dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf981b58918d46a4bf6543e26edf77e6 | CC1(C)CCC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>CC1(C)CCC[C@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C(=O)N1 | C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1.O.NN.C1(C=2C(C(N1[C@H]1CCCC(NC1=O)(C)C)=O)=CC=CC2)=O.C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>>C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@H]1CCCC(NC1=O)(C)C | O=C1c2ccccc2C(=O)[N:8]1[C@H:7]1[CH2:6][CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[NH:30][C:28]1=[O:29].Cl[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][C@H:7]([NH:8][C:9]([c:10]2[cH:11][cH:... | CC1(C)CCC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | CC1(C)CCC[C@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C(=O)N1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a12cf7af8efc46e68d61b624fd0d279b6a62dfdd51fa9a2ebdb998fdcdd29be7 | 28b72e46db2638ded4e9272b0bcac45fdcf86b73ced593a7dbbac98cf9ed0efd | O=C1NCCCC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].O=C1-[N;H0;D3;+0:11](-[C:12](-[C:13])-[C:14](=[O;D1;H0:15])-[#7:16]-[C:17])-C(=O)-c2:c:c:c:c:c:2-1>>[C:17]-[#7:16]-[C:14](=[O;D1;H0:15])-[C:12](-[NH;D2;+0:11]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10... | null | [] | null | null | 72 | HOUR | Hydrazine monohydrate (4.59 ml., 94.6 mmol.) was added to a solution of (S)-hexahydro-6-phthalimido-2,2-dimethyl-2H-azepine-7-one [preparred as described in Example 66(e), 19.98 g., 68.76 mmol.] in methanol (250 ml.) at room temperature under argon. The resulting mixture was stirred for 72 hours then filtered to remove... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Substituted dicarboximide | Secondary amine | c1ccc2c(c1)C[NH]C2 | null | C1CCCNCC1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CO | null | 72 | CC1(C)CCC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>CO>CC1(C)CCC[C@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C(=O)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa67e58f427c410f88c862b2ce6dc73e | ClP(Cl)Cl.Oc1ccccc1-c1ccccc1O>>Clp1oc2ccccc2c2ccccc2o1 | C=1(C(=CC=CC1)C=1C(=CC=CC1)O)O.P(Cl)(Cl)Cl>>P1(OC2=C(C=CC=C2)C2=C(C=CC=C2)O1)Cl | Cl[P:2](Cl)[Cl:1].[OH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[OH:16]>>[Cl:1][p:2]1[o:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[o:16]1 | ClP(Cl)Cl.Oc1ccccc1-c1ccccc1O | Clp1oc2ccccc2c2ccccc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1388d467c73a45f8728568ec2382b0e62344af6950e7aad2f3a259e6a6f7af96 | 8a2ce476a1d993ef0eccc79c0116619b23ccd96544c672b2781b24ef0818f555 | c1ccc2c(c1)o[pH]oc1ccccc12 | Cl-[P;H0;D3;+0:1](-Cl)-[Cl;D1;H0:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]):[c:13]:[c:14]>>[Cl;D1;H0:2]-[p;H0;D3;+0:1]1:[o;H0;D2;+0:3]:[c:4](:[c:5]):[c;H0;D3;+0:6](:[c:13]:[c:14]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](:[c:12]):[o;H0;D2;+0:11]:1 | 81 | [{"value": 81.0, "product": "P1(OC2=C(C=CC=C2)C2=C(C=CC=C2)O1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,2'-biphenol (28.1 g, 0.151 mol) in 49 mL phosphorus trichloride was heated at reflux for 2 hr. The excess PC13 was removed by distillation. The residue was purified by vacuum distillation (140°-143° C. at 0.5 mm Hg) to give 30.70 g (81% yield) 1,1'-biphenyl-2,2'-diyl phosphorochloridite (as a clear visc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | null | c1ccccc1.c1ccccc1 | c1ccc2c(c1)opoc1ccccc12 | c1ccc2c(c1)opoc1ccccc12 | HCl | null | null | null | ClP(Cl)Cl.Oc1ccccc1-c1ccccc1O>>Clp1oc2ccccc2c2ccccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-440b49e065434692a260e63870f36ce7 | Fc1cc(Br)ccc1CBr.OCc1ccccc1>>O=C(NCc1ccc(Br)cc1F)OCc1ccccc1 | C(C1=CC=CC=C1)O.O([K])C#N.BrC1=CC(=C(CBr)C=C1)F>>BrC1=CC(=C(CNC(OCC2=CC=CC=C2)=O)C=C1)F | Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[F:12].[OH:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[F:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | Fc1cc(Br)ccc1CBr.OCc1ccccc1 | O=C(NCc1ccc(Br)cc1F)OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 1c5f0b45e080118803b9e15ddb72c3da01ea2f14018cf1d8ca981d3ed00fe7f9 | 5e1dd53cff58b3c5481a3ca8392554a4f9cbbc0fad5e63854b46344482c9bd4c | O=C(NCc1ccccc1)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:8]=[C:9](-[#7:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[O;H0;D2;+0:5]-[C:6]-[c:7] | null | [] | 110 | CELSIUS | null | null | Anhydrous and amine-free DMF (180 ml) and benzyl alcohol (28 ml) and KOCN (0.247 mol, 20 g) are charged into a 500 ml 2-neck round bottom flask having a reflux condenser and drying tube. A solution of 4-bromo-2-fluorobenzyl bromide (0.075 mol, 20 g) in DMF (20 ml) is added rapidly (in the course of 1 min) at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Carbamic ester.Ether | null | null | c1ccccc1.c1ccccc1 | Br- | CN(C)C=O | 110 | null | Fc1cc(Br)ccc1CBr.OCc1ccccc1>CN(C)C=O>O=C(NCc1ccc(Br)cc1F)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50401cea459a444786f5e8507d29997b | CCOC(=O)Cc1cccc(Br)c1>>O=CCc1cccc(Br)c1 | [H-].C(C(C)C)[Al+]CC(C)C.[H][H].BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC=1C=C(C=CC1)CC(=O)OCC.BrC=1C=C(C=CC1)CC(=O)OCC>>BrC=1C=C(C=CC1)CC=O | CCO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1>>[O:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1 | CCOC(=O)Cc1cccc(Br)c1 | O=CCc1cccc(Br)c1 | null | null | null | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]>>[O;D1;H0:2]=[CH;D2;+0:1]-[C:3]-[c:4] | null | [] | null | null | null | null | In the preferred compounds of the invention the two R1 substituents are methyl, and the R2 and R3 substituents are hydrogen. Reaction Scheme 4 illustrates a synthetic process for preparing 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one (Compound G) which serves as a starting material for the synthesis of several pref... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)Cc1cccc(Br)c1>>O=CCc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81448799139447a985ca454877c95d87 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 | BrC=1C=C(C=CC1)CC=O.C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>BrC=1C=C(C=CC1)CCCC(=O)OCC | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[CH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1cccc(Br)c1 | CCOC(=O)CCCc1cccc(Br)c1 | null | null | null | C-C Coupling | OtherReaction | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | In the preferred compounds of the invention the two R1 substituents are methyl, and the R2 and R3 substituents are hydrogen. Reaction Scheme 4 illustrates a synthetic process for preparing 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one (Compound G) which serves as a starting material for the synthesis of several pref... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c9f9ed9d7a3470fad54d7ea759b23b8 | CCO.O=C(O)Cc1ccc(Br)cc1>>CCOC(=O)Cc1ccc(Br)cc1 | BrC1=CC=C(C=C1)CC(=O)O.OS(=O)(=O)O.C(C)O.C(=O)([O-])[O-].[K+].[K+]>>BrC1=CC=C(C=C1)CC(=O)OCC | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1 | CCO.O=C(O)Cc1ccc(Br)cc1 | CCOC(=O)Cc1ccc(Br)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[C;D1;H3:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | null | null | A solution of 43 g (200 mmol) of 4-bromophenylacetic acid and 0.2 g of conc. H2SO4 in 470 ml of ethanol was refluxed for 16 hours. The reaction mixture was cooled to ambient temperature, stirred with 6 g of solid K2CO3 for 30 minutes and then filtered. The filtrate was concentrated in vacuo, diluted with Et2O (200 ml),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)Cc1ccc(Br)cc1>>CCOC(=O)Cc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e43ff72352bb417281bdb41c9d85b8ca | CCOC(=O)Cc1ccc(Br)cc1.O=C(O)Cc1cccc(Br)c1>>CCOC(=O)Cc1cccc(Br)c1 | BrC1=CC=C(C=C1)CC(=O)OCC.BrC1=CC=C(C=C1)CC(=O)OCC.BrC=1C=C(C=CC1)CC(=O)O>>BrC=1C=C(C=CC1)CC(=O)OCC | O=C(Cc1ccc(Br)cc1)O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[cH:13]1 | CCOC(=O)Cc1ccc(Br)cc1.O=C(O)Cc1cccc(Br)c1 | CCOC(=O)Cc1cccc(Br)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 042509afb850b7ae8d1b416db2a7d99308189364e9a5fcf96184b5eead3a8ee2 | b4a89122cda2e12df412f0af60b7839f49d2933dbee64ad6cf28e3443255e82d | c1ccccc1 | Br-c1:c:c:c(-C-C(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2]):c:c:1.[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl (4-bromophenyl)acetate (Compound A), 100 g (463 mmol) of 3-bromophenylacetic acid was converted into the title compound (yellow oil) using 2 g of conc. H2SO4 and 500 ml of ethanol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Ester | Ester | c1ccccc1 | null | c1ccccc1 | HBr | null | null | null | CCOC(=O)Cc1ccc(Br)cc1.O=C(O)Cc1cccc(Br)c1>>CCOC(=O)Cc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33aa1937ff844517b2312155507524cc | CCOC(=O)Cc1ccc(Br)cc1>>O=CCc1ccc(Br)cc1 | [H-].C(C(C)C)[Al+]CC(C)C.BrC1=CC=C(C=C1)CC(=O)OCC.BrC1=CC=C(C=C1)CC(=O)OCC.[H-].C(C(C)C)[Al+]CC(C)C>>BrC1=CC=C(C=C1)CC=O | CCO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>>[O:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1 | CCOC(=O)Cc1ccc(Br)cc1 | O=CCc1ccc(Br)cc1 | null | null | C(Cl)Cl | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]>>[O;D1;H0:2]=[CH;D2;+0:1]-[C:3]-[c:4] | null | [] | -78 | CELSIUS | null | null | To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl (4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutyl aluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccccc1 | HO- | C(Cl)Cl | -78 | null | CCOC(=O)Cc1ccc(Br)cc1>C(Cl)Cl>O=CCc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-da2fa25d7948417ea3bceca3d031dfb8 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1ccc(Br)cc1>>CCOC(=O)C=CCc1ccc(Br)cc1 | BrC1=CC=C(C=C1)CC=O.ClCl.C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>BrC1=CC=C(C=C1)CC=CC(=O)OCC | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[CH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1ccc(Br)cc1 | CCOC(=O)C=CCc1ccc(Br)cc1 | null | null | C(Cl)Cl | C-C Coupling | Wittig reaction with triphenylphosphorane | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | 16 | HOUR | To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl (4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutyl aluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | C(Cl)Cl | null | 16 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1ccc(Br)cc1>C(Cl)Cl>CCOC(=O)C=CCc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbd2b45e8f9b4d7dbebe53c304885efe | CCOC(=O)CCCc1ccc(Br)cc1.CCOC(=O)Cc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 | BrC1=CC=C(C=C1)CCCC(=O)OCC.BrC1=CC=C(C=C1)CCCC(=O)OCC.BrC=1C=C(C=CC1)CC(=O)OCC.BrC=1C=C(C=CC1)CC(=O)OCC>>BrC=1C=C(C=CC1)CCCC(=O)OCC | Br[c:12]1[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:15][cH:13]1.CCOC(=O)Cc1cccc([Br:14])c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | CCOC(=O)CCCc1ccc(Br)cc1.CCOC(=O)Cc1cccc(Br)c1 | CCOC(=O)CCCc1cccc(Br)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 434198cbd735c3e210a63326c76eb747349a83f3c9f01bbe2eff06a955199ae4 | d0508361c24262840b1fde4be03be16061d0fd8ada9f40d1b6c5100911d70222 | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.C-C-O-C(=O)-C-c1:c:c:c:c(-[Br;H0;D1;+0:7]):c:1>>[Br;H0;D1;+0:7]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | Employing the same general multistep preparation as for ethyl 4-(4-bromophenyl)butanoate (Compound C), 60 g (246 mmol) of ethyl (3-bromophenyl)acetate (Compound B) was converted into the title compound (oil) using 255 ml (255 mmol) of diisobutyl aluminum hydride (DIBAL-H, 1M in hexane), 85.8 g (250 mmol) of (carbethoxy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | null | null | CCOC(=O)CCCc1ccc(Br)cc1.CCOC(=O)Cc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7d11788629c4e828999fce2494a1099 | CC(C)(O)CCCc1cccc(Br)c1>>CC1(C)CCCc2cc(Br)ccc21 | BrC=1C=C(C=CC1)CCCC(C)(O)C.BrC=1C=C(C=CC1)CCCC(C)(O)C.OS(=O)(=O)O>>BrC=1C=C2CCCC(C2=CC1)(C)C | O[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12][cH:13]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21 | CC(C)(O)CCCc1cccc(Br)c1 | CC1(C)CCCc2cc(Br)ccc21 | null | null | O | Functional Group Interconversion | OtherReaction | 9c1fb3695518f6dccadbe5ee73c6321afbfb380fa2ad5c0f3b619c242d912134 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | c1ccc2c(c1)CCCC2 | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9]-1:[c:10]:[c:11] | null | [] | null | null | 2.5 | HOUR | 15.0 g (58.3 mmol) of 5-(3-bromophenyl)-2-methyl-pentan-2-ol (Compound E) was cooled to 0° C. and then 2.8 ml of conc. H2SO4 was added. The mixture was stirred for 2.5 hours, diluted with water (20 ml) and extracted with Et2O (3×40 ml). The combined organic layers were washed with water, sat. aqueous NaHCO3 and brine, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | O | null | 2.5 | CC(C)(O)CCCc1cccc(Br)c1>O>CC1(C)CCCc2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f2e1f01e7ab4687bdbd97f9472f7215 | CC(=O)O.CC1(C)CCCc2cc(Br)ccc21>>CC1(C)CCC(=O)c2cc(Br)ccc21 | C(C)(=O)OC(C)=O.C(C)(=O)O.BrC=1C=C2CCCC(C2=CC1)(C)C.BrC=1C=C2CCCC(C2=CC1)(C)C>>BrC1=CC=C2C(CCC(C2=C1)=O)(C)C | CC(O)=[O:7].[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21 | CC(=O)O.CC1(C)CCCc2cc(Br)ccc21 | CC1(C)CCC(=O)c2cc(Br)ccc21 | null | [O-2].[O-2].[O-2].[Cr+6] | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 06b75b2d4fdd308e9ae14eb39d86aacd806c7aa02919897cbe294a3bc24409c8 | bd34f155ea119239d8395e98fadac5c7a5507ae7ce37531b09373c8830fc562b | O=C1CCCc2ccccc21 | C-C(-O)=[O;H0;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:1])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | To a cold mixture (0° C.) of 209 g (200 mmol) of chromium trioxide, 100 ml (1.06 mol) of acetic anhydride and 200 ml (3.5 mol) of acetic acid was added a solution of 10 g (41.8 mmol) of 6-bromo-1,2,3,4-tet-rahydro-1,1-dimethylnaphthalene (Compound F) in 125 ml of benzene. The reaction mixture was stirred for 1 hour, qu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | [O-2].[O-2].[O-2].[Cr+6].C1=CC=CC=C1 | null | 1 | CC(=O)O.CC1(C)CCCc2cc(Br)ccc21>[O-2].[O-2].[O-2].[Cr+6].C1=CC=CC=C1>CC1(C)CCC(=O)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d35af9b12f1b47e88a643494fdc123b8 | CC1(C)CCCc2cc(Br)ccc21.O=C1CCC(=O)N1Br>>CC1(C)CCC(Br)c2cc(Br)ccc21 | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.BrC=1C=C2CCCC(C2=CC1)(C)C.BrC=1C=C2CCCC(C2=CC1)(C)C.BrN1C(CCC1=O)=O>>BrC1CCC(C2=CC=C(C=C12)Br)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21.O=C1CCC(=O)N1[Br:7]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH:6]([Br:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21 | CC1(C)CCCc2cc(Br)ccc21.O=C1CCC(=O)N1Br | CC1(C)CCC(Br)c2cc(Br)ccc21 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl secondary | 17739125d8cd5498d2767e5d914bf11a628d3cd4978506b1472183bfc6cb0caf | d425bc7fa712969b9477dfeabb5ca2470f442214b30503c51715e13a06c60154 | c1ccc2c(c1)CCCC2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[Br;H0;D1;+0:1]-[CH;D3;+0:4](-[C:3]-[C:2])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | To a solution of 1.2 g (5.0 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F) in 20 ml of CCl4 was added 0.97 g (5.5 mmol) of N-bromosuccinimide followed by 20 mg (0.08 mmol ) of benzoylperoxide. The mixture was refluxed for 3 hours, filtered and the filtrate washed with water (5 ml). The organic... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Secondary halide | c1ccc2c(c1)CCCC2.C1CCNC1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | CC1(C)CCCc2cc(Br)ccc21.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CC1(C)CCC(Br)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9d51c679b094d58b2ae53013e4113f3 | CC1(C)CCC(Br)c2cc(Br)ccc21.OC1CCCCC1>>CC1(C)CCC(OC2CCCCC2)c2cc(Br)ccc21 | BrC1CCC(C2=CC=C(C=C12)Br)(C)C.BrC1CCC(C2=CC=C(C=C12)Br)(C)C.C1(CCCCC1)O.[Na].[Na].C1(CCCCC1)O>>BrC=1C=C2C(CCC(C2=CC1)(C)C)OC1CCCCC1 | Br[CH:6]1[CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[c:20]2[c:14]1[cH:15][c:16]([Br:17])[cH:18][cH:19]2.[OH:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | CC1(C)CCC(Br)c2cc(Br)ccc21.OC1CCCCC1 | CC1(C)CCC(OC2CCCCC2)c2cc(Br)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 34d15a16c487cc76959b4148d45a121e70900b63e696306f158d56c902806bae | ea93f50d7d0ba6e1a92e059c8905ace57b0b1cde9cb71b1ee64fbecaa8f468bb | c1ccc2c(c1)CCCC2OC1CCCCC1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6])-[C:10] | null | [] | 70 | CELSIUS | 12 | HOUR | To 9 g (89.9 mmol) of cyclohexanol was added 160 mg (7.0 mmol) of sodium metal and the mixture was stirred at 70° C. for 12 hours. After all of the sodium dissolved the reaction mixture was cooled to ambient temperature and then a solution of 1 g (3.2 mmol) of 4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Com... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary alcohol | Ether | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | C1CCCCC1.c1ccc2c(c1)CCCC2 | HBr | null | 70 | 12 | CC1(C)CCC(Br)c2cc(Br)ccc21.OC1CCCCC1>>CC1(C)CCC(OC2CCCCC2)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5100f97ff6524472837ccd21fd6bb444 | CC1(C)CCC(=O)c2ccc(Br)cc21>>C#Cc1ccc2c(c1)C(C)(C)CCC2=O | C[Si](C)(C)C#C.BrC=1C=C2C(CCC(C2=CC1)=O)(C)C.BrC=1C=C2C(CCC(C2=CC1)=O)(C)C.C(=O)([O-])[O-].[K+].[K+]>>C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C | Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][C:14]2=[O:15]>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][C:14]2=[O:15] | CC1(C)CCC(=O)c2ccc(Br)cc21 | C#Cc1ccc2c(c1)C(C)(C)CCC2=O | 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 | CO.