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-02ee2261663048188cf6d85d2cc96e3f | ord-f9b363bf630049efa482b18098a1d4e7 | CCBr.COC(=O)CC(C)=O>>CCC(C(C)=O)C(=O)OC | C(CC(=O)C)(=O)OC.C(C)Br.C[O-].[Na+]>>C(C)(=O)C(C(=O)OC)CC | Br[CH2:2][CH3:1].[CH2:3]([C:4]([CH3:5])=[O:6])[C:7](=[O:8])[O:9][CH3:10]>>[CH3:1][CH2:2][CH:3]([C:4]([CH3:5])=[O:6])[C:7](=[O:8])[O:9][CH3:10] | CCBr.COC(=O)CC(C)=O | CCC(C(C)=O)C(=O)OC | null | null | CO | C-C Coupling | OtherReaction | eb3faf2a43700925ab4f46cf65072b7145e4e060dba25a917e6b7428f38e349e | 61bad66347ae366bfd0a2cd3779dd3d0c29125e97564b97243e11258be3b2a9f | null | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])=[O;D1;H0:10]>>[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:8](-[C;D1;H3:9])=[O;D1;H0:10] | 56.9 | [{"value": 56.9, "product": "C(C)(=O)C(C(=O)OC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "C(C)(=O)C(C(=O)OC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 465 g of methyl acetoacetate and then 458 g of ethyl bromide were added under nitrogen to 720 g of 30% sodium methylate solution in 1200 ml of methanol. The reaction mixture was subsequently boiled at reflux. After distillation of the methanol the residue was poured on to ice-water. It was then extracted with n-hexane ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | null | null | null | HBr | CO | null | null | CCBr.COC(=O)CC(C)=O>CO>CCC(C(C)=O)C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e4259a4f0b9499a99678dde8cd38979 | Cc1ccccc1.Cc1ccccc1.O=C(OC(=O)c1ccccc1)c1ccccc1.[O-][Cl+3]([O-])([O-])O>>CCCCCCCCCCCCCCCCCC1CC(OC(=O)c2ccccc2)C(CC)C(=O)O1 | C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)=O.Cl(=O)(=O)(=O)O.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C>>C(C1=CC=CC=C1)(=O)OC1C(C(=O)OC(C1)CCCCCCCCCCCCCCCCC)CC | [cH:2]1[cH:3][cH:4][cH:5][cH:19][c:18]1[CH3:17].[CH3:1][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[cH:6]1[cH:10][cH:32][cH:31][c:30]([C:33]([O:21][C:22](=[O:23])[c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)=[O:34])[cH:20]1.[O-][Cl+3]([O-])([O-])[OH:35]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH... | Cc1ccccc1.Cc1ccccc1.O=C(OC(=O)c1ccccc1)c1ccccc1.[O-][Cl+3]([O-])([O-])O | CCCCCCCCCCCCCCCCCC1CC(OC(=O)c2ccccc2)C(CC)C(=O)O1 | null | null | null | C-C Coupling | OtherReaction | 30e563bf7876a285eec0ff6a012176ea7508c1dae6b3dd779a4a24201bcb01ec | f4f0e4933e28ad003609fc57514057fc8dd4673f5e354908bb247868372e8d2b | O=C1CC(OC(=O)c2ccccc2)CCO1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:1.[CH3;D1;+0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:1.[O-]-[Cl+3](-[O-])(-[O-])-[OH;D1;+0:15].[O;D1;H0:16]=[C:17](-[c:18])-[O;H0;D2;+0:19]-[C;H0;D3;+0:20](=[O;D1;H0:21])-[c;H0... | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)(=O)OC1C(C(=O)OC(C1)CCCCCCCCCCCCCCCCC)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 138.5 g of benzoic anhydride and subsequently 2.5 ml of perchloric acid 70% were added to a suspension of 191.3 g of the δ-lactone from c) in 1250 ml of toluene. After stirring for 2.5 hours the reaction mixture in toluene was extracted with 1N sodium hydroxide solution in 20% sodium chloride solution and then with sat... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester | Ester.Ester | c1ccccc1.c1ccccc1.c1ccccc1 | C1CCOCC1 | C1CCOCC1.c1ccccc1 | Other | null | null | null | Cc1ccccc1.Cc1ccccc1.O=C(OC(=O)c1ccccc1)c1ccccc1.[O-][Cl+3]([O-])([O-])O>>CCCCCCCCCCCCCCCCCC1CC(OC(=O)c2ccccc2)C(CC)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3baf013c7faa44a8a67c3c1de075f233 | CC1(C)OC(=O)CC(=O)O1.CCCCCCCCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCCCCCCCC(=O)CC(=O)OC | CC1(OC(=O)CC(=O)O1)C.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>COC(CC(CCCCCCCCCCCCCCCCC)=O)=O | C[C:24]1(C)OC(=O)[CH2:20][C:21](=[O:22])[O:23]1.Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17... | CC1(C)OC(=O)CC(=O)O1.CCCCCCCCCCCCCCCCCC(=O)Cl | CCCCCCCCCCCCCCCCCC(=O)CC(=O)OC | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | e5ee695d1d78743b8608798a0e36af6a72f4664706b9ea57fe3da683aa6eeb71 | 0b98f3c92810ed1bd18934df20e2dc11eaf0d97d7f977f2dab53d6a8a4ca8348 | null | C-[C;H0;D4;+0:1]1(-C)-O-C(=O)-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-1.Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]-[C:9]>>[C:9]-[C:8]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[CH3;D1;+0:1] | null | [] | null | null | null | null | To a solution of 117 g of Meldrum's acid and 131 ml of pyridine in 1.5 1 of methylene chloride, 270 ml of stearic acid chloride were added dropwise at a maximum temperature of 15° C. After stirring, the reaction mixture was washed with 4N hydrochloric acid, the aqueous phase was extracted with methylene chloride, the m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone.Ester | C1COCOC1 | null | null | HCl | C(Cl)Cl | null | null | CC1(C)OC(=O)CC(=O)O1.CCCCCCCCCCCCCCCCCC(=O)Cl>C(Cl)Cl>CCCCCCCCCCCCCCCCCC(=O)CC(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1e30286531164f3e818011ff3a8385c4 | C1=COCCC1.CCCCCCCCCCCC1CC(O)C(CCCCCC)C(=O)O1.[OH-]>>CCCCCCC(C(=O)O)C(O)CC(CCCCC)OCc1ccccc1 | [OH-].[Na+].C(CCCCC)C1C(=O)OC(CC1O)CCCCCCCCCCC.O1CCCC=C1.[NH+]1=CC=CC=C1>>C(C1=CC=CC=C1)OC(CC(C(C(=O)O)CCCCCC)O)CCCCC | O1[CH:21]=[CH:22][CH2:27][CH2:26][CH2:25]1.C(CCC[CH2:17][CH2:18][CH3:19])CC[CH2:16][CH2:15][CH:14]1[CH2:13][CH:11]([OH:12])[CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:8](=[O:9])[O:20]1.[OH-:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([C:8](=[O:9])[OH:10])[CH:11]([OH:12])[CH2:13][CH:14]([CH2:15][CH2:1... | C1=COCCC1.CCCCCCCCCCCC1CC(O)C(CCCCCC)C(=O)O1.[OH-] | CCCCCCC(C(=O)O)C(O)CC(CCCCC)OCc1ccccc1 | null | null | CC(C)(C)OC | Acylation | OtherReaction | 6ae66847291765dddb107b03d860fc912695196e22097d203726531586920b9a | 9e710d8ca83c6866df2ded3c535f6910cb326e50e3befe16fa342ba965613aaf | c1ccccc1 | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[C:6]-[C:7]1-[C:8]-[C:9]-[C:10](-[C:11]-[CH2;D2;+0:12]-C-C-C-C-C-C-[CH2;D2;+0:13]-[C:14]-[C;D1;H3:15])-[O;H0;D2;+0:16]-[C;H0;D3;+0:17]-1=[O;D1;H0:18].[OH-;D0:19]>>[C:6]-[C:7](-[C:8]-[C:9]-[C:10](-[C:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[C:14]-[C;D1;H... | null | [] | null | null | 2.5 | HOUR | 177.3 mg of rac-(2RS,3RS,5SR)-2-hexyl-3-hydroxy-5-undecyl-δ-valerolactone (Example 1c)), 750 ml of TBME, 86.7 g of 97% 3,4-dihydro-2H-pyran and 0.314 g of pyridinium p-toluenesulphone were stirred at 50° under argon for 20 hours. 500 ml of 2N sodium hydroxide solution were added to the reaction solution. After stirring... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Ether | C1=COCCC1.C1CCOCC1 | c1ccccc1 | c1ccccc1 | HO- | CC(C)(C)OC | null | 2.5 | C1=COCCC1.CCCCCCCCCCCC1CC(O)C(CCCCCC)C(=O)O1.[OH-]>CC(C)(C)OC>CCCCCCC(C(=O)O)C(O)CC(CCCCC)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d6aa1484224448e995eff7bbe4db6fd5 | CC(C)=CCCC(C)=CCCC(C)=CCO>>CC(C)CCCC(C)CCCC(C)CCO | OCC=C(C)CCC=C(C)CCC=C(C)C>>CC(CCO)CCCC(CCCC(C)C)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH2:10][CH2:11][C:12]([CH3:13])=[CH:14][CH2:15][OH:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH2:14][CH2:15][OH:16] | CC(C)=CCCC(C)=CCCC(C)=CCO | CC(C)CCCC(C)CCCC(C)CCO | null | [Pt]=O | C(C)O | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C:3]-[C:4]-[CH;D2;+0:5]=[C;H0;D3;+0:6](-[C;D1;H3:7])-[C:8]-[C:9]-[CH;D2;+0:10]=[C;H0;D3;+0:11](-[C;D1;H3:12])-[C;D1;H3:13])=[CH;D2;+0:14]-[C:15]-[O;D1;H1:16]>>[C;D1;H3:1]-[CH;D3;+0:2](-[C:3]-[C:4]-[CH2;D2;+0:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[C:8]-[C:9]-[CH2;D2;+0:10]-[CH;D3;+0:11](-[C;D1;H3:12... | 94.9 | [{"value": 94.9, "product": "CC(CCO)CCCC(CCCC(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Farnesol (200 g) was dissolved in ethanol (1000 ml), added with platinum oxide (1 g) and stirred for 24 hours at room temperature under hydrogen atmosphere. After the completion of the reaction, insoluble material was removed by filtration through a Celite layer and the filtrate was concentrated under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | [Pt]=O.C(C)O | null | 24 | CC(C)=CCCC(C)=CCCC(C)=CCO>[Pt]=O.C(C)O>CC(C)CCCC(C)CCCC(C)CCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c0dfd353e6324d3daf2c3d50805ae08b | CC(C)=CCC/C(C)=C/CO>>CC(C)CCCC(C)CCO | CC(C)=CCC\C(\C)=C\CO>>CC(CCO)CCCC(C)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[CH2:10][OH:11]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][OH:11] | CC(C)=CCC/C(C)=C/CO | CC(C)CCCC(C)CCO | null | [Pt]=O | C(C)O | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[C:5]-[C:6]/[C;H0;D3;+0:7](-[C;D1;H3:8])=[CH;D2;+0:9]/[C:10]-[O;D1;H1:11]>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[C:5]-[C:6]-[CH;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[C:10]-[O;D1;H1:11] | 97.5 | [{"value": 97.5, "product": "CC(CCO)CCCC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Geraniol (100 g) was dissolved in ethanol (500 ml), added with platinum oxide (500 mg) and stirred for 24 hours at room temperature under hydrogen atmosphere. After the completion of the reaction, insoluble material was removed by filtration through a Celite layer and the filtrate was concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | [Pt]=O.C(C)O | null | 24 | CC(C)=CCC/C(C)=C/CO>[Pt]=O.C(C)O>CC(C)CCCC(C)CCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-90e6615f1f7643cdaa5aff37c3329be7 | COCCl.O=C(NC(=O)c1c(Cl)cccc1Cl)Nc1ccc(Cl)cc1>>COCN(C(=O)Nc1ccc(Cl)cc1)C(=O)c1c(Cl)cccc1Cl | COCCl.ClC1=C(C(=O)NC(=O)NC2=CC=C(C=C2)Cl)C(=CC=C1)Cl.[OH-].[K+].CI>>ClC1=C(C(=O)N(C(=O)NC2=CC=C(C=C2)Cl)COC)C(=CC=C1)Cl | Cl[CH2:3][O:2][CH3:1].[NH:4]([C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[C:15](=[O:16])[c:17]1[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]1[Cl:24]>>[CH3:1][O:2][CH2:3][N:4]([C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[C:15](=[O:16])[c:17]1[c:18]([Cl:19])[cH:20][cH:21][cH... | COCCl.O=C(NC(=O)c1c(Cl)cccc1Cl)Nc1ccc(Cl)cc1 | COCN(C(=O)Nc1ccc(Cl)cc1)C(=O)c1c(Cl)cccc1Cl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d6d8ab12c940ea72d62283b53492e38d28a4af252a026a3ef9133a123c951446 | f4cf4267f5c9296df9060197435985b3e2de54a17a90ceac7a87601161e72831 | O=C(NC(=O)c1ccccc1)Nc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[O;D1;H0:4]=[C:5](-[c:6])-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[c:11]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:5](=[O;D1;H0:4])-[c:6])-[C:8](=[O;D1;H0:9])-[#7:10]-[c:11] | null | [] | null | null | 2 | HOUR | 10.3 g of N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)-urea and 1.88 g of powdered potassium hydroxide (90% are dissolved 40 ml of dimethyl formamide, after which 4.7 of methyl iodide are added drop by drop to the clear solution. The resulting reaction is exothermic. After stirring for two hours the solution is diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Urea | Ether.Urea | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | 2 | COCCl.O=C(NC(=O)c1c(Cl)cccc1Cl)Nc1ccc(Cl)cc1>CN(C=O)C>COCN(C(=O)Nc1ccc(Cl)cc1)C(=O)c1c(Cl)cccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4b7507acb22e4bf8a1321040f57cb521 | N#CCNc1ccc(Cl)cc1.O=C=NC(=O)c1c(Cl)cccc1Cl>>N#CCN(C(=O)NC(=O)c1c(Cl)cccc1Cl)c1ccc(Cl)cc1 | ClC1=C(C(=O)N=C=O)C(=CC=C1)Cl.ClC1=CC=C(NCC#N)C=C1>>ClC1=C(C(=O)NC(=O)N(C2=CC=C(C=C2)Cl)CC#N)C(=CC=C1)Cl | [N:1]#[C:2][CH2:3][NH:4][c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1.