | null | C-C Coupling | Chlorination | 63a5bbb7584869c734c57121d2a924fb323d55cf29a98933c11896490672bc05 | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1CCCCC1 | C-C(-C)(-C)-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6].O=C1-C-C-C-C-C-1-[CH;D3;+0:7](-[C;D1;H3:8])-[C:9]-[C;D1;H3:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[CH;D3;+0:7](-[C;D1;H3:8])-[C:9]-[C;D1;H3:10])-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | The chlorination of 2-sec-butylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)(C)C1CCCC(Cl)C1=O.CCC(C)C1CCCCC1=O>>CCC(C)C1CCCC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-07a93d26942c48389645f5e8ecd4937f | CC(C)(C)C1CCCC(Cl)C1=O.O=C1CCCCC1Cc1ccccc1>>O=C1C(Cl)CCCC1Cc1ccccc1 | C(C1=CC=CC=C1)C1C(CCCC1)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>C(C1=CC=CC=C1)C1C(C(CCC1)Cl)=O | CC(C)(C)C1CCCC([Cl:4])C1=O.[O:1]=[C:2]1[CH2:3][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[C:2]1[CH:3]([Cl:4])[CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(C)(C)C1CCCC(Cl)C1=O.O=C1CCCCC1Cc1ccccc1 | O=C1C(Cl)CCCC1Cc1ccccc1 | null | null | null | Functional Group Interconversion | Chlorination | a46c7dc769608b8ec35dadd804e0f7a74a028f2146ee0122a9c24d2aaae96684 | af6f895a0e88516f0a2e7e54838a1e72c142a95d71091e6b02ff568a7310f7ea | O=C1CCCCC1Cc1ccccc1 | C-C(-C)(-C)-C1-C-C-C-C(-[Cl;H0;D1;+0:1])-C-1=O.[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7]>>[C:2]-[C:3]-[CH;D3;+0:4](-[Cl;H0;D1;+0:1])-[C:5](=[O;D1;H0:6])-[C:7] | null | [] | null | null | null | null | The chlorination of 2-benzylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)C1CCCC(Cl)C1=O.O=C1CCCCC1Cc1ccccc1>>O=C1C(Cl)CCCC1Cc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-852db3603ad6437c85542cb40eaff3e5 | C=CCC1CCCCC1=O.CC(C)(C)C1CCCC(Cl)C1=O>>C=CCC1CCCC(Cl)C1=O | C(C=C)C1C(CCCC1)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>C(C=C)C1C(C(CCC1)Cl)=O | O=C1CCCCC1[CH2:3][CH:2]=[CH2:1].CC(C)(C)[CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([Cl:9])[C:10]1=[O:11]>>[CH2:1]=[CH:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([Cl:9])[C:10]1=[O:11] | C=CCC1CCCCC1=O.CC(C)(C)C1CCCC(Cl)C1=O | C=CCC1CCCC(Cl)C1=O | null | null | null | C-C Coupling | Chlorination | c4a895f1c1f52b347a59f746ff5e631a0e8a0b4d3136cafad19b06f703b40e3f | 940e9d9ead9edc923b2b550708cac04806d787002c86a8649805e86750b645dc | O=C1CCCCC1 | C-C(-C)(-C)-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6].O=C1-C-C-C-C-C-1-[CH2;D2;+0:7]-[C:8]=[C;D1;H2:9]>>[C:3]-[C:2]-[CH;D3;+0:1](-[CH2;D2;+0:7]-[C:8]=[C;D1;H2:9])-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | The chlorination of 2-allylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Allyl | Ketone.Allyl | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | C=CCC1CCCCC1=O.CC(C)(C)C1CCCC(Cl)C1=O>>C=CCC1CCCC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c503a5a1adda4c4797e232ba621b6b4b | CC(C)(C)C1CCCC(Cl)C1=O.O=C1CCCCC1c1ccccc1>>O=C1C(Cl)CCCC1c1ccccc1 | C1(=CC=CC=C1)C1C(CCCC1)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>ClC1C(C(CCC1)C1=CC=CC=C1)=O | CC(C)(C)C1CCCC([Cl:4])C1=O.[O:1]=[C:2]1[CH2:3][CH2:5][CH2:6][CH2:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]1[CH:3]([Cl:4])[CH2:5][CH2:6][CH2:7][CH:8]1[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | CC(C)(C)C1CCCC(Cl)C1=O.O=C1CCCCC1c1ccccc1 | O=C1C(Cl)CCCC1c1ccccc1 | null | null | null | Functional Group Interconversion | Chlorination | a46c7dc769608b8ec35dadd804e0f7a74a028f2146ee0122a9c24d2aaae96684 | af6f895a0e88516f0a2e7e54838a1e72c142a95d71091e6b02ff568a7310f7ea | O=C1CCCCC1c1ccccc1 | C-C(-C)(-C)-C1-C-C-C-C(-[Cl;H0;D1;+0:1])-C-1=O.