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 9818ebb8d5fc33ce3a31bcb4fdc7e5e2df1ec512dcedf969889ca1e8c4b90a40 | 3328c8f87c438567981cd74666102f3c9878dcf86df57abda9cd69bae6cfdc49 | O=C1CCCc2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[C;D1;H1:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 24 | HOUR | To a solution (flushed for 15 minutes with a stream of argon) of 13.55 g (53.8 mmol) of 6-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound H) in 280 ml of triethylamine was added 1.87 g (2.66 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.53 g (2.66 mmol) of cuprous iodide. The solution mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Alkyne | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Br- | 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.CO.C(C)N(CC)CC | null | 24 | CC1(C)CCC(=O)c2ccc(Br)cc21>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.CO.C(C)N(CC)CC>C#Cc1ccc2c(c1)C(C)(C)CCC2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37e5f74403034441b8cb09beed7ae702 | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CC1(C)CCC(=O)c2cc(Br)ccc21>>C#Cc1ccc2c(c1)C(=O)CCC2(C)C | C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C>>C(#C)C1=CC=C2C(CCC(C2=C1)=O)(C)C | C#Cc1ccc2c(c1)C(C)([CH3:15])CCC2=O.C[C:9]1(C)[c:7]2[c:6]([cH:5][cH:4][c:3]([C:2]#[CH:1])[cH:8]2)[C:13](=O)[CH2:12][CH2:11]1.CC1([CH3:14])CCC(=[O:10])c2cc(Br)ccc21>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12][C:13]2([CH3:14])[CH3:15] | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CC1(C)CCC(=O)c2cc(Br)ccc21 | C#Cc1ccc2c(c1)C(=O)CCC2(C)C | null | null | null | C-C Coupling | OtherReaction | 1365b500a0241976737dfb6a369761907f8fb54b4f9ffb3c30402e49bd252bc2 | 92eb20c58f7702e061d6464afba78c5922cec9ff6753b5109e17ff517e1560ff | O=C1CCCc2ccccc21 | Br-c1:c:c:c2:c(:c:1)-C(=[O;H0;D1;+0:1])-C-C-C-2(-C)-[CH3;D1;+0:2].C-C1(-[CH3;D1;+0:3])-C-C-C(=O)-c2:c:c:c(-C#C):c:c:2-1.C-[C;H0;D4;+0:4]1(-C)-[C:5]-[C:6]-[C;H0;D3;+0:7](=O)-[c:8](:[c:9]):[c:10]-1:[c:11]>>[CH3;D1;+0:2]-[C;H0;D4;+0:7]1(-[CH3;D1;+0:3])-[C:6]-[C:5]-[C;H0;D3;+0:4](=[O;H0;D1;+0:1])-[c:10](:[c:11]):[c:8]-1:[c... | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound K), 7 g (27.6 mmol) of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) was converted into the title compound using 39 ml (36.6 mmol) of trimethylsilyl acetylene, 0.97 g (1.3 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ketone.Ketone.Alkyne | Ketone | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HBr | null | null | null | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CC1(C)CCC(=O)c2cc(Br)ccc21>>C#Cc1ccc2c(c1)C(=O)CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-084c85907fd245078e2f7acbc10ccaab | C#Cc1ccc2c(c1)C(C)(C)CCC2=O>>C#Cc1ccc2c(c1)C(C)(C)CCC2 | C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.BrC1=CC=C2CCCC(C2=C1)(C)C>>C(#C)C1=CC=C2CCCC(C2=C1)(C)C | O=[C:14]1[c:6]2[cH:5][cH:4][c:3]([C:2]#[CH:1])[cH:8][c:7]2[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][CH2:14]2 | C#Cc1ccc2c(c1)C(C)(C)CCC2=O | C#Cc1ccc2c(c1)C(C)(C)CCC2 | null | null | null | Reduction | OtherReaction | 468c83eaa3986920e31d657ce80fb6963b17b14c1dd69f3228a474d350fb1bc7 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc2c(c1)CCCC2 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound K), 2.1 g (8.8 mmol) of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene was converted into the title compound using 10 ml (93.9 mmol) of trimethylsilyl acetylene, 1.25 g (1.8 mmol) of bis(t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Other | null | null | null | C#Cc1ccc2c(c1)C(C)(C)CCC2=O>>C#Cc1ccc2c(c1)C(C)(C)CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0079b2bf1e1f4513a61d1b8da92b8460 | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CC1(C)CCC(OC2CCCCC2)c2cc(Br)ccc21>>C#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2(C)C | C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.BrC=1C=C2C(CCC(C2=CC1)(C)C)OC1CCCCC1.BrC=1C=C2C(CCC(C2=CC1)(C)C)OC1CCCCC1>>C1(CCCCC1)OC1CCC(C2=CC=C(C=C12)C#C)(C)C | CC1(C)CCC(=O)c2ccc([C:2]#[CH:1])cc21.Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([O:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[CH2:17][CH2:18][C:19]2([CH3:20])[CH3:21]>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([O:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[CH2:17][CH2:18][C:19]2(... | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CC1(C)CCC(OC2CCCCC2)c2cc(Br)ccc21 | C#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2(C)C | null | null | null | C-C Coupling | OtherReaction | 31a3474e92ab2e8b85367011ff722b53d568044350671cd066f20ddbecb87843 | a0646be30f9e286d895567733705df3a31f14d5a6362370a8a4aee5300c33666 | c1ccc2c(c1)CCCC2OC1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C1(-C)-C-C-C(=O)-c2:c:c:c(-[C;H0;D2;+0:6]#[C;D1;H1:7]):c:c:2-1>>[C;D1;H1:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound K), 2.1 g (8.8 mmol) of 6-bromo-4-cyclohexyloxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Compound J) was converted into the title compound using 1 g (10.2 mmol) of trimethylsilyl acetylene,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Alkyne | Alkyne | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | C1CCCCC1.c1ccc2c(c1)CCCC2 | HBr | null | null | null | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CC1(C)CCC(OC2CCCCC2)c2cc(Br)ccc21>>C#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a6411cd1b2143cf95c4b57b2c8fb6d3 | CC1(C)CCCc2cc(Br)ccc21.O=C1CCC(=O)N1Br>>CC1(C)CCC(Br)c2cc(Br)ccc21 | C1=CC=CC2=CC=CC=C12.BrC=1C=C2CCCC(C2=CC1)(C)C.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C1=CC=CC2=CC=CC=C12.BrC=1C=C2CCCC(C2=CC1)(C)C.C1=CC=CC2=CC=CC=C12.BrC=1C=C2CCCC(C2=CC1)(C)C.BrN1C(CCC1=O)=O.BrC1=C(C2=CC=CC=C2C=C1)Br>>BrC1CCC(C2=CC=C(C=C12)Br)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21.O=C1CCC(=O)N1[Br:7]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH:6]([Br:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21 | CC1(C)CCCc2cc(Br)ccc21.O=C1CCC(=O)N1Br | CC1(C)CCC(Br)c2cc(Br)ccc21 | null | null | null | Functional Group Interconversion | Wohl-Ziegler bromination benzyl secondary | 17739125d8cd5498d2767e5d914bf11a628d3cd4978506b1472183bfc6cb0caf | d425bc7fa712969b9477dfeabb5ca2470f442214b30503c51715e13a06c60154 | c1ccc2c(c1)CCCC2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[Br;H0;D1;+0:1]-[CH;D3;+0:4](-[C:3]-[C:2])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Employing the above-described procedure for the conversion of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene (Compound F) to the dibromonaphthalene derivative (Compond I), 3.5 g (14.6 mmol) of (Compound F), 2.86 g (16.1 mmol) of N-bromosuccinimide and 150 mg (0.62 mmol ) of benzoylperoxide gave crude 4,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Secondary halide | c1ccc2c(c1)CCCC2.C1CCNC1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | null | null | null | CC1(C)CCCc2cc(Br)ccc21.O=C1CCC(=O)N1Br>>CC1(C)CCC(Br)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ad41e85bae94573960b3d36e878b3e1 | CC1(C)CCC(Br)c2cc(Br)ccc21>>CC(=S)C1CCC(C)(C)c2ccc(Br)cc21 | BrC1CCC(C2=CC=C(C=C12)Br)(C)C.BrC1CCC(C2=CC=C(C=C12)Br)(C)C.C(C)(=S)[O-].[K+]>>BrC=1C=C2C(CCC(C2=CC1)(C)C)C(C)=S | Br[CH:4]1[CH2:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21>>[CH3:1][C:2](=[S:3])[CH:4]1[CH2:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21 | CC1(C)CCC(Br)c2cc(Br)ccc21 | CC(=S)C1CCC(C)(C)c2ccc(Br)cc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 9454b75fa71245ad89b40fe3c2db4bb90e1d43bd9cae8b3499d53736938dead0 | 9559467ca5e8c56c867a7f0b1d7590b92ee0338e4bcca9d01df5ba4df2a7cb1f | c1ccc2c(c1)CCCC2 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]>>[C:3]-[C:2]-[CH;D3;+0:1](-[C:7](-[C;D1;H3:8])=[S;D1;H0:9])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Employing the above-described procedure for the conversion of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene (Compound F) to the dibromonaphthalene derivative (Compond I), 3.5 g (14.6 mmol) of (Compound F), 2.86 g (16.1 mmol) of N-bromosuccinimide and 150 mg (0.62 mmol ) of benzoylperoxide gave crude 4,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Thiocarbonyl | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Br- | C1CCOC1 | null | null | CC1(C)CCC(Br)c2cc(Br)ccc21>C1CCOC1>CC(=S)C1CCC(C)(C)c2ccc(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6724f220dc7c4e89ac64b79ac6a33d74 | CCO.O=C(O)c1ccc(I)cc1>>CCOC(=O)c1ccc(I)cc1 | IC1=CC=C(C(=O)O)C=C1.C(C)O.S(=O)(Cl)Cl>>C(C)OC(C1=CC=C(C=C1)I)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([I:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([I:10])[cH:11][cH:12]1 | CCO.O=C(O)c1ccc(I)cc1 | CCOC(=O)c1ccc(I)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a suspension of 10 g (40.32 mmol) of 4-iodobenzoic acid in 100 ml absolute ethanol was added 2 ml thionyl chloride and the mixture was then heated at reflux for 3 hours. Solvent was removed in vacuo and the residue was dissolved in 100 ml ether. The ether solution was washed with saturated NaHCO3 and saturated NaCl ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)c1ccc(I)cc1>>CCOC(=O)c1ccc(I)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-314d43ab585348f7bd5e6d904c0e5adc | CCO.O=C(O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(Cl)nc1 | ClC1=NC=C(C(=O)O)C=C1.C(C)O.C1(CCCCC1)N=C=NC1CCCCC1.CN(C)C1=NC=CC=C1>>ClC1=NC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1 | CCO.O=C(O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(Cl)nc1 | null | null | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and the residue subjected to flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | null | CCO.O=C(O)c1ccc(Cl)nc1>C(Cl)Cl>CCOC(=O)c1ccc(Cl)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9bd2bc35b4cb41778d4b4e86c4962f24 | I.O=C(O)c1ccc(Cl)nc1>>O=C(O)c1ccc(I)nc1 | [I-].[Na+].I.ClC1=NC=C(C(=O)O)C=C1>>IC1=NC=C(C(=O)O)C=C1 | [IH:8].Cl[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:10][n:9]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([I:8])[n:9][cH:10]1 | I.O=C(O)c1ccc(Cl)nc1 | O=C(O)c1ccc(I)nc1 | null | null | CC(=O)C | Miscellaneous | OtherReaction | b82d7209d2f0845b6d508d9b5d94221ef0c6a7295c1411bdc2d44fbaafae04d9 | 50b3263108b11afcbe25d1a908d5d62fc9b7a01756ee297f5e635ade1a0cdefb | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[IH;D0;+0:6]>>[I;H0;D1;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 5 | MINUTE | To 27.97 g (186.6 mmol) of sodium iodide cooled to -78° C. was added 121.77 g (71.6 ml, 952.0 mmol) of hydriodic acid (57 wt %). The reaction mixture was allowed to warm slightly with stirring for 5 minutes, and then 30.00 g (190.4 mmol) of 6-chloronicotinic acid was added. The resulting mixture was allowed to warm to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CC(=O)C | null | 0.083333 | I.O=C(O)c1ccc(Cl)nc1>CC(=O)C>O=C(O)c1ccc(I)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2fe08cc9e6c748808fe5a8679bdd3bfb | CCO.O=C(O)c1ccc(I)nc1>>CCOC(=O)c1ccc(I)nc1 | IC1=NC=C(C(=O)O)C=C1.C(C)O.Cl.CN(CCCN=C=NCC)C>>IC1=NC=C(C(=O)OCC)C=C1 | O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([I:10])[n:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([I:10])[n:11][cH:12]1 | CCO.O=C(O)c1ccc(I)nc1 | CCOC(=O)c1ccc(I)nc1 | null | CN(C1=CC=NC=C1)C | ClCCl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccncc1 | O-[CH2;D2;+0:1]-[C;D1;H3:2].[#7;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[#7;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | 50 | CELSIUS | null | null | To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (95%) and 1.15 g (9.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | 50 | null | CCO.O=C(O)c1ccc(I)nc1>CN(C1=CC=NC=C1)C.ClCCl>CCOC(=O)c1ccc(I)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-445de8cff1a04382843fe36a0a03ecd1 | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CCOC(=O)c1ccc(I)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C.IC1=CC=C(C(=O)OCC)C=C1>>CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C | [CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]2=[O:24].I[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:26][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])(... | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CCOC(=O)c1ccc(I)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | 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 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C1CCCc2cc(C#Cc3ccccc3)ccc21 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 18 | HOUR | To a solution of 8.8 g (47.8 mmol) of 6-ethynyl-1,2,3,4-tetrahydro-4,4-dimethylnaphthalen-1-one (Compound K) flushed for 15 minutes with a stream of argon, and 13.2 g (47.8 mmol) of ethyl 4-iodobenzoate in 200 ml of triethylamine was added 1.1 g (1.6 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.30 g (1.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCC2 | HI | 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.C(C)N(CC)CC | null | 18 | C#Cc1ccc2c(c1)C(C)(C)CCC2=O.CCOC(=O)c1ccc(I)cc1>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.C(C)N(CC)CC>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e299c501d96048db89b08fd31ee6b9bf | C#Cc1ccc2c(c1)C(=O)CCC2(C)C.C#Cc1ccc2c(c1)C(=O)CCC2(C)C.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)cc1 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.C(#C)C1=CC=C2C(CCC(C2=C1)=O)(C)C.C(#C)C1=CC=C2C(CCC(C2=C1)=O)(C)C>>CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C | C#Cc1ccc2c(c1)C(=[O:19])CCC2(C)C.C#Cc1ccc2c(c1)C(=O)CCC2([CH3:23])[CH3:24].C[C:18]1(C)[c:16]2[c:15]([cH:14][cH:13][c:12]([C:11]#[C:10][c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:26][cH:25]3)[cH:17]2)[C:22](=O)[CH2:21][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]... | C#Cc1ccc2c(c1)C(=O)CCC2(C)C.C#Cc1ccc2c(c1)C(=O)CCC2(C)C.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)cc1 | null | null | null | C-C Coupling | OtherReaction | dc33cab0b77d3fb96b3667c72300820592501c9c2e822167612a009d145b0c83 | 885371fb4e33873f638094be96087519d7dde6b81c0705bbbf7b5f832f94f13e | O=C1CCCc2ccc(C#Cc3ccccc3)cc21 | C#C-c1:c:c:c2:c(:c:1)-C(=O)-C-C-C-2(-[CH3;D1;+0:1])-[CH3;D1;+0:2].C-C1(-C)-C-C-C(=[O;H0;D1;+0:3])-c2:c:c(-C#C):c:c:c:2-1.C-[C;H0;D4;+0:4]1(-C)-[C:5]-[C:6]-[C;H0;D3;+0:7](=O)-[c:8](:[c:9]):[c:10]-1:[c:11]>>[CH3;D1;+0:1]-[C;H0;D4;+0:7]1(-[CH3;D1;+0:2])-[C:6]-[C:5]-[C;H0;D3;+0:4](=[O;H0;D1;+0:3])-[c:10](:[c:11]):[c:8]-1:[... | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1), 4 g (21.7 mmol) of 7-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound L) was converted into the title compound using 6 g (21.7 mmol) of ethyl 4-iodobenzo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ketone.Alkyne.Alkyne | Ketone | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | C#Cc1ccc2c(c1)C(=O)CCC2(C)C.C#Cc1ccc2c(c1)C(=O)CCC2(C)C.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ccf8d7ba858a4a1d98efae7e84bea37c | C#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2(C)C.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(OC2CCCCC2)CCC3(C)C)cc1 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.C1(CCCCC1)OC1CCC(C2=CC=C(C=C12)C#C)(C)C.C1(CCCCC1)OC1CCC(C2=CC=C(C=C12)C#C)(C)C>>C1(CCCCC1)OC1C=2C=C(C=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1 | C#Cc1ccc2c(c1)[CH:18]([O:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:26][CH2:27][C:28]2([CH3:29])[CH3:30].CC1(C)CCC(=O)[c:15]2[cH:14][cH:13][c:12]([C:11]#[C:10][c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:32][cH:31]3)[cH:17][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](... | C#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2(C)C.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(OC2CCCCC2)CCC3(C)C)cc1 | null | null | null | C-C Coupling | OtherReaction | 2b8579d1dea69c0d1f699de464a260c5b1c7d6aa0ee7dc7df5152b5133779971 | 94a676fe3e982ab149a6f97d161c48e0feb67671b52e80ae2dc697687e7b886e | C(#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2)c1ccccc1 | C#C-c1:c:c:c2:c(:c:1)-[CH;D3;+0:1](-[#8:2]-[C:3])-[C:4]-[C:5]-[C;H0;D4;+0:6]-2(-[C;D1;H3:7])-[C;D1;H3:8].C-C1(-C)-C-C-C(=O)-[c;H0;D3;+0:9]2:[c:10]:[c:11]:[c:12](-[C:13]#[C:14]):[c:15]:[c;H0;D3;+0:16]:2-1>>[C:14]#[C:13]-[c:12]1:[c:11]:[c:10]:[c;H0;D3;+0:9]2:[c;H0;D3;+0:16](:[c:15]:1)-[CH;D3;+0:1](-[#8:2]-[C:3])-[C:4]-[C... | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1), 90 mg (0.3 mmol) of 4-cyclohexyloxy-6-ethynyl-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound N) was converted into the title compound using 88 mg (0.32 mmol) of ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Alkyne | Ether | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.C1CCCCC1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | C#Cc1ccc2c(c1)C(OC1CCCCC1)CCC2(C)C.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(OC2CCCCC2)CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7c746e75636433f9e27f8624b0dcadb | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.[Li+].[OH-]>>CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C | CC[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([C:13]#[C:12][c:11]2[cH:10][cH:9][c:8]3[c:24]([cH:23]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3=[O:7])[cH:22][cH:21]1)=[O:19]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]#[C:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | null | null | C(C)O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCCc2cc(C#Cc3ccccc3)ccc21 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 4 | HOUR | To a suspension of 0.30 g (0.87 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 4 ml of THF and 2 ml of ethanol was added 2 ml (2 mmol) of LiOH (1N aqueous solution). The reaction mixture was stirred at room temperature for 4 hours, concentrated in vacuo to near dryn... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | Other | C(C)O.C1CCOC1 | null | 4 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>C(C)O.C1CCOC1>CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9e18f2a2e4df4babb93886c7acc67a7c | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21.CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21>>CC1(C)CCC(=O)c2cc(C#Cc3ccc(C(=O)O)cc3)ccc21 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C>>CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C | CC1(C)CCC(=O)[c:24]2[c:8]1[cH:9][c:10]([C:11]#[C:12][c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21]1)[cH:22][cH:23]2.O=C(O)c1ccc(C#Cc2ccc3c(c2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3=[O:7])cc1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]#[C:12][c:13]3[cH:14][cH:15][c... | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21.CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | CC1(C)CCC(=O)c2cc(C#Cc3ccc(C(=O)O)cc3)ccc21 | null | null | null | C-C Coupling | OtherReaction | d3f6d1903ff582380fc39e7e066afb4d2aef58322140d130a8213d57d545b6c1 | d308d6d88bdc2680ebd4a0ac133a9fce7c59d78c57c9b8a8e267f80ef25c594e | O=C1CCCc2ccc(C#Cc3ccccc3)cc21 | C-C1(-C)-C-C-C(=O)-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4](-[C:5]#[C:6]):[c:7]:[c;H0;D3;+0:8]:2-1.O-C(=O)-c1:c:c:c(-C#C-c2:c:c:c3:c(:c:2)-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C:12]-[C:13]-[C;H0;D3;+0:14]-3=[O;D1;H0:15]):c:c:1>>[C:6]#[C:5]-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1]2:[c;H0;D3;+0:8](:[c:7]:1)-[C;H0;D3;+0:14](=[... | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl) ethynyl]benzoic acid (Compound 7), 500 mg (1.45 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) was converted into the title compound using 4 ml (4 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone.Alkyne | Ketone | c1ccc2c(c1)CCCC2.c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | null | null | null | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21.CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21>>CC1(C)CCC(=O)c2cc(C#Cc3ccc(C(=O)O)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bb6edbcef5bb4a6484ddbb61dc2f5b2b | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.