[C:5](=[O:6])=[N:7][C:8](=[O:9])[c:10]1[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]1[Cl:17]>>[N:1]#[C:2][CH2:3][N:4]([C:5](=[O:6])[NH:7][C:8](=[O:9])[c:10]1[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]1[Cl:17])[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH... | N#CCNc1ccc(Cl)cc1.O=C=NC(=O)c1c(Cl)cccc1Cl | N#CCN(C(=O)NC(=O)c1c(Cl)cccc1Cl)c1ccc(Cl)cc1 | null | null | C1=CC=CC=C1 | Acylation | Urea synthesis via isocyanate and secondary amine | 288f31369c46060b9009e57afc96d52a76d6a0243a2e1197ab47b0221bb8a3ee | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC(=O)c1ccccc1)Nc1ccccc1 | [N;D1;H0:1]#[C:2]-[C:3]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[C:11](=[O;D1;H0:12])-[c:13]>>[N;D1;H0:1]#[C:2]-[C:3]-[N;H0;D3;+0:4](-[C;H0;D3;+0:9](=[O;D1;H0:8])-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[c:13])-[c:5](:[c:6]):[c:7] | 80 | [{"value": 80.0, "product": "ClC1=C(C(=O)NC(=O)N(C2=CC=C(C=C2)Cl)CC#N)C(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 16.0 g of 2,6-dichlorobenzoylisocyanate are added in small portions to a solution of 11.66 g of p-chloroaniline-acetonitrile in 100 ml of dry benzene with moderate cooling. After some time a substance crystallizes out, which after about 12 hours is drawn off and washed with benzene. After drying the weight is 25.25 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | null | null | c1ccccc1.c1ccccc1 | null | C1=CC=CC=C1 | null | 12 | N#CCNc1ccc(Cl)cc1.O=C=NC(=O)c1c(Cl)cccc1Cl>C1=CC=CC=C1>N#CCN(C(=O)NC(=O)c1c(Cl)cccc1Cl)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b3cdc8bc250746f0a9b4b3f1f74ac0a5 | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 | C1(=CC=CC=C1)O.C(C)(=O)OC(C)=O>>CC(=O)C=1C=CC(=CC1)O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1 | CC(=O)OC(C)=O.Oc1ccccc1 | CC(=O)c1ccc(O)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | d99b77b773ef3c26c74d2c747a21e4608137c0863599d8a950dc561200cf7372 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | null | [] | null | null | null | null | acylating phenol with acetic anhydride to produce 4-hydroxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bcdb5ae725174952a7db67b730b792e9 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 | CC(=O)C=1C=CC(=CC1)O.C(C)(=O)OC(C)=O>>CC(=O)C1=CC=C(C=C1)OC(=O)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1 | CC(=O)Oc1ccc(C(C)=O)cc1 | null | null | null | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | acylating the 4-hydroxyacetophenone with acetic anhydride to form 4-acetoxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f7e1cedbe0254d16a188644db0d854a4 | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 | C1(=CC=CC=C1)O.C(C)(=O)OC(C)=O>>CC(=O)C=1C=CC(=CC1)O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1 | CC(=O)OC(C)=O.Oc1ccccc1 | CC(=O)c1ccc(O)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | d99b77b773ef3c26c74d2c747a21e4608137c0863599d8a950dc561200cf7372 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | null | [] | null | null | null | null | acylating phenol with acetic anhydride to produce 4-hydroxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-010d0cbee04b4a92809fa94ff301ca99 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 | CC(=O)C=1C=CC(=CC1)O.C(C)(=O)OC(C)=O>>CC(=O)C1=CC=C(C=C1)OC(=O)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1 | CC(=O)Oc1ccc(C(C)=O)cc1 | null | null | null | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | acylating the 4-hydroxyacetophenone with acetic anhydride to form 4-acetoxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8b54166452fb459c93d14a8e1befbd38 | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 | C1(=CC=CC=C1)O.C(C)(=O)OC(C)=O>>CC(=O)C=1C=CC(=CC1)O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1 | CC(=O)OC(C)=O.Oc1ccccc1 | CC(=O)c1ccc(O)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | d99b77b773ef3c26c74d2c747a21e4608137c0863599d8a950dc561200cf7372 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | null | [] | null | null | null | null | acylating phenol with acetic anhydride to produce 4-hydroxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d906db6505034d9995ee812c94fcf991 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 | CC(=O)C=1C=CC(=CC1)O.C(C)(=O)OC(C)=O>>CC(=O)C1=CC=C(C=C1)OC(=O)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1 | CC(=O)Oc1ccc(C(C)=O)cc1 | null | null | null | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | acylating the 4-hydroxyacetophenone with acetic anhydride to form 4-acetoxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-91606507d9c8452b9a5af7f7c1fbb1a1 | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 | C1(=CC=CC=C1)O.C(C)(=O)OC(C)=O>>CC(=O)C=1C=CC(=CC1)O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1 | CC(=O)OC(C)=O.Oc1ccccc1 | CC(=O)c1ccc(O)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | d99b77b773ef3c26c74d2c747a21e4608137c0863599d8a950dc561200cf7372 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | null | [] | null | null | null | null | acylating phenol with acetic anhydride to produce 4-hydroxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Oc1ccccc1>>CC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-064db5386d114ce1804f7bd4fad2f2e3 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 | CC(=O)C=1C=CC(=CC1)O.C(C)(=O)OC(C)=O>>CC(=O)C1=CC=C(C=C1)OC(=O)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][cH:13]1 | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1 | CC(=O)Oc1ccc(C(C)=O)cc1 | null | null | null | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | acylating the 4-hydroxyacetophenone with acetic anhydride to form 4-acetoxyacetophenone; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7856edbcbd4d46f3915e152d225502ee | C1=CCCC=CCC1.CCCCCCCCCCC.Pc1ccccc1>>c1ccc(P2CCCCCCCC2C2CCCCCCCC2)cc1 | C(C)(C)(C)OOC(C)(C)C.C1=CCCC=CCC1.C1(=CC=CC=C1)P.C(C)(C)(C)OOC(C)(C)C.CCCCCCCCCCC>>C1(=CC=CC=C1)P1CCCCCCCC1C1CCCCCCCC1 | [CH:9]1=[CH:10][CH2:11][CH2:12][CH:13]=[CH:14][CH2:22][CH2:21]1.C(C[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[CH2:8][CH2:7][CH3:6].[cH:1]1[cH:2][cH:3][c:4]([PH2:5])[cH:23][cH:24]1>>[cH:1]1[cH:2][cH:3][c:4]([P:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]2[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][... | C1=CCCC=CCC1.CCCCCCCCCCC.Pc1ccccc1 | c1ccc(P2CCCCCCCC2C2CCCCCCCC2)cc1 | null | null | null | C-C Coupling | OtherReaction | be1d173849f16ff1060ba715577cda0de8e611ef7aca87a92a5afae86a84b925 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc(P2CCCCCCCC2C2CCCCCCCC2)cc1 | [CH3;D1;+0:1]-[C:2]-[C:3]-[C:4]-[C:5]-[CH2;D2;+0:6]-C-C-[CH2;D2;+0:7]-[C:8]-[CH3;D1;+0:9].[C:10]1-[C:11]-[CH;D2;+0:12]=[CH;D2;+0:13]-[C:14]-[CH2;D2;+0:15]-[CH;D2;+0:16]=[CH;D2;+0:17]-1.[PH2;D1;+0:18]-[c:19](:[c:20]):[c:21]>>[c:20]:[c:19](-[P;H0;D3;+0:18]1-[CH2;D2;+0:9]-[C:8]-[CH2;D2;+0:7]-[CH2;D2;+0:16]-[CH2;D2;+0:17]-... | null | [] | 135 | CELSIUS | 2 | HOUR | This procedure is a modification of Mason and Van Winkle's. See U.S. Pat. No. 3,400,163. All glassware is dried at 120° C. and assembled hot under a purge of argon. A 250 mL, 3-neck flask is fitted with magnetic spin bar, thermometer, reflux condenser, a rubber syringe septum, argon inlet, and flowmeter. The reactor sy... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCC=CCC1 | C1CCCC[P]CCC1.C1CCCCCCCC1 | c1ccccc1.C1CCCC[P]CCC1.C1CCCCCCCC1 | Other | null | 135 | 2 | C1=CCCC=CCC1.CCCCCCCCCCC.Pc1ccccc1>>c1ccc(P2CCCCCCCC2C2CCCCCCCC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fdacc60898794503bab31670ff34e1da | CC1(C)C(C(=O)[O-])C1C(OS(C)(=O)=O)C(Cl)(Br)C(F)(F)F>>CC1(C)C(C(=O)O)C1C(C(Cl)(Br)C(F)(F)F)S(C)(=O)=O | C1(=CC=C(C=C1)S(=O)(=O)O)C.CC1(C(C1C(C(Cl)(Br)C(F)(F)F)OS(=O)(=O)C)C(=O)[O-])C>>CC1(C(C1C(C(Cl)(Br)C(F)(F)F)S(=O)(=O)C)C(=O)O)C | O([CH:9]([CH:8]1[C:2]([CH3:1])([CH3:3])[CH:4]1[C:5](=[O:6])[O-:7])[C:10]([Cl:11])([Br:12])[C:13]([F:14])([F:15])[F:16])[S:17]([CH3:18])(=[O:19])=[O:20]>>[CH3:1][C:2]1([CH3:3])[CH:4]([C:5](=[O:6])[OH:7])[CH:8]1[CH:9]([C:10]([Cl:11])([Br:12])[C:13]([F:14])([F:15])[F:16])[S:17]([CH3:18])(=[O:19])=[O:20] | CC1(C)C(C(=O)[O-])C1C(OS(C)(=O)=O)C(Cl)(Br)C(F)(F)F | CC1(C)C(C(=O)O)C1C(C(Cl)(Br)C(F)(F)F)S(C)(=O)=O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 1f48ed6130e0b7a10053eb41dbcc5f70632d6d58be34803a057c297ee65ab43e | 90218b4dd4eb4abbfbf76919a6bc1199330074d5824290bf04b81d71532d84d1 | C1CC1 | [Br;D1;H0:1]-[C:2](-[Cl;D1;H0:3])(-[CH;D3;+0:4](-O-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-1-[C:12](-[O-;H0;D1:13])=[O;D1;H0:14])-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]>>[Br;D1;H0:1]-[C:2](-[Cl;D1;H0:3])(-[CH;D3;+0:4](-[C:9]1-[C:10]-[C:11]-1-[C:12](=[O;D1;H0:14])-[OH;D1;+... | null | [] | 40 | CELSIUS | null | null | 30 mg of p-toluene sulfonic acid were added at 40° C. to a solution of 1 g of the product of Step B and 10 ml of methylene chloride and the reaction mixture was heated for 5 hours at 40° C., then poured on to ice, and decanted. The organic phase was washed with water, dried on sodium sulfate and evaporated to dryness u... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Carboxylic acid.Sulfone | null | null | C1CC1 | Other | C(Cl)Cl | 40 | null | CC1(C)C(C(=O)[O-])C1C(OS(C)(=O)=O)C(Cl)(Br)C(F)(F)F>C(Cl)Cl>CC1(C)C(C(=O)O)C1C(C(Cl)(Br)C(F)(F)F)S(C)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29c831e9f5614f9b8eb8037523a00d0e | CC(C)c1cccc(C(C)C)c1O.CCCCCCCCCCCCOC(=O)NS(=O)(=O)Cl>>CCCCCCCCCCCCOC(=O)NS(=O)(=O)Oc1c(C(C)C)cccc1C(C)C | C(CCCCCCCCCCC)OC(NS(=O)(=O)Cl)=O.C(C)(C)C1=C(C(=CC=C1)C(C)C)O.C(C)N(CC)CC>>CC(C)C1=C(OS(=O)(=O)NC(OCCCCCCCCCCCC)=O)C(=CC=C1)C(C)C | [OH:20][c:21]1[c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27][cH:28][c:29]1[CH:30]([CH3:31])[CH3:32].Cl[S:17]([NH:16][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:15])(=[O:18])=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:... | CC(C)c1cccc(C(C)C)c1O.CCCCCCCCCCCCOC(=O)NS(=O)(=O)Cl | CCCCCCCCCCCCOC(=O)NS(=O)(=O)Oc1c(C(C)C)cccc1C(C)C | null | null | C1CCOC1 | Acylation | Formation of Sulfonic Esters | 20981640fc119f2a042d405c20d8668ba133c9ad0e4b08eb8b727bb015482008 | 3fc12f522d8c129031348b23ecc6689626c35c95b5c7f49458f64f73f8885a8a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4]-[C:5](-[#8:6])=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[#7:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 59.7 | [{"value": 5.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.7, "product": "CC(C)C1=C(OS(=O)(=O)NC(OCCCCCCCCCCCC)=O)C(=CC=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of n-dodecyl(chlorosulfonyl)carbamate (5.0 g, 15.2 mmoles) in 80 mL THF was added dropwise to a solution of 2,6-diisopropyl phenol (2.72 g, 15.2 mmoles) and excess triethylamine in 100 mL THF at room temperature under an atmosphere of N2. The mixture was stirred for 16 hours and then concentrated in vacuo. T... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic alcohol | Sulfonamide | null | null | c1ccccc1 | HCl | C1CCOC1 | null | 16 | CC(C)c1cccc(C(C)C)c1O.CCCCCCCCCCCCOC(=O)NS(=O)(=O)Cl>C1CCOC1>CCCCCCCCCCCCOC(=O)NS(=O)(=O)Oc1c(C(C)C)cccc1C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-77906ee1bea24ed3b1e739a1dc11b691 | CCCCCCCCCCCCO.O=C(NS(=O)(=O)Cl)Oc1c(-c2ccccc2)cccc1-c1ccccc1>>CCCCCCCCCCCCOS(=O)(=O)NC(=O)Oc1c(-c2ccccc2)cccc1-c1ccccc1 | ClS(=O)(=O)NC(OC1=C(C=CC=C1C1=CC=CC=C1)C1=CC=CC=C1)=O.C(CCCCCCCCCCC)O.C(C)N(CC)CC>>C1(=CC=CC=C1)C1=C(C(=CC=C1)C1=CC=CC=C1)OC(NS(=O)(=O)OCCCCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].Cl[S:14](=[O:15])(=[O:16])[NH:17][C:18](=[O:19])[O:20][c:21]1[c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30][cH:31][c:32]1-[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH... | CCCCCCCCCCCCO.O=C(NS(=O)(=O)Cl)Oc1c(-c2ccccc2)cccc1-c1ccccc1 | CCCCCCCCCCCCOS(=O)(=O)NC(=O)Oc1c(-c2ccccc2)cccc1-c1ccccc1 | null | null | C1CCOC1 | Acylation | Formation of Sulfonic Esters | 2bc98381358be8e8663931daf0aadb124ab25c618b5eb396473354572ff70e65 | 305049ec2c503dead98023ef3c4902a17a57f1dc8fe61364861a85b85787f4de | c1ccc(-c2cccc(-c3ccccc3)c2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:6]-[C:5](=[O;D1;H0:7])-[#7:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:10]-[C:9]-[C:8] | 42.5 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.5, "product": "C1(=CC=CC=C1)C1=C(C(=CC=C1)C1=CC=CC=C1)OC(NS(=O)(=O)OCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of [1,1':3',1"-terphenyl]-2'-yl (chlorosulfonyl)carbamate (5.0 g, 12.9 mmoles) in 75 mL THF was added dropwise to a solution of n-dodecyl alcohol (2.4 g, 12.9 mmoles) and triethylamine (1.3 g, 12.9 mmoles) in 100 mL THF at ~15° C. under an atmosphere of N2. The mixture was allowed to warm to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | null | CCCCCCCCCCCCO.O=C(NS(=O)(=O)Cl)Oc1c(-c2ccccc2)cccc1-c1ccccc1>C1CCOC1>CCCCCCCCCCCCOS(=O)(=O)NC(=O)Oc1c(-c2ccccc2)cccc1-c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5b876d1b98bf447b958335604e70efcd | CO.O=C=NS(=O)(=O)Cl>>COC(=O)NS(=O)(=O)Cl | CO.ClS(=O)(=O)N=C=O>>COC(NS(=O)(=O)Cl)=O | [CH3:1][OH:2].[C:3](=[O:4])=[N:5][S:6](=[O:7])(=[O:8])[Cl:9]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][S:6](=[O:7])(=[O:8])[Cl:9] | CO.O=C=NS(=O)(=O)Cl | COC(=O)NS(=O)(=O)Cl | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | c7bfad7dec4bcd80555d5f761b49ca955fd13442c4972ed7e74bfa630ed5a8c7 | e0e55f411343a2fb7d353b5b4db135cf580a86689522a7d164c3268acd586115 | null | [C;D1;H3:1]-[OH;D1;+0:2].