[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7]>>[C:2]-[C:3]-[CH;D3;+0:4](-[Cl;H0;D1;+0:1])-[C:5](=[O;D1;H0:6])-[C:7] | null | [] | null | null | null | null | The chlorination of 2-phenylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)C1CCCC(Cl)C1=O.O=C1CCCCC1c1ccccc1>>O=C1C(Cl)CCCC1c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1b11742f473c477887fee3c6574fe70c | CC(C)(C)C1CCCC(Cl)C1=O.CCOC(=O)CC1CCCCC1=O>>CCOC(=O)CC1CCCC(Cl)C1=O | C(C)OC(CC1C(CCCC1)=O)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>C(C)OC(CC1C(C(CCC1)Cl)=O)=O | CC(C)(C)C1C[CH2:9][CH2:10][CH:11]([Cl:12])[C:13]1=[O:14].O=C1CCC[CH2:8][CH:7]1[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH:11]([Cl:12])[C:13]1=[O:14] | CC(C)(C)C1CCCC(Cl)C1=O.CCOC(=O)CC1CCCCC1=O | CCOC(=O)CC1CCCC(Cl)C1=O | null | null | null | C-C Coupling | Chlorination | 63a5bbb7584869c734c57121d2a924fb323d55cf29a98933c11896490672bc05 | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1CCCCC1 | C-C(-C)(-C)-C1-C-[CH2;D2;+0:1]-[C:2]-[C:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5]-1=[O;D1;H0:6].O=C1-C-C-C-[CH2;D2;+0:7]-[CH;D3;+0:8]-1-[C:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C:9]-[CH;D3;+0:8]1-[CH2;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | null | [] | null | null | null | null | The chlorination of ethyl(2-oxo-cyclohexyl)-acetate takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)(C)C1CCCC(Cl)C1=O.CCOC(=O)CC1CCCCC1=O>>CCOC(=O)CC1CCCC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7fd1a39939ab4c2897ab649df14746c2 | CC(C)(C)C1CCCC(Cl)C1=O.N#CCCC1CCCCC1=O>>N#CCCC1CCCC(Cl)C1=O | O=C1C(CCCC1)CCC#N.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>ClC1C(C(CCC1)CCC#N)=O | CC(C)(C)[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([Cl:10])[C:11]1=[O:12].O=C1CCCCC1[CH2:4][CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([Cl:10])[C:11]1=[O:12] | CC(C)(C)C1CCCC(Cl)C1=O.N#CCCC1CCCCC1=O | N#CCCC1CCCC(Cl)C1=O | null | null | null | C-C Coupling | Chlorination | 63a5bbb7584869c734c57121d2a924fb323d55cf29a98933c11896490672bc05 | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1CCCCC1 | C-C(-C)(-C)-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6].O=C1-C-C-C-C-C-1-[CH2;D2;+0:7]-[C:8]-[C:9]#[N;D1;H0:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[CH2;D2;+0:7]-[C:8]-[C:9]#[N;D1;H0:10])-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | The chlorination of 2-oxo-1-cyclohexanepropionitrile takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)(C)C1CCCC(Cl)C1=O.N#CCCC1CCCCC1=O>>N#CCCC1CCCC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-04f249f2864a4c3b83c80561d0cd17d0 | CC(C)(C)C1CCCC(Cl)C1=O.CC1CCCCC1=O>>CC1CCCC(Cl)C1=O | CC1C(CCCC1)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>ClC1C(C(CCC1)C)=O | CC(C)(C)[CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([Cl:7])[C:8]1=[O:9].O=C1CCCCC1[CH3:1]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([Cl:7])[C:8]1=[O:9] | CC(C)(C)C1CCCC(Cl)C1=O.CC1CCCCC1=O | CC1CCCC(Cl)C1=O | null | null | null | C-C Coupling | Chlorination | 63a5bbb7584869c734c57121d2a924fb323d55cf29a98933c11896490672bc05 | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1CCCCC1 | C-C(-C)(-C)-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6].O=C1-C-C-C-C-C-1-[CH3;D1;+0:7]>>[C:3]-[C:2]-[CH;D3;+0:1](-[CH3;D1;+0:7])-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | The chlorination of 2-methylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)(C)C1CCCC(Cl)C1=O.CC1CCCCC1=O>>CC1CCCC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-86101b2e7f9945179d50d853ef03d403 | CC1CCCCC1=O.CI>>CC1(C)CCCCC1=O | CI.