[BH4-].[Na+]>>OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]3=[O:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1 | null | null | C(C)O.C1CCOC1.O | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 6 | HOUR | To a cold solution (0° C.) of 980 mg (2.8 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 5 ml of THF and 10 ml of ethanol was added 78 mg (2 mmol) of sodium borohydride. The mixture was stirred for 6 hours, diluted with water (10 ml) and extracted with Et2O (4×40 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | null | C(C)O.C1CCOC1.O | null | 6 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>C(C)O.C1CCOC1.O>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29ccf8ac4f5a4867bec6dfaabe5da5da | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(O)CCC3(C)C)cc1 | OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1.OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1.CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C>>OC1C=2C=C(C=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3([CH3:23])[CH3:24])cc1.C[C:18]1(C)[c:16]2[c:15]([cH:14][cH:13][c:12]([C:11]#[C:10][c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:26][cH:25]3)[cH:17]2)[CH:22]([OH:19])[CH2:21][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(O)CCC3(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c5e6bbc7a9a06463d1cfdc9e7f078d26c8f4b38b4024a0aa1c7dfced71cf66c1 | 022be287155c79a6d0a8de717f678014006ca37ac9cbb0d100f44924121a0883 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | C-C-O-C(=O)-c1:c:c:c(-C#C-c2:c:c:c3:c(:c:2)-C(=O)-C-C-C-3(-[CH3;D1;+0:1])-[CH3;D1;+0:2]):c:c:1.C-[C;H0;D4;+0:3]1(-C)-[C:4]-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[CH3;D1;+0:1]-[C;H0;D4;+0:6]1(-[CH3;D1;+0:2])-[C:5]-[C:4]-[CH;D3;+0:3](-[OH;D1;+0:7])-[c:10](:[c:11]):[c:8]-1:[c:9] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9), 1 g (2.88 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) (was converted into the title compound using 60 mg (1.6... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Secondary alcohol.Alkyne | Secondary alcohol | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(O)CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a309b213ee744acf9636717f3498282d | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)nc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(O)CCC3(C)C)nc1 | OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1.OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1.CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=O)C>>OC1C=2C=C(C=CC2C(CC1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18](=[O:19])[CH2:20][CH2:21][C:22]3([CH3:23])[CH3:24])[n:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[CH:18]([OH:19])[CH2:... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)nc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(O)CCC3(C)C)nc1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C(#Cc1ccccn1)c1ccc2c(c1)CCCC2 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9), 700 mg (2 mmol) of ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate (Compound 4) was converted into the title compound using 60 mg (1.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccncc1.c1ccc2c(c1)CCCC2 | null | null | null | null | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)nc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(O)CCC3(C)C)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b29fc3fad974c179356548ebb415dfd | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)nc1>>CC1(C)CCC(=O)c2cc(C#Cc3ccc(C(=O)O)cn3)ccc21 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=O)C>>CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)O)C=C1)=O)C | CC[O:19][C:17]([c:16]1[cH:15][cH:14][c:13]([C:12]#[C:11][c:10]2[cH:9][c:8]3[c:24]([cH:23][cH:22]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3=[O:7])[n:21][cH:20]1)=[O:18]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]#[C:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][n:21]3)[... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)nc1 | CC1(C)CCC(=O)c2cc(C#Cc3ccc(C(=O)O)cn3)ccc21 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCCc2ccc(C#Cc3ccccn3)cc21 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of 4-[[5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl]ethynyl]benzoic acid (Compound 7), 300 mg (0.86 mmol) of ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate (Compound 3) was converted into the title compound (pale yellow solid... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CCCC2.c1ccncc1 | Other | null | null | null | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(=O)CCC3(C)C)nc1>>CC1(C)CCC(=O)c2cc(C#Cc3ccc(C(=O)O)cn3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-312409619c75422fbcb4db7823828526 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1.C[Si](C)(C)Cl>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O[Si](C)(C)C)cc1 | Cl[Si](C)(C)C.OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1.OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1.C(C)N(CC)CC>>CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)O[Si](C)(C)C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][CH:23]3[OH:24])[cH:29][cH:30]1.Cl[Si:25]([CH3:26])([CH3:27])[CH3:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:1... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1.C[Si](C)(C)Cl | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O[Si](C)(C)C)cc1 | null | null | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](-[OH;D1;+0:7])-[c:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4])-[c:8] | null | [] | null | null | null | null | To a solution of 0.23 g (0.54 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9) in 4 ml of dry CH2Cl2 was added 0.06 ml of triethylamine (0.81 mmol). The solution was flushed with nitrogen and then 0.12 g (0.81 mmol) of chlorotrimethylsilane was slowly added by syring... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccccc1.c1ccc2c(c1)CCCC2 | HCl | C(Cl)Cl | null | null | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O)cc1.C[Si](C)(C)Cl>C(Cl)Cl>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O[Si](C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f42f93a338f24d7caa512d7d1159c4df | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O[Si](C)(C)C)cc1>>CC1(C)CCC(O[Si](C)(C)C)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)O[Si](C)(C)C)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)O[Si](C)(C)C)C.OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1.OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1>>CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)O[Si](C)(C)C)C | CC[O:24][C:22]([c:21]1[cH:20][cH:19][c:18]([C:17]#[C:16][c:15]2[cH:14][cH:13][c:12]3[c:28]([cH:27]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][CH:6]3[O:7][Si:8]([CH3:9])([CH3:10])[CH3:11])[cH:26][cH:25]1)=[O:23]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH:6]([O:7][Si:8]([CH3:9])([CH3:10])[CH3:11])[c:12]2[cH:13][cH:14][c:15]([C... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O[Si](C)(C)C)cc1 | CC1(C)CCC(O[Si](C)(C)C)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-trimethylsiloxynaphth-2-yl)ethynyl]benzoate (Compound 111), 83 mg (0.26 mmol) of 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid (Compound 42) was converted into the title compound (w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | Other | null | null | null | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3O[Si](C)(C)C)cc1>>CC1(C)CCC(O[Si](C)(C)C)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3bc3da49cb6b461196d4eaac084da60d | CCOC(=O)CBr.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>>CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21 | BrCC(=O)OCC.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C>>OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[C:7]1(=[O:8])[CH2:9][CH2:10][C:11]([CH3:12])([CH3:13])[c:14]2[cH:15][c:16]([C:17]#[C:18][c:19]3[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH2:26][CH3:27])[cH:28][cH:29]3)[cH:30][cH:31][c:32]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1([OH:8])[CH2:9][CH2:10][C:11]([CH3:12]... | CCOC(=O)CBr.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1 | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21 | null | [Zn] | C1=CC=CC=C1 | C-C Coupling | Grignard_alcohol | ae6802bc43630c235b581c1f69ee3f400dd59564bb5948df811879329723b99c | 86d8e63c1eeb9e82c583fd2409352b28a569a3f780f9f297e86b8d2f688ca9d6 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7]-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | To a refluxing solution of 1.00 g (15.30 mmol) of 20 mesh, granular zinc (activated prior to use by washing with 2% HCl, water, 95% ethanol, acetone, anhydrous Et2O and then dried in vacuum for several hours) in 20 ml of dry benzene was slowly added a mixture of 0.23 ml (1.62 mmol) of ethyl bromoacetate, 0.28 g (0.81 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ester.Tertiary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | Br- | [Zn].C1=CC=CC=C1 | null | null | CCOC(=O)CBr.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3=O)cc1>[Zn].C1=CC=CC=C1>CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-558960f60108438697a2928369019551 | CC(O)[Si](C)(C)C.CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21>>CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)cc21 | CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C.CN(C)C1=NC=CC=C1.C[Si](C)(C)C(C)O.Cl.CN(CCCN=C=NCC)C>>CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)=O)C | O[CH:22]([CH3:21])[Si:23]([CH3:24])([CH3:25])[CH3:26].[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]#[C:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:27][cH:28]3)[cH:29][c:30]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]#[C:13][c:14]... | CC(O)[Si](C)(C)C.CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21 | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)cc21 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 55fde8dca0a408407bb776c4e1e9a22d6eeb5c734b0d7975d23baba4292968d2 | 505f7b4da8def84a80ac616845cb7b0566b14f3232b5b9d3480d84d3e0d284a0 | O=C1CCCc2cc(C#Cc3ccccc3)ccc21 | O-[CH;D3;+0:1](-[CH3;D1;+0:2])-[#14:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[O;D1;H0:7]=[C:8](-[OH;D1;+0:9])-[c:10]>>[C;D1;H3:4]-[#14:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:9]-[C:8](=[O;D1;H0:7])-[c:10] | null | [] | 25 | CELSIUS | 5 | HOUR | To a solution of 0.24 g (0.73 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid (Compound 7) in 10 ml of dry CH2Cl2 was added 0.09 g (0.74 mmol) of dimethylaminopyridine, 0.115 ml (0.80 mmol) of trimethylsilylethanol and 0.17 g (0.88 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | C(Cl)Cl | 25 | 5 | CC(O)[Si](C)(C)C.CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)O)cc3)cc21>C(Cl)Cl>CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c1a4e1e535804129a0f31d37c5904ccb | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)cc21.CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21>>CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 | OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC.OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)=O)C.CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)=O)C>>OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)CC(=O)... | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)[O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:30])[CH3:31])cc3)cc21.CCO[C:23]([c:22]1[cH:21][cH:20][c:19]([C:18]#[C:17][c:16]2[cH:15][c:14]3[c:36]([cH:35][cH:34]2)[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])([OH:8])[CH2:9][CH2:10][C:11]3([CH3:12])[CH3:13])[cH:33][cH:32]1)=[O:24]>>[CH3:... | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)cc21.CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21 | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 | null | null | null | Acylation | OtherReaction | 5649976c68db781128c5e8fe1133b554cbbb509205645293d888ba70e249ea5b | 9d3a8d45a08916f563b73b1fec78d20ccc19f70a36752aa400881ecf9d6765b1 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].C-C1(-C)-C-C-C(=O)-c2:c:c:c(-C#C-c3:c:c:c(-C(=O)-[O;H0;D2;+0:6]-[C:7]-[C:8]):c:c:3):c:c:2-1>>[C:8]-[C:7]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoate (Compound 113), 0.38 g (0.89 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 116), was converted... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester.Alkyne | Ester | c1ccc2c(c1)CCCC2.c1ccccc1 | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | null | null | null | CC1(C)CCC(=O)c2ccc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)cc21.CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21>>CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78663f7332f8419998daa1598e9a7019 | CCOC(=O)C1(O)CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C.CCOC(=O)C1(O)CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C>>CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)O)cc3)ccc21 | OC1(C=2C=CC(=C(C2C(CC1)(C)C)C)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)C(=O)OCC.OC1(C=2C=CC(=C(C2C(CC1)(C)C)C)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)C(=O)OCC.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1)CC(=O)OCC | CCOC(=O)[C:7]1([OH:8])CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C.C[Si](C)(C)CC[O:25][C:23]([c:22]1[cH:21][cH:20][c:19]([C:18]#[C:17][c:16]2[c:15](C)[c:14]3[c:30]([cH:29][cH:28]2)[C:6](O)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:9][CH2:10][C:11]3([CH3:12])[CH3:13])[cH:27][cH:26]1)=[O:24]>>[CH3:1][CH2:2][O:3][C:4... | CCOC(=O)C1(O)CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C.CCOC(=O)C1(O)CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)O)cc3)ccc21 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 5e6086f67bb351dc4b0e6d73161fa1416f05d08374ce8c5066c53fbd31042a7a | 44b4ae204a13468e8ec96b5abf6014d1bfbaaea3ec420cf0ca0799433fb2a4cb | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | C-C-O-C(=O)-[C;H0;D4;+0:1]1(-[O;D1;H1:2])-C-C-C(-C)(-C)-c2:c-1:c:c:c(-C#C-c1:c:c:c(-C(=O)-O-C-C-[Si](-C)(-C)-C):c:c:1):c:2-C.C-[Si](-C)(-C)-C-C-[O;H0;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6].C-[c;H0;D3;+0:7]1:[c:8]2:[c;H0;D3;+0:9](:[c:10]:[c:11]:[c:12]:1-[C:13]#[C:14]-[c:15])-[C;H0;D4;+0:16](-O)(-[C:17](=[O;D1;H0:18])-[#8:19... | null | [] | null | null | 12 | HOUR | To a solution of 0.25 g (0.49 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate (Compound 117) in 5 ml of dry THF (flushed with argon) was added 1.48 ml (1.5 mmol) of tetrabutyl ammonium fluoride (1M solution in THF). The reaction mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester.Tertiary alcohol.Tertiary alcohol.Alkyne.Silyl protective group.Silyl protective group | Carboxylic acid.Ester.Tertiary alcohol | c1ccc2c(c1)CCCC2.c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | C1CCOC1 | null | 12 | CCOC(=O)C1(O)CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C.CCOC(=O)C1(O)CCC(C)(C)c2c1ccc(C#Cc1ccc(C(=O)OCC[Si](C)(C)C)cc1)c2C>C1CCOC1>CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)O)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6dac85cc0d34ff6820bdd2f7d903d31 | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21.CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21>>CCOC(=O)CC1(O)CCC(C)(C)c2ccc(C#Cc3ccc(C(=O)OCC)cc3)cc21 | OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC.OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC.CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C.CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C>>OC1(C=2C=C(C=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC | CCOC(=O)c1ccc(C#Cc2cc[c:32]3[c:14](c2)[C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][C:7]3([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[OH:8])cc1.CCOC(=O)CC1(O)CCC(C)(C)c2c1[cH:15][cH:16][c:17]([C:18]#[C:19][c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[O:26][CH2:27][CH3:28])[cH:29][cH:30]1)[cH:31]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5... | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21.CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21 | CCOC(=O)CC1(O)CCC(C)(C)c2ccc(C#Cc3ccc(C(=O)OCC)cc3)cc21 | null | null | null | Miscellaneous | OtherReaction | c2e278b01ce4d9711febfb131346be5a90905ed19322581b1150e5fa51455d26 | 0af981d09dd6a64dfd59aae9124418845f9a67f7be038caa795d2225b5703624 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | C-C-O-C(=O)-C-C1(-O)-C-C-C(-C)(-C)-c2:[cH;D2;+0:1]:[c:2](-[C:3]#[C:4]-[c:5]):[c:6]:[cH;D2;+0:7]:c:2-1.C-C-O-C(=O)-c1:c:c:c(-C#C-c2:c:c:[c;H0;D3;+0:8]3:[c;H0;D3;+0:9](:c:2)-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C:13]-[C:14]-[C:15]-3(-[O;D1;H1:16])-[C:17]-[C:18](-[#8:19])=[O;D1;H0:20]):c:c:1>>[#8:19]-[C:18](=[O;D1;H0:20]... | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl 4-[(7,8-dihydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoate (Compound 113), 1.00 g (2.88 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) was converted into the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Tertiary alcohol.Alkyne | null | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | null | null | null | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21.CCOC(=O)CC1(O)CCC(C)(C)c2cc(C#Cc3ccc(C(=O)OCC)cc3)ccc21>>CCOC(=O)CC1(O)CCC(C)(C)c2ccc(C#Cc3ccc(C(=O)OCC)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a56f7e2293dc4862a8c854ae1b1ae4b3 | CC([O-])=S.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3C(C)=S)cc1 | CC1(CCCC=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)C.CC1(CCCC=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(C)(=S)[O-].[K+]>>CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)C(C)=S)C | [O-][C:24]([CH3:25])=[S:26].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][CH2:23]3)[cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17... | CC([O-])=S.