[Cl;D1;H0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C;D1;H3:1]-[O;H0;D2;+0:2]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[#16:4](-[Cl;D1;H0:3])(=[O;D1;H0:5])=[O;D1;H0:6] | 75.4 | [{"value": 75.4, "product": "COC(NS(=O)(=O)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The mixture was removed from the cooling bath and stirred for one-half hour at room temperature, then cooled to 0° C. and 65 mL ice cold hexanes was... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Sulfonamide.Carbamic ester | null | null | null | null | C1(=CC=CC=C1)C | null | null | CO.O=C=NS(=O)(=O)Cl>C1(=CC=CC=C1)C>COC(=O)NS(=O)(=O)Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0b945865b6ed43e89b1d0e52682f9023 | CCCCCCCCCCCCO.O=C=NS(=O)(=O)Cl>>CCCCCCCCCCCCOC(=O)NS(=O)(=O)Cl | C(CCCCCCCCCCC)O.ClS(=O)(=O)N=C=O>>C(CCCCCCCCCCC)OC(NS(=O)(=O)Cl)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[C:14](=[O:15])=[N:16][S:17](=[O:18])(=[O:19])[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14](=[O:15])[NH:16][S:17](=[O:18])(=[O:19])[Cl:20] | CCCCCCCCCCCCO.O=C=NS(=O)(=O)Cl | CCCCCCCCCCCCOC(=O)NS(=O)(=O)Cl | null | null | CCOCC | Protection | OtherReaction | 5903472f7fde872c0e2c01c89ed6188579dca0b618d750fc8f4727ce6f8df9e4 | 9b07b5c64086b5fa83ceb215f711b596c3e070d0d9c870e61dc7f6592ff6725e | null | [C:1]-[C:2]-[OH;D1;+0:3].[Cl;D1;H0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:8]-[#16:5](-[Cl;D1;H0:4])(=[O;D1;H0:6])=[O;D1;H0:7] | 101.6 | [{"value": 101.6, "product": "C(CCCCCCCCCCC)OC(NS(=O)(=O)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of n-dodecyl alcohol (10.7 g, 57.4 mmoles) in 100 mL Et2O was added dropwise to a solution of chlorosulfonyl isocyanate (5.0 mL, 57.4 mmoles) in 100 mL Et2O at ~15° C. under an atmosphere of N2. The resulting mixture was stirred for 2 hours and concentrated in vacuo. The residue was triturated with cold hexa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Sulfonamide.Carbamic ester | null | null | null | null | CCOCC | null | 2 | CCCCCCCCCCCCO.O=C=NS(=O)(=O)Cl>CCOCC>CCCCCCCCCCCCOC(=O)NS(=O)(=O)Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-042fbd86b6fe436b88f44678e39f7b6d | CC(C)(C)OC(=O)NCC(=O)O.C[C@@H](N)C(=O)OCc1ccccc1.ClCCl>>C[C@@H](NC(=O)CN)C(=O)OCc1ccccc1.Cl | C1(CCCCC1)N=C=NC1CCCCC1.C(C)(C)(C)OC(=O)NCC(=O)O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC([C@H](N)C)=O.C(Cl)Cl.C(C)N(CC)CC>>Cl.C(C1=CC=CC=C1)OC([C@H](NC(CN)=O)C)=O | CC(C)(C)OC(=O)[NH:7][CH2:6][C:4](O)=[O:5].[CH3:1][C@@H:2]([NH2:3])[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.ClC[Cl:18]>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[CH2:6][NH2:7])[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[ClH:18] | CC(C)(C)OC(=O)NCC(=O)O.C[C@@H](N)C(=O)OCc1ccccc1.ClCCl | C[C@@H](NC(=O)CN)C(=O)OCc1ccccc1.Cl | null | null | null | Acylation | OtherReaction | c4b6ff1c5a86405f86fe4a3d689987915e1ddb8ecb5b8ab8c4aa3d729fe0ceef | c73530b43160ba59e35b2ca368dd7f9e092fe1309aabd3f94299d7158bc36c97 | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].Cl-C-[Cl;H0;D1;+0:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1].[ClH;D0;+0:5] | 70 | [{"value": 70.0, "product": "Cl.C(C1=CC=CC=C1)OC([C@H](NC(CN)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a cold (0° C.) solution of 100 ml. methylene chloride containing 10 g. (57 mmol) of N-t-butyloxycarbonylglycine, 20 g. (57 mmol) of D-alanine benzyl ester p-toluene sulfonic acid salt and 5.77 g. (57 mmol) of triethylamine was added 12.3 g. (60 mmol) of dicyclohexylcarbodiimide and the resulting reaction mixture all... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1 | HCl | null | null | 0.5 | CC(C)(C)OC(=O)NCC(=O)O.C[C@@H](N)C(=O)OCc1ccccc1.ClCCl>>C[C@@H](NC(=O)CN)C(=O)OCc1ccccc1.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-88228e4040e04ab3b2c5db9f2b2006b0 | CCOC(=O)C1=C(CSC(=N)N)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1.ClCc1ccc[nH+]c1>>CCOC(=O)C1=C(CSCc2cccnc2)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1 | C(#N)C=1C(C(=C(NC1C)CSC(N)=N)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-].Cl.ClCC=1C=[NH+]C=CC1.[Cl-].[OH-].[K+]>>N1=CC(=CC=C1)CSCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C#N)C | N=C(N)[S:9][CH2:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:23]([c:24]2[cH:25][cH:26][cH:27][c:28]([N+:29](=[O:30])[O-:31])[cH:32]2)[C:20]([C:21]#[N:22])=[C:18]([CH3:19])[NH:17]1.Cl[CH2:10][c:11]1[cH:12][cH:13][cH:14][nH+:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][S:9][CH2:10][c:11]2[cH:1... | CCOC(=O)C1=C(CSC(=N)N)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1.ClCc1ccc[nH+]c1 | CCOC(=O)C1=C(CSCc2cccnc2)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1 | null | null | C1=CC=CC=C1 | Protection | OtherReaction | 70f18c6c601403236489898fd734999936ff4ca727b7c885dbee21a3ca2ea4d4 | 32eca1c585c6d7dc700e5c0638a80d0372911ccbc04d35b8abd663aac090c78e | C1=CC(c2ccccc2)C=C(CSCc2cccnc2)N1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]:[nH+;D2:6]:[c:7]:1.N-C(=N)-[S;H0;D2;+0:8]-[C:9]-[C:10]1=[C:11](-[C:12](-[#8:13])=[O;D1;H0:14])-[C:15]-[C:16]=[C:17]-[#7:18]-1>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]1=[C:10](-[C:9]-[S;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2]2:[c:3]:[c:4]:[c:5]:[n;H0;D2;+0:6]:[c:7]:2)-[#7:18]-[C:17]=[C:16]... | null | [] | null | null | 15 | MINUTE | A mixture of (-)-S-[(5-cyano-3-carboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridin-2-yl)methyl]isothiourea (mg 500), 3-chloromethylpyridinium hydrochloride (mg 190), benzylthriethylammonium chloride (BTEAC mg 80), KOH (4M, ml 2) and benzene (ml 5) is stirred at room temperature for 15 minutes to separate a precip... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine.Monosulfide | Monosulfide | c1cc[n+]cc1 | c1ccncc1 | C1=CNC=CC1.c1ccncc1.c1ccccc1 | HCl | C1=CC=CC=C1 | null | 0.25 | CCOC(=O)C1=C(CSC(=N)N)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1.ClCc1ccc[nH+]c1>C1=CC=CC=C1>CCOC(=O)C1=C(CSCc2cccnc2)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7e2beb4a11a24e89994da680a2a56493 | CCOC(=O)C1=C(CSC2=NCCCN2)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1.NCCBr>>CCOC(=O)C1=C(CSCCN)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | C(\C=C\C(=O)O)(=O)O.N1C(=NCCC1)SCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C.Br.BrCCN.[OH-].[Na+]>>C(\C=C\C(=O)O)(=O)O.NCCSCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C | C1CN=C([S:9][CH2:8][C:7]2=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:21]([c:22]3[cH:23][cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30]3)[C:16]([C:17](=[O:18])[O:19][CH3:20])=[C:14]([CH3:15])[NH:13]2)NC1.Br[CH2:10][CH2:11][NH2:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])[N... | CCOC(=O)C1=C(CSC2=NCCCN2)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1.NCCBr | CCOC(=O)C1=C(CSCCN)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 | null | [Br-].C(CCCCCCCCCCCCCCC)[P+](CCCC)(CCCC)CCCC | CO.C1=CC=CC=C1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | fba53c3c4214f1fcd959477421a5709143a57e1c9356333fc559e964ce1217f5 | 0519c430f59fb89c5f53eabf5ea78fcdfd16cd01595a9a3717fd7a8fb3a5d0f3 | C1=CC(c2ccccc2)C=CN1 | Br-[CH2;D2;+0:1]-[C:2]-[N;D1;H2:3].[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]1=[C:8](-[C:9]-[S;H0;D2;+0:10]-C2=N-C-C-C-N-2)-[#7:11]-[C:12]=[C:13]-[C:14]-1>>[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]1=[C:8](-[C:9]-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2]-[N;D1;H2:3])-[#7:11]-[C:12]=[C:13]-[C:14]-1 | null | [] | null | null | 40 | MINUTE | A mixture of (-)-2-[(1,4,5,6-tetrahydropyrimidin-2-yl)thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (g 2), hexadecyltributyl phosphonium bromide (mg 180), 2-bromoethylaminehydrobromide (mg 900), NaOH (35%, ml 8) and benzene is stirred for 40 minutes at room temperature. After t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Monosulfide | Monosulfide | C1=NCCCN1 | null | C1=CNC=CC1.c1ccccc1 | HBr | [Br-].C(CCCCCCCCCCCCCCC)[P+](CCCC)(CCCC)CCCC.CO.C1=CC=CC=C1.C(C)(=O)OCC | null | 0.666667 | CCOC(=O)C1=C(CSC2=NCCCN2)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1.NCCBr>[Br-].C(CCCCCCCCCCCCCCC)[P+](CCCC)(CCCC)CCCC.CO.C1=CC=CC=C1.C(C)(=O)OCC>CCOC(=O)C1=C(CSCCN)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-51111519c1874c0c8735f605cc74cf63 | CCOC(=O)C1=C(CSCC)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1 | C(C)SCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)Cl)C(=O)OC)C>>CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)Cl)C(=O)OC)C | CCS[CH2:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:17]([c:18]2[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]2)[C:12]([C:13](=[O:14])[O:15][CH3:16])=[C:10]([CH3:11])[NH:9]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH3:16])[CH:17]1[c:18]1[cH:19][cH:20... | CCOC(=O)C1=C(CSCC)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1 | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1 | null | null | CO | Reduction | OtherReaction | 4b57e24218e2409c207dcfe624aba83448b3ad4b3549d9bc7855651565b7e76d | 32a5269109432865a866e9a2b5da238f4471b13dee7daf193dc4e8c41b091706 | C1=CC(c2ccccc2)C=CN1 | C-C-S-[CH2;D2;+0:1]-[C:2]1=[C:3](-[C:4](-[#8:5])=[O;D1;H0:6])-[C:7]-[C:8]=[C:9]-[#7:10]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]1=[C:2](-[CH3;D1;+0:1])-[#7:10]-[C:9]=[C:8]-[C:7]-1 | null | [] | null | null | null | null | Under nitrogen atmosphere and stirring, a MeOH solution (15 ml) of g 0.85 of (+)2-ethylthiomethyl-3-carboethoxy-5-carbomethoxy-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine, cooled at 30° C. is treated with NaH2PO4 (g 1.45) and with Na/Hg amalgam (2.64 g) (10% in Na). After 15 minutes the solution is filtered and eva... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | null | null | C1=CNC=CC1.c1ccccc1 | Other | CO | null | null | CCOC(=O)C1=C(CSCC)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1>CO>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9c4c8e8f7f234b989171bc299cf5fb6f | CC(=O)OC(C)=O.CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(N)c1>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(NC(C)=O)c1 | CC(=O)OC(=O)C.CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)N)C(=O)OC)C>>CC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)NC(C)=O)C(=O)OC)C | CC(=O)O[C:24]([CH3:25])=[O:26].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH3:16])[CH:17]1[c:18]1[cH:19][cH:20][cH:21][c:22]([NH2:23])[cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([CH3:11])=[C:12]([C:13](=[O:14])[O:15][CH3:16])[... | CC(=O)OC(C)=O.CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(N)c1 | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(NC(C)=O)c1 | null | null | N1=CC=CC=C1 | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | C1=CC(c2ccccc2)C=CN1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Under inert gas atmosphere Ac2O (43 mcl) is added to a stirred solution of (-)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-aminophenyl)-1,4-dihydropyridine (100 mg) in pyridine (ml 1). 90 minutes after dilution with water (ml 50), extraction with AcOEt (3×10 ml) and crystallization from Et2O 70/EtOH 10, give mg 85 o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | C1=CNC=CC1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | CC(=O)OC(C)=O.CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(N)c1>N1=CC=CC=C1>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(NC(C)=O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c49a90aeb7b4f16adbda904ec4ca422 | C=CCOC(=O)C1=C(C)NC(CSC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(CSC)NC(C)=C(C(=O)O)C1c1cccc([N+](=O)[O-])c1 | Cl.CSCC=1NC(=C(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC=C)C.C(=O)[O-].