[H-].[K+].CC1C(CCCC1)=O.C(C)B(CC)CC>>CC1(C(CCCC1)=O)C | [CH3:1][CH:2]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1=[O:9].I[CH3:3]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1=[O:9] | CC1CCCCC1=O.CI | CC1(C)CCCCC1=O | null | null | O1CCCC1 | C-C Coupling | Methylation with MeI_tertiary | 4a8411eb6f8e0f1911d82c64ff7bdbf7273fee73d2c750190adc2ec2b5d8008a | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1CCCCC1 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[CH;D3;+0:4](-[C;D1;H3:5])-[C:6](=[O;D1;H0:7])-[C:8]>>[C:2]-[C:3]-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[CH3;D1;+0:1])-[C:6](=[O;D1;H0:7])-[C:8] | null | [] | null | null | 30 | MINUTE | A suspension of potassium hydride (5.5 mmol) and 2-methylcyclohexanone (5 mmol) in dry tetrahydrofuran (10 ml) is stirred for 30 mins at room temperature. Triethylborane (6.25 mmol) is slowly added dropwise and the mixture is stirred for 16 hours at room temperature. After addition of methyl iodide stirring is continue... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HI | O1CCCC1 | null | 0.5 | CC1CCCCC1=O.CI>O1CCCC1>CC1(C)CCCCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9e0f4e40a8f64237bd9ed880f5977340 | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CCCCC1=O>>CC1(C)CCCC(Br)C1=O | CC1(C(CCCC1)=O)C.BrC1C(CCC(C1)C(C)C)=O>>BrC1CCCC(C1=O)(C)C | CC(C)C1CCC(=O)[CH:7]([Br:8])C1.C1[CH2:6][CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[C:9]1=[O:10]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([Br:8])[C:9]1=[O:10] | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CCCCC1=O | CC1(C)CCCC(Br)C1=O | null | null | null | C-C Coupling | Bromination | b51efa558fa8fcc06d635bb9582af5d9535e70b2d77b877bfb91954c1bd42275 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCCCC1 | C-C(-C)-C1-C-C-C(=O)-[CH;D3;+0:1](-[Br;D1;H0:2])-C-1.[C;D1;H3:3]-[C:4]1(-[C;D1;H3:5])-[C:6]-[C:7]-[CH2;D2;+0:8]-C-[C;H0;D3;+0:9]-1=[O;D1;H0:10]>>[Br;D1;H0:2]-[CH;D3;+0:1]1-[CH2;D2;+0:8]-[C:7]-[C:6]-[C:4](-[C;D1;H3:3])(-[C;D1;H3:5])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | The bromination of 2,2-dimethyl-cyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CCCCC1=O>>CC1(C)CCCC(Br)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f9806c1703d24d3e95559c9a94bcdb30 | CC1(C)CCCCC1=O.CCI>>CCC1(C)CCCCC1=O | CC1C(CCCC1)=O.C(C)I.CC1(C(CCCC1)=O)C>>C(C)C1(C(CCCC1)=O)C | C[C:3]1([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:10].I[CH2:2][CH3:1]>>[CH3:1][CH2:2][C:3]1([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:10] | CC1(C)CCCCC1=O.CCI | CCC1(C)CCCCC1=O | null | null | null | C-C Coupling | C-methylation | 054c40a29a9c4e7d7190d9f2c2209b70e51db1b7252a5e41d135490be0aeff3d | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | O=C1CCCCC1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C:3]-[C:4])-[C:5](=[O;D1;H0:6])-[C:7].I-[CH2;D2;+0:8]-[C;D1;H3:9]>>[C:4]-[C:3]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[CH2;D2;+0:8]-[C;D1;H3:9])-[C:5](=[O;D1;H0:6])-[C:7] | null | [] | null | null | null | null | The alkylation of 2-methylcyclohexanone with ethyl iodide takes place in a manner similar to that described above for the preparation of 2,2-dimethyl-cyclohexanone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HI | null | null | null | CC1(C)CCCCC1=O.CCI>>CCC1(C)CCCCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e248eb24780740e1a7701f3626904618 | CC(C)C1CCC(=O)C(Br)C1.CCC1(C)CCCCC1=O>>CCC1(C)CCCC(Br)C1=O | C(C)C1(C(CCCC1)=O)C.BrC1C(CCC(C1)C(C)C)=O>>BrC1CCCC(C1=O)(C)CC | CC(C)C1CC[C:10](=[O:11])[CH:8]([Br:9])C1.O=C1C[CH2:7][CH2:6][CH2:5][C:3]1([CH2:2][CH3:1])[CH3:4]>>[CH3:1][CH2:2][C:3]1([CH3:4])[CH2:5][CH2:6][CH2:7][CH:8]([Br:9])[C:10]1=[O:11] | CC(C)C1CCC(=O)C(Br)C1.CCC1(C)CCCCC1=O | CCC1(C)CCCC(Br)C1=O | null | null | null | C-C Coupling | Bromination | b51efa558fa8fcc06d635bb9582af5d9535e70b2d77b877bfb91954c1bd42275 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCCCC1 | C-C(-C)-C1-C-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[Br;D1;H0:4])-C-1.O=C1-C-[CH2;D2;+0:5]-[C:6]-[C:7]-[C;H0;D4;+0:8]-1(-[C;D1;H3:9])-[C:10]-[C;D1;H3:11]>>[Br;D1;H0:4]-[CH;D3;+0:3]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C:10]-[C;D1;H3:11])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | The bromination of 2-ethyl-2-methyl-cyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CCC1(C)CCCCC1=O>>CCC1(C)CCCC(Br)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bd3218b3ece74055bcb848851a34a235 | CC(C)CI.CC1CCCCC1=O>>CC(C)CC1(C)CCCCC1=O | CC1C(CCCC1)=O.ICC(C)C.CC1(C(CCCC1)=O)C>>C(C(C)C)C1(C(CCCC1)=O)C | I[CH2:4][CH:2]([CH3:1])[CH3:3].[CH:5]1([CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1=[O:12]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5]1([CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1=[O:12] | CC(C)CI.CC1CCCCC1=O | CC(C)CC1(C)CCCCC1=O | null | null | null | C-C Coupling | OtherReaction | 054c40a29a9c4e7d7190d9f2c2209b70e51db1b7252a5e41d135490be0aeff3d | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | O=C1CCCCC1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C;D1;H3:9])-[C:10]-[C:11]>>[C:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:10]-[C:11] | null | [] | null | null | null | null | The alkylation of 2-methylcyclohexanone with 1-iodo-2-methyl-propane takes place in a manner similar to that described above for the preparation of 2,2-dimethyl-cyclohexanone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HI | null | null | null | CC(C)CI.CC1CCCCC1=O>>CC(C)CC1(C)CCCCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4d4fb1c5b4544e7dbd181e62a3b29bdf | CC(C)C1CCC(=O)C(Br)C1.CC(C)CC1(C)CCCCC1=O>>CC(C)CC1(C)CCCC(Br)C1=O | C(C(C)C)C1(C(CCCC1)=O)C.BrC1C(CCC(C1)C(C)C)=O>>BrC1CCCC(C1=O)(C)CC(C)C | CC(C)C1CC[C:12](=[O:13])[CH:10]([Br:11])C1.O=C1C[CH2:9][CH2:8][CH2:7][C:5]1([CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:6]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5]1([CH3:6])[CH2:7][CH2:8][CH2:9][CH:10]([Br:11])[C:12]1=[O:13] | CC(C)C1CCC(=O)C(Br)C1.CC(C)CC1(C)CCCCC1=O | CC(C)CC1(C)CCCC(Br)C1=O | null | null | null | C-C Coupling | Bromination | b51efa558fa8fcc06d635bb9582af5d9535e70b2d77b877bfb91954c1bd42275 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCCCC1 | C-C(-C)-C1-C-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[Br;D1;H0:4])-C-1.O=C1-C-[CH2;D2;+0:5]-[C:6]-[C:7]-[C;H0;D4;+0:8]-1(-[C;D1;H3:9])-[C:10]-[C:11]>>[Br;D1;H0:4]-[CH;D3;+0:3]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C:10]-[C:11])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | The bromination of 2-isobutyl-2-methyl-cyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CC(C)CC1(C)CCCCC1=O>>CC(C)CC1(C)CCCC(Br)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-93005017ea044c5cabef79e419509e07 | CC1(C)CCCCC1=O.CCCI>>CCCC1(C)CCCCC1=O | CC1C(CCCC1)=O.ICCC.CC1(C(CCCC1)=O)C>>CC1(C(CCCC1)=O)CCC | C[C:4]1([CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1=[O:11].I[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][C:4]1([CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1=[O:11] | CC1(C)CCCCC1=O.CCCI | CCCC1(C)CCCCC1=O | null | null | null | C-C Coupling | OtherReaction | 054c40a29a9c4e7d7190d9f2c2209b70e51db1b7252a5e41d135490be0aeff3d | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | O=C1CCCCC1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C:3]-[C:4])-[C:5](=[O;D1;H0:6])-[C:7].I-[CH2;D2;+0:8]-[C:9]-[C;D1;H3:10]>>[C:4]-[C:3]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[CH2;D2;+0:8]-[C:9]-[C;D1;H3:10])-[C:5](=[O;D1;H0:6])-[C:7] | null | [] | null | null | null | null | The alkylation of 2-methylcyclohexanone with 1-iodopropane takes place in a manner similar to that described above for the preparation of 2,2-dimethyl-cyclohexanone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HI | null | null | null | CC1(C)CCCCC1=O.CCCI>>CCCC1(C)CCCCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-88d89b5b81314a39a92b474967b1b8e2 | CC(C)C1CCC(=O)C(Br)C1.CCCC1(C)CCCCC1=O>>CCCC1(C)CCCC(Br)C1=O | CC1(C(CCCC1)=O)CCC.BrC1C(CCC(C1)C(C)C)=O>>BrC1CCCC(C1=O)(CCC)C | CC(C)C1CC[C:11](=[O:12])[CH:9]([Br:10])C1.O=C1C[CH2:8][CH2:7][CH2:6][C:4]1([CH2:3][CH2:2][CH3:1])[CH3:5]>>[CH3:1][CH2:2][CH2:3][C:4]1([CH3:5])[CH2:6][CH2:7][CH2:8][CH:9]([Br:10])[C:11]1=[O:12] | CC(C)C1CCC(=O)C(Br)C1.CCCC1(C)CCCCC1=O | CCCC1(C)CCCC(Br)C1=O | null | null | null | C-C Coupling | Bromination | b51efa558fa8fcc06d635bb9582af5d9535e70b2d77b877bfb91954c1bd42275 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCCCC1 | C-C(-C)-C1-C-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[Br;D1;H0:4])-C-1.O=C1-C-[CH2;D2;+0:5]-[C:6]-[C:7]-[C;H0;D4;+0:8]-1(-[C;D1;H3:9])-[C:10]-[C:11]>>[Br;D1;H0:4]-[CH;D3;+0:3]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C:10]-[C:11])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | The bromination of 2-methyl-2-propyl-cyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CCCC1(C)CCCCC1=O>>CCCC1(C)CCCC(Br)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b69ffd70b70b453990f6ee758973e6dd | CCOC(=O)C1CCCC(Br)C1=O.NC(=S)N=C(N)N>>CCOC(=O)C1CCCc2sc(NC(=N)N)nc21 | C(C)OC(=O)C1C(C(CCC1)Br)=O.C(=NC(=S)N)(N)N>>C(C)OC(=O)C1CCCC2=C1N=C(S2)NC(=N)N | O=[C:18]1[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][CH2:9][CH:10]1Br.[S:11]=[C:12]([N:13]=[C:14]([NH2:15])[NH2:16])[NH2:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][c:10]2[s:11][c:12]([NH:13][C:14](=[NH:15])[NH2:16])[n:17][c:18]21 | CCOC(=O)C1CCCC(Br)C1=O.NC(=S)N=C(N)N | CCOC(=O)C1CCCc2sc(NC(=N)N)nc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 373f7dad3b93db51a4eb7c72e5b9d2383177f968f1532a60649d983079a4e4eb | b2acdbda34ff0f9c191e84f29366b133b5877f45419e401e78a1fee07acd5878 | c1nc2c(s1)CCCC2 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C;H0;D3;+0:10]-1=O.[N;D1;H2:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[N;H0;D2;+0:14]-[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[S;H0;D1;+0:17]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[c;H0;D3;+0:1]2:[s;H0;D2;+0:17]:[c;H0;D3;+0:15](-[NH;D... | null | [] | null | null | null | null | Analogously to the preparation of Example C-01, 3-bromo-2-oxo-cyclohexane carboxylic acid ethyl ester is reacted with 2-imino-4-thiobiuret to produce the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Thioamide.Primary amine | Secondary amine | C1CCCCC1 | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | HBr | null | null | null | CCOC(=O)C1CCCC(Br)C1=O.NC(=S)N=C(N)N>>CCOC(=O)C1CCCc2sc(NC(=N)N)nc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-37fb364ca93b408f8103ecfca7b9d4ae | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1CCCCC1=O>>CCOC(=O)C1CCCC(Br)C1=O | C(C)OC(=O)C1C(CCCC1)=O.BrC1C(CCC(C1)C(C)C)=O>>C(C)OC(=O)C1C(C(CCC1)Br)=O | CC(C)C1CCC(=O)C([Br:11])C1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:12]1=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH:10]([Br:11])[C:12]1=[O:13] | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1CCCCC1=O | CCOC(=O)C1CCCC(Br)C1=O | null | null | null | Functional Group Interconversion | Bromination | a46c7dc769608b8ec35dadd804e0f7a74a028f2146ee0122a9c24d2aaae96684 | af6f895a0e88516f0a2e7e54838a1e72c142a95d71091e6b02ff568a7310f7ea | O=C1CCCCC1 | C-C(-C)-C1-C-C-C(=O)-C(-[Br;H0;D1;+0:1])-C-1.[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9]-[C:10]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[Br;H0;D1;+0:1])-[C:9]-[C:10] | null | [] | null | null | null | null | The bromination of 2-oxo-cyclohexane carboxylic acid ethyl ester takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1CCCCC1=O>>CCOC(=O)C1CCCC(Br)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-33413e6dcbc0448487ecea1669d7ccf7 | CCOC(=O)C1CCCc2sc(NC(=N)N)nc21>>N=C(N)Nc1nc2c(s1)CCCC2C(=O)O | C(C)OC(=O)C1CCCC2=C1N=C(S2)NC(=N)N.[OH-].[Na+].Cl>>N(C(=N)N)C=1SC2=C(N1)C(CCC2)C(=O)O | CC[O:16][C:14]([CH:13]1[c:7]2[n:6][c:5]([NH:4][C:2](=[NH:1])[NH2:3])[s:9][c:8]2[CH2:10][CH2:11][CH2:12]1)=[O:15]>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)[CH2:10][CH2:11][CH2:12][CH:13]2[C:14](=[O:15])[OH:16] | CCOC(=O)C1CCCc2sc(NC(=N)N)nc21 | N=C(N)Nc1nc2c(s1)CCCC2C(=O)O | null | null | CO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1nc2c(s1)CCCC2 | 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] | 56 | [{"value": 56.0, "product": "N(C(=N)N)C=1SC2=C(N1)C(CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of 2-guanidino-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester (5 mmol) and sodium hydroxide (20 mmol) in methanol/water (4:1, 10 ml) is stirred overnight at room temperature. The pH is set at 5 by adding 25% hydrochloric acid and the precipitated product is filtered off. In this way the tit... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1nc2c(s1)CCCC2 | Other | CO.O | null | 8 | CCOC(=O)C1CCCc2sc(NC(=N)N)nc21>CO.O>N=C(N)Nc1nc2c(s1)CCCC2C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-36e7a4e2ac1d496fa174c9edc625682a | CCOC(=O)C1CCC(=O)C(Br)C1.NC(=S)N=C(N)N>>CCOC(=O)C1CCc2nc(NC(=N)N)sc2C1 | C(C)OC(=O)C1CC(C(CC1)=O)Br.C(=NC(=S)N)(N)N>>C(C)OC(=O)C1CC2=C(N=C(S2)NC(=N)N)CC1 | O=[C:9]1[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:18][CH:17]1Br.[NH2:10][C:11]([N:12]=[C:13]([NH2:14])[NH2:15])=[S:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][c:9]2[n:10][c:11]([NH:12][C:13](=[NH:14])[NH2:15])[s:16][c:17]2[CH2:18]1 | CCOC(=O)C1CCC(=O)C(Br)C1.NC(=S)N=C(N)N | CCOC(=O)C1CCc2nc(NC(=N)N)sc2C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 373f7dad3b93db51a4eb7c72e5b9d2383177f968f1532a60649d983079a4e4eb | b2acdbda34ff0f9c191e84f29366b133b5877f45419e401e78a1fee07acd5878 | c1nc2c(s1)CCCC2 | Br-[CH;D3;+0:1]1-[C:2]-[C:3](-[C:4](-[#8:5])=[O;D1;H0:6])-[C:7]-[C:8]-[C;H0;D3;+0:9]-1=O.