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3C(C)=S)cc1 | null | null | C(Cl)(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 21fe3870b4af9b152fbe9a5de671668cd64bbcc171946f688076c59d13f4f553 | 55d778e3faa8ee35a0df7132afa41f23510972a70b1f5f04051088f634cdee47 | C(#Cc1ccc2c(c1)CCCC2)c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[O-])=[S;D1;H0:3].[C:4]-[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:5]-[CH;D3;+0:6](-[C;H0;D3;+0:2](-[C;D1;H3:1])=[S;D1;H0:3])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | To a solution of 543 mg (1.64 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (obtainable from Compound M by coupling with ethyl-4-iodobenzoate) in 20 ml of CCl4 was added 320 mg (1.81 mmol) of N-bromosuccinimide and 26 mg (0.11 mmol) of benzoyl peroxide. The mixture was refluxed for 3 ho... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Thiocarbonyl | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | CC([O-])=S.CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3)cc1>C(Cl)(Cl)(Cl)Cl>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCC3C(C)=S)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cfae32b2602f43d987a2a67d53a3bee8 | CC(C)C=C=O.FC(F)(F)C(Cl)Br>>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | CC(C)([O-])C.[Na+].BrC(C(F)(F)F)Cl.CC(C=C=O)C.O1CCCC1>>BrC(C(C=C(C)C)O)(C(F)(F)F)Cl | [CH3:1][CH:2]([CH3:3])[CH:4]=[C:5]=[O:6].[CH:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH:5]([OH:6])[C:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13] | CC(C)C=C=O.FC(F)(F)C(Cl)Br | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | null | null | CN(C=O)C | C-C Coupling | OtherReaction | a555a0218c8ffda0a8d9ad72f436a897605d75c2ecc35d1571cb0a895708f2b6 | c0aafa762e8e97773a571cd9698e9eec9342bb07704960a5a3263af845ada306 | null | [Br;D1;H0:1]-[CH;D3;+0:2](-[Cl;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[C;D1;H3:8]-[CH;D3;+0:9](-[C;D1;H3:10])-[CH;D2;+0:11]=[C;H0;D2;+0:12]=[O;H0;D1;+0:13]>>[Br;D1;H0:1]-[C;H0;D4;+0:2](-[Cl;D1;H0:3])(-[CH;D3;+0:12](-[OH;D1;+0:13])-[CH;D2;+0:11]=[C;H0;D3;+0:9](-[C;D1;H3:8])-[C;D1;H3:10])-[C:4](-[F;D1;H0... | null | [] | -78 | CELSIUS | 40 | MINUTE | Sodium t-butoxide (1.39 g of a 42% solution in dry dimethyl formamide was added dropwise over a period of 5 minutes to a stirred mixture of 1-bromo-1-chloro-2,2,2-trifluoroethane (0.535 ml), 3-methylbut-1-en-1-al (0.538 ml) and dry tetrahydrofuran (10 ml) maintained at a temperature of -78° C. by external cooling under... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Tertiary halide.Tertiary halide.Secondary alcohol | null | null | null | null | CN(C=O)C | -78 | 0.666667 | CC(C)C=C=O.FC(F)(F)C(Cl)Br>CN(C=O)C>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-56961baabfe2420f864e8e6d0f4d6728 | CC(C)=CC=O.FC(F)(F)C(Cl)Br>>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | BrC(C(F)(F)F)Cl.C(C=C(C)C)=O.CC(C)([O-])C.[Na+]>>BrC(C(C=C(C)C)O)(C(F)(F)F)Cl | [CH3:1][C:2]([CH3:3])=[CH:4][CH:5]=[O:6].[CH:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH:5]([OH:6])[C:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13] | CC(C)=CC=O.FC(F)(F)C(Cl)Br | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 5435d0ec6b37aa9738fb0b43202d46adad1fb62e47985a626acc8e0a0b0a1203 | cb00fcdc041dbd2da5d224bc1b019b9ae570e5bc5d8f0a5146770346817407c6 | null | [Br;D1;H0:1]-[CH;D3;+0:2](-[Cl;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])=[C:11]-[CH;D2;+0:12]=[O;H0;D1;+0:13]>>[Br;D1;H0:1]-[C;H0;D4;+0:2](-[Cl;D1;H0:3])(-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:11]=[C:9](-[C;D1;H3:8])-[C;D1;H3:10])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7] | 73.8 | [{"value": 70.0, "product": "BrC(C(C=C(C)C)O)(C(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "BrC(C(C=C(C)C)O)(C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -60 | CELSIUS | null | null | Tetrahydrofuran (230 ml) and sodium t-butoxide (57.6 g; 40% w/v solution in dimethylformamide) was charged to a split-neck reaction flask, and cooled to -60° C. with stirring. 1-Bromo-1-chloro-2,2,2-trifluorethane (47.6 g) and senecialdehyde (20.9 g) were charged simultaneously over 25 minutes, then the mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Aldehyde | Tertiary halide.Tertiary halide.Secondary alcohol | null | null | null | null | O1CCCC1 | -60 | null | CC(C)=CC=O.FC(F)(F)C(Cl)Br>O1CCCC1>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-08430d7f4e5041b2a041747d195c0a59 | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>>COC(C)(OC)OC(C=C(C)C)C(Cl)(Br)C(F)(F)F | BrC(C(C=C(C)C)O)(C(F)(F)F)Cl.C(C)(OC)(OC)OC.C(C(C)C)(=O)O>>BrC(C(C=C(C)C)OC(C)(OC)OC)(C(F)(F)F)Cl | [OH:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH3:12])[C:13]([Cl:14])([Br:15])[C:16]([F:17])([F:18])[F:19].CO[C:3]([O:2][CH3:1])([CH3:4])[O:5][CH3:6]>>[CH3:1][O:2][C:3]([CH3:4])([O:5][CH3:6])[O:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH3:12])[C:13]([Cl:14])([Br:15])[C:16]([F:17])([F:18])[F:19] | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC | COC(C)(OC)OC(C=C(C)C)C(Cl)(Br)C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | da59a6e496e58629453a78c5e1487b31b25688d768592f6d7000493943d39c02 | 9cde3f0ce3308e8c18bafc8301e5ba0177f0ef4f63237b39a252a2d6edcd92fd | null | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[#8:3]-[C;D1;H3:4])-[#8:5]-[C;D1;H3:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]=[C:11](-[C;D1;H3:12])-[C;D1;H3:13]>>[C:7]-[C:8](-[C:10]=[C:11](-[C;D1;H3:12])-[C;D1;H3:13])-[O;H0;D2;+0:9]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[#8:3]-[C;D1;H3:4])-[#8:5]-[C;D1;H3:6] | null | [] | 111 | CELSIUS | null | null | 5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (48.0 g) and isobutyric acid (0.29 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and Dean and Stark received packed with 5A molecular seives. The mixture was heated with agitation t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Ether.Ether.Ether | null | null | null | HO- | null | 111 | null | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>>COC(C)(OC)OC(C=C(C)C)C(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d60f1ea20aa0467e8d0f2bb79c4451e3 | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>>COC(=O)CC(C)(C)C=CC(Cl)(Br)C(F)(F)F | BrC(C(C=C(C)C)O)(C(F)(F)F)Cl.C(C)(OC)(OC)OC>>BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl | O[CH:10]([CH:9]=[C:6]([CH3:7])[CH3:8])[C:11]([Cl:12])([Br:13])[C:14]([F:15])([F:16])[F:17].CO[C:3]([O:2][CH3:1])([O:4]C)[CH3:5]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]([CH3:7])([CH3:8])[CH:9]=[CH:10][C:11]([Cl:12])([Br:13])[C:14]([F:15])([F:16])[F:17] | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC | COC(=O)CC(C)(C)C=CC(Cl)(Br)C(F)(F)F | null | O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3] | null | Acylation | OtherReaction | 62d15542be43b94a80da01568db53380356499d771ca28bc7e0ff722d34a5863 | 98ff49def7e6e395079390a512d545b9d4d6c593686e816bc1a43a7ae419027a | null | C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[#8:3]-[C;D1;H3:4])-[O;H0;D2;+0:5]-C.O-[CH;D3;+0:6](-[CH;D2;+0:7]=[C;H0;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[Br;D1;H0:12])(-[Cl;D1;H0:13])-[C:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[F;D1;H0:17]>>[Br;D1;H0:12]-[C:11](-[Cl;D1;H0:13])(-[CH;D2;+0:6]=[CH;D2;+0:7]-[C;H0;D4;+0:8](-[C;D1... | 65 | [{"value": 59.0, "product": "BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 111 | CELSIUS | 1 | HOUR | 5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (16.0 g) and Montmorillonite KSF (0.5 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and still-head. The mixture was heated with agitation, and the methanol-trimethyl orthoacetate di... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Ester | null | null | null | HO- | O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3] | 111 | 1 | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>COC(=O)CC(C)(C)C=CC(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d42202fb4a7943b3bbc1a6d0fce478fe | CC(C)=CC(O)C(Cl)(Cl)C(F)(F)F.CCOC(C)(OCC)OCC>>CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F | C(C)(OCC)(OCC)OCC.ClC(C(C=C(C)C)O)(C(F)(F)F)Cl.C(C(C)C)(=O)O>>ClC(C=CC(CC(=O)OCC)(C)C)(C(F)(F)F)Cl | O[CH:11]([CH:10]=[C:7]([CH3:8])[CH3:9])[C:12]([Cl:13])([Cl:14])[C:15]([F:16])([F:17])[F:18].CCO[C:4]([O:3][CH2:2][CH3:1])([O:5]CC)[CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]([CH3:8])([CH3:9])[CH:10]=[CH:11][C:12]([Cl:13])([Cl:14])[C:15]([F:16])([F:17])[F:18] | CC(C)=CC(O)C(Cl)(Cl)C(F)(F)F.CCOC(C)(OCC)OCC | CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F | null | null | null | Acylation | OtherReaction | 62d15542be43b94a80da01568db53380356499d771ca28bc7e0ff722d34a5863 | 98ff49def7e6e395079390a512d545b9d4d6c593686e816bc1a43a7ae419027a | null | C-C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[#8:3]-[C:4])-[O;H0;D2;+0:5]-C-C.O-[CH;D3;+0:6](-[CH;D2;+0:7]=[C;H0;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[Cl;D1;H0:12])(-[Cl;D1;H0:13])-[C:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[F;D1;H0:17]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;H0;D1;+0:5])-[CH2;D2;+0:2]-[C;H0;D4;+0:8](-[C;D1;H3:9])... | null | [] | null | null | null | null | A mixture of triethyl orthoacetate (25 ml), 5,5-dichloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (3.5 g), and isobutyric acid (0.11 g) was heated at the reflux temperature. The refluxing volatiles were condensed and collected in a Dean & Stark apparatus containing molecular sieves (4A) to collect the by-product eth... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Ester | null | null | null | HO- | null | null | null | CC(C)=CC(O)C(Cl)(Cl)C(F)(F)F.CCOC(C)(OCC)OCC>>CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70ae7882edfe4b59882bded66d4f531c | CC1(C)OC(CO)C(CO)O1.CCOC(=O)CC(=O)CCl>>CCOC(=O)CC(=O)COCC1OC(C)(C)OC1COCC(=O)CC(=O)OCC | [H-].[Na+].ClCC(CC(=O)OCC)=O.CC1(OC(C(O1)CO)CO)C>>C(C)OC(CC(COCC1OC(OC1COCC(CC(=O)OCC)=O)(C)C)=O)=O | [CH3:1][C:14]1([CH3:16])[O:13][CH:12]([CH2:2][OH:3])[CH:18]([CH2:19][OH:20])[O:17]1.Cl[CH2:21][C:22](=[O:23])[CH2:24][C:25](=[O:26])[O:27][CH2:28][CH3:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][O:10][CH2:11][CH:12]1[O:13][C:14]([CH3:15])([CH3:16])[O:17][CH:18]1[CH2:19][O:20][CH2:21][C:22](=[O:23])... | CC1(C)OC(CO)C(CO)O1.CCOC(=O)CC(=O)CCl | CCOC(=O)CC(=O)COCC1OC(C)(C)OC1COCC(=O)CC(=O)OCC | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0344072df22acf89147411ca83c03c260456897ced6262baad4d664f99cc7453 | 6718608c291f284d92dbc0a9a9fe817322a6ccdd03478eb057cf50201a353fab | C1COCO1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C;D1;H3:8]-[C;H0;D4;+0:9]1(-[CH3;D1;+0:10])-[#8:11]-[CH;D3;+0:12](-[CH2;D2;+0:13]-[OH;D1;+0:14])-[C:15](-[C:16]-[OH;D1;+0:17])-[#8:18]-1>>[#8:19]-[C:20]-[CH;D3;+0:12]1-[#8:11]-[C;H0;D4;+0:9](-[C;D1;H3:21])(-[C;D1;H3:8])-[#8:18]-[C:15]-1-[C:16]-[O;H0... | 43.7 | [{"value": 43.7, "product": "C(C)OC(CC(COCC1OC(OC1COCC(CC(=O)OCC)=O)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of sodium hydride (4.0 g, 60% dispersion in oil) in tetrahydrofuran (150 mL) under a nitrogen atmosphere was added a solution of 2,2-dimethyl-[1,3]dioxolane-4,5-dimethanol (VII, 4.05 g) in tetrahydrofuran (25 mL) over 2 min at room temperature, followed by solid tetrabutylammonium hydrogen sulfate (0.4 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether.Ether.Primary alcohol.Primary alcohol | Ketone.Ketone.Ester.Ether.Ether.Ether.Ether | C1COCO1 | C1COCO1 | C1COCO1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCCC1 | null | null | CC1(C)OC(CO)C(CO)O1.CCOC(=O)CC(=O)CCl>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCCC1>CCOC(=O)CC(=O)COCC1OC(C)(C)OC1COCC(=O)CC(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bcfe7e4ce5914fd798eabd94aed3d84f | CC1(C)OCC(CO)O1.CCOC(=O)CC(=O)CCl>>CCOC(=O)CC(=O)COCC1COC(C)(C)O1 | ClCC(CC(=O)OCC)=O.CC1(OCC(O1)CO)C.[H-].[Na+]>>C(C)OC(CC(COCC1OC(OC1)(C)C)=O)=O | [OH:10][CH2:11][CH:12]1[CH2:13][O:14][C:15]([CH3:16])([CH3:17])[O:18]1.Cl[CH2:9][C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][O:10][CH2:11][CH:12]1[CH2:13][O:14][C:15]([CH3:16])([CH3:17])[O:18]1 | CC1(C)OCC(CO)O1.CCOC(=O)CC(=O)CCl | CCOC(=O)CC(=O)COCC1COC(C)(C)O1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fbcfc5578f28d9d8930a708c71944acf35323dc567d3a35141adc89c3fb4ae9e | 7d4d679c705f72095ba1d241e831385ef35d8aef34f3127d947d089fa3227973 | C1COCO1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7] | 50.1 | [{"value": 50.1, "product": "C(C)OC(CC(COCC1OC(OC1)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a suspension of sodium hydride (55 g, 60% dispersion in oil) in tetrahydrofuran (1L) under a nitrogen atmosphere was added a solution of 2,2-dimethyl-[1,3]dioxolane-4-methanol (XV, 102.4 g) in tetrahydrofuran (250 mL) over 15 min at room temperature. The resulting mixture was cooled in an ice bath and a solution of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary alcohol | Ketone.Ether | null | null | C1COCO1 | HCl | O1CCCC1 | null | 20 | CC1(C)OCC(CO)O1.CCOC(=O)CC(=O)CCl>O1CCCC1>CCOC(=O)CC(=O)COCC1COC(C)(C)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df519091f55147ec9c9c3a495aefb74e | CCOC(=O)C1=C(COCC(O)CO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl>>CCOC(=O)C1=C(COCC=O)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | [Cl-].[NH4+].COC(=O)C=1C(C(=C(NC1C)COCC(CO)O)C(=O)OCC)C1=C(C=CC=C1)Cl.I(=O)(=O)(=O)[O-].[Na+]>>COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)COCC=O)C | OC[CH:11]([CH2:10][O:9][CH2:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:21]([c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[Cl:28])[C:16]([C:17](=[O:18])[O:19][CH3:20])=[C:14]([CH3:15])[NH:13]1)[OH:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][O:9][CH2:10][CH:11]=[O:12])[NH:13][C:14]([CH3:15])=[C:16]([C:... | CCOC(=O)C1=C(COCC(O)CO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | CCOC(=O)C1=C(COCC=O)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | null | null | CO.O | Miscellaneous | OtherReaction | 6b26fe5aae922ff894047a49926c0aceb5638cd263aa19950a2aab435845c036 | 1f7d0f705fc2b6dec522235bbfa5fd9d570e6409417a0c4e8313976c2a5c011a | C1=CC(c2ccccc2)C=CN1 | O-C-[CH;D3;+0:1](-[OH;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH;D2;+0:1]=[O;H0;D1;+0:2] | 97.9 | [{"value": 97.9, "product": "COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)COCC=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To an ice-cooled solution of 4-(2-chlorophenyl)-2-(2,3-dihydroxypropoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IC, 13.0 g) in methanol (150 mL) was added a solution of sodium periodate (7.6 g) dissolved in water (100 mL) dropwise over 15 min. After stirring for 10 min, a satur... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol | Aldehyde | null | null | C1=CNC=CC1.c1ccccc1 | HO- | CO.O | null | 0.166667 | CCOC(=O)C1=C(COCC(O)CO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl>CO.O>CCOC(=O)C1=C(COCC=O)NC(C)=C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4264e1627523496cb0a0bc9ac274b94e | CCOC(=O)C1=C(COCC=O)NC(C)=C(C(=O)OC)C1c1ccccc1Cl.[NH3+]O>>CCOC(=O)C1=C(COCC=NO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)COCC=O)C.Cl.O[NH3+].C(C)N(CC)CC>>COC(=O)C=1C(C(=C(NC1C)COCC=NO)C(=O)OCC)C1=C(C=CC=C1)Cl | O=[CH:11][CH2:10][O:9][CH2:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[Cl:29])[C:17]([C:18](=[O:19])[O:20][CH3:21])=[C:15]([CH3:16])[NH:14]1.[NH3+:12][OH:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][O:9][CH2:10][CH:11]=[N:12][OH:13])[NH:14][C:15]([CH3:... | CCOC(=O)C1=C(COCC=O)NC(C)=C(C(=O)OC)C1c1ccccc1Cl.[NH3+]O | CCOC(=O)C1=C(COCC=NO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | null | null | CO | Functional Group Interconversion | OtherReaction | 9575b3f7e9975c02abe24e99b2681a2813f6f73af9b27467491bf10c6c26ae48 | 5ddad3e703fe819c706f37fb03eddf29d0a60c973b030a231bcdc1b66cd51b53 | C1=CC(c2ccccc2)C=CN1 | O=[CH;D2;+0:1]-[C:2]-[#8:3].[NH3+;D1:4]-[O;D1;H1:5]>>[#8:3]-[C:2]-[CH;D2;+0:1]=[N;H0;D2;+0:4]-[O;D1;H1:5] | null | [] | null | null | 6 | HOUR | A mixture of 4-(2-chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester (ID, 6.2 g), hydroxylammonium hydrochloride (1.27 g) and triethylamine (1.85 g) in methanol (100 mL) was stirred at room temperature for 6 h. Methanol was removed under reduced pressure and t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Oxime | null | null | C1=CNC=CC1.c1ccccc1 | HO- | CO | null | 6 | CCOC(=O)C1=C(COCC=O)NC(C)=C(C(=O)OC)C1c1ccccc1Cl.[NH3+]O>CO>CCOC(=O)C1=C(COCC=NO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db51435d97f64dfb86f4de59e3efb185 | CCOC(=O)C1=C(COCC=NO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl>>CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | COC(=O)C=1C(C(=C(NC1C)COCC=NO)C(=O)OCC)C1=C(C=CC=C1)Cl.C(=O)[O-].[NH4+]>>COC(=O)C=1C(C(=C(NC1C)COCCN)C(=O)OCC)C1=C(C=CC=C1)Cl | O[N:12]=[CH:11][CH2:10][O:9][CH2:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:21]([c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[Cl:28])[C:16]([C:17](=[O:18])[O:19][CH3:20])=[C:14]([CH3:15])[NH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][O:9][CH2:10][CH2:11][NH2:12])[NH:13][C:14]([CH3:15])=[C:16]([C:1... | CCOC(=O)C1=C(COCC=NO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | null | [OH-].[OH-].[Pd+2] | CO | Reduction | OtherReaction | 2911de7676f9c054838849cab652dcb324de4944866edb887235c5bf7854a715 | 4a7bf747f64425b21ceaa04fbc4c046ccf522c774aa5649ec92eba03e46bfee5 | C1=CC(c2ccccc2)C=CN1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:2]-[NH2;D1;+0:1] | 60.7 | [{"value": 60.7, "product": "COC(=O)C=1C(C(=C(NC1C)COCCN)C(=O)OCC)C1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IBa, 150 mg), palladium hydroxide on carbon (10 mg) and ammonium formate (224 mg) in methanol (10 mL) was refluxed for 5 h under a nitrogen atmosphere. On cooling to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Primary amine | null | null | C1=CNC=CC1.c1ccccc1 | Other | [OH-].[OH-].[Pd+2].CO | null | null | CCOC(=O)C1=C(COCC=NO)NC(C)=C(C(=O)OC)C1c1ccccc1Cl>[OH-].[OH-].