[NH4+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(=O)(O)C=1C(C(=C(NC1C)CSC)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-] | C=[CH:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:13])[NH:11][C:12]([CH2:8][S:9][CH3:10])=[C:14]([C:15](=[O:16])[O:17]CC)[CH:18]1[c:19]1[cH:20][cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH2:8][S:9][CH3:10])[NH:11][C:12]([CH3:13])=[C:14]([C:15](=[O:16])[OH:17])[... | C=CCOC(=O)C1=C(C)NC(CSC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(CSC)NC(C)=C(C(=O)O)C1c1cccc([N+](=O)[O-])c1 | null | [Pd] | O1CCOCC1 | Miscellaneous | Ester saponification (alkyl deprotection) | 8a1d32a94cb1de8e1bdd3bf605726c54998d0a57b2b31af51fef8c2b878ee3b9 | c9b951964c21be5248721f8f1dd37c5226680f11de85d5a02577cb0f311eee2e | C1=CC(c2ccccc2)C=CN1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]1=[C;H0;D3;+0:5](-[CH2;D2;+0:6]-[#16:7]-[C;D1;H3:8])-[#7:9]-[C;H0;D3;+0:10](-[CH3;D1;+0:11])=[C:12](-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]-[CH;D2;+0:17]=C)-[C:18]-1>>[C;D1;H3:8]-[#16:7]-[CH2;D2;+0:6]-[C;H0;D3;+0:10]1=[C:12](-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]-[CH3;D1;+0:17])... | null | [] | null | null | null | null | A suspension of 2-methylthiomethyl-6-methyl-4-(3-nitrophenyl)-3-carboethoxy-5-carboallyloxy-1,4-dihydropyridine (g 0.27), palladium on charcoal (10% 6 mg), ammonium formate (mg 71) and triphenylphosphine (mg 3) in anhydrous 1,4-dioxane, is heated at the reflux temperature for 8 hours. The reaction mixture is cooled at ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ester.Monosulfide.Allyl | Enamine.Enamine.Carboxylic acid.Monosulfide | C1=CNC=CC1 | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1 | Other | [Pd].O1CCOCC1 | null | null | C=CCOC(=O)C1=C(C)NC(CSC)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>[Pd].O1CCOCC1>CCOC(=O)C1=C(CSC)NC(C)=C(C(=O)O)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6cc3dc8dfa924976a59acdde99fd9910 | CC1=C(C(=O)[O-])C(c2ccccc2)C(C(=O)OCC=CC(C)(C)C)=C(C)N1>>CC1=C(C(=O)O)C(c2ccccc2)C(C(=O)OC(C)(C)C)=C(C)N1 | CC=1NC(=C(C(C1C(=O)OCC=CC(C)(C)C)C1=CC=CC=C1)C(=O)[O-])C.C(=O)[O-].[NH4+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CC=1NC(=C(C(C1C(=O)OC(C)(C)C)C1=CC=CC=C1)C(=O)O)C | C(=C[C:18]([CH3:19])([CH3:20])[CH3:21])C[O:17][C:15]([C:14]1=[C:22]([CH3:23])[NH:24][C:2]([CH3:1])=[C:3]([C:4](=[O:5])[O-:6])[CH:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:16]>>[CH3:1][C:2]1=[C:3]([C:4](=[O:5])[OH:6])[CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH... | CC1=C(C(=O)[O-])C(c2ccccc2)C(C(=O)OCC=CC(C)(C)C)=C(C)N1 | CC1=C(C(=O)O)C(c2ccccc2)C(C(=O)OC(C)(C)C)=C(C)N1 | null | [Pd] | O1CCOCC1 | Miscellaneous | OtherReaction | 6964d317f96e5ec443b628aa20adcf9ce59df51c6e752f0ba688d0106c9a8846 | 25b53624051778d7b93b11291d8ead79ccbffb1e81819be753f1ab1ae25d1334 | C1=CC(c2ccccc2)C=CN1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-C=C-C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[#7:11]-[C:12](-[C;D1;H3:13])=[C:14](-[C:15](-[O-;H0;D1:16])=[O;D1;H0:17])-[C:18]-1>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H... | null | [] | null | null | null | null | A sample of (+) tertbutyl,allyl 2,6-dimethyl-4phenyl-1,4-dihydropyridine-3,5-dicarboxylate is treated in dioxane with 10% Pd on C, ammonium formate and triphenylphospine to give (+)-tertbutyl 2,6-dimethyl-4-phenyl-5-carboxy-1,4-dihydropyridine-3-carboxylate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid.Ester | null | null | C1=CNC=CC1.c1ccccc1 | Other | [Pd].O1CCOCC1 | null | null | CC1=C(C(=O)[O-])C(c2ccccc2)C(C(=O)OCC=CC(C)(C)C)=C(C)N1>[Pd].O1CCOCC1>CC1=C(C(=O)O)C(c2ccccc2)C(C(=O)OC(C)(C)C)=C(C)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-80a36a4efaf343448d7ae9f9feb6eb02 | CC(=O)OCC=C(C)CCC=C(C)CO.CC(C)(C)[Si](C)(C)Cl>>CC(=O)OCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C | O.N1C=NC=C1.Cl[Si](C(C)(C)C)(C)C.C(C)(=O)OCC=C(CCC=C(CO)C)C>>C(C)(=O)OCC=C(CCC=C(CO[Si](C(C)(C)C)(C)C)C)C | [CH3:1][C:2](=[O:3])[O:4][CH2:5][CH:6]=[C:7]([CH3:8])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][OH:15].Cl[Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH:6]=[C:7]([CH3:8])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20... | CC(=O)OCC=C(C)CCC=C(C)CO.CC(C)(C)[Si](C)(C)Cl | CC(=O)OCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C | null | null | CN(C=O)C | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]=[C:10](-[C;D1;H3:11])-[C:12]-[OH;D1;+0:13]>>[C:8]-[C:9]=[C:10](-[C;D1;H3:11])-[C:12]-[O;H0;D2;+0:13]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 75 | [{"value": 75.0, "product": "C(C)(=O)OCC=C(CCC=C(CO[Si](C(C)(C)C)(C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 8-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol in dimethylformamide (4 ml) was stirred on an ice bath. To the solution were added imidazole (338 mg, 4.96 mmol) and chlorodimethyl t-butylsilane (410 mg, 2.73 mmol), and the mixture was stirred at room temperature for one hour. After addition of water (30 ml) to the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | CN(C=O)C | null | 1 | CC(=O)OCC=C(C)CCC=C(C)CO.CC(C)(C)[Si](C)(C)Cl>CN(C=O)C>CC(=O)OCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-653cf78642b64e369dbc6c4aa0830f0e | COC(=O)C(CC=C(C)CCC=C(C)COC1CCCCO1)C(C)=O>>CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1 | O.C(C)(=O)C(C(=O)OC)CC=C(CCC=C(COC1OCCCC1)C)C.[Cl-].[Na+].O>>CC(=CCCC(C)=O)CCC=C(COC1OCCCC1)C | COC(=O)[CH:4]([C:2]([CH3:1])=[O:3])[CH2:5][CH:6]=[C:7]([CH3:8])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH:6]=[C:7]([CH3:8])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1 | COC(=O)C(CC=C(C)CCC=C(C)COC1CCCCO1)C(C)=O | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1 | null | null | CS(=O)C | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | C1CCOCC1 | C-O-C(=O)-[CH;D3;+0:1](-[C:2]-[C:3]=[C:4](-[C:5])-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[C:5]-[C:4](-[C;D1;H3:6])=[C:3]-[C:2]-[CH2;D2;+0:1]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 70 | [{"value": 70.0, "product": "CC(=CCCC(C)=O)CCC=C(COC1OCCCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 4 | HOUR | To a solution of methyl 2-acetyl-5,9-dimethyl-10-(2-tetrahydropyranyl)oxy-4,8-decadienate (370 mg, 1.05 mmol) in methylsulfoxide (2 ml) were added sodium chloride (180 mg, 3.08 mmol)and water (0.1 ml), and the mixture was stirred at 150° C. After four hours, the reaction mixture was allowed to cool to room temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | C1CCOCC1 | HO- | CS(=O)C | 150 | 4 | COC(=O)C(CC=C(C)CCC=C(C)COC1CCCCO1)C(C)=O>CS(=O)C>CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c92ff85cd307478d8567de5bbe8a6be1 | COCOCC(C)=CCCC(C)=CCC(C(C)=O)C(=O)OC>>COCOCC(C)=CCCC(C)=CCCC(C)=O | O.C(C)(=O)C(C(=O)OC)CC=C(CCC=C(COCOC)C)C.[Cl-].[Na+].O>>CC(=CCCC(C)=O)CCC=C(COCOC)C | COC(=O)[CH:15]([CH2:14][CH:13]=[C:11]([CH2:10][CH2:9][CH:8]=[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[CH3:7])[CH3:12])[C:16]([CH3:17])=[O:18]>>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]([CH3:7])=[CH:8][CH2:9][CH2:10][C:11]([CH3:12])=[CH:13][CH2:14][CH2:15][C:16]([CH3:17])=[O:18] | COCOCC(C)=CCCC(C)=CCC(C(C)=O)C(=O)OC | COCOCC(C)=CCCC(C)=CCCC(C)=O | null | null | CS(=O)C | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | null | C-O-C(=O)-[CH;D3;+0:1](-[C:2]-[C:3]=[C:4](-[C:5])-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[C:5]-[C:4](-[C;D1;H3:6])=[C:3]-[C:2]-[CH2;D2;+0:1]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 102.7 | [{"value": 67.0, "product": "CC(=CCCC(C)=O)CCC=C(COCOC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.7, "product": "CC(=CCCC(C)=O)CCC=C(COCOC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 5 | HOUR | To a solution of methyl 2-acetyl-5,9-dimethyl-10-(methoxymethyl)oxy-4,8-decadienate (420 mg, 1.37 mmol) in methylsulfoxide (4 ml) were added sodium chloride (160 mg, 2.74 mmol) and water (0.1 ml), and the mixture was stirred at 150° C. After five hours, the reaction mixture was allowed to cool to room temperature, and ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | null | HO- | CS(=O)C | 150 | 5 | COCOCC(C)=CCCC(C)=CCC(C(C)=O)C(=O)OC>CS(=O)C>COCOCC(C)=CCCC(C)=CCCC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-df3ec79a7f2a4004a3d61a7c5b0fd4ee | COC(=O)C(CC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C)C(C)=O>>CC(=O)CCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C | O.C(C)(=O)C(C(=O)OC)CC=C(CCC=C(CO[Si](C(C)(C)C)(C)C)C)C.[I-].[Na+].O>>CC(=CCCC(C)=O)CCC=C(CO[Si](C(C)(C)C)(C)C)C | COC(=O)[CH:4]([C:2]([CH3:1])=[O:3])[CH2:5][CH:6]=[C:7]([CH3:8])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH:6]=[C:7]([CH3:8])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH2:14][O:15][Si:16]([CH3:17])([CH3:18])[C:19]... | COC(=O)C(CC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C)C(C)=O | CC(=O)CCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C | null | null | CN(P(N(C)C)(N(C)C)=O)C | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | null | C-O-C(=O)-[CH;D3;+0:1](-[C:2]-[C:3]=[C:4](-[C:5])-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[C:5]-[C:4](-[C;D1;H3:6])=[C:3]-[C:2]-[CH2;D2;+0:1]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 70.2 | [{"value": 70.0, "product": "CC(=CCCC(C)=O)CCC=C(CO[Si](C(C)(C)C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.2, "product": "CC(=CCCC(C)=O)CCC=C(CO[Si](C(C)(C)C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 2 | HOUR | To a solution of methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate (96 mg, 0.25 mmol) in hexamethylphosphoric triamide (0.5 ml) were added sodium iodide (45 mg, 0.30 mmol) and water (0.01 ml), and the mixture was stirred at 150° C. After two hours, the reaction mixture was allowed to cool to ro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | null | HO- | CN(P(N(C)C)(N(C)C)=O)C | 150 | 2 | COC(=O)C(CC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C)C(C)=O>CN(P(N(C)C)(N(C)C)=O)C>CC(=O)CCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-def7012a35b24ca7acecda3599d33a87 | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1>>C#CC(C)(O)CCC=C(C)CCC=C(C)COC1CCCCO1 | CC(=CCCC(C)=O)CCC=C(COC1OCCCC1)C.O1CCCC1.[Cl-].[NH4+]>>CC(C#C)(CCC=C(CCC=C(COC1OCCCC1)C)C)O | [C:3]([CH3:4])(=[O:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][O:23]1>>[CH:1]#[C:2][C:3]([CH3:4])([OH:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH... | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1 | C#CC(C)(O)CCC=C(C)CCC=C(C)COC1CCCCO1 | null | null | null | Miscellaneous | OtherReaction | b0261a6e0833c38ef685714207caa8eb2984374d2381857280475311e93c5865 | c16f001d888fd5760355ab07c7cbeeb3916cb313ce8e69caceb96e11c3db56ee | C1CCOCC1 | [C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7]>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[C:8]#[C;D1;H1:9] | 75 | [{"value": 75.0, "product": "CC(C#C)(CCC=C(CCC=C(COC1OCCCC1)C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (90 mg, 0.31 mmol) in tetrahydrofuran (5 ml) was stirred on an ice bath under argon atmosphere. To the solution was added lithium acetylide ethylenediamine complex (180 mg, 1.95 mmol), and the mixture was warmed to room temperature and stirre... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol.Alkyne | null | null | C1CCOCC1 | Other | null | null | 3 | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1>>C#CC(C)(O)CCC=C(C)CCC=C(C)COC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fb88b86a266648a883be899ba27a392c | COCOCC(C)=CCCC(C)=CCCC(C)=O>>C#CC(C)(O)CCC=C(C)CCC=C(C)COCOC | CC(=CCCC(C)=O)CCC=C(COCOC)C.O1CCCC1.[Cl-].[NH4+]>>CC(C#C)(CCC=C(CCC=C(COCOC)C)C)O | [CH2:2]([C:3]([CH3:4])=[O:5])[CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH2:18][O:19][CH3:20]>>[CH:1]#[C:2][C:3]([CH3:4])([OH:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH2:18][O:19][CH3:20] | COCOCC(C)=CCCC(C)=CCCC(C)=O | C#CC(C)(O)CCC=C(C)CCC=C(C)COCOC | null | null | null | Functional Group Interconversion | OtherReaction | 8a55e49129533797495405ac892f36c90b40dc368c5851091ae8cfd74e4d6cce | b4d3f12699d73dfe9326ff386e682fbe0707faa6a3b5de0b1e494f2c54861252 | null | [C:1]-[C:2](-[C;D1;H3:3])=[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9]>>[C:1]-[C:2](-[C;D1;H3:3])=[C:4]-[CH2;D2;+0:5]-[C:10]-[C;H0;D4;+0:7](-[C;D1;H3:8])(-[OH;D1;+0:9])-[C;H0;D2;+0:6]#[C;D1;H1:11] | 83 | [{"value": 83.0, "product": "CC(C#C)(CCC=C(CCC=C(COCOC)C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 6,10-dimethyl-11-(methoxymethyl)oxy-5,9-undecadien-2-one (67 mg, 0.26 mmol) in tetrahydrofuran (2 ml) was stirred on an ice bath under argon atmosphere. To the solution was added lithium acetylide ethylenediamine complex (30 mg, 0.33 mmol), and the mixture was warmed to room temperature and stirred for 3 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol.Alkyne | null | null | null | Other | null | null | 3 | COCOCC(C)=CCCC(C)=CCCC(C)=O>>C#CC(C)(O)CCC=C(C)CCC=C(C)COCOC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cfc0a82347d8454ea67b3ecfbd841139 | CC(=O)CCC=C(C)CCC=C(C)COC(=O)c1ccccc1.CC(=O)CCC=C(C)CCC=C(C)COC(C)=O>>C#CC(C)(O)CCC=C(C)CCC=C(C)COC(=O)c1ccccc1.C#CC(C)(O)CCC=C(C)CCC=C(C)COC(C)=O | CC(=CCCC(C)=O)CCC=C(COC(C)=O)C.CC(=CCCC(C)=O)CCC=C(COC(C1=CC=CC=C1)=O)C>>CC(C#C)(CCC=C(CCC=C(COC(C)=O)C)C)O.CC(C#C)(CCC=C(CCC=C(COC(C1=CC=CC=C1)=O)C)C)O | [cH:1]1[cH:23][cH:22][cH:21][c:20]([C:18]([O:17][CH2:16][C:14](=[CH:13][CH2:12][CH2:11][C:9](=[CH:8][CH2:7][CH2:6][C:3]([CH3:2])=[O:5])[CH3:10])[CH3:15])=[O:19])[cH:25]1.