[N;D1;H2:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[N;H0;D2;+0:13]-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[S;H0;D1;+0:16]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]1-[C:2]-[c;H0;D3;+0:1]2:[s;H0;D2;+0:16]:[c;H0;D3;+0:14](-[NH;D2;+0:13]-[C;H0;D3;+0:11](... | null | [] | null | null | null | null | Analogously to the preparation of Example C-01, 3-bromo-4-oxo-cyclohexane carboxylic acid ethyl ester is reacted with 2-imino-4-thiobiuret to form the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Thioamide.Primary amine | Secondary amine | C1CCCCC1 | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | HBr | null | null | null | CCOC(=O)C1CCC(=O)C(Br)C1.NC(=S)N=C(N)N>>CCOC(=O)C1CCc2nc(NC(=N)N)sc2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aa5614f3adf74aaeaa8e0d65a3012e4f | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1CCC(=O)CC1>>CCOC(=O)C1CCC(=O)C(Br)C1 | C(C)OC(=O)C1CCC(CC1)=O.BrC1C(CCC(C1)C(C)C)=O>>C(C)OC(=O)C1CC(C(CC1)=O)Br | CC(C)[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[CH:11]([Br:12])[CH2:13]1.O=C1CCC([C:4]([O:3][CH2:2][CH3:1])=[O:5])CC1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[CH:11]([Br:12])[CH2:13]1 | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1CCC(=O)CC1 | CCOC(=O)C1CCC(=O)C(Br)C1 | null | null | null | C-C Coupling | Bromination | 859f4e276d02eca86bbd5435dc5917b8c946fcb6ddfe252a81c131d1156bebcb | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | O=C1CCCCC1 | C-C(-C)-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1.O=C1-C-C-C(-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11])-C-C-1>>[C:11]-[#8:10]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1 | null | [] | null | null | null | null | The bromination of 4-oxo-cyclohexane carboxylic acid ethyl ester takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1CCC(=O)CC1>>CCOC(=O)C1CCC(=O)C(Br)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-abac6013fd7b43ea93290638b29d1aeb | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCC12CCCCC2>>O=C1C(Br)CCCC12CCCCC2 | C1(CCCCC12CCCCC2)=O.BrC1C(CCC(C1)C(C)C)=O>>BrC1C(C2(CCC1)CCCCC2)=O | CC(C)C1CC[C:2](=[O:1])[CH:3]([Br:4])[CH2:5]1.O=C1CC[CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2>>[O:1]=[C:2]1[CH:3]([Br:4])[CH2:5][CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2 | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCC12CCCCC2 | O=C1C(Br)CCCC12CCCCC2 | null | null | null | C-C Coupling | Bromination | c78bcfd0979853cad17bbe220f813cb70b348a4c2023ed6f6b5ba48e2bb9137b | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1CCCCC12CCCCC2 | C-C(-C)-C1-C-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Br;D1;H0:4])-[CH2;D2;+0:5]-1.O=C1-C-C-[CH2;D2;+0:6]-[C:7]-[C;H0;D4;+0:8]-1(-[C:9]-[C:10])-[C:11]-[C:12]>>[Br;D1;H0:4]-[C:3]1-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7]-[C;H0;D4;+0:8](-[C:9]-[C:10])(-[C:11]-[C:12])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | The bromination of spiro[5.5]undecan-1-one takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | C1CCCCC1.C1CCC2(CC1)CCCCC2 | C1CCC2(CC1)CCCCC2 | C1CCC2(CC1)CCCCC2 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCC12CCCCC2>>O=C1C(Br)CCCC12CCCCC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dc56b055e1544a4a8c8c799f73e8849d | CCC(Br)(Br)CC.O=C1CCCCC1>>O=C1CCCCC12CCCCC2 | Cl.BrC(CC)(CC)Br.C1(CCCCC1)=O.[K].C(C)(C)(C)[O-]>>C1(CCCCC12CCCCC2)=O | Br[C:7](Br)([CH2:6][CH3:5])[CH2:8][CH3:9].[O:1]=[C:2]1[CH2:3][CH2:4][CH2:10][CH2:11][CH2:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]12[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2 | CCC(Br)(Br)CC.O=C1CCCCC1 | O=C1CCCCC12CCCCC2 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 1984e377c5a53864ac597b345147e25f85c928fce3b4d3326f7184a4390f7151 | 900fcca56a30780c8a6389aaff7b67bf15bb816c9cda74c5539c23c6ec184457 | O=C1CCCCC12CCCCC2 | Br-[C;H0;D4;+0:1](-Br)(-[C:2]-[CH3;D1;+0:3])-[C:4]-[CH3;D1;+0:5].