[Pd+2].CO>CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b853575abe94e7c8c35c82d1e1ed7b0 | CCOC(=O)C1=C(COCC(OC)OC)NC(C)=C(C(=O)OC)C1c1ccccc1Cl>>CCOC(=O)C1=C2COC=CN2C(C)=C(C(=O)OC)C1c1ccccc1Cl | COC(=O)C=1C(C(=C(NC1C)COCC(OC)OC)C(=O)OCC)C1=C(C=CC=C1)Cl.Cl>>COC(=O)C=1C(C(=C2COC=CN2C1C)C(=O)OCC)C1=C(C=CC=C1)Cl | CO[CH:11](OC)[CH2:10][O:9][CH2:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[Cl:27])[C:15]([C:16](=[O:17])[O:18][CH3:19])=[C:13]([CH3:14])[NH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]2[CH2:8][O:9][CH:10]=[CH:11][N:12]2[C:13]([CH3:14])=[C:15]([C:16](=[O:17])[... | CCOC(=O)C1=C(COCC(OC)OC)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | CCOC(=O)C1=C2COC=CN2C(C)=C(C(=O)OC)C1c1ccccc1Cl | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | ff6e2150b37df9c6c7faec8b31e0ff9a35bb825185a402a3b3e4ef2fea8d8338 | de73217b601b2798317d9de7c02a4c2a49bf20113d826b0123ad95bf25a4855f | C1=CN2C=CC(c3ccccc3)C=C2CO1 | C-O-[CH;D3;+0:1](-O-C)-[CH2;D2;+0:2]-[#8:3]-[C:4]-[C:5]1=[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10]-[C:11](-[C:12](-[#8:13])=[O;D1;H0:14])=[C:15](-[C;D1;H3:16])-[NH;D2;+0:17]-1>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]1=[C:15](-[C;D1;H3:16])-[N;H0;D3;+0:17]2-[CH;D2;+0:1]=[CH;D2;+0:2]-[#8:3]-[C:4]-[C:5]-2=[C:6](-[C:7](-[#8:8... | 65.8 | [{"value": 65.8, "product": "COC(=O)C=1C(C(=C2COC=CN2C1C)C(=O)OCC)C1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-(2-chlorophenyl)-2-(2,2-dimethoxy-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (XX, 9.2 g) in tetrahydrofuran (200 mL) was added 3N hydrochloric acid (40 mL). The mixture was then refluxed for 4 h. On cooling to room temperature, tetrahydrofuran was removed ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ether.Ether.Ether | Enamine.Enamine.Enamine | C1=CNC=CC1 | C1=CN2C=COCC2=CC1 | C1=CN2C=COCC2=CC1.c1ccccc1 | HO- | O1CCCC1 | null | null | CCOC(=O)C1=C(COCC(OC)OC)NC(C)=C(C(=O)OC)C1c1ccccc1Cl>O1CCCC1>CCOC(=O)C1=C2COC=CN2C(C)=C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1e2912f9b2444eeb1e5ad64e18d1404 | CCOC(=O)CC(=O)CCl.COC(=O)C=C(C)NCCO.O=Cc1ccccc1Cl>>CCOC(=O)C1=C(CCl)N2CCOC2(C)C(C(=O)OC)C1c1ccccc1Cl | ClC1=C(C=O)C=CC=C1.ClCC(CC(=O)OCC)=O.COC(C=C(C)NCCO)=O>>COC(=O)C1C2(N(C(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)CCl)CCO2)C | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8][Cl:9].[NH:10]([CH2:11][CH2:12][OH:13])[C:14]([CH3:15])=[CH:16][C:17](=[O:18])[O:19][CH3:20].O=[CH:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[Cl:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][Cl:9])[N:10]2[CH2:11][CH2:12][O:13][C:14]2([CH3:15])[CH:16]... | CCOC(=O)CC(=O)CCl.COC(=O)C=C(C)NCCO.O=Cc1ccccc1Cl | CCOC(=O)C1=C(CCl)N2CCOC2(C)C(C(=O)OC)C1c1ccccc1Cl | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 45bba53f2703211ee8e72a28add2f98a7e77aabd35fbf31ad11867ca7492972e | 1b0a543a218938f814aab8e10edc774aa5e088d2d7ffce8b04acddeef534f28b | C1=CN2CCOC2CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[Cl;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[C;D1;H3:13]-[C;H0;D3;+0:14](=[CH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19])-[NH;D2;+0:20]-[C:21]-[C:22]-[OH;D1;+0:23]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:4]1=[C;H0;D3;+0:1](-[... | 17.6 | [{"value": 17.6, "product": "COC(=O)C1C2(N(C(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)CCl)CCO2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A mixture of 2-chlorobenzaldehyde (XI, 57.0 g), ethyl 4-chloroacetoacetate (VIII, 69.3 g) and 3-(2-hydroxyethylamino)-but-2-enoic acid methyl ester (XXIII, 63.2 g) in methanol (800 mL) was stirred at room temperature for 48 h. Methanol was removed under reduced pressure and the residue dissolved in ethyl acetate (400 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone.Ester.Ester.Primary alcohol | Enamine.Ester.Ester.Ether | null | C1=CN2CCOC2CC1 | C1=CN2CCOC2CC1.c1ccccc1 | HO- | CO | null | 48 | CCOC(=O)CC(=O)CCl.COC(=O)C=C(C)NCCO.O=Cc1ccccc1Cl>CO>CCOC(=O)C1=C(CCl)N2CCOC2(C)C(C(=O)OC)C1c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69d79d7234c34dfc9b1df959b118c003 | COC(=O)CC(C)=O.NCCO>>COC(=O)C=C(C)NCCO | C(O)CN.C(CC(=O)C)(=O)OC>>COC(C=C(C)NCCO)=O | O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH3:7].[NH2:8][CH2:9][CH2:10][OH:11]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH3:7])[NH:8][CH2:9][CH2:10][OH:11] | COC(=O)CC(C)=O.NCCO | COC(=O)C=C(C)NCCO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2308c5562a388f5a3972b1c218a1d28a1c29d68e0019b4c583e0642f86effe2c | 386abf15293513363decea2e36c34c5591e7bebcecf634963fbfb09ec1e3b1bc | null | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | 91.2 | [{"value": 91.2, "product": "COC(C=C(C)NCCO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice-cooled sample of ethanolamine (6.1 g) was added methyl acetoacetate (11.6 g) dropwise. Compound (XXIII 14.5 g) was formed within 30 min (U.S. Pat. No. 1102800).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Enamine | null | null | null | HO- | null | null | null | COC(=O)CC(C)=O.NCCO>>COC(=O)C=C(C)NCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54b03352f0df47deb65aac6e35fc4ae0 | CCC(Cc1ccccc1-c1ccccc1)C(=O)O.O=S(Cl)Cl>>CCC(Cc1ccccc1-c1ccccc1)C(=O)Cl | C1(=C(C=CC=C1)CC(C(=O)O)CC)C1=CC=CC=C1.S(=O)(Cl)Cl>>C1(=C(C=CC=C1)CC(C(=O)Cl)CC)C1=CC=CC=C1 | O[C:17]([CH:3]([CH2:2][CH3:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[O:18].O=S(Cl)[Cl:19]>>[CH3:1][CH2:2][CH:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[Cl:19] | CCC(Cc1ccccc1-c1ccccc1)C(=O)O.O=S(Cl)Cl | CCC(Cc1ccccc1-c1ccccc1)C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc(-c2ccccc2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C:6])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | 106.3 | [{"value": 106.3, "product": "C1(=C(C=CC=C1)CC(C(=O)Cl)CC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 100-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a thermometer and a NaOH trap was charged with 13.3 g (52.4 mmol) of 3-(2-biphenylyl)-2-ethylpropionic acid and 25.9 ml (355 mmol) of thionyl chloride, and the resulting mixture was stirred under reflux for 2.5 hours under a nitrogen a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CCC(Cc1ccccc1-c1ccccc1)C(=O)O.O=S(Cl)Cl>>CCC(Cc1ccccc1-c1ccccc1)C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-09d8e89ed27a4556962f79ec5f092948 | CCC1Cc2c(cccc2-c2ccccc2)C1=O>>CCC1=Cc2c(-c3ccccc3)cccc2C1O | CC(=O)C.[BH4-].[Na+].C(C)C1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)=O.[BH4-].[Na+]>>C(C)C=1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)O | [CH3:1][CH2:2][CH:3]1[CH2:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][CH2:2][C:3]1=[CH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[CH:17]1[OH:18] | CCC1Cc2c(cccc2-c2ccccc2)C1=O | CCC1=Cc2c(-c3ccccc3)cccc2C1O | null | null | C(C)O | Miscellaneous | OtherReaction | 1c8237a20e7497d53def9024475d65ea3729a4e2375df0c6e7118649b93b9d03 | 65c0f1e474134afe581396038c9eec1081d3cf2c66a067b33a419661521d5253 | C1=Cc2c(cccc2-c2ccccc2)C1 | [C;D1;H3:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C;D1;H3:1]-[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8])-[CH;D3;+0:9]-1-[OH;D1;+0:10] | 100.1 | [{"value": 99.0, "product": "C(C)C=1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "C(C)C=1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 0.85 g (22.6 mmol) of sodium borohydride and 28 ml of ethanol. To the mixture was dropwise added a solution containing 10.6 g (45.1 mmol) of the above-obtained 2-ethyl-4-phenyl-1-ind... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | c1ccccc1.C1=Cc2ccccc2C1 | null | C(C)O | null | 3.5 | CCC1Cc2c(cccc2-c2ccccc2)C1=O>C(C)O>CCC1=Cc2c(-c3ccccc3)cccc2C1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a1bc6cce7d6438fb61cdd07c56a6ee6 | CCC1Cc2c(-c3ccccc3)cccc2C1O>>CCC1=Cc2c(cccc2-c2ccccc2)C1 | C(C)C1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)C=1CC2=CC=CC(=C2C1)C1=CC=CC=C1 | O[CH:4]1[CH:3]([CH2:2][CH3:1])[CH2:17][c:6]2[c:5]1[cH:7][cH:8][cH:9][c:10]2-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][C:3]1=[CH:4][c:5]2[c:6]([cH:7][cH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1 | CCC1Cc2c(-c3ccccc3)cccc2C1O | CCC1=Cc2c(cccc2-c2ccccc2)C1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 77cbac765057fd7cdc9bab7700bc44fd842074b8261be2244e17dfd2370accb3 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | C1=Cc2c(cccc2-c2ccccc2)C1 | O-[CH;D3;+0:1]1-[CH;D3;+0:2](-[C:3]-[C;D1;H3:4])-[C:5]-[c;H0;D3;+0:6]2:[c;H0;D3;+0:7](-[c:8](:[c:9]):[c:10]):[c:11]:[c:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14]:2-1>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:2]1=[CH;D2;+0:1]-[c;H0;D3;+0:14]2:[c;H0;D3;+0:7](-[c:8](:[c:9]):[c:10]):[c:11]:[c:12]:[cH;D2;+0:13]:[c;H0;D3;+0:6]:2-[C:5]-1 | 73 | [{"value": 73.0, "product": "C(C)C=1CC2=CC=CC(=C2C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "C(C)C=1CC2=CC=CC(=C2C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | A 300-ml four-necked round flask equipped with a stirring bar, a dropping funnel and a thermometer was charged with 9.78 g (41.3 mmol) of 2-ethyl-1-hydroxy-4-phenylindane, 17.2 ml (123.8 mmol) of triethylamine, 0.25 g (2.1 mmol) of 4-dimethylaminopyridine and 98 ml of methylene chloride. To the mixture was dropwise add... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 3.5 | CCC1Cc2c(-c3ccccc3)cccc2C1O>CN(C1=CC=NC=C1)C.C(Cl)Cl>CCC1=Cc2c(cccc2-c2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f4401e734f84a7c9ca25250dd8869e3 | CCCC(Cc1ccccc1Br)C(=O)O.O=S(Cl)Cl>>CCCC(Cc1ccccc1Br)C(=O)Cl | BrC1=C(C=CC=C1)CC(C(=O)O)CCC.S(=O)(Cl)Cl>>BrC1=C(C=CC=C1)CC(C(=O)Cl)CCC | O[C:13]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Br:12])=[O:14].O=S(Cl)[Cl:15]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Br:12])[C:13](=[O:14])[Cl:15] | CCCC(Cc1ccccc1Br)C(=O)O.O=S(Cl)Cl | CCCC(Cc1ccccc1Br)C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C:6])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | A 500-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a thermometer and a NaOH trap was charged with 277 mmol of 3-(2-bromophenyl)-2-propylpropionic acid and 200 ml of thionyl chloride, and the mixture was heated under reflux for 2 hours. Then, the excess thionyl chloride was removed by a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | CCCC(Cc1ccccc1Br)C(=O)O.O=S(Cl)Cl>>CCCC(Cc1ccccc1Br)C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c816ac4ef7654d68886954c067ebcb25 | CCC1Cc2c(-c3cc4ccccc4c4ccccc34)cccc2C1O>>CCC1=Cc2c(cccc2-c2cc3ccccc3c3ccccc23)C1 | C(C)C1C(C2=CC=CC(=C2C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1)O.C(C)N(CC)CC.C([O-])(O)=O.[Na+].CS(=O)(=O)Cl>>C(C)C=1CC2=CC=CC(=C2C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1 | O[CH:25]1[CH:3]([CH2:2][CH3:1])[CH2:4][c:5]2[c:6]1[cH:7][cH:8][cH:9][c:10]2-[c:11]1[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][CH2:2][C:3]1=[CH:4][c:5]2[c:6]([cH:7][cH:8][cH:9][c:10]2-[c:11]2[cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]3[cH:20][cH:21][... | CCC1Cc2c(-c3cc4ccccc4c4ccccc34)cccc2C1O | CCC1=Cc2c(cccc2-c2cc3ccccc3c3ccccc23)C1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5614d5e5fab02a31ec0e60c576932a05bb07db160a8bb51ea2a91a8018c587db | f944c3c276bd629b2b018acd321b0523075bf7bf55eb7a9350e06e053a9e137b | C1=Cc2c(cccc2-c2cc3ccccc3c3ccccc23)C1 | O-[CH;D3;+0:1]1-[CH;D3;+0:2](-[C:3]-[C;D1;H3:4])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:2]1=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9])-[CH2;D2;+0:1]-1 | 83 | [{"value": 83.0, "product": "C(C)C=1CC2=CC=CC(=C2C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C(C)C=1CC2=CC=CC(=C2C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 12.3 g (36.3 mmol) of 2-ethyl-1-hydroxy-4-(9-phenanthryl)indane, 19.7 ml (142 mmol) of triethylamine and 61.5 ml of methylene chloride. To the mixture was gradually dropwise added a ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.c1ccc2c(c1)ccc1ccccc12 | HO- | C(Cl)Cl | null | 4 | CCC1Cc2c(-c3cc4ccccc4c4ccccc34)cccc2C1O>C(Cl)Cl>CCC1=Cc2c(cccc2-c2cc3ccccc3c3ccccc23)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9622eb5e098b43e1961ca5b2635ecda8 | CCC(CC)(C(=O)O)C(O)C(=O)O.O=Cc1ccccc1Br>>CCC(CC=Cc1ccccc1Br)(C(=O)O)C(=O)O | BrC1=C(C=O)C=CC=C1.C(C)C(C(C(=O)O)O)(C(=O)O)CC.N1CCCCC1.C(C)(=O)O>>BrC1=C(C=CCC(C(=O)O)(C(=O)O)CC)C=CC=C1 | OC([CH:17]([C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[C:14](=[O:15])[OH:16])[OH:19])=[O:18].O=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Br:13]>>[CH3:1][CH2:2][C:3]([CH2:4][CH:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Br:13])([C:14](=[O:15])[OH:16])[C:17](=[O:18])[OH:19] | CCC(CC)(C(=O)O)C(O)C(=O)O.O=Cc1ccccc1Br | CCC(CC=Cc1ccccc1Br)(C(=O)O)C(=O)O | null | null | CCOCC.C1=CC=CC=C1 | C-C Coupling | OtherReaction | bc1ed0b41ecf79b9ddc55b089d04a1ea8dac22b572a01624651ce6a04c592e6c | 1312feaf05378fecf324ae29885ffdc6b26a5bce74a717a259b939d2a1b7fbb8 | c1ccccc1 | O-C(=[O;H0;D1;+0:1])-[CH;D3;+0:2](-[O;D1;H1:3])-[C:4](-[C:5])(-[C:6]-[CH3;D1;+0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].O=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C:5]-[C:4](-[C:6]-[CH;D2;+0:7]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14])(-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[C;H0;D3;+0:2](-[O;D1;H1:3])=[O;H0;D1;+0:1] | 90 | [{"value": 90.0, "product": "BrC1=C(C=CCC(C(=O)O)(C(=O)O)CC)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | A 500-ml three-necked round flask (Dean & Stark) equipped with a stirring bar, a Dimroth condenser and a thermometer was charged with 74.0 g (400 mmol) of 2-bromobenzaldehyde, 70.48 g (440 mmol) of diethylmaloic acid, 1.6 ml of piperidine, 4.8 ml of acetic acid and 80 ml of benzene. The mixture was subjected to azeotor... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Secondary alcohol | Carboxylic acid | null | null | c1ccccc1 | HO- | CCOCC.C1=CC=CC=C1 | null | 7 | CCC(CC)(C(=O)O)C(O)C(=O)O.O=Cc1ccccc1Br>CCOCC.C1=CC=CC=C1>CCC(CC=Cc1ccccc1Br)(C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-720d56245d524a16b94637dbc351cd6f | CCCCC(Cc1ccccc1Br)C(=O)Cl>>CC(C)CC1Cc2c(Br)cccc2C1=O | C(=S)=S.BrC1=C(C=CC=C1)CC(C(=O)Cl)CCCC.[Cl-].[Al+3].[Cl-].[Cl-].C(=S)=S>>BrC1=C2CC(C(C2=CC=C1)=O)CC(C)C | Cl[C:14]([CH:5]([CH2:4][CH2:2][CH2:3][CH3:1])[CH2:6][c:7]1[c:8]([Br:9])[cH:10][cH:11][cH:12][cH:13]1)=[O:15]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([Br:9])[cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15] | CCCCC(Cc1ccccc1Br)C(=O)Cl | CC(C)CC1Cc2c(Br)cccc2C1=O | null | null | null | Functional Group Interconversion | OtherReaction | 7b9734e58924bc575a74e807adf26a9823112e4889035db5164e883ac041f237 | f6f1db2fb6b7641a5cc9b525399565f319b23dea2171a8a2e15ad3fed644bcab | O=C1CCc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7])-[C:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[CH3;D1;+0:7]-[CH;D3;+0:5](-[CH3;D1;+0:6])-[C:4]-[C:3]1-[C:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](:[c:12]:[c:13])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | 1 | HOUR | A 500-ml four-necked round flask equipped with a stirrer, a Dimroth condenser, a dropping funnel, a thermometer and a NaOH trap was charged with 20.33 g (152.5 mmol) of anhydrous aluminum chloride and 70 ml of carbon disulfide. To the mixture was added dropwise a solution containing 40.2 g (132.6 mmol) of the above-obt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HCl | null | null | 1 | CCCCC(Cc1ccccc1Br)C(=O)Cl>>CC(C)CC1Cc2c(Br)cccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4507c8e738e140f981dfa47144c9fc10 | CC(C)CC1Cc2c(Br)cccc2C1=O>>CC(C)CC1Cc2c(Br)cccc2C1O | B.[Na].BrC1=C2CC(C(C2=CC=C1)=O)CC(C)C>>BrC1=C2CC(C(C2=CC=C1)O)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([Br:9])[cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([Br:9])[cH:10][cH:11][cH:12][c:13]2[CH:14]1[OH:15] | CC(C)CC1Cc2c(Br)cccc2C1=O | CC(C)CC1Cc2c(Br)cccc2C1O | null | null | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 0a3f398c63bd0c6cfcdf56758ab675b7848fb8b1a73b3840e22b4343df98b04f | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCC2 | [C:1]-[C:2]1-[C:3]-[c:4]:[c:5](:[c:6])-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8]>>[C:1]-[C:2]1-[C:3]-[c:4]:[c:5](:[c:6])-[CH;D3;+0:7]-1-[OH;D1;+0:8] | 96.4 | [{"value": 96.0, "product": "BrC1=C2CC(C(C2=CC=C1)O)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.4, "product": "BrC1=C2CC(C(C2=CC=C1)O)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 2.51 g (66.3 mmol) of sodium boron hydride and 85 ml of ethanol. To the mixture was added dropwise a solution containing 37.0 g (132.6 mmol) of the above-obtained 4-bromo-2-i-butyl-1... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | C(C)O | null | 16 | CC(C)CC1Cc2c(Br)cccc2C1=O>C(C)O>CC(C)CC1Cc2c(Br)cccc2C1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69eb7f64dea14051acb42ba139e8579c | CC(C)CC1Cc2c(Br)cccc2C1O.C[Si](C)(C)Cl>>CC(C)CC1Cc2c(Br)cccc2C1O[Si](C)(C)C | C([O-])(O)=O.[Na+].BrC1=C2CC(C(C2=CC=C1)O)CC(C)C.C(C)N(CC)CC.C[Si](C)(C)Cl>>BrC1=C2CC(C(C2=CC=C1)O[Si](C)(C)C)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([Br:9])[cH:10][cH:11][cH:12][c:13]2[CH:14]1[OH:15].Cl[Si:16]([CH3:17])([CH3:18])[CH3:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([Br:9])[cH:10][cH:11][cH:12][c:13]2[CH:14]1[O:15][Si:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)CC1Cc2c(Br)cccc2C1O.C[Si](C)(C)Cl | CC(C)CC1Cc2c(Br)cccc2C1O[Si](C)(C)C | null | null | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | c1ccc2c(c1)CCC2 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](-[OH;D1;+0:7])-[c:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4])-[c:8] | 96 | [{"value": 96.0, "product": "BrC1=C2CC(C(C2=CC=C1)O[Si](C)(C)C)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "BrC1=C2CC(C(C2=CC=C1)O[Si](C)(C)C)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 34.4 g (127.8 mmol) of 4-bromo-2-i-butyl-1-hydoxyindane, 23.1 ml (166.2 mmol) of triethylamine and 118 ml of methylene chloride. To the mixture was added dropwise 20 ml of a methylen... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccc2c(c1)CCC2 | HCl | C(Cl)Cl | null | 1.5 | CC(C)CC1Cc2c(Br)cccc2C1O.C[Si](C)(C)Cl>C(Cl)Cl>CC(C)CC1Cc2c(Br)cccc2C1O[Si](C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fb06eeebdaf54faba40d9313cc436031 | CC(C)CC1=Cc2c(-c3cccc4ccccc34)cccc2C1O>>CC(C)CC1=Cc2c(cccc2-c2cccc3ccccc23)C1 | O.C(C(C)C)C=1C(C2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C(C)C)C=1CC2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12 | O[CH:23]1[C:5]([CH2:4][CH:2]([CH3:1])[CH3:3])=[CH:6][c:7]2[c:8]1[cH:9][cH:10][cH:11][c:12]2-[c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5]1=[CH:6][c:7]2[c:8]([cH:9][cH:10][cH:11][c:12]2-[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]23)[... | CC(C)CC1=Cc2c(-c3cccc4ccccc34)cccc2C1O | CC(C)CC1=Cc2c(cccc2-c2cccc3ccccc23)C1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Reduction | OtherReaction | e9b6a42e50b8eac49607046617d0205c14a3425da3a513186e1138d5359ba2a3 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | C1=Cc2c(cccc2-c2cccc3ccccc23)C1 | O-[CH;D3;+0:1]1-[C:2](-[C:3])=[C:4]-[c:5]:[c:6]-1:[c:7]>>[C:3]-[C:2]1=[C:4]-[c:5]:[c:6](:[c:7])-[CH2;D2;+0:1]-1 | 93 | [{"value": 93.0, "product": "C(C(C)C)C=1CC2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "C(C(C)C)C=1CC2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 4.54 g (14.4 mmol) of 2-i-butyl-1-hydroxy-4-(1-naphthyl)indene, 5.13 g (50.8 mmol) of triethylamine, 0.10 g (0.82 mmol) of 4-dimethylaminopyridine and 57.7 ml of methylene chloride. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.c1ccc2ccccc2c1 | Other | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 3 | CC(C)CC1=Cc2c(-c3cccc4ccccc34)cccc2C1O>CN(C1=CC=NC=C1)C.C(Cl)Cl>CC(C)CC1=Cc2c(cccc2-c2cccc3ccccc23)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f88ac48b7e45476aa2b72c1493bc7762 | O=C(O)CN(CC(O)CCl)CC(O)CCl>>O=C(O)CN(CC1CO1)CC1CO1 | ClCC(CN(CC(=O)O)CC(CCl)O)O.[Na].[OH-].[Na+]>>O1C(CN(CC(=O)O)CC2CO2)C1 | Cl[CH2:8][CH:7]([CH2:6][N:5]([CH2:4][C:2](=[O:1])[OH:3])[CH2:10][CH:11]([CH2:12]Cl)[OH:13])[OH:9]>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]([CH2:6][CH:7]1[CH2:8][O:9]1)[CH2:10][CH:11]1[CH2:12][O:13]1 | O=C(O)CN(CC(O)CCl)CC(O)CCl | O=C(O)CN(CC1CO1)CC1CO1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 2ec9e41df1eaed03dcbceb90354f5fc8e8bacbfa8468fa18185c2ec00f0def46 | cbf4463e0bad0be7f9ea06a8484ca48c009710e8fe37e8786de0b77d450609b7 | C(NCC1CO1)C1CO1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[OH;D1;+0:4].Cl-[CH2;D2;+0:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1.[C:7]-[C:6]1-[CH2;D2;+0:5]-[O;H0;D2;+0:8]-1 | 84 | [{"value": 84.0, "product": "O1C(CN(CC(=O)O)CC2CO2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "O1C(CN(CC(=O)O)CC2CO2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A reactor was charged with 20 g (0.07 mole) of sodium N,N-bis(3-chloro-2-hydroxypropyl)glycine obtained in the same manner as in Referential Example 1 and 100 g of water, and the contents were kept at 50° C., to which 35 ml of a 4N aqueous solution of sodium hydroxide were added. After the mixture was stirred for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1CO1.C1CO1 | C1CO1.C1CO1 | HCl | O | null | 0.5 | O=C(O)CN(CC(O)CCl)CC(O)CCl>O>O=C(O)CN(CC1CO1)CC1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fee902400dd24de2890c72bb0aeb17a9 | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.O=C1CCC(=O)O1>>CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)CCC(=O)O)C(=O)CCC(=O)O | OC(CNCCCCCCCC)CN(CC(CNCCCCCCCC)O)CCS(=O)(=O)O.C1(CCC(=O)O1)=O>>OC(CN(C(CCC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(CCC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH2:13][N:14]([CH2:15][CH2:16][S:17](=[O:18])(=[O:19])[OH:20])[CH2:21][CH:22]([OH:23])[CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[CH2:34]1[C:38](=[O:39])[O:40][C:45](=[O:46])[CH2:44]1>>[CH3:1][CH2... | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.O=C1CCC(=O)O1 | CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)CCC(=O)O)C(=O)CCC(=O)O | null | null | C=1(C(=CC=CC1)C)C | Functional Group Addition | OtherReaction | 3bb26b2855a96a180ebf1f241af912f3509a997494f1dbeb14302538de5c1750 | 4c4c310a2e25b44b6a153f73ca33f28376363c37984b1851430357fdf169a55b | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10].[O;D1;H0:11]=[C;H0;D3;+0:12]1-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[C;H0;D3;+0:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-1>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:13](=[O;D1;H0:18])-[C:19]-[C:20]-[C;H0;D3;+0:12](=[O;D1;H0:11])-[OH;D1;+0:17].[C:... | 80.5 | [{"value": 76.0, "product": "OC(CN(C(CCC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(CCC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "OC(CN(C(CCC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(CCC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A reactor was charged with 27 g (0.05 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane and 100 g of xylene, to which 12 g (0.12 mole) of succinic anhydride were then added with stirring to conduct a reaction at 50° C. for 6 hours. After xylene was distilled off under reduced pressure, 300 ml of water we... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amide.Tertiary amide | C1CCOC1 | null | null | Other | C=1(C(=CC=CC1)C)C | null | null | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.O=C1CCC(=O)O1>C=1(C(=CC=CC1)C)C>CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)CCC(=O)O)C(=O)CCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-edde2bbf24c7456a8918ccba8422abf0 | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.O=C1C=CC(=O)O1>>CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)C=CC(=O)O)C(=O)C=CC(=O)O | OC(CNCCCCCCCC)CN(CC(CNCCCCCCCC)O)CCS(=O)(=O)O.C1(\C=C/C(=O)O1)=O>>OC(CN(C(C=CC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(C=CC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH2:13][N:14]([CH2:15][CH2:16][S:17](=[O:18])([OH:20])=[O:46])[CH2:21][CH:22]([OH:23])[CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[CH:34]1=[CH:44][C:45](=[O:47])[O:40][C:38]1=[O:39]>>[CH3:1][CH2:2]... | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.O=C1C=CC(=O)O1 | CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)C=CC(=O)O)C(=O)C=CC(=O)O | null | null | C=1(C(=CC=CC1)C)C | Functional Group Addition | OtherReaction | dc140d5ed9dd6ad3cb833885cee8553db570545e53b2e43473a6d4d501dc3140 | 259d608df1616a51b4b4055e626ee8b0d431be26ac17083f0a7d17f76ab6069e | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10].[C:11]-[C:12]-[S;H0;D4;+0:13](=[O;D1;H0:14])(-[O;D1;H1:15])=[O;H0;D1;+0:16].[O;D1;H0:17]=[C;H0;D3;+0:18]1-[CH;D2;+0:19]=[CH;D2;+0:20]-[C;H0;D3;+0:21](=[O;H0;D1;+0:22])-[O;H0;D2;+0:23]-1>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:19](... | 80 | [{"value": 80.0, "product": "OC(CN(C(C=CC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(C=CC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "OC(CN(C(C=CC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(C=CC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | A reactor was charged with 20 g (0.04 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane and 100 g of xylene, to which 10 g (0.1 mole) of maleic anhydride were then added with stirring to conduct a reaction at 50° C. for 6 hours. After xylene was distilled off under reduced pressure, 300 ml of water were ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine.Secondary amine.Sulfonic acid | Carboxylic acid.Carboxylic acid.Tertiary amide.Tertiary amide.Sulfonic acid | C1=CCOC1 | null | null | Other | C=1(C(=CC=CC1)C)C | null | null | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.O=C1C=CC(=O)O1>C=1(C(=CC=CC1)C)C>CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)C=CC(=O)O)C(=O)C=CC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7c6c206c7c6b448dac5969421cf30787 | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.CCOC(=O)CO>>CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)CO)C(=O)CO | OC(CNCCCCCCCC)CN(CC(CNCCCCCCCC)O)CCS(=O)(=O)O.C(CO)(=O)OCC>>C(CCCCCCC)N(C(CO)=O)CC(CN(CC(CN(C(CO)=O)CCCCCCCC)O)CCS(=O)(=O)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH2:13][N:14]([CH2:15][CH2:16][S:17](=[O:18])([OH:20])=[O:35])[CH2:21][CH:22]([OH:23])[CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[CH3:34][CH2:36][O:37][C:38](=[O:39])[CH2:40][OH:41]>>[CH3:1][CH2:2... | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.CCOC(=O)CO | CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)CO)C(=O)CO | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | a734285b9b0266344aeed8bc0a479ce60148c2ec41457be505e12de4ce92c30b | 8d2d16edbc74466c428de7493aa2e86ef74b2ac3164ce0df05133be761f835c3 | null | [CH3;D1;+0:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[O;D1;H1:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17].[C:18]-[C:19]-[S;H0;D4;+0:20](=[O;D1;H0:21])(-[O;D1;H1:22])=[O;H0;D1;+0:23]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-... | 91 | [{"value": 91.0, "product": "C(CCCCCCC)N(C(CO)=O)CC(CN(CC(CN(C(CO)=O)CCCCCCCC)O)CCS(=O)(=O)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "C(CCCCCCC)N(C(CO)=O)CC(CN(CC(CN(C(CO)=O)CCCCCCCC)O)CCS(=O)(=O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 7.5 | HOUR | A reactor was charged with 10 g (0.02 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane, 50 ml of toluene and 5.1 ml (0.05 mole) of ethyl glycolate, and the contents were heated to 100° C. and continuously stirred for 7.5 hours while purging ethanol formed with a nitrogen stream. After completion of a re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Secondary amine.Sulfonic acid | Tertiary amide.Tertiary amide.Primary alcohol.Sulfonic acid | null | null | null | Other | C1(=CC=CC=C1)C | 100 | 7.5 | CCCCCCCCNCC(O)CN(CCS(=O)(=O)O)CC(O)CNCCCCCCCC.CCOC(=O)CO>C1(=CC=CC=C1)C>CCCCCCCCN(CC(O)CN(CCS(=O)(=O)O)CC(O)CN(CCCCCCCC)C(=O)CO)C(=O)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd7b84cd2bdd41c8acecfbb08583d7c0 | CSC.Nc1cc(F)c(F)cc1F>>CSCc1c(N)c(F)cc(F)c1F | [OH-].[Na+].FC1=C(N)C=C(C(=C1)F)F.CSC.ClN1C(CCC1=O)=O>>CSCC1=C(N)C(=CC(=C1F)F)F | [CH3:1][S:2][CH3:3].[cH:4]1[c:5]([NH2:6])[c:7]([F:8])[cH:9][c:10]([F:11])[c:12]1[F:13]>>[CH3:1][S:2][CH2:3][c:4]1[c:5]([NH2:6])[c:7]([F:8])[cH:9][c:10]([F:11])[c:12]1[F:13] | CSC.Nc1cc(F)c(F)cc1F | CSCc1c(N)c(F)cc(F)c1F | null | null | ClCCl.C(C)N(CC)CC | C-C Coupling | OtherReaction | 85a8db8ffc07fc3b1bc470aedfdb3564a15505e4228e084fe460beeb91f08127 | 3ec03d96d3f7f1d21fd396735dd73d6cac136a1c01b9b5cbf8cabc89b6a4b631 | c1ccccc1 | [C;D1;H3:1]-[#16:2]-[CH3;D1;+0:3].[F;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[N;D1;H2:9]):[c:10]>>[C;D1;H3:1]-[#16:2]-[CH2;D2;+0:3]-[c;H0;D3;+0:7](:[c:5](-[F;D1;H0:4]):[c:6]):[c:8](-[N;D1;H2:9]):[c:10] | null | [] | 0 | CELSIUS | 15 | MINUTE | To 2,4,5-trifluoroaniline (35.0 g) are added anhydrous dichloromethane (530 ml) and dimethyl sulfide (24.6 ml) and the mixture is cooled to 0° C. Thereto N-chlorosuccinimide (38.2 g) is gradually added below 5° C. After the mixture is stirred at the same temperature for 15 minutes, triethylamine (47.7 ml) is gradually ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | ClCCl.C(C)N(CC)CC | 0 | 0.25 | CSC.Nc1cc(F)c(F)cc1F>ClCCl.C(C)N(CC)CC>CSCc1c(N)c(F)cc(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ef792f7c5b74d278abb8630ab09df7e | CSCc1c(N)c(F)cc(F)c1F>>Cc1c(N)c(F)cc(F)c1F | CSCC1=C(N)C(=CC(=C1F)F)F>>CC1=C(N)C(=CC(=C1F)F)F | CS[CH2:1][c:2]1[c:3]([NH2:4])[c:5]([F:6])[cH:7][c:8]([F:9])[c:10]1[F:11]>>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]([F:6])[cH:7][c:8]([F:9])[c:10]1[F:11] | CSCc1c(N)c(F)cc(F)c1F | Cc1c(N)c(F)cc(F)c1F | null | [Ni] | C(C)O | Reduction | OtherReaction | 4b57e24218e2409c207dcfe624aba83448b3ad4b3549d9bc7855651565b7e76d | 32a5269109432865a866e9a2b5da238f4471b13dee7daf193dc4e8c41b091706 | c1ccccc1 | C-S-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | 71.3 | [{"value": 71.3, "product": "CC1=C(N)C(=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To 2-methylthiomethyl-3,4,6-trifluoroaniline (22.2 g) are added ethanol (400 ml) and Raney nickel (200 g) and the mixture is stirred at room temperature for 30 minutes. After the catalyst is filtered off, the filtrate is added with water and extracted with dichloromethane. The is dried over magnesium sulfate and concen... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | null | null | c1ccccc1 | Other | [Ni].C(C)O | null | 0.5 | CSCc1c(N)c(F)cc(F)c1F>[Ni].C(C)O>Cc1c(N)c(F)cc(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e9ca78c8b7943d3b81ed784f0fbf2a2 | Cc1c(N)c(F)cc(F)c1F.[C-]#N>>Cc1c(F)c(F)cc(F)c1C#N | [C-]#N.[K+].[OH-].[NH4+].CC1=C(N)C(=CC(=C1F)F)F.S(O)(O)(=O)=O.N(=O)[O-].[Na+]>>CC1=C(C#N)C(=CC(=C1F)F)F | N[c:10]1[c:2]([CH3:1])[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]1[F:9].[C-:11]#[N:12]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]([F:9])[c:10]1[C:11]#[N:12] | Cc1c(N)c(F)cc(F)c1F.[C-]#N | Cc1c(F)c(F)cc(F)c1C#N | null | S(=O)(=O)([O-])[O-].[Cu+2] | O | C-C Coupling | OtherReaction | b30bff3fbe81433a7565d8ffcdad0af1ed80d4d9274730f7a6e26aad2e552e05 | 6febc4a6ed64b39af6e5a12de3ade52adc549644adf3ef1f7265276b39762a0d | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C-;H0;D1:8]#[N;D1;H0:9]>>[C;D1;H3:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[C;H0;D2;+0:8]#[N;D1;H0:9]):[c:5](-[F;D1;H0:6]):[c:7] | 38.2 | [{"value": 38.2, "product": "CC1=C(C#N)C(=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 2-methyl-3,4,6-trifluoroaniline (10.6 g) is added a mixture of conc. sulfuric acid (13.8 ml) and water (46 ml) and the mixture is cooled. Thereto an aqueous solution (20 ml) of sodium nitrite (5.5 g) is added dropwise at 0°-5° C. The solution is gradually added to a mixture of copper (II) sulfate 5 hydrate (41 g), p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | S(=O)(=O)([O-])[O-].[Cu+2].O | null | null | Cc1c(N)c(F)cc(F)c1F.[C-]#N>S(=O)(=O)([O-])[O-].[Cu+2].O>Cc1c(F)c(F)cc(F)c1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-141b4f862c4146f6950ca566cd749152 | Cc1c(F)c(F)cc(F)c1C(=O)O.[Cl-]>>Cc1c(F)c(F)cc(F)c1C(=O)Cl | CC1=C(C(=O)O)C(=CC(=C1F)F)F.[Cl-]>>CC1=C(C(=O)Cl)C(=CC(=C1F)F)F | O[C:11]([c:10]1[c:2]([CH3:1])[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]1[F:9])=[O:12].[Cl-:13]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]([F:9])[c:10]1[C:11](=[O:12])[Cl:13] | Cc1c(F)c(F)cc(F)c1C(=O)O.[Cl-] | Cc1c(F)c(F)cc(F)c1C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_Salt | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[Cl-;H0;D0:6]>>[Cl;H0;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To 2-methyl-3,4,6-trifluorobenzoic acid (3.2 g) is added thiony chloride (7 ml) and the mixture is refluxed for 1 hour. After concentrating, 2-methyl-3,4,6-trifluorobenzoyl chloride (3.3 g) is obtained.
Conditions: See reaction.notes.procedure_details.
Workup: the mixture is refluxed for 1 hour; After concentrating | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HO- | null | null | null | Cc1c(F)c(F)cc(F)c1C(=O)O.[Cl-]>>Cc1c(F)c(F)cc(F)c1C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c7533e52831442a89bfed399496e97e | CCOC(=O)CC(=O)OCC.Cc1c(F)c(F)cc(F)c1C(=O)Cl>>CCOC(=O)C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)Cl)C(=CC(=C1F)F)F.S(O)(O)(=O)=O.[Mg].C(CC(=O)OCC)(=O)OCC>>CC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=CC(=C1F)F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[C:12](=[O:13])[c:14]1[c:15]([F:16])[cH:17][c:18]([F:19])[c:20]([F:21])[c:22]1[CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[C:12](=[O:13])[c:14]1[c:15]([F:16])[cH:17][c:18]([F:19])[c:20]([F:21])[c:22]1[CH3... | CCOC(=O)CC(=O)OCC.Cc1c(F)c(F)cc(F)c1C(=O)Cl | CCOC(=O)C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | null | C(Cl)(Cl)(Cl)Cl | C(C)O.C1(=CC=CC=C1)C.O | C-C Coupling | OtherReaction | 872dd4ea89053916cf9ee557745988425973a0fb6c3fde7e681bde82864a0018 | a7050091370b27e4945622bf444949c46249e49bd26e357ae44671cc72030a02 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | 1 | HOUR | Separately, two drops of carbon tetrachloride are added to a solution of metallic magnesium (0.4 g) in absolute ethanol (0.9 ml). When the reaction starts, a mixture of diethyl malonate (2.6 ml), absolute ethanol (1.6 ml) and anhydrous toluene (6 ml) is added dropwise below 60° C. After stirring at 60° C. for 1 hour, t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone | null | null | c1ccccc1 | HCl | C(Cl)(Cl)(Cl)Cl.C(C)O.C1(=CC=CC=C1)C.O | 60 | 1 | CCOC(=O)CC(=O)OCC.Cc1c(F)c(F)cc(F)c1C(=O)Cl>C(Cl)(Cl)(Cl)Cl.C(C)O.C1(=CC=CC=C1)C.O>CCOC(=O)C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2da68ab0871c4a05aa3d4f9224f8df1c | CCOC(=O)C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C>>CCOC(=O)CC(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=CC(=C1F)F)F.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F | CCOC(=O)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[c:9]1[c:10]([F:11])[cH:12][c:13]([F:14])[c:15]([F:16])[c:17]1[CH3:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[c:10]([F:11])[cH:12][c:13]([F:14])[c:15]([F:16])[c:17]1[CH3:18] | CCOC(=O)C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | CCOC(=O)CC(=O)c1c(F)cc(F)c(F)c1C | null | null | O | Reduction | Decarboxylation | c8cf2024f85522a1f5dc304862ec185b9ba9539171a955fed5fc95020255a5b8 | 92cfcced8d7e743a323bd1528115ee07546647fe3eca55d712fbb9eefe0c9e22 | c1ccccc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[c:8]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C:6](=[O;D1;H0:7])-[c:8] | 82.6 | [{"value": 82.6, "product": "CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.1 g) are added water (20 ml) and p-toluenesulfonic acid (30 mg) and the mixture is refluxed for 2.5 hours. After cooling, the resultant is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give ethyl 2-methyl-3,4,6-tri... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CCOC(=O)C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C>O>CCOC(=O)CC(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c88fe3c527448899e928f57e94a62f9 | CCOC(=O)CC(=O)c1c(F)cc(F)c(F)c1C.CCOC(OCC)OCC>>CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F.C(C)(=O)OC(C)=O.C(C)OC(OCC)OCC>>CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F | [CH2:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[c:14]([F:15])[cH:16][c:17]([F:18])[c:19]([F:20])[c:21]1[CH3:22].CCO[CH:4](OCC)[O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[c:14]([F:15])[cH:16][c:17]([F:18])[c:19]([F:20])[c:21]1[CH3:22] | CCOC(=O)CC(=O)c1c(F)cc(F)c(F)c1C.CCOC(OCC)OCC | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | null | null | null | C-C Coupling | OtherReaction | 7cfff3053680512afd8f3daf149645dfb2cfa4c9c32bf9b885b72097190aacf2 | 9164ecc9bc41a60ea056ee2b5a56d6c3899e2ff7c236ad9974338a128257f79c | c1ccccc1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[#8:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:3]-[#8:2]-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4] | 90 | [{"value": 90.0, "product": "CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (3.2 g) are added acetic anhydride (3.0 g) and triethoxymethane (2.7 g) and the mixture is refluxed for 1 hour. After concentrating, ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (3.5 g) is obtained.