[C:28]([CH3:29])(=[O:30])[CH2:31][CH2:32][CH:33]=[C:34]([CH3:35])[CH2:36][CH2:37][CH:38]=[C:39]([CH3:40])[CH2:41][O:42][C:43]([CH3:44])=[O:45]>>[CH:1]... | CC(=O)CCC=C(C)CCC=C(C)COC(=O)c1ccccc1.CC(=O)CCC=C(C)CCC=C(C)COC(C)=O | C#CC(C)(O)CCC=C(C)CCC=C(C)COC(=O)c1ccccc1.C#CC(C)(O)CCC=C(C)CCC=C(C)COC(C)=O | null | null | null | C-C Coupling | OtherReaction | 17288995bb1a9c607a11923137046d5c90731afcbc2f95b933a88848cff5ca74 | 25227984e902301059084be4a97e52fb59f6c543f8c093a2759edd287f18a0ab | c1ccccc1 | [C:1]=[C:2]-[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1.[C:13]=[C:14]-[C:15]-[C:16]-[C;H0;D3;+0:17](-[CH3;D1;+0:18])=[O;H0;D1;+0:19].[C:20]=[C:21]-[C:22]-[C:23]-[C;H0;D3;+0:24](-[C;D1;H3:25])=[O;H0;D1;+0:26]>>[C:1]=[C:2]-[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[... | null | [] | null | null | null | null | The procedure described in Example 9 was repeated except that 6,10-dimethyl-11-acetoxy-5,9-undecadien-2-on or 6,10-dimethyl-11-(benzoyl)oxy-5,9-undecadien-2-one was employed as a starting amterial to give 3,7,11-trimethyl-12-acetoxy-6,10-dodecadien-1-in-3-ol and 3,7,11-trimethyl-12-(benzoyl)oxy-6,10-dodecadien-1-in-3-o... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Tertiary alcohol.Tertiary alcohol.Alkyne.Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | null | null | null | CC(=O)CCC=C(C)CCC=C(C)COC(=O)c1ccccc1.CC(=O)CCC=C(C)CCC=C(C)COC(C)=O>>C#CC(C)(O)CCC=C(C)CCC=C(C)COC(=O)c1ccccc1.C#CC(C)(O)CCC=C(C)CCC=C(C)COC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-040d953b7c4342fe86b15659471a5179 | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1>>C=CC(C)(O)CCC=C(C)CCC=C(C)COC1CCCCO1 | CC(=CCCC(C)=O)CCC=C(COC1OCCCC1)C.C(=C)[Mg]Br.[Cl-].[NH4+]>>CC(C=C)(CCC=C(CCC=C(COC1OCCCC1)C)C)O | [C:3]([CH3:4])(=[O:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][O:23]1>>[CH2:1]=[CH:2][C:3]([CH3:4])([OH:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH:18]1[CH2:19][CH2:20][CH2:21][... | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1 | C=CC(C)(O)CCC=C(C)CCC=C(C)COC1CCCCO1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | e4a1e0cd9d6dfd9db238e7c2c1de7c3e0737df0f5a991ca26c06602eed667e3f | 2ce956c609b76ee2dc626ad09e785d954b7df9a7379fec6f4a0d038e8e2d1b2b | C1CCOCC1 | [C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7]>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[C:8]=[C;D1;H2:9] | 70 | [{"value": 70.0, "product": "CC(C=C)(CCC=C(CCC=C(COC1OCCCC1)C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0 M), and the mixture was warmed to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol.Vinyl | null | null | C1CCOCC1 | Other | O1CCCC1 | null | 10 | CC(=O)CCC=C(C)CCC=C(C)COC1CCCCO1>O1CCCC1>C=CC(C)(O)CCC=C(C)CCC=C(C)COC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-abf89943068e44e4b243d8981907c802 | COCOCC(C)=CCCC(C)=CCCC(C)=O>>C=CC(C)(O)CCC=C(C)CCC=C(C)COCOC | CC(=CCCC(C)=O)CCC=C(COCOC)C.C(=C)[Mg]Br.[Cl-].[NH4+]>>CC(C=C)(CCC=C(CCC=C(COCOC)C)C)O | [C:3]([CH3:4])(=[O:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH2:18][O:19][CH3:20]>>[CH2:1]=[CH:2][C:3]([CH3:4])([OH:5])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][O:17][CH2:18][O:19][CH3:20] | COCOCC(C)=CCCC(C)=CCCC(C)=O | C=CC(C)(O)CCC=C(C)CCC=C(C)COCOC | null | null | O1CCCC1 | Miscellaneous | OtherReaction | e4a1e0cd9d6dfd9db238e7c2c1de7c3e0737df0f5a991ca26c06602eed667e3f | 2ce956c609b76ee2dc626ad09e785d954b7df9a7379fec6f4a0d038e8e2d1b2b | null | [C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7]>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[C:8]=[C;D1;H2:9] | 80 | [{"value": 80.0, "product": "CC(C=C)(CCC=C(CCC=C(COCOC)C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 6,10-dimethyl-11-(methoxymethyl)oxy-5,9-undecadien-2-one (60 mg, 0.24 mmol) in tetrahydrofuran (2 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (1.0 ml, 1.0 mmol, 1.0 M), and the mixture was warmed to room temperature and stirred... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol.Vinyl | null | null | null | Other | O1CCCC1 | null | 4 | COCOCC(C)=CCCC(C)=CCCC(C)=O>O1CCCC1>C=CC(C)(O)CCC=C(C)CCC=C(C)COCOC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d8573869d08e470baf695611eb541645 | CC(C)=CCC/C(C)=C/C=O.CCOP(=O)(OCC)C(C#N)C(C)C>>CC(C)=CCCC(C)=CC=C(C#N)C(C)C | CC(C)=CCC\C(\C)=C\C=O.C(C)OP(=O)(OCC)C(C#N)C(C)C.C[Si](C)(C)[N-][Si](C)(C)C.[K+].O>>CC(C)C(C#N)=CC=C(CCC=C(C)C)C | O=[CH:10]/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8].CCOP(=O)(OCC)[CH:11]([C:12]#[N:13])[CH:14]([CH3:15])[CH3:16]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH:10]=[C:11]([C:12]#[N:13])[CH:14]([CH3:15])[CH3:16] | CC(C)=CCC/C(C)=C/C=O.CCOP(=O)(OCC)C(C#N)C(C)C | CC(C)=CCCC(C)=CC=C(C#N)C(C)C | null | null | CCCCCC.C(C)(=O)OCC.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | df44814facebff896c2ad69cee6ae7fa6f5dde76efe90a5256e518ed7e917e1c | d70fa5718646c1ca7d5c68acab5b524370b238501cb432d711539d0f01ee6d2b | null | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6].O=[CH;D2;+0:7]/[C:8]=[C:9](\[C;D1;H3:10])-[C:11]-[C:12]-[C:13]=[C:14]>>[C:14]=[C:13]-[C:12]-[C:11]-[C:9](-[C;D1;H3:10])=[C:8]-[CH;D2;+0:7]=[C;H0;D3;+0:1](-[C:2]#[N;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6] | 90 | [{"value": 90.0, "product": "CC(C)C(C#N)=CC=C(CCC=C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "CC(C)C(C#N)=CC=C(CCC=C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 30 | MINUTE | To a solution of 2-(diethylphosphono)isovaleronitrile (6.54 g, 30 mmol) in toluene (55 ml) was added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (56 ml) with stirring on a cooling bath at -70° C. After 30 minutes, geranial (3.80 g, 25 mmol) was added thereto with continuous stirring at the same te... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Conjugated diene | null | null | null | HO- | CCCCCC.C(C)(=O)OCC.C1(=CC=CC=C1)C | -70 | 0.5 | CC(C)=CCC/C(C)=C/C=O.CCOP(=O)(OCC)C(C#N)C(C)C>CCCCCC.C(C)(=O)OCC.C1(=CC=CC=C1)C>CC(C)=CCCC(C)=CC=C(C#N)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e71dfe02ed7a4998a002c61663dd0167 | CC(C)=CCCC(C)=CC=C(C#N)C(C)C.O>>CC(C)=CCCC(C)=CC=C(C=O)C(C)C | O.CC(C)C(C#N)=CC=C(CCC=C(C)C)C.[H-].C(C(C)C)[Al+]CC(C)C>>CC(C)C(C=O)=CC=C(CCC=C(C)C)C | N#[C:12][C:11](=[CH:10][CH:9]=[C:7]([CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8])[CH:14]([CH3:15])[CH3:16].[OH2:13]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH:10]=[C:11]([CH:12]=[O:13])[CH:14]([CH3:15])[CH3:16] | CC(C)=CCCC(C)=CC=C(C#N)C(C)C.O | CC(C)=CCCC(C)=CC=C(C=O)C(C)C | null | null | C1(=CC=CC=C1)C.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | null | N#[C;H0;D2;+0:1]-[C:2](-[C:3])=[C:4]-[C:5]=[C:6].[OH2;D0;+0:7]>>[C:3]-[C:2](=[C:4]-[C:5]=[C:6])-[CH;D2;+0:1]=[O;H0;D1;+0:7] | 90 | [{"value": 90.0, "product": "CC(C)C(C=O)=CC=C(CCC=C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | null | null | To a solution of 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitril (2Z compound, 217 mg, 1 mmol) in n-hexane (4 ml) was added a 1 M solution of diisobutylaluminium hydride in toluene (2 ml) with stirring under argon atmosphere at -70° C. After two-hour-stirring at the same temperature, water (0.8 ml) was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | null | Other | C1(=CC=CC=C1)C.CCCCCC | -70 | null | CC(C)=CCCC(C)=CC=C(C#N)C(C)C.O>C1(=CC=CC=C1)C.CCCCCC>CC(C)=CCCC(C)=CC=C(C=O)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d891efc28e36422aa4bc843ada73ddc3 | CC(C)=CCCC(C)=CCCC(C)=CCO.CCOP(=O)(OCC)C(C#N)C(C)C>>CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C | OCC=C(C)CCC=C(C)CCC=C(C)C.C(C)OP(=O)(OCC)C(C#N)C(C)C.C[Si](C)(C)[N-][Si](C)(C)C.[K+].O>>CC(C)C(C#N)=CC=C(CCC=C(CCC=C(C)C)C)C | O[CH2:15][CH:14]=[C:12]([CH2:11][CH2:10][CH:9]=[C:7]([CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8])[CH3:13].CCOP(=O)(OCC)[CH:16]([C:17]#[N:18])[CH:19]([CH3:20])[CH3:21]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH2:10][CH2:11][C:12]([CH3:13])=[CH:14][CH:15]=[C:16]([C:17]#[N:18])[CH:19]([CH3:... | CC(C)=CCCC(C)=CCCC(C)=CCO.CCOP(=O)(OCC)C(C#N)C(C)C | CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 5233481be9d92617a5762cf9702e2cf42d3320e3895b7f4ba4ce43d8d71559dc | b035c718464f22a2fee64a10728df89061c9f6b680353f0d59daf6bbab2893d1 | null | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6].O-[CH2;D2;+0:7]-[C:8]=[C:9](-[C:10])-[C;D1;H3:11]>>[C:10]-[C:9](-[C;D1;H3:11])=[C:8]-[CH;D2;+0:7]=[C;H0;D3;+0:1](-[C:2]#[N;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6] | 96 | [{"value": 96.0, "product": "CC(C)C(C#N)=CC=C(CCC=C(CCC=C(C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "CC(C)C(C#N)=CC=C(CCC=C(CCC=C(C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | null | null | To a solution of 2-(diethylphosphono)isovaleronitrile (8.72 g, 40 mmol) in toluene (75 ml) was gradually added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (75 ml) with stirring at -70° C. under argon atmosphere. The cooling bath was removed, and the reaction mixture was stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Conjugated diene | null | null | null | HO- | C1(=CC=CC=C1)C | -70 | null | CC(C)=CCCC(C)=CCCC(C)=CCO.CCOP(=O)(OCC)C(C#N)C(C)C>C1(=CC=CC=C1)C>CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1beec0472a4d456a82991908e309a084 | CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C.O>>CC(C)=CCCC(C)=CCCC(C)=CC=C(C=O)C(C)C | O.C(C(=O)O)(=O)O.CC(C)C(C#N)=CC=C(CCC=C(CCC=C(C)C)C)C.[H-].C(C(C)C)[Al+]CC(C)C>>CC(C)C(C=O)=CC=C(CCC=C(CCC=C(C)C)C)C | N#[C:17][C:16](=[CH:15][CH:14]=[C:12]([CH2:11][CH2:10][CH:9]=[C:7]([CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8])[CH3:13])[CH:19]([CH3:20])[CH3:21].[OH2:18]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH2:10][CH2:11][C:12]([CH3:13])=[CH:14][CH:15]=[C:16]([CH:17]=[O:18])[CH:19]([CH3:20])[CH3:21... | CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C.O | CC(C)=CCCC(C)=CCCC(C)=CC=C(C=O)C(C)C | null | null | C1(=CC=CC=C1)C.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | null | N#[C;H0;D2;+0:1]-[C:2](-[C:3])=[C:4]-[C:5]=[C:6].[OH2;D0;+0:7]>>[C:6]=[C:5]-[C:4]=[C:2](-[C:3])-[CH;D2;+0:1]=[O;H0;D1;+0:7] | 84 | [{"value": 84.0, "product": "CC(C)C(C=O)=CC=C(CCC=C(CCC=C(C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 1 | HOUR | To a solution of 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (856 mg, 3.0 mmol) in n-hexane (30 ml) was added a 0.5 M solution of diisobutylaluminium hydride in toluene (6 ml) with stirring at -70° C. under argon atmosphere. After one hour, water (3 ml) was added, the cooling bath was removed, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | null | Other | C1(=CC=CC=C1)C.CCCCCC | -70 | 1 | CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C.O>C1(=CC=CC=C1)C.CCCCCC>CC(C)=CCCC(C)=CCCC(C)=CC=C(C=O)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cd445a28a1bf4a1d9e7cefe6eaf0f6bc | CC(C)(C)OO.CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C>>CC(C)=CCCC(C)=CCCC(C)=C(O)C=C(C#N)C(C)C | C(C)(C)(C)OO.OC1=C(C(=O)O)C=CC=C1.CC(C)C(C#N)=CC=C(CCC=C(CCC=C(C)C)C)C>>OC(C=C(C#N)C(C)C)=C(CCC=C(CCC=C(C)C)C)C | CC(C)(C)O[OH:15].[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH2:10][CH2:11][C:12]([CH3:13])=[CH:14][CH:16]=[C:17]([C:18]#[N:19])[CH:20]([CH3:21])[CH3:22]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C:7]([CH3:8])=[CH:9][CH2:10][CH2:11][C:12]([CH3:13])=[C:14]([OH:15])[CH:16]=[C:17]([C:18]#[N:19])[CH:... | CC(C)(C)OO.CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C | CC(C)=CCCC(C)=CCCC(C)=C(O)C=C(C#N)C(C)C | null | [Se](=O)=O | C(Cl)Cl | Acylation | OtherReaction | 51ed781db2c0c42bd775cd01d66bf0748da484e9d31940e46bd96a8bcc3fb0cc | 8cee6fe1e6e705aeea84c9464ad19dd199049631903fc4aa30ed3747cd3b3ab6 | null | C-C(-C)(-C)-O-[OH;D1;+0:1].