[O;D1;H0:6]=[C;H0;D3;+0:7]1-[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C;H0;D3;+0:7]1-[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:3]-[C:2]-[C;H0;D4;+0:1]-12-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:10]-[C:11]-[CH2;D2;+0:12]-2 | null | [] | null | null | null | null | Dibromopentane (5 mmol) is added to a solution of cyclohexanone (5 mmol) and potassium-tert-butanolate (10 mmol) in toluene (7.5 ml) and the reaction mixture is refluxed for 48 hours. After cooling to room temperature 25% hydrochloric acid is added and extraction is carried out with diethyl ether. The combined organic ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone | Ketone | C1CCCCC1 | C1CCC2(CC1)CCCCC2 | C1CCC2(CC1)CCCCC2 | HBr | C1(=CC=CC=C1)C | null | null | CCC(Br)(Br)CC.O=C1CCCCC1>C1(=CC=CC=C1)C>O=C1CCCCC12CCCCC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-81e44d8726b64ed0be920b284fd3b62f | CC(C)C1CCC(=O)C(Br)C1.O=C1CCC(c2ccccc2)(c2ccccc2)CC1>>O=C1CCC(c2ccccc2)(c2ccccc2)CC1Br | C1(=CC=CC=C1)C1(CCC(CC1)=O)C1=CC=CC=C1.BrC1C(CCC(C1)C(C)C)=O>>BrC1C(CCC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O | CC(C)[CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[CH:19]([Br:20])[CH2:18]1.O=C1CCC([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)CC1>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH:19]1[Br:20] | CC(C)C1CCC(=O)C(Br)C1.O=C1CCC(c2ccccc2)(c2ccccc2)CC1 | O=C1CCC(c2ccccc2)(c2ccccc2)CC1Br | null | null | null | C-C Coupling | Bromination | 28a75d7de73b1abb39336eed518e8fb0d047c9efdefbfb8db611d57a55121780 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=C1CCC(c2ccccc2)(c2ccccc2)CC1 | C-C(-C)-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1.O=C1-C-C-C(-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])(-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17])-C-C-1>>[O;D1;H0:5]=[C:4]1-[C:3]-[C:2]-[C;H0;D4;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])(-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17])-... | null | [] | null | null | null | null | The bromination of 4,4-diphenylcyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1.C1CCCCC1.c1ccccc1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.O=C1CCC(c2ccccc2)(c2ccccc2)CC1>>O=C1CCC(c2ccccc2)(c2ccccc2)CC1Br |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-61c17b37e0774a4e826e87fd4f6dbcec | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1(c2ccccc2)CCC(=O)CC1>>CCOC(=O)C1(c2ccccc2)CCC(=O)C(Br)C1 | C(C)OC(=O)C1(CCC(CC1)=O)C1=CC=CC=C1.BrC1C(CCC(C1)C(C)C)=O>>C(C)OC(=O)C1(CC(C(CC1)=O)Br)C1=CC=CC=C1 | CC(C)C1[CH2:13][CH2:14][C:15](=[O:16])[CH:17]([Br:18])[CH2:19]1.O=C1CC[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)CC1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][C:15](=[O:16])[CH:17]([Br:18])[CH2:19]1 | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1(c2ccccc2)CCC(=O)CC1 | CCOC(=O)C1(c2ccccc2)CCC(=O)C(Br)C1 | null | null | null | C-C Coupling | Bromination | 859f4e276d02eca86bbd5435dc5917b8c946fcb6ddfe252a81c131d1156bebcb | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | O=C1CCC(c2ccccc2)CC1 | C-C(-C)-C1-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[C:5](-[Br;D1;H0:6])-[CH2;D2;+0:7]-1.O=C1-C-C-[C;H0;D4;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])(-[c:13](:[c:14]):[c:15])-C-C-1>>[Br;D1;H0:6]-[C:5]1-[CH2;D2;+0:7]-[C;H0;D4;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])(-[c:13](:[c:14]):[c:15])-[CH2;D2;+0:1]-[C:2]-[C:3]-... | null | [] | null | null | null | null | The bromination of 4-oxo-1-phenyl-cyclohexane carboxylic acid ethyl ester takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CCOC(=O)C1(c2ccccc2)CCC(=O)CC1>>CCOC(=O)C1(c2ccccc2)CCC(=O)C(Br)C1 |
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