Conditions: See reaction.notes.procedure_details.
Workup: t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Ether | Ketone.Ester.Ether | null | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)CC(=O)c1c(F)cc(F)c(F)c1C.CCOC(OCC)OCC>>CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6bc9092d4d54296b6f4a8701204549f | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.NC1CC1>>CCOC(=O)C(=CNC1CC1)C(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F.C1(CC1)N>>CC1=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=CC(=C1F)F)F | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:12](=[O:13])[c:14]1[c:15]([F:16])[cH:17][c:18]([F:19])[c:20]([F:21])[c:22]1[CH3:23].[NH2:8][CH:9]1[CH2:10][CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][NH:8][CH:9]1[CH2:10][CH2:11]1)[C:12](=[O:13])[c:14]1[c:15]([F:16])[cH:17][c:18]([F:19])[c:20]([F:21])[c:2... | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.NC1CC1 | CCOC(=O)C(=CNC1CC1)C(=O)c1c(F)cc(F)c(F)c1C | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | cd3db327c21c90c24d38808dacb2ed3fbf57044150e5b341d88de9389ff3759d | 54aca1a08d403c8dd5c375df3e63fffc5027b15326b2523cf980a4a251290495 | O=C(C=CNC1CC1)c1ccccc1 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3](=[O;D1;H0:4])-[c:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[NH2;D1;+0:10]-[C:11]1-[C:12]-[C:13]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:2](=[CH;D2;+0:1]-[NH;D2;+0:10]-[C:11]1-[C:12]-[C:13]-1)-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 30 | MINUTE | Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (3.5 g) is dissolved in ethanol (25 ml) and thereto cyclopropylamine (0.84 ml) is added dropwise under ice-cooling. After stirring at room temperature for 30 minutes, the mixture is concentrated and the residue is purified with column chromatography (silica-gel... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Enamine | null | null | C1CC1.c1ccccc1 | HO- | C(C)O | null | 0.5 | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.NC1CC1>C(C)O>CCOC(=O)C(=CNC1CC1)C(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8baad9aabd414b21a6bb786ba650a995 | CCOC(=O)C(=CNC1CC1)C(=O)c1c(F)cc(F)c(F)c1C>>CCOC(=O)c1cn(C2CC2)c2cc(F)c(F)c(C)c2c1=O | CC1=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=CC(=C1F)F)F.[H-].[Na+]>>C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC | F[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([CH3:19])[c:20]1[C:21]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][NH:8][CH:9]1[CH2:10][CH2:11]1)=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11]2)[c:12]2[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([CH3:19])[c:20]2[c:21]1=[O:22] | CCOC(=O)C(=CNC1CC1)C(=O)c1c(F)cc(F)c(F)c1C | CCOC(=O)c1cn(C2CC2)c2cc(F)c(F)c(C)c2c1=O | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | f1bb464adea8e64c138d384f2f02c35f1978964fc9c160676d8ef60c68e5e3df | ecabf5a50b4453255d534845e8b1084d96a0aaf957abdb24947c6089ec559e5f | O=c1ccn(C2CC2)c2ccccc12 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](=[CH;D2;+0:8]-[NH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]):[c:17]>>[C:16]-[#8:15]-[C:13](=[O;D1;H0:14])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D3;+0:9](-[C:10]2-[C:11]-[C:12]-2):[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4... | 81.9 | [{"value": 81.9, "product": "C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-cyclopropylaminoacrylate (2.6 g) is dissolved in anhydrous dioxane (26 ml) and thereto 60% sodium hydride (0.38 g) is gradully added under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture is poured into ice-water and extracted with dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone | Ester | c1ccccc1 | c1ccc2ncccc2c1 | C1CC1.c1ccc2ncccc2c1 | HF | O1CCOCC1 | null | 0.5 | CCOC(=O)C(=CNC1CC1)C(=O)c1c(F)cc(F)c(F)c1C>O1CCOCC1>CCOC(=O)c1cn(C2CC2)c2cc(F)c(F)c(C)c2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4ccefd875914706b84816f471c88bad | CCOC(=O)c1cn(C2CC2)c2cc(F)c(F)c(C)c2c1=O>>Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC.Cl>>C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O | CC[O:15][C:13]([c:12]1[c:10](=[O:11])[c:9]2[c:2]([CH3:1])[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]2[n:17]([CH:18]2[CH2:19][CH2:20]2)[cH:16]1)=[O:14]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]2[c:9]1[c:10](=[O:11])[c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]2[CH:18]1[CH2:19][CH2:20]1 | CCOC(=O)c1cn(C2CC2)c2cc(F)c(F)c(C)c2c1=O | Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccn(C2CC2)c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 92.7 | [{"value": 92.7, "product": "C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.9 g) are added 90% acetic acid (20 ml) and conc. hydrochloric acid (5 ml) and the mixture is refluxed for 2 hours. After cooling, the precipitated crystals are isolated, washed with water, ethanol, and diethyl ether in this order t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1.C1CC1 | Other | C(C)(=O)O | null | null | CCOC(=O)c1cn(C2CC2)c2cc(F)c(F)c(C)c2c1=O>C(C)(=O)O>Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ca06de262c0c42b696248fd0b6d115dc | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.Nc1ccc(F)cc1>>CCOC(=O)C(=CNc1ccc(F)cc1)C(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F.FC1=CC=C(N)C=C1>>CC1=C(C(=O)C(C(=O)OCC)=CNC2=CC=C(C=C2)F)C(=CC(=C1F)F)F | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:16](=[O:17])[c:18]1[c:19]([F:20])[cH:21][c:22]([F:23])[c:24]([F:25])[c:26]1[CH3:27].[NH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[C:16](=[O:17])[c:18]1[c:... | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.Nc1ccc(F)cc1 | CCOC(=O)C(=CNc1ccc(F)cc1)C(=O)c1c(F)cc(F)c(F)c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cd3db327c21c90c24d38808dacb2ed3fbf57044150e5b341d88de9389ff3759d | 54aca1a08d403c8dd5c375df3e63fffc5027b15326b2523cf980a4a251290495 | O=C(C=CNc1ccccc1)c1ccccc1 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3](=[O;D1;H0:4])-[c:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:2](=[CH;D2;+0:1]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and p-fluoroaniline (0.39 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-fluorophenyl)aminoacrylate, which is then treated with 60% sodium hydride (0.15 g) as in Reference Example 9 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Enamine | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.Nc1ccc(F)cc1>>CCOC(=O)C(=CNc1ccc(F)cc1)C(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ae2d2dcbbfdb4f1f9dfb58ab8ece22a4 | CCOC(=O)c1cn(-c2ccc(F)cc2)c2cc(F)c(F)c(C)c2c1=O>>Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1 | FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC.Cl>>FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O | CC[O:15][C:13]([c:12]1[c:10](=[O:11])[c:9]2[c:2]([CH3:1])[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]2[n:17](-[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[cH:16]1)=[O:14]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([F:6])[cH:7][c:8]2[c:9]1[c:10](=[O:11])[c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]2-[c:18]1[cH:19][cH:20][c:21]([F:22])... | CCOC(=O)c1cn(-c2ccc(F)cc2)c2cc(F)c(F)c(C)c2c1=O | Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccn(-c2ccccc2)c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 94.9 | [{"value": 94.9, "product": "FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Employing ethyl 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.56 g), conc. hydrochloric acid (1.5 ml), and 90% acetic acid (6 ml), the procedure of Reference Example 10 is repeated to give 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.49 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1.c1ccccc1 | Other | C(C)(=O)O | null | null | CCOC(=O)c1cn(-c2ccc(F)cc2)c2cc(F)c(F)c(C)c2c1=O>C(C)(=O)O>Cc1c(F)c(F)cc2c1c(=O)c(C(=O)O)cn2-c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ed5758e449440ffbc8cbb4a1a1e12a0 | CCN.CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C>>CCNC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F.C(C)N>>CC1=C(C(=O)C(C(=O)OCC)=CNCC)C(=CC(=C1F)F)F | [CH3:1][CH2:2][NH2:3].CCO[CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[c:14]([F:15])[cH:16][c:17]([F:18])[c:19]([F:20])[c:21]1[CH3:22]>>[CH3:1][CH2:2][NH:3][CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[c:14]([F:15])[cH:16][c:17]([F:18])[c:19]([F:20])[c:21]1[CH3:22] | CCN.CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | CCNC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cd3db327c21c90c24d38808dacb2ed3fbf57044150e5b341d88de9389ff3759d | 54aca1a08d403c8dd5c375df3e63fffc5027b15326b2523cf980a4a251290495 | c1ccccc1 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3](=[O;D1;H0:4])-[c:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[C;D1;H3:10]-[C:11]-[NH2;D1;+0:12]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:2](=[CH;D2;+0:1]-[NH;D2;+0:12]-[C:11]-[C;D1;H3:10])-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and 70% aqueous ethylamine solution (0.24 ml), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethylaminoacrylate, which is then treated with 60 % sodium hydride (0.15 g) as in Reference Exa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Enamine | null | null | c1ccccc1 | HO- | null | null | null | CCN.CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C>>CCNC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ced401958df14107b84014195a09d50e | CCOC(=O)c1cn(CC)c2cc(F)c(F)c(C)c2c1=O>>CCn1cc(C(=O)O)c(=O)c2c(C)c(F)c(F)cc21 | C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC.Cl>>C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O | CC[O:8][C:6]([c:5]1[cH:4][n:3]([CH2:2][CH3:1])[c:19]2[c:11]([c:9]1=[O:10])[c:12]([CH3:13])[c:14]([F:15])[c:16]([F:17])[cH:18]2)=[O:7]>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[c:11]2[c:12]([CH3:13])[c:14]([F:15])[c:16]([F:17])[cH:18][c:19]12 | CCOC(=O)c1cn(CC)c2cc(F)c(F)c(C)c2c1=O | CCn1cc(C(=O)O)c(=O)c2c(C)c(F)c(F)cc21 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc[nH]c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 80.4 | [{"value": 80.4, "product": "C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Employing ethyl 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.55 g), conc. hydrochloric acid (1.5 ml) and 90% acetic acid (6 ml), the procedure of Reference Example 10 is repeated to give 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3- carboxylic acid (0.40 g), as white crystals,... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1 | Other | C(C)(=O)O | null | null | CCOC(=O)c1cn(CC)c2cc(F)c(F)c(C)c2c1=O>C(C)(=O)O>CCn1cc(C(=O)O)c(=O)c2c(C)c(F)c(F)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6d1437bef5145cca37826ac5ae090f0 | CO.Cc1c(C(=O)O)cccc1[N+](=O)[O-]>>COC(=O)c1cccc([N+](=O)[O-])c1C | CC1=C(C(=O)O)C=CC=C1[N+](=O)[O-].CO.S(=O)(Cl)Cl>>CC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-] | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[CH3:14] | CO.Cc1c(C(=O)O)cccc1[N+](=O)[O-] | COC(=O)c1cccc([N+](=O)[O-])c1C | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To 2-methyl-3-nitrobenzoic acid (10.0 g) is added methanol (100 ml) and thereto thionyl chloride (8 ml) is added dropwise at room temperature. After reflux for 2 hours, the reaction mixture is poured into ice-water and extracted with dichloromethane. The solvent is concentrated to give methyl 2-methyl-3-nitrobenzoate (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Cc1c(C(=O)O)cccc1[N+](=O)[O-]>>COC(=O)c1cccc([N+](=O)[O-])c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a382dee7401645edb9da6c1fce7078a0 | COC(=O)c1cccc([N+](=O)[O-])c1C>>COC(=O)c1cccc(N)c1C | CC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]>>CC1=C(C(=O)OC)C=CC=C1N | O=[N+:10]([O-])[c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]1[CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[c:11]1[CH3:12] | COC(=O)c1cccc([N+](=O)[O-])c1C | COC(=O)c1cccc(N)c1C | null | [Pd] | C(C)(=O)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] | 101.6 | [{"value": 101.6, "product": "CC1=C(C(=O)OC)C=CC=C1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Methyl 2-methyl-3-nitrobenzoate (10.0 g) is dissolved in acetic acid (50 ml) and thereto 5% Pd-C (1 g) is added to carry out catalytic reduction at room temperature under 1 atm. After 1.5 hours, the catalyst is filtered off. The reaction mixture is concentrated, and thereto is added water, and the mixture is made alkal... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)O | null | 1.5 | COC(=O)c1cccc([N+](=O)[O-])c1C>[Pd].C(C)(=O)O>COC(=O)c1cccc(N)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b1dfc28218048f1b96339ca5954f763 | COC(=O)c1c(Br)cc(Br)c(F)c1C>>Cc1c(F)c(Br)cc(Br)c1C(=O)O | CC1=C(C(=O)OC)C(=CC(=C1F)Br)Br.C(C)O.[OH-].[Na+]>>CC1=C(C(=O)O)C(=CC(=C1F)Br)Br | C[O:13][C:11]([c:10]1[c:2]([CH3:1])[c:3]([F:4])[c:5]([Br:6])[cH:7][c:8]1[Br:9])=[O:12]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([Br:6])[cH:7][c:8]([Br:9])[c:10]1[C:11](=[O:12])[OH:13] | COC(=O)c1c(Br)cc(Br)c(F)c1C | Cc1c(F)c(Br)cc(Br)c1C(=O)O | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 84.4 | [{"value": 84.4, "product": "CC1=C(C(=O)O)C(=CC(=C1F)Br)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To methyl 2-methyl-3-fluoro-4,6-dibromobenzoate (75.5 g) are added ethanol (460 ml) and 10% aqueous solution of sodium hydroxide (460 ml) and the mixture is refluxed for 2 hours. After cooling, the reaction mixture is diluted with water and extracted with diethyl ether. The aqueous layer is made acidic with conc. hydro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O | null | null | COC(=O)c1c(Br)cc(Br)c(F)c1C>O>Cc1c(F)c(Br)cc(Br)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54a17c6717d34e7dab9d9ee4a4d665b8 | CCOC(=O)C(=CNC1CC1)C(=O)c1c(Br)cc(Br)c(F)c1C>>CCOC(=O)c1cn(C2CC2)c2cc(Br)c(F)c(C)c2c1=O | BrC1=C(C(=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C1)Br)C)F.C([O-])([O-])=O.[K+].[K+]>>C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Br)F)C)=O)C(=O)OCC | Br[c:12]1[cH:13][c:14]([Br:15])[c:16]([F:17])[c:18]([CH3:19])[c:20]1[C:21]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][NH:8][CH:9]1[CH2:10][CH2:11]1)=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11]2)[c:12]2[cH:13][c:14]([Br:15])[c:16]([F:17])[c:18]([CH3:19])[c:20]2[c:21]1=[O:22] | CCOC(=O)C(=CNC1CC1)C(=O)c1c(Br)cc(Br)c(F)c1C | CCOC(=O)c1cn(C2CC2)c2cc(Br)c(F)c(C)c2c1=O | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | f1bb464adea8e64c138d384f2f02c35f1978964fc9c160676d8ef60c68e5e3df | ecabf5a50b4453255d534845e8b1084d96a0aaf957abdb24947c6089ec559e5f | O=c1ccn(C2CC2)c2ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](=[CH;D2;+0:8]-[NH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]):[c:17]>>[C:16]-[#8:15]-[C:13](=[O;D1;H0:14])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D3;+0:9](-[C:10]2-[C:11]-[C:12]-2):[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:... | 91.1 | [{"value": 91.1, "product": "C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Br)F)C)=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture comprising ethyl 2-(4,6-dibromo-3-fluoro-2-methylbenzoyl)-3-cyclopropylaminoacrylate (45.0 g), potassium carbonate (16.7 g) and dimethylformamide (450 ml) is reacted at 140° C. for 30 minutes. After cooling, the reaction mixture is poured into ice-water and the precipitated crystals are filtered, which are re... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone | Ester | c1ccccc1 | c1ccc2ncccc2c1 | C1CC1.c1ccc2ncccc2c1 | HBr | CN(C=O)C | null | null | CCOC(=O)C(=CNC1CC1)C(=O)c1c(Br)cc(Br)c(F)c1C>CN(C=O)C>CCOC(=O)c1cn(C2CC2)c2cc(Br)c(F)c(C)c2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f9699d46336a408a989760bcba92ed2e | Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1.O=S(Cl)Cl>>Cc1c(F)c(Cl)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | [OH-].[Na+].C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Br)F)C)=O)C(=O)O.S(=O)(Cl)Cl>>C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Cl)F)C)=O)C(=O)O | Br[c:5]1[c:3]([F:4])[c:2]([CH3:1])[c:9]2[c:8]([cH:7]1)[n:17]([CH:18]1[CH2:19][CH2:20]1)[cH:16][c:12]([C:13](=[O:14])[OH:15])[c:10]2=[O:11].O=S(Cl)[Cl:6]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([Cl:6])[cH:7][c:8]2[c:9]1[c:10](=[O:11])[c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17]2[CH:18]1[CH2:19][CH2:20]1 | Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1.O=S(Cl)Cl | Cc1c(F)c(Cl)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | null | null | null | Functional Group Interconversion | OtherReaction | e284eb1a1a2e6a7ff4d99faedbf4df50ba8c3875dc22e9335e645ef3c2dbcb0e | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | O=c1ccn(C2CC2)c2ccccc12 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1-[F;D1;H0:7]):[#7;a:8](-[C:9]):[c:10].Cl-S(=O)-[Cl;H0;D1;+0:11]>>[C:9]-[#7;a:8](:[c:10]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[Cl;H0;D1;+0:11]):[c:6](-[F;D1;H0:7]):[c:5]:[c:4]:1 | null | [] | null | null | 30 | MINUTE | To 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4- dihydro-4-oxoquinoline-3-carboxylic acid (0.2 g) is added thionyl chloride (2 ml) and the mixture is refluxed for 1 hour. After cooling, the reaction mixture is poured into ice-water and made alkaline with 10% aqueous sodium hydroxide solution. After stirring for 30 minut... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CC1 | Br- | null | null | 0.5 | Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1.O=S(Cl)Cl>>Cc1c(F)c(Cl)cc2c1c(=O)c(C(=O)O)cn2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b88a2a6137fb40db944423fb5f4a79e9 | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.Nc1ccc(F)cc1F>>CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(F)c(F)c1C | CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F.FC1=C(N)C=CC(=C1)F>>CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)F)F | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17](=[O:18])[c:19]1[c:20]([F:21])[cH:22][c:23]([F:24])[c:25]([F:26])[c:27]1[CH3:28].[NH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16])[C:17](=[O:18])... | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.Nc1ccc(F)cc1F | CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(F)c(F)c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cd3db327c21c90c24d38808dacb2ed3fbf57044150e5b341d88de9389ff3759d | 54aca1a08d403c8dd5c375df3e63fffc5027b15326b2523cf980a4a251290495 | O=C(C=CNc1ccccc1)c1ccccc1 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3](=[O;D1;H0:4])-[c:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:2](=[CH;D2;+0:1]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:3](=[O;D1;H0:4])-[c:5] | 87.1 | [{"value": 87.1, "product": "CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and 2,4-difluoroaniline (0.5 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate (1.1 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Enamine | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C.Nc1ccc(F)cc1F>>CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(F)c(F)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2cec4d8016440a8aabfc36afde71b94 | CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(F)c(F)c1C>>CCOC(=O)c1cn(-c2ccc(F)cc2F)c2cc(F)c(F)c(C)c2c1=O | CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)F)F.