[C:2]-[C:3](-[C;D1;H3:4])=[CH;D2;+0:5]-[C:6]=[C:7](-[C:8])-[C:9]#[N;D1;H0:10]>>[C:2]-[C:3](-[C;D1;H3:4])=[C;H0;D3;+0:5](-[OH;D1;+0:1])-[C:6]=[C:7](-[C:8])-[C:9]#[N;D1;H0:10] | 317.6 | [{"value": 31.0, "product": "OC(C=C(C#N)C(C)C)=C(CCC=C(CCC=C(C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 317.6, "product": "OC(C=C(C#N)C(C)C)=C(CCC=C(CCC=C(C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of selenium dioxide (58 mg) and 2-hydroxybenzoic acid (365 mg) in methylene chloride (10.5 ml) was gradually added an aqueous solution of 80% t-butyl hydroperoxide (11.6 ml) with stirring on a water bath. After 30 minutes, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (7.56 g, 26.... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Conjugated diene | Enol | null | null | null | HO- | [Se](=O)=O.C(Cl)Cl | null | 0.5 | CC(C)(C)OO.CC(C)=CCCC(C)=CCCC(C)=CC=C(C#N)C(C)C>[Se](=O)=O.C(Cl)Cl>CC(C)=CCCC(C)=CCCC(C)=C(O)C=C(C#N)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8c3070185c0c485e916e3d80a6ea4995 | C#CC(C)(O)CCC=C(C)CCC=C(C)COCOC>>COCOCC(C)=CCCC(C)=CCCC(C)=CC=O | CC(C#C)(CCC=C(CCC=C(COCOC)C)C)O.C(C1=CC=CC=C1)(=O)O>>COCOCC(=CCCC(=CCCC(=CC=O)C)C)C | [CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]([CH3:7])=[CH:8][CH2:9][CH2:10][C:11]([CH3:12])=[CH:13][CH2:14][CH2:15][C:16]([CH3:17])([C:18]#[CH:19])[OH:20]>>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]([CH3:7])=[CH:8][CH2:9][CH2:10][C:11]([CH3:12])=[CH:13][CH2:14][CH2:15][C:16]([CH3:17])=[CH:18][CH:19]=[O:20] | C#CC(C)(O)CCC=C(C)CCC=C(C)COCOC | COCOCC(C)=CCCC(C)=CCCC(C)=CC=O | null | null | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | 08cc8b5aba5ce7cacff262de7e593f47308e73def414aa0cc722c2ea5b3c7fb9 | 10bef8ecdd241dd96ab9e8e5993d81e2c6bfde8d842f397a5970db62c104b881 | null | [C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[C;H0;D2;+0:8]#[CH;D1;+0:9]>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[CH;D2;+0:8]-[CH;D2;+0:9]=[O;H0;D1;+0:7] | 506.2 | [{"value": 50.0, "product": "COCOCC(=CCCC(=CCCC(=CC=O)C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 506.2, "product": "COCOCC(=CCCC(=CCCC(=CC=O)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,7,11-trimethyl-12-(methoxymethyl)oxy-6,10-dodecadien-1-in-3-ol (175 mg, 0.62 mmol), tris (triphenylsilyl)vanadate (49 mg, 0.062 mmol), and benzoic acid (7.6 mg, 0.062 mmol) in xylene (2 ml) was stirred on an oil bath at 140° C. After two-hour-stirring, the solution was allowed to cool to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Alkyne | Aldehyde | null | null | null | null | C=1(C(=CC=CC1)C)C | null | null | C#CC(C)(O)CCC=C(C)CCC=C(C)COCOC>C=1(C(=CC=CC1)C)C>COCOCC(C)=CCCC(C)=CCCC(C)=CC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be061f6076814d3eb2e7884b9794b2d8 | C=CC(C)(O)CCC=C(C)CCC=C(C)COCOC>>COCOCC(C)=CCCC(C)=CCCC(C)=CC=O | CCCCCC.C(C)(=O)OCC.CC(C=C)(CCC=C(CCC=C(COCOC)C)C)O.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>COCOCC(=CCCC(=CCCC(=CC=O)C)C)C | [CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]([CH3:7])=[CH:8][CH2:9][CH2:10][C:11]([CH3:12])=[CH:13][CH2:14][CH2:15][C:16]([CH3:17])([CH:18]=[CH2:19])[OH:20]>>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]([CH3:7])=[CH:8][CH2:9][CH2:10][C:11]([CH3:12])=[CH:13][CH2:14][CH2:15][C:16]([CH3:17])=[CH:18][CH:19]=[O:20] | C=CC(C)(O)CCC=C(C)CCC=C(C)COCOC | COCOCC(C)=CCCC(C)=CCCC(C)=CC=O | null | null | ClCCl.CCOCC | Functional Group Interconversion | OtherReaction | 932573158b7f38b60e75f42220ad1f7790a69a05f1655d0d3e24a0fae37f96bf | ffe5565d98f0f079bc523aca6dc82f3c8ed848b415f8e29cf6fb99a9e0fdd5d7 | null | [C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[CH;D2;+0:8]-[CH;D2;+0:9]=[O;H0;D1;+0:7] | 52 | [{"value": 52.0, "product": "COCOCC(=CCCC(=CCCC(=CC=O)C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "COCOCC(=CCCC(=CCCC(=CC=O)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 3,7,11-trimethyl-12-(methoxymethyl)oxy-1,6,10-dodecatrien-3-ol (460 mg, 1.6 mmol) in dichloromethane (30 ml) was added pyridinium chlorochromate (690 mg, 3.2 mmol), and the mixture was stirred at room temperature for 8 hours. After addition of a mixture of hexane, ethyl acetate, and ether (3:1:1) (100 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Vinyl | Aldehyde | null | null | null | null | ClCCl.CCOCC | null | 8 | C=CC(C)(O)CCC=C(C)CCC=C(C)COCOC>ClCCl.CCOCC>COCOCC(C)=CCCC(C)=CCCC(C)=CC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b97247ada82742289e9ba7217c2fbcc9 | CC1=CC=C(C(C)C)C(C#N)(O[Si](C)(C)C)CC(C)=CCCC(C)=CCC1>>CC1=CC=C(C(C)C)C(=O)CC(C)=CCCC(C)=CCC1 | CC(C)C=1C(CC(=CCCC(=CCCC(=CC1)C)C)C)(C#N)O[Si](C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CC(C)C=1C(CC(=CCCC(=CCCC(=CC1)C)C)C)=O | C[Si](C)(C)[O:10][C:9]1(C#N)[C:5]([CH:6]([CH3:7])[CH3:8])=[CH:4][CH:3]=[C:2]([CH3:1])[CH2:21][CH2:20][CH:19]=[C:17]([CH3:18])[CH2:16][CH2:15][CH:14]=[C:12]([CH3:13])[CH2:11]1>>[CH3:1][C:2]1=[CH:3][CH:4]=[C:5]([CH:6]([CH3:7])[CH3:8])[C:9](=[O:10])[CH2:11][C:12]([CH3:13])=[CH:14][CH2:15][CH2:16][C:17]([CH3:18])=[CH:19][C... | CC1=CC=C(C(C)C)C(C#N)(O[Si](C)(C)C)CC(C)=CCCC(C)=CCC1 | CC1=CC=C(C(C)C)C(=O)CC(C)=CCCC(C)=CCC1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 6b55fd76f4c9622a5dddd188d879d316f2b68abed37dc3ccc386d8985cd7a63e | 61b2d875aaccd8e93cf051a19a569cff9a172d59692ce05315f24e7065ab3279 | O=C1C=CC=CCCC=CCCC=CC1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C#N)(-[C:3]-[C:4](-[C;D1;H3:5])=[C:6]-[C:7])-[C:8](-[C:9])=[C:10]-[C:11]=[C:12]>>[C:7]-[C:6]=[C:4](-[C;D1;H3:5])-[C:3]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[C:8](-[C:9])=[C:10]-[C:11]=[C:12] | 85 | [{"value": 85.0, "product": "CC(C)C=1C(CC(=CCCC(=CCCC(=CC1)C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "CC(C)C=1C(CC(=CCCC(=CCCC(=CC1)C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | The above cyanohydrine trimethylsilyl ether compound, 2-(1-methylethyl)-5,9,13-trimethyl-1-trimethylsiloxy-2,4,8,12-cyclotetradecatetraen-1-carbonitrile (657 mg, 1.7 mmol) was dissolved in 10% aqueous tetrahydrofuran (10 ml). To the solution on an ice-water bath was added a solution of 1M tetra n-butylammonium fluoride... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Silyl protective group | Ketone | C1=CCCC=CCCC=CCCC=C1 | C1=CCCC=CCCC=CCCC=C1 | C1=CCCC=CCCC=CCCC=C1 | Other | O1CCCC1 | null | 48 | CC1=CC=C(C(C)C)C(C#N)(O[Si](C)(C)C)CC(C)=CCCC(C)=CCC1>O1CCCC1>CC1=CC=C(C(C)C)C(=O)CC(C)=CCCC(C)=CCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-afd51883db244e12b7b5da102322d549 | CC1=CC=C(C(C)C)C(=O)CC(C)=CCCC(C)=CCC1>>C/C1=C\CC/C(C)=C/C=C(/C(C)C)[C@@H](O)C/C(C)=C/CC1 | O.CC(C)C=1C(CC(=CCCC(=CCCC(=CC1)C)C)C)=O.[H-].C(C(C)C)[Al+]CC(C)C.CCCCCC.C(C)(=O)OCC>>C/C/1=C\CC/C(=C/C=C(\[C@H](C/C(=C/CC1)/C)O)/C(C)C)/C | [CH3:1][C:2]1=[CH:3][CH:4]=[C:5]([CH:6]([CH3:7])[CH3:8])[C:9](=[O:10])[CH2:11][C:12]([CH3:13])=[CH:14][CH2:15][CH2:16][C:17]([CH3:18])=[CH:19][CH2:20][CH2:21]1>>[CH3:1]/[C:2]1=[CH:3]\[CH:4]=[C:5](\[CH:6]([CH3:7])[CH3:8])[C@@H:9]([OH:10])[CH2:11]/[C:12]([CH3:13])=[CH:14]/[CH2:15][CH2:16]/[C:17]([CH3:18])=[CH:19]/[CH2:20... | CC1=CC=C(C(C)C)C(=O)CC(C)=CCCC(C)=CCC1 | C/C1=C\CC/C(C)=C/C=C(/C(C)C)[C@@H](O)C/C(C)=C/CC1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ketone to secondary alcohol | 0f564bc62a8b76684fdd2bc57d3bb69c6079fe08170eab268dcc00bbdb253ba1 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCC/C=C/CC/C=C/CCC=C1 | [C:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8](-[C:9])=[C:10]-[C:11]=[C:12]>>[C:1]/[C:2]=[C:3](\[C;D1;H3:4])-[C:5]-[C@H;D3;+0:6](-[OH;D1;+0:7])/[C:8](-[C:9])=[C:10]\[C:11]=[C:12] | 90.3 | [{"value": 88.0, "product": "C/C/1=C\\CC/C(=C/C=C(\\[C@H](C/C(=C/CC1)/C)O)/C(C)C)/C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "C/C/1=C\\CC/C(=C/C=C(\\[C@H](C/C(=C/CC1)/C)O)/C(C)C)/C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To the above ketone compound, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one (137 mg, 0.48 mmol) in dry toluene (2.5 ml) was dropwise added with stirring on a cooling bath at -70° C. a solution of 1M diisobutyl aluminium hydride in toluene (0.6 ml). One hour later, disappearance of the starting... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC=CCCC=CCCC=C1 | C1=CCC/C=C/CC/C=C/CCC=C1 | C1=CCC/C=C/CC/C=C/CCC=C1 | null | C1(=CC=CC=C1)C | null | null | CC1=CC=C(C(C)C)C(=O)CC(C)=CCCC(C)=CCC1>C1(=CC=CC=C1)C>C/C1=C\CC/C(C)=C/C=C(/C(C)C)[C@@H](O)C/C(C)=C/CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ff3a359235274b109e5176e13886b94a | CC1(C)COB(c2ccc(CBr)cc2)OC1.CCC1=Nc2ccccc2C(=O)C1>>CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1 | C(C)C1=NC2=CC=CC=C2C(C1)=O.Cl.NC1=CC=CC=C1.C(CC)(=O)CC(=O)OCC.[H-].[Na+].BrN1C(CCC1=O)=O.BrCC1=CC=C(C=C1)B1OCC(CO1)(C)C.CC1=CC=C(C=C1)B(O)O.CC(CO)(CO)C>>Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)B(O)O | CC1(C)C[O:13][B:12]([c:11]2[cH:10][cH:9][c:8]([CH2:7]Br)[cH:16][cH:15]2)[O:14]C1.[CH3:1][CH2:2][C:3]1=[N:23][c:22]2[c:17]([cH:18][cH:19][cH:20][cH:21]2)[C:5](=[O:6])[CH2:4]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([B:12]([OH:13])[OH:14])[cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][... | CC1(C)COB(c2ccc(CBr)cc2)OC1.CCC1=Nc2ccccc2C(=O)C1 | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1 | null | N(=NC(C#N)(C)C)C(C#N)(C)C | C1CCCCC1.O.C(C)(=O)OCC.CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | 730b0718ada63f168f56f3b1b9c07f5618f8e6fe7aeaf6c4752f4d2344e38544 | 9f12664b446dee6f8942935b54b2d5c54bf5b5402981628b5dbcff82bf213981 | c1ccc(COc2ccnc3ccccc23)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C1(-C)-C-[O;H0;D2;+0:5]-[#5:6](-[c:7])-[O;H0;D2;+0:8]-C-1.[C;D1;H3:9]-[C:10]-[C;H0;D3;+0:11]1=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15](:[c:16])-[C;H0;D3;+0:17](=[O;H0;D1;+0:18])-[CH2;D2;+0:19]-1>>[C;D1;H3:9]-[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:19]:[c;H0;D3;+0:17](-[O;H0;D2;+0:18]-[CH2... | null | [] | null | null | 20 | MINUTE | A solution of 2-ethyl-4-quinolone (6.9 g; 0.04 mole), (prepared using a similar procedure to that described in Org. Syn., Coll., Vol. III, p. 374 and p. 593 from aniline and ethyl propionylacetate) in (NMP) (50 ml) was added over 30 minutes to a stirred suspension of sodium hydride (1.6 g of a 60% dispersion in mineral... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Substituted imine | Ether.Boronic acid | [B]1OCCCO1.C1=Nc2ccccc2CC1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr | N(=NC(C#N)(C)C)C(C#N)(C)C.C1CCCCC1.O.C(C)(=O)OCC.CN1CCCC1=O | null | 0.333333 | CC1(C)COB(c2ccc(CBr)cc2)OC1.CCC1=Nc2ccccc2C(=O)C1>N(=NC(C#N)(C)C)C(C#N)(C)C.C1CCCCC1.O.C(C)(=O)OCC.CN1CCCC1=O>CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2590efa2e9e45318afc6a859630a380 | BrBr.Cc1ccc(B(O)O)cc1>>OB(O)c1ccc(CBr)cc1 | BrBr.CC1=CC=C(C=C1)B(O)O.BrBr.O.O>>BrCC1=CC=C(C=C1)B(O)O | Br[Br:9].[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:10][cH:11]1>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]1 | BrBr.Cc1ccc(B(O)O)cc1 | OB(O)c1ccc(CBr)cc1 | null | N(=NC(C#N)(C)C)C(C#N)(C)C | CC(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | a15881996473f5a1ce0bccff03f7e43814dbff6603523dd7ef3da5577a9ef0c0 | 66c56de4857c93aad279a9723c5dc81ded09ca7f36c2d38768545aa0b6ab7f0a | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 67.5 | [{"value": 67.5, "product": "BrCC1=CC=C(C=C1)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 4-methylphenylboronic acid (27.2 g; 0.2 mole) in methyl chloroform (250 ml) was heated at reflux with azeotropic removal of water until approximately 2.5 ml of water was collected and a crystalline slurry was formed. A solution of azo(bisisobutyronitrile) (1.0 g) and bromine (32 g) in methyl chloroform (25... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary halide | null | null | c1ccccc1 | HBr | N(=NC(C#N)(C)C)C(C#N)(C)C.CC(Cl)(Cl)Cl | null | 0.5 | BrBr.Cc1ccc(B(O)O)cc1>N(=NC(C#N)(C)C)C(C#N)(C)C.CC(Cl)(Cl)Cl>OB(O)c1ccc(CBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-453bbeae00f848f6ad982371dbf56ba9 | CCc1cc(=O)c2c([nH]1)CCCC2.OB(O)c1ccc(CBr)cc1>>CCc1cc(OCc2ccc(B(O)O)cc2)c2c(n1)CCCC2 | O.[H-].