[H-].[Na+]>>FC1=C(C=CC(=C1)F)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC | F[c:17]1[cH:18][c:19]([F:20])[c:21]([F:22])[c:23]([CH3:24])[c:25]1[C:26]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]1[F:16])=[O:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]2[F:16])[c:17]2[cH:18][c:19]([F:2... | CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(F)c(F)c1C | CCOC(=O)c1cn(-c2ccc(F)cc2F)c2cc(F)c(F)c(C)c2c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f1bb464adea8e64c138d384f2f02c35f1978964fc9c160676d8ef60c68e5e3df | ecabf5a50b4453255d534845e8b1084d96a0aaf957abdb24947c6089ec559e5f | O=c1ccn(-c2ccccc2)c2ccccc12 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](=[CH;D2;+0:8]-[NH;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[F;D1;H0:14]):[c:15])-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19]):[c:20]>>[C:19]-[#8:18]-[C:16](=[O;D1;H0:17])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D3;+0:9](-[c;H0;D3;+0:10](:[c:1... | 67 | [{"value": 67.0, "product": "FC1=C(C=CC(=C1)F)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate (1.1 g) and 60% sodium hydride (0.13 g), the procedure of Reference Example 9 is repeated to give ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.7 g).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone | Ester | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HF | null | null | null | CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(F)c(F)c1C>>CCOC(=O)c1cn(-c2ccc(F)cc2F)c2cc(F)c(F)c(C)c2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4ea23bfddc534be9b03e25cecadbc056 | CCOC=C(C(=O)OCC)C(=O)OCC.Cc1c(F)c(N2CCNCC2)cc(NC2CC2)c1[N+](=O)[O-]>>CCOC(=O)C(=CN(c1cc(N2CCNCC2)c(F)c(C)c1[N+](=O)[O-])C1CC1)C(=O)OCC | N1(CCNCC1)C=1C=C(NC2CC2)C(=C(C1F)C)[N+](=O)[O-].C(C)OC=C(C(=O)OCC)C(=O)OCC>>C1(CC1)N(C1=CC(=C(C(=C1[N+](=O)[O-])C)F)N1CCNCC1)C=C(C(=O)OCC)C(=O)OCC | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:29](=[O:30])[O:31][CH2:32][CH3:33].[NH:8]([c:9]1[cH:10][c:11]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[c:18]([F:19])[c:20]([CH3:21])[c:22]1[N+:23](=[O:24])[O-:25])[CH:26]1[CH2:27][CH2:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][c:11]... | CCOC=C(C(=O)OCC)C(=O)OCC.Cc1c(F)c(N2CCNCC2)cc(NC2CC2)c1[N+](=O)[O-] | CCOC(=O)C(=CN(c1cc(N2CCNCC2)c(F)c(C)c1[N+](=O)[O-])C1CC1)C(=O)OCC | null | null | null | Functional Group Addition | OtherReaction | 38cce29c47a06422870d2b994c7fc6572611707b1fe155de9452da80a160e466 | 575ae94c9a30081d7737dec981506212ab231d10166b2bd9b7134947ffcd0ce1 | c1cc(NC2CC2)cc(N2CCNCC2)c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[c:12]:[c:13](-[NH;D2;+0:14]-[C:15]1-[C:16]-[C:17]-1):[c:18]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C:3](=[CH;D2;+0:4]-[N;H0;D3;+0:14](-[C:15]1-[C:16]-[C:17]-1)-[c:13](:[c:12]):[c:18])-[C;H0;D3;+0:1... | null | [] | 150 | CELSIUS | null | null | To 3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitro-N-cyclopropylaniline (1.57 g) is added diethyl ethoxymethylenemalonate (1.45 ml) and the mixture is heated at 150° C. for 25 hours. After cooling, the reaction product is purified by silica-gel column-chromatography (dichloromethane:methanol=100:1) to give diethyl [N-cyclo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1.C1C[NH]CCN1.C1CC1 | HO- | null | 150 | null | CCOC=C(C(=O)OCC)C(=O)OCC.Cc1c(F)c(N2CCNCC2)cc(NC2CC2)c1[N+](=O)[O-]>>CCOC(=O)C(=CN(c1cc(N2CCNCC2)c(F)c(C)c1[N+](=O)[O-])C1CC1)C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf9ee368bd9548f6bc7d6beba130ae9b | CCOC(=O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)c(C)c2c1=O>>Cc1c(F)c(N2CCNCC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)OCC)=O)C)F.[OH-].[Na+].C(C)O>>N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F | CC[O:20][C:18]([c:17]1[c:15](=[O:16])[c:14]2[c:2]([CH3:1])[c:3]([F:4])[c:5]([N:6]3[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)[cH:12][c:13]2[n:22]([CH:23]2[CH2:24][CH2:25]2)[cH:21]1)=[O:19]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][c:13]2[c:14]1[c:15](=[O:16])[c:17]([C:18](=[O:19])[O... | CCOC(=O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)c(C)c2c1=O | Cc1c(F)c(N2CCNCC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccn(C2CC2)c2cc(N3CCNCC3)ccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 56.4 | [{"value": 56.4, "product": "N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To ethyl 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (23 mg) are added 10% aqueous solution of sodium hydroxide (3 ml) and ethanol (3 ml), and the mixture is refluxed for 1 hour. After cooling, the reaction mixture is diluted with water and washed with dichloromethane. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CCN1.c1ccc2ncccc2c1.C1CC1 | Other | O | null | null | CCOC(=O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)c(C)c2c1=O>O>Cc1c(F)c(N2CCNCC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2010b52898404086bd489885248322bd | Cc1c(F)c(N2CC(C)C(NC(=O)OC(C)(C)C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1>>Cc1c(F)c(N2CC(C)C(N)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | C(C)(C)(C)OC(=O)NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F.Cl>>Cl.NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F | CC(C)(C)OC(=O)[NH:11][CH:10]1[CH:8]([CH3:9])[CH2:7][N:6]([c:5]2[c:3]([F:4])[c:2]([CH3:1])[c:15]3[c:14]([cH:13]2)[n:23]([CH:24]2[CH2:25][CH2:26]2)[cH:22][c:18]([C:19](=[O:20])[OH:21])[c:16]3=[O:17])[CH2:12]1>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([N:6]2[CH2:7][CH:8]([CH3:9])[CH:10]([NH2:11])[CH2:12]2)[cH:13][c:14]2[c:15]1[c:16... | Cc1c(F)c(N2CC(C)C(NC(=O)OC(C)(C)C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | Cc1c(F)c(N2CC(C)C(N)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1ccn(C2CC2)c2cc(N3CCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3] | null | [] | null | null | null | null | A mixture comprising 7-(3-t-butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (trans form) (120 mg), ethanol (4 ml) and 10% hydrochloric acid (4 ml) is refluxed for 30 minutes. After concentrating, the obtained residue is recrystallized from methan... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HO- | C(C)O | null | null | Cc1c(F)c(N2CC(C)C(NC(=O)OC(C)(C)C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1>C(C)O>Cc1c(F)c(N2CC(C)C(N)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4f5c585a2f143a1af864ac4739e3c74 | CC(=O)OC(C)=O.Cc1c(F)c(N2CCNCC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1>>CC(=O)N1CCN(c2cc3c(c(C)c2F)c(=O)c(C(=O)O)cn3C2CC2)CC1 | Cl.N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F.C(C)(=O)OC(C)=O>>C(C)(=O)N1CCN(CC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F | CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][c:10]3[c:11]([c:12]([CH3:13])[c:14]2[F:15])[c:16](=[O:17])[c:18]([C:19](=[O:20])[OH:21])[cH:22][n:23]3[CH:24]2[CH2:25][CH2:26]2)[CH2:27][CH2:28]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][c:10]3[c:11]([c:12]([CH3:13])[c:14]2[F:15])[c:... | CC(=O)OC(C)=O.Cc1c(F)c(N2CCNCC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | CC(=O)N1CCN(c2cc3c(c(C)c2F)c(=O)c(C(=O)O)cn3C2CC2)CC1 | null | null | [OH-].[Na+] | Acylation | Aminolysis of esters | b3be41bbcee62996e53bc3035dc7cc02d97d5bc8a1e1c9b0ca187f26f9fbfafa | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | O=c1ccn(C2CC2)c2cc(N3CCNCC3)ccc12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | To a solution of 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (40 mg) in 5% sodium hydroxide (2 ml) is added acetic anhydride (0.1 ml) at room temperature. After the mixture is made acidic with dilute hydrochloric acid, the resultant is extracted with dichloromethane an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1.C1CC1 | HO- | [OH-].[Na+] | null | null | CC(=O)OC(C)=O.Cc1c(F)c(N2CCNCC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1>[OH-].[Na+]>CC(=O)N1CCN(c2cc3c(c(C)c2F)c(=O)c(C(=O)O)cn3C2CC2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4dd793d179ff43a5b9d3cc139df171bf | Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1.O=C1CCNCC1>>Cc1c(F)c(N2CCC(=O)CC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Br)F)C)=O)C(=O)O.O=C1CCNCC1>>C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)N1CCC(CC1)=O)F)C)=O)C(=O)O | Br[c:5]1[c:3]([F:4])[c:2]([CH3:1])[c:15]2[c:14]([cH:13]1)[n:23]([CH:24]1[CH2:25][CH2:26]1)[cH:22][c:18]([C:19](=[O:20])[OH:21])[c:16]2=[O:17].[NH:6]1[CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH2:12]1>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([N:6]2[CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH2:12]2)[cH:13][c:14]2[c:15]1[c:16](=[O:17])[c:18... | Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1.O=C1CCNCC1 | Cc1c(F)c(N2CCC(=O)CC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1CCN(c2ccc3c(=O)ccn(C4CC4)c3c2)CC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1-[F;D1;H0:7]):[#7;a:8](-[C:9]):[c:10].[O;D1;H0:11]=[C:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:9]-[#7;a:8](:[c:10]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[C:12](=[O;D1;H0:11])-[C:17]-[C:16]-2):[c:6](-[F;D1;H0:7]):[c:5]:[c:4]:1 | 37.6 | [{"value": 37.6, "product": "C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)N1CCC(CC1)=O)F)C)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.58 g) in N-methyl-2-pyrrolidone (5 ml) is added 4-oxopiperidine (0.64 g) and the mixture is heated at 90° C. for 20 minutes. The solvent is distilled off under reduced pressure. To the resulting residue is added eth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CCNCC1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.C1CC1 | HBr | CN1C(CCC1)=O | 90 | null | Cc1c(F)c(Br)cc2c1c(=O)c(C(=O)O)cn2C1CC1.O=C1CCNCC1>CN1C(CCC1)=O>Cc1c(F)c(N2CCC(=O)CC2)cc2c1c(=O)c(C(=O)O)cn2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-05149c9288364f2583be374274cc2755 | CC(C)(C)C(=O)C(=O)[O-].NO>>CC(C)(C)C(=NO)C(=O)O | [Na+].CC(C(C(=O)[O-])=O)(C)C.Cl.NO>>CC(C(C(=O)O)=NO)(C)C | O=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:8](=[O:9])[O-:10].[NH2:6][OH:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[N:6][OH:7])[C:8](=[O:9])[OH:10] | CC(C)(C)C(=O)C(=O)[O-].NO | CC(C)(C)C(=NO)C(=O)O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 563f6a8535c43609e054d888343590b2682c219f195349290c332185db5b558f | e64636ca549954a90be725fde08b07bc1a3f451bbed63061829d2618f80d2516 | null | O=[C;H0;D3;+0:1](-[C:2](-[O-;H0;D1:3])=[O;D1;H0:4])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[O;D1;H1:10]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[O;D1;H1:10])-[C:2](=[O;D1;H0:4])-[OH;D1;+0:3] | 81.2 | [{"value": 81.0, "product": "CC(C(C(=O)O)=NO)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "CC(C(C(=O)O)=NO)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 163 g (1 mole) 93.5% trimethylpyruvic acid sodium salt and 69.5 g (1 mole) hydroxylamine hydrochloride were dissolved at 40° C. in 450 ml water. The product crystallized out during slow cooling under agitation. After 1.5 h agitation in an ice bath the crystals were filtered off, washed with 150 ml ice water, dried in a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Carboxylic acid.Oxime | null | null | null | HO- | O | null | null | CC(C)(C)C(=O)C(=O)[O-].NO>O>CC(C)(C)C(=NO)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd9603f73e7d4c139f69155d33de1172 | CC(C)(C)[C@@H](N)CO.CCOC(=O)Cl>>CC(C)(C)[C@@H]1COC(=O)N1 | [OH-].[Na+].N[C@H](C(C)(C)C)CO.O.C(C)OC(=O)Cl>>C(C)(C)(C)[C@H]1NC(OC1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]([CH2:6][OH:7])[NH2:10].CCO[C:8](Cl)=[O:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]1[CH2:6][O:7][C:8](=[O:9])[NH:10]1 | CC(C)(C)[C@@H](N)CO.CCOC(=O)Cl | CC(C)(C)[C@@H]1COC(=O)N1 | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | f9d29bd4817ea47fcfe120b170cfc227567f09cb92c6b107b13832ce06e891fc | 09b7218caca4bbcd940f7b50cdf774e76319a49137d8b21f1dade5f374345a97 | O=C1NCCO1 | C-C-O-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[C:3]-[C:4](-[NH2;D1;+0:5])-[C:6]-[OH;D1;+0:7]>>[C:3]-[C:4]1-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-1 | 80 | [{"value": 80.0, "product": "C(C)(C)(C)[C@H]1NC(OC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "C(C)(C)(C)[C@H]1NC(OC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | 73 g (containing 0.25 mole (R)-tert-leucinol) of the filtrate cited in example 6 was taken up with 27 ml water and 200 ml toluene. 25 ml (0.26 mole) chloroformic acid ethyl ester were then added dropwise at 20°-25° C., during which the pH was maintained at 7-8.5 by the addition of 10 M sodium hydroxide solution. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol.Primary amine | Carbamic ester | null | C1COCN1 | C1COCN1 | HCl | C1(=CC=CC=C1)C | 65 | null | CC(C)(C)[C@@H](N)CO.CCOC(=O)Cl>C1(=CC=CC=C1)C>CC(C)(C)[C@@H]1COC(=O)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84448ea235a5434095bfa277b099b79d | Cc1ccc(Nc2ccc(C)c(C)c2)cc1C.Ic1ccc(-c2ccccc2)cc1>>Cc1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc(C)c(C)c2)cc1C | N1=CC=CC2=CC=C3C=CC=NC3=C12.CC=1C=C(C=CC1C)NC1=CC(=C(C=C1)C)C.IC1=CC=C(C=C1)C1=CC=CC=C1.[OH-].[K+]>>CC=1C=C(C=CC1C)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC(=C(C=C1)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:19]2[cH:20][cH:21][c:22]([CH3:23])[c:24]([CH3:25])[cH:26]2)[cH:27][c:28]1[CH3:29].I[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH... | Cc1ccc(Nc2ccc(C)c(C)c2)cc1C.Ic1ccc(-c2ccccc2)cc1 | Cc1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc(C)c(C)c2)cc1C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]:[c:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:12]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:8](-[c:7](:[c:6]):[c:12])-[c:9](:[c:10]):[c:11]):[c:4]:[c:5] | null | [] | 120 | CELSIUS | 3 | HOUR | In a 500 milliliter round bottomed flask equipped with mechanical stirrer and fitted with a Dean-Stark trap under a reflux condenser were placed 12.39 grams (0.055 mole) of bis(3,4-dimethylphenyl)amine, 14 grams (0.050 mole) of 4-iodobiphenyl, 0.25 gram (0.0025 mole) of cuprous chloride, 0.45 gram (0,0025 mole) of 1,10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI | C1(=CC=CC=C1)C | 120 | 3 | Cc1ccc(Nc2ccc(C)c(C)c2)cc1C.Ic1ccc(-c2ccccc2)cc1>C1(=CC=CC=C1)C>Cc1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc(C)c(C)c2)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c73a1583f23e4b29be1a2f3ab4c01786 | Cc1ccc(I)cc1C.Nc1ccc(-c2ccccc2)cc1>>Cc1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc(C)c(C)c2)cc1C | [OH-].[K+].NC1=CC=C(C=C1)C1=CC=CC=C1.IC=1C=C(C(=CC1)C)C>>CC=1C=C(C=CC1C)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC(=C(C=C1)C)C | I[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:28]([CH3:29])[cH:27]1.[NH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][c:22]([CH3:23])[c:24]([... | Cc1ccc(I)cc1C.Nc1ccc(-c2ccccc2)cc1 | Cc1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc(C)c(C)c2)cc1C | null | N1=CC=CC2=CC=C3C=CC=NC3=C12 | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 850bf8b88603759e93e21aa4bc6ea75b619f817ec1a4a2b605bfab9b13302179 | 4798700b8674842eb5bdd2fe41a2eb48ecea3f9c3ee8f644eef6be0214075a26 | c1ccc(-c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6](-[c:10](:[c:11]):[c:12])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 70 | [{"value": 70.0, "product": "CC=1C=C(C=CC1C)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC(=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "CC=1C=C(C=CC1C)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC(=C(C=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 3 | HOUR | In a 250 milliliter round-bottomed flask equipped with mechanical stirrer and fitted with a Dean-Stark trap under a reflux condenser were placed 8.46 grams (0.05 mole) of 4-aminobiphenyl, 25.53 grams (0.11 mole) of 4-iodo-ortho-xylene, 0.25 gram (0.0025 mole) of cuprous chloride, 0.45 gram (0.0025 mole) of 1,10-phenant... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Tertiary amine | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | N1=CC=CC2=CC=C3C=CC=NC3=C12.C1(=CC=CC=C1)C | 130 | 3 | Cc1ccc(I)cc1C.Nc1ccc(-c2ccccc2)cc1>N1=CC=CC2=CC=C3C=CC=NC3=C12.C1(=CC=CC=C1)C>Cc1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc(C)c(C)c2)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d880e525dd19411dbb94deface4386f9 | Fc1ccc(Cc2ccc(F)cc2)cc1.O=S(=O)(O)O>>O=C(c1ccc(F)cc1)c1ccc(F)cc1 | C1=CC(=CC=C1CC2=CC=C(C=C2)F)F.OS(=O)(=O)O.C1(=CC=CC=C1)C.OS(=O)(=O)O>>FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1 | [CH2:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.O=S(=O)(O)[OH:1]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | Fc1ccc(Cc2ccc(F)cc2)cc1.O=S(=O)(O)O | O=C(c1ccc(F)cc1)c1ccc(F)cc1 | null | O=[Mn]=O | O | Heteroatom Alkylation and Arylation | OtherReaction | 7a0b8463d98f4c7b922b16e60aaf09698e9f90cf246a26e079db9b5cbdeab585 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C(c1ccccc1)c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[c:2]:[c:3](-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:4](-[c:3](:[c:2]):[c:8])-[c:5](:[c:6]):[c:7] | 69.2 | [{"value": 68.0, "product": "FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | null | null | To a 250 mL round bottomed flask equipped with a heating mantle, overhead agitator, thermometer, condenser, and addition funnel with a tube protruding below the liquid level was added 10.6 g 4,4'-difluorodiphenylmethane (0.051 moles). Agitation was begun and a slurry of 20.5 g MnO2 (0.195 moles) in 30 g water was added... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | O=[Mn]=O.O | 125 | null | Fc1ccc(Cc2ccc(F)cc2)cc1.O=S(=O)(O)O>O=[Mn]=O.O>O=C(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f59502531b224cbdb38244051ab9c738 | Fc1ccc(Cc2ccc(F)cc2)cc1.O>>O=C(c1ccc(F)cc1)c1ccc(F)cc1 | C1=CC(=CC=C1CC2=CC=C(C=C2)F)F.O>>FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1 | [CH2:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.[OH2:1]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | Fc1ccc(Cc2ccc(F)cc2)cc1.O | O=C(c1ccc(F)cc1)c1ccc(F)cc1 | null | O=[Mn]=O | null | Heteroatom Alkylation and Arylation | OtherReaction | 7a0b8463d98f4c7b922b16e60aaf09698e9f90cf246a26e079db9b5cbdeab585 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C(c1ccccc1)c1ccccc1 | [OH2;D0;+0:1].[c:2]:[c:3](-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:4](-[c:3](:[c:2]):[c:8])-[c:5](:[c:6]):[c:7] | 95 | [{"value": 95.0, "product": "FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 1 was used except that 20 g 4,4'-difluorodiphenylmethane, 30 g water, 31 g MnO2 and 50 g H2 SO4 were used. 20 g off-white solids, after toluene removal, afforded 95% pure 4,4'-difluorobenzophenone in a 90% yield.
Conditions: See reaction.notes.procedure_details.
Workup: 20 g off-white solids, a... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | null | null | c1ccccc1.c1ccccc1 | null | O=[Mn]=O | null | null | Fc1ccc(Cc2ccc(F)cc2)cc1.O>O=[Mn]=O>O=C(c1ccc(F)cc1)c1ccc(F)cc1 |
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