[Na+].C(C)C=1NC=2CCCCC2C(C1)=O.BrCC1=CC=C(C=C1)B(O)O>>C(C)C1=NC=2CCCCC2C(=C1)OCC1=CC=C(C=C1)B(O)O | [CH3:1][CH2:2][c:3]1[cH:4][c:5](=[O:6])[c:17]2[c:18]([nH:19]1)[CH2:20][CH2:21][CH2:22][CH2:23]2.Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([B:12]([OH:13])[OH:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([B:12]([OH:13])[OH:14])[cH:15][cH:16]2)[c:17]2[c:18]([n:19]1)[CH2:20][CH2:21][C... | CCc1cc(=O)c2c([nH]1)CCCC2.OB(O)c1ccc(CBr)cc1 | CCc1cc(OCc2ccc(B(O)O)cc2)c2c(n1)CCCC2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f6a6be0d29c91f8530666945cc5a8e53fa06cd4a125b146335c05ec503f5b978 | 62c7c72c35b09d63ca1131e6cd8c0b88a31e29901d660456b77319cfd78354c7 | c1ccc(COc2ccnc3c2CCCC3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[nH;D2;+0:7]:[c:8](-[C:9]):[c:10]:[c;H0;D3;+0:11](=[O;H0;D1;+0:12]):[c:13]:1-[C:14]>>[C:5]-[c:6]1:[n;H0;D2;+0:7]:[c:8](-[C:9]):[c:10]:[c;H0;D3;+0:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:13]:1-[C:14] | 99.3 | [{"value": 99.3, "product": "C(C)C1=NC=2CCCCC2C(=C1)OCC1=CC=C(C=C1)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | Sodium hydride (60% dispersion in oil; 180 mg) was added to a mixture of 2-ethyl-5,6,7,8-tetrahydro-4(1H)-quinolone (660 mg) and 4-bromomethylphenylboronic acid (800 mg) (obtained as described in J. Amer. Chem. Soc. 1958, 80, 835) in DMF (12 ml) under an atmosphere of argon. The mixture was stirred for 40 hours and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | c1ccc2c(n1)CCCC2 | c1cnc2c(c1)CCCC2 | c1ccccc1.c1cnc2c(c1)CCCC2 | HBr | CN(C)C=O | null | 40 | CCc1cc(=O)c2c([nH]1)CCCC2.OB(O)c1ccc(CBr)cc1>CN(C)C=O>CCc1cc(OCc2ccc(B(O)O)cc2)c2c(n1)CCCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-46152c9e14d74da38cf75a60bb4c02b6 | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1.O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1>>CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1 | C([O-])([O-])=O.[K+].[K+].BrC1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-].BrC1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-].O.Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)B(O)O>>C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-] | OB(O)[c:11]1[cH:10][cH:9][c:8]([CH2:7][O:6][c:5]2[cH:4][c:3]([CH2:2][CH3:1])[n:40][c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)[cH:33][cH:32]1.Br[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1-[c:18]1[n:19][n:20][n:21][n:22]1-[c:23]1[cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]... | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1.O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1 | CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.CO | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-n2nnnc2-c2ccccc2-c2ccc(COc3ccnc4ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[#7;a:9]:1):[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:4](-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[#7;a:9]:1):[c:10] | 65 | [{"value": 65.0, "product": "C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of potassium carbonate (5.8 g), 5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole (5.81 g) (Compound B), water (43 ml), toluene (43 ml), and methanol (43 ml) was heated to 60° C. to give a clear solution. 4-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (4.3 g) and tetrakis(triphenylphosphin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO | 60 | null | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1.O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO>CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])c... |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55c8dbdb7e544eb9a79fb8565a5af017 | Nc1ccc([N+](=O)[O-])cc1.O=C(O)c1ccccc1Br>>O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1Br | [N+](=O)([O-])C1=CC=C(N)C=C1.S(=O)(Cl)Cl.BrC1=C(C(=O)O)C=CC=C1>>BrC1=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=CC=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1.O[C:2](=[O:1])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Br:19]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Br:19] | Nc1ccc([N+](=O)[O-])cc1.O=C(O)c1ccccc1Br | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1Br | null | null | CN(C=O)C.C1(=CC=CC=C1)C.CN1CCCC1=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 87 | [{"value": 87.0, "product": "BrC1=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 24 | HOUR | Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and N,N-dimethylformamide (DMF) (5 ml) and the mixture heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and NMP (120 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C=O)C.C1(=CC=CC=C1)C.CN1CCCC1=O | 80 | 24 | Nc1ccc([N+](=O)[O-])cc1.O=C(O)c1ccccc1Br>CN(C=O)C.C1(=CC=CC=C1)C.CN1CCCC1=O>O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1Br |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-22c770c71f534618af7b4271c7bca75d | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1Br.[N-]=[N+]=[N-]>>O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1 | S(=O)(Cl)Cl.[N-]=[N+]=[N-].[Na+].C(C)N(CC)CC.BrC1=C(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])C=CC=C1.CN(C)C=O.C(C)N(CC)CC>>BrC1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-] | O=[C:12]([NH:8][c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][cH:20]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Br:19].[N-:9]=[N+:10]=[N-:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][n:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Br:19])[cH:20][cH:21]1 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1Br.[N-]=[N+]=[N-] | O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)#N.O | Aromatic Heterocycle Formation | OtherReaction | 44c51fa4775381974c36b821e53a168b7c1999527620818cbf27ff54b30f0148 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | c1ccc(-c2nnnn2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[Br;D1;H0:12]):[c:13].[N-;H0;D1:14]=[N+;H0;D2:15]=[N-;H0;D1:16]>>[Br;D1;H0:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[n;H0;D2;+0:15]:[n;H0;D2;+0:16]:[n;H0;D3;+0:2]:1-[c;H0;D3;+0:3](:[... | 73 | [{"value": 73.0, "product": "BrC1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "BrC1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 90 | MINUTE | Triethylamine (1.04 g; 10.38 mmol) was added to a mixture of 2-bromo-N-(4-nitrophenyl)benzamide (3 g; 9.35 mmol) in acetonitrile (12 ml) and DMF (0.189 g; 2.58 mmol) and the mixture was stirred for 90 minutes. Thionyl chloride (1.44 g; 12.14 mmol) was then added slowly keeping the reaction temperature below 25° C. The ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.c1ccccc1 | HO- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N.O | 10 | 1.5 | O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1Br.[N-]=[N+]=[N-]>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N.O>O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8c3949dd42b847749d5aa5ec9d9df23e | CCc1cc(OCc2ccc(B3OCC(C)(C)CO3)cc2)c2ccccc2n1.O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1>>CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1 | C([O-])([O-])=O.[K+].[K+].BrC1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-].O.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)B1OCC(CO1)(C)C>>C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-] | CC1(C)COB([c:11]2[cH:10][cH:9][c:8]([CH2:7][O:6][c:5]3[cH:4][c:3]([CH2:2][CH3:1])[n:40][c:39]4[c:34]3[cH:35][cH:36][cH:37][cH:38]4)[cH:33][cH:32]2)OC1.Br[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1-[c:18]1[n:19][n:20][n:21][n:22]1-[c:23]1[cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][c:3]1[c... | CCc1cc(OCc2ccc(B3OCC(C)(C)CO3)cc2)c2ccccc2n1.O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1 | CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.CO | C-C Coupling | Suzuki coupling with boronic esters | 6645429072e9cb23849faae8b2d240e8cdc660fd04d4135f8e93c07af10093d5 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-n2nnnc2-c2ccccc2-c2ccc(COc3ccnc4ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[#7;a:9]:1):[c:10].C-C1(-C)-C-O-B(-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15])-O-C-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:4](-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[#7;a:9]:1):[c:10] | 58.2 | [{"value": 58.2, "product": "C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of potassium carbonate (1.08 g; 7.8 mmol), 5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole (1.16 g; 3.2 mmol) water (10 ml), toluene (10 ml), and methanol (10 ml) was heated to 60° C. to give a clear solution. 2-(4-[(2-Ethylquinolin-4-yloxy)-methyl]phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (1.0 g; 2.6 mmol) a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | B1OCCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO | 60 | null | CCc1cc(OCc2ccc(B3OCC(C)(C)CO3)cc2)c2ccccc2n1.O=[N+]([O-])c1ccc(-n2nnnc2-c2ccccc2Br)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO>CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](... |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a42eab0e9842413eba4f462da9863058 | CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1>>CCc1cc(OCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c2ccccc2n1 | Cl.C(CC)S.[H-].[Na+].C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1C1=CC=C(C=C1)[N+](=O)[O-]>>Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1 | O=[N+]([O-])c1ccc(-[n:22]2[c:18](-[c:17]3[c:12](-[c:11]4[cH:10][cH:9][c:8]([CH2:7][O:6][c:5]5[cH:4][c:3]([CH2:2][CH3:1])[n:31][c:30]6[c:25]5[cH:26][cH:27][cH:28][cH:29]6)[cH:24][cH:23]4)[cH:13][cH:14][cH:15][cH:16]3)[n:19][n:20][n:21]2)cc1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[... | CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1 | CCc1cc(OCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c2ccccc2n1 | null | null | CCCCCC.O.CN1C(CCC1)=O | Reduction | OtherReaction | ac42d4b6686e6b85ce90266c83918d48acf1a2a7658b21f88754f025785eb771 | a48304f1d491232fd73e82261ecea998a2c4787d8fac4a6a0f69a35adfcacd2c | c1ccc(-c2nnn[nH]2)c(-c2ccc(COc3ccnc4ccccc34)cc2)c1 | O=[N+](-[O-])-c1:c:c:c(-[n;H0;D3;+0:1]2:[#7;a:2]:[#7;a:3]:[#7;a:4]:[c:5]:2-[c:6]):c:c:1>>[c:6]-[c:5]1:[#7;a:4]:[#7;a:3]:[#7;a:2]:[nH;D2;+0:1]:1 | 64 | [{"value": 64.0, "product": "Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Sodium hydride (50% dispersion in mineral oil; 0.091 g; 1.9 mmol) was washed with hexane, dried with a stream of nitrogen and covered with N-methylpyrrolidone (NMP) (5 ml). The mixture was cooled to below 10° C. and propanethiol (0.145 g; 1.9 mmol) was added slowly with stirring. After 15 minutes, a solution of 2-ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | null | c1ccccc1.c1nnn[nH]1 | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccc2ncccc2c1 | HO- | CCCCCC.O.CN1C(CCC1)=O | null | 0.25 | CCc1cc(OCc2ccc(-c3ccccc3-c3nnnn3-c3ccc([N+](=O)[O-])cc3)cc2)c2ccccc2n1>CCCCCC.O.CN1C(CCC1)=O>CCc1cc(OCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c2ccccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-19b3524e42254cd798a618b4d5e376b5 | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1.N#Cc1ccccc1Br>>CCc1cc(OCc2ccc(-c3ccccc3C#N)cc2)c2ccccc2n1 | C(C)N(CC)CC.Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)B(O)O.BrC1=C(C#N)C=CC=C1>>C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C=1C(=CC=CC1)C#N | OB(O)[c:11]1[cH:10][cH:9][c:8]([CH2:7][O:6][c:5]2[cH:4][c:3]([CH2:2][CH3:1])[n:28][c:27]3[c:22]2[cH:23][cH:24][cH:25][cH:26]3)[cH:21][cH:20]1.Br[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:18]#[N:19]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18]... | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1.N#Cc1ccccc1Br | CCc1cc(OCc2ccc(-c3ccccc3C#N)cc2)c2ccccc2n1 | null | [Pd](Cl)Cl | O.C(CCC)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(COc3ccnc4ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | 91.1 | [{"value": 91.1, "product": "C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C=1C(=CC=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Triethylamine (13.8 ml) was added to a mixture of 4-[(2-ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (12.74 g), 2-bromobenzonitrile (5.92 g) and palladium chloride (0.13 g) in butanol (80 ml) and water (40 ml) and the mixture was heated at reflux for 3 hours. The hot reaction mixture was filtered throu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | [Pd](Cl)Cl.O.C(CCC)O | null | null | CCc1cc(OCc2ccc(B(O)O)cc2)c2ccccc2n1.N#Cc1ccccc1Br>[Pd](Cl)Cl.O.C(CCC)O>CCc1cc(OCc2ccc(-c3ccccc3C#N)cc2)c2ccccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f2e47c7899134a9295da63016e60ddb0 | CCc1cc(OCc2ccc(B(O)O)cc2)c2c(n1)CCCC2.N#Cc1ccccc1Br>>CCc1cc(OCc2ccc(-c3ccccc3C#N)cc2)c2c(n1)CCCC2 | C(C)C1=NC=2CCCCC2C(=C1)OCC1=CC=C(C=C1)B(O)O.BrC1=C(C#N)C=CC=C1>>C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)COC1=CC(=NC=2CCCCC12)CC | OB(O)[c:11]1[cH:10][cH:9][c:8]([CH2:7][O:6][c:5]2[cH:4][c:3]([CH2:2][CH3:1])[n:24][c:23]3[c:22]2[CH2:28][CH2:27][CH2:26][CH2:25]3)[cH:21][cH:20]1.Br[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:18]#[N:19]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C... | CCc1cc(OCc2ccc(B(O)O)cc2)c2c(n1)CCCC2.N#Cc1ccccc1Br | CCc1cc(OCc2ccc(-c3ccccc3C#N)cc2)c2c(n1)CCCC2 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(COc3ccnc4c3CCCC4)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | 49.4 | [{"value": 49.4, "product": "C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)COC1=CC(=NC=2CCCCC12)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetrakis(triphenylphosphine)palladium (40 mg) was added to a suspension of 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]-phenylboronic acid (200 mg) and 2-bromobenzonitrile (106 mg) in toluene (2 ml) ethanol (0.5 ml) and 2M aqueous sodium carbonate (0.58 ml). The mixture was degassed and placed under an atmosp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1cnc2c(c1)CCCC2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C | null | null | CCc1cc(OCc2ccc(B(O)O)cc2)c2c(n1)CCCC2.N#Cc1ccccc1Br>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>CCc1cc(OCc2ccc(-c3ccccc3C#N)cc2)c2c(n1)CCCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-832ff61cff804954b0b824263d4250bb | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[n]1nnc(-c2ccccc2-c2ccc(COc3cc(CC)nc4ccccc34)cc2)n1>>CCc1cc(OCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c2ccccc2n1 | N(=O)[O-].[Na+].Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C=1C(=CC=CC1)C#N.C(CCC)[Sn](CCCC)(CCCC)N=[N+]=[N-].C(CCC)[Sn](CCCC)(CCCC)Cl.[N-]=[N+]=[N-].[Na+].S(N)(O)(=O)=O.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C=1N=NN(N1)[Sn](CCCC)(CCCC)CCCC>>Cl.C(C)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[n:20]1[n:19][c:18](-[c:17]2[c:12](-[c:11]3[cH:10][cH:9][c:8]([CH2:7][O:6][c:5]4[cH:4][c:3]([CH2:2][CH3:1])[n:31][c:30]5[c:25]4[cH:26][cH:27][cH:28][cH:29]5)[cH:24][cH:23]3)[cH:13][cH:14][cH:15][cH:16]2)[n:22][n:21]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][c:11](... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[n]1nnc(-c2ccccc2-c2ccc(COc3cc(CC)nc4ccccc34)cc2)n1 | CCc1cc(OCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c2ccccc2n1 | null | null | C1(=CC=CC=C1)C.O | Miscellaneous | OtherReaction | 0a9371a4e95c0c666f605b5b7552272ca5aa6515f1d058621b39dc3fa43a9ee3 | 0a43800783b8b35c229f6662ca603d845499733b0931b52000994d05a7b14c6d | c1ccc(-c2nnn[nH]2)c(-c2ccc(COc3ccnc4ccccc34)cc2)c1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[n;H0;D2;+0:5]:[#7;a:6]:1>>[c:4]-[c:3]1:[#7;a:2]:[n;H0;D2;+0:1]:[#7;a:6]:[nH;D2;+0:5]:1 | null | [] | null | null | 1 | HOUR | A solution of 2-ethyl-4-[(2'-(2-tributylstannyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline in toluene (15 ml), prepared in situ by refluxing for 90 hours a mixture of 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile (0.9 g) and a solution of tributyltin azide in toluene (15 ml) [the latter prepared by ... | 10.6084/m9.figshare.5104873.v1 | null | Tin | null | c1nnn[nH]1 | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccc2ncccc2c1 | Sn | C1(=CC=CC=C1)C.O | null | 1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[n]1nnc(-c2ccccc2-c2ccc(COc3cc(CC)nc4ccccc34)cc2)n1>C1(=CC=CC=C1)C.O>CCc1cc(OCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c2ccccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-28eff96ac1a74bc0827f6036314dc85e | CC(C)(C)C(C(=O)O)C(=O)O.CC(C)(C)C(C(=O)O)C(=O)O.CC(C)(C)[Si](C)(C)O[C@H](CC#N)CC(=O)O>>CC(C)(C)OC(=O)CC(=O)C[C@@H](CC#N)O[Si](C)(C)C(C)(C)C | Cl.[Cl-].[Mg+2].[Cl-].C(C)(C)N(CC)C(C)C.O=C1C(O)=C(O)[C@H](O1)[C@@H](O)CO.CC(C)(C)C(C(=O)O)C(=O)O.[K].C([C@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O.C(#N)C[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1.CC(C)(C)C(C(=O)O)C(=O)O>>C(#N)C[C@H](CC(CC(=O)OC(C)(C)C)=O)O[Si](C)(C)C(C)(C)C | O=C(O)C(C(=O)O)[C:2]([CH3:1])([CH3:3])[CH3:4].CC(C)(C)[CH:8](C(=O)O)[C:6]([OH:5])=[O:7].O[C:9](=[O:10])[CH2:11][C@@H:12]([CH2:13][C:14]#[N:15])[O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@@H:12]([CH2:13][C:14]#[N:15]... | CC(C)(C)C(C(=O)O)C(=O)O.CC(C)(C)C(C(=O)O)C(=O)O.CC(C)(C)[Si](C)(C)O[C@H](CC#N)CC(=O)O | CC(C)(C)OC(=O)CC(=O)C[C@@H](CC#N)O[Si](C)(C)C(C)(C)C | null | null | C(C)#N.C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | d450ad79c5f4d0beaa4c5de00ae2db10230626063b3a87b7e19e4b8ec5a9c5da | 7068fba248159e8633a87fcd42bed155c4e815f98058291361e5a887b8b35b32 | null | C-C(-C)(-C)-[CH;D3;+0:1](-C(-O)=O)-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].O-C(=O)-C(-C(-O)=O)-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[C:12]>>[C:12]-[C:11]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H... | null | [] | 25 | CELSIUS | null | null | Thus, the optically active compounds are prepared from the known isoascorbic acid using the methodology described by Volante R. P. et al., in U.S. Pat. No. 4,611,067 but in that case starting with ascorbic acid. This establishes the optically active centers desired in Formula XXVa and Formula XXIIIa as R. Thus, the (R)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid | Ketone.Ester | null | null | null | HO- | C(C)#N.C(C)(=O)OCC.O1CCCC1 | 25 | null | CC(C)(C)C(C(=O)O)C(=O)O.CC(C)(C)C(C(=O)O)C(=O)O.CC(C)(C)[Si](C)(C)O[C@H](CC#N)CC(=O)O>C(C)#N.C(C)(=O)OCC.O1CCCC1>CC(C)(C)OC(=O)CC(=O)C[C@@H](CC#N)O[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-030dd67a47da476ca971ca42ed1f5543 | CC(C)C(=O)CC(=O)Nc1ccccc1.O=Cc1ccccc1>>CC(C)C(=O)C(=Cc1ccccc1)C(=O)Nc1ccccc1 | CC(C(CC(=O)NC1=CC=CC=C1)=O)C.CC(C(CC(=O)NC1=CC=CC=C1)=O)C.C(C1=CC=CC=C1)=O.N1CCCCC1.C(CN)N.NCCC(=O)O.CC(C(CC(=O)OC)=O)C.NC1=CC=CC=C1.C(CN)N>>CC(C(C(C(=O)NC1=CC=CC=C1)=CC1=CC=CC=C1)=O)C | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[CH2:6][C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[C:6](=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(C)C(=O)CC(=O)Nc1ccccc1.O=Cc1ccccc1 | CC(C)C(=O)C(=Cc1ccccc1)C(=O)Nc1ccccc1 | null | null | C(C)(=O)O.CCCCCC.C1(=CC=CC=C1)C.CCCCCCC.O | C-C Coupling | Aldol condensation | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1ccccc1)Nc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[c:12]>>[C:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#7:11]-[c:12] | null | [] | null | null | null | null | 4-Methyl-3-oxo-N-phenylpentanamide (XIX) is obtained by heating a mixture of methyl 4-methyl-3-oxopentanoate (XX), aniline and ethylene diamine in toluene. 4-Methyl-3-oxo-N-phenylpentanamide (XIX) is subsequently reacted with benzaldehyde in the presence of a catalyst such as, for example, piperidine and glacial acetic... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.CCCCCC.C1(=CC=CC=C1)C.CCCCCCC.O | null | null | CC(C)C(=O)CC(=O)Nc1ccccc1.O=Cc1ccccc1>C(C)(=O)O.CCCCCC.C1(=CC=CC=C1)C.CCCCCCC.O>CC(C)C(=O)C(=Cc1ccccc1)C(=O)Nc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-05456a5bf1634b1fb36ce4b30e08ab37 | C=CCC(O)CC=C>>C=CC[C@@H](O)C[C@@H]1CO1 | O1CCCC1.C(CCC)[Li].C=CCC(CC=C)O.C1(=CC=CC=C1)C(C1=CC=CC=C1)C1=CC=CC=C1>>C(C=C)[C@H](C[C@H]1OC1)O | [CH2:1]=[CH:2][CH2:3][CH:4]([OH:5])[CH2:6][CH:7]=[CH2:8]>>[CH2:1]=[CH:2][CH2:3][C@@H:4]([OH:5])[CH2:6][C@@H:7]1[CH2:8][O:9]1 | C=CCC(O)CC=C | C=CC[C@@H](O)C[C@@H]1CO1 | null | null | null | Oxidation | OtherReaction | ccc410867e4c89598d5079c0dfc27f7bc863046b1c1459e93fa3815bf371d797 | 38c38e5e943ba321612c1e8763ee5b6d3bec0e5b922509df80b788fc9703980f | C1CO1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4]>>[C:1]-[C:2]-[C@H;D3;+0:3]1-[#8:5]-[CH2;D2;+0:4]-1 | null | [] | null | null | 30 | MINUTE | n-Butyllithium, 129 mL (200 mmol), is added dropwise to a 0° C. solution of 1,6-heptadien-4-ol, 22.4 g (0.2 mol), in 200 mL of anhydrous tetrahydrofuran until the triphenylmethane indicator turned red. Carbon dioxide is then bubbled in for 30 minutes (lecture bottle carbon dioxide passed through drierite) and the light... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Ether | null | C1CO1 | C1CO1 | Other | null | null | 0.5 | C=CCC(O)CC=C>>C=CC[C@@H](O)C[C@@H]1CO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a3a4fee475da4c86890db66cdc3aa76f | C=CC[C@@H](O)C[C@@H]1CO1.CC(C)O.[C-]#N>>C=CC[C@@H]1C[C@H](CC#N)OC(C)(C)O1 | [C-]#N.[K+].C(C=C)[C@H](C[C@H]1OC1)O.C(C)(C)O.O>>CC1(O[C@@H](C[C@@H](O1)CC#N)CC=C)C | O1[C@H:6]([CH2:5][C@@H:4]([CH2:3][CH:2]=[CH2:1])[OH:14])[CH2:7]1.[OH:10][CH:11]([CH3:12])[CH3:13].[C-:8]#[N:9]>>[CH2:1]=[CH:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8]#[N:9])[O:10][C:11]([CH3:12])([CH3:13])[O:14]1 | C=CC[C@@H](O)C[C@@H]1CO1.CC(C)O.[C-]#N | C=CC[C@@H]1C[C@H](CC#N)OC(C)(C)O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4c15f157a12f53c42684a56c8c1dc0ee43b25d3db1e9bf3482f1a71033594b9c | b2727f0507fdca4a006da10729db27fe4375933b6c39a949f86c89c9d12de99b | C1COCOC1 | [C-;H0;D1:1]#[N;D1;H0:2].[C;D1;H2:3]=[C:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-[C@H;D3;+0:9]1-O-[CH2;D2;+0:10]-1.[C;D1;H3:11]-[CH;D3;+0:12](-[C;D1;H3:13])-[OH;D1;+0:14]>>[C;D1;H2:3]=[C:4]-[C:5]-[C:6]1-[C:8]-[C@H;D3;+0:9](-[CH2;D2;+0:10]-[C;H0;D2;+0:1]#[N;D1;H0:2])-[O;H0;D2;+0:14]-[C;H0;D4;+0:12](-[C;D1;H3:11])(-[C;D1;H3:1... | null | [] | null | null | 20 | HOUR | Potassium cyanide, 1.3 g (20 mmol), is added to a room temperature solution of (R*,R*)-α-2-propenyloxiraneethanol, 2.56 g (20 mmol), in 25 mL of 4:1 isopropanol-water. The solution is stirred for 20 hours at ambient temperature, concentrated, and partitioned between ethyl acetate and brine. The aqueous layer is extract... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Secondary alcohol | Ether.Ether.Nitrile | C1CO1 | C1COCOC1 | C1COCOC1 | HO- | null | null | 20 | C=CC[C@@H](O)C[C@@H]1CO1.CC(C)O.[C-]#N>>C=CC[C@@H]1C[C@H](CC#N)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b6eb58361dae4facaccd1c29d8d6a8b6 | C=CC[C@@H]1C[C@H](CC#N)OC(C)(C)O1>>CC1(C)O[C@H](CC=O)C[C@H](CC#N)O1 | CC1(O[C@@H](C[C@@H](O1)CC#N)CC=C)C.O=[O+][O-].O=[O+][O-]>>O=CC[C@@H]1C[C@@H](OC(O1)(C)C)CC#N | C=[CH:7][CH2:6][C@H:5]1[O:4][C:2]([CH3:1])([CH3:3])[O:14][C@@H:10]([CH2:11][C:12]#[N:13])[CH2:9]1>>[CH3:1][C:2]1([CH3:3])[O:4][C@H:5]([CH2:6][CH:7]=[O:8])[CH2:9][C@H:10]([CH2:11][C:12]#[N:13])[O:14]1 | C=CC[C@@H]1C[C@H](CC#N)OC(C)(C)O1 | CC1(C)O[C@H](CC=O)C[C@H](CC#N)O1 | null | null | ClCCl | Oxidation | Alkene oxidation to aldehyde | bba9eb9a112fc7573e22f83c2d00d38db23db9bd0c71632ed02baac3559c409c | 32819d6b5381845ad0bcd88c90cc74f19ec27991c6c1ce562774976396f3fe8e | C1COCOC1 | C=[CH;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[CH;D2;+0:1]=[O;D1;H0:5] | null | [] | null | null | null | null | A solution of (±)-cis-2,2-dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 3 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsbach generator, flow rate 0.1, voltage=90 V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone appear... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Aldehyde | null | null | C1COCOC1 | null | ClCCl | null | null | C=CC[C@@H]1C[C@H](CC#N)OC(C)(C)O1>ClCCl>CC1(C)O[C@H](CC=O)C[C@H](CC#N)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3e866dd73b724ce1babaa729046e5dfa | CC(C)I.CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1>>CC(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)O.N12CCCCCC2=NCCC1.IC(C)C>>C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)C | I[CH:2]([CH3:1])[CH3:3].[OH:4][C:5](=[O:6])[CH2:7][C@H:8]1[CH2:9][C@@H:10]([CH2:11][C:12]#[N:13])[O:14][C:15]([CH3:16])([CH3:17])[O:18]1>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C@H:8]1[CH2:9][C@@H:10]([CH2:11][C:12]#[N:13])[O:14][C:15]([CH3:16])([CH3:17])[O:18]1 | CC(C)I.CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1 | CC(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | null | null | C(C)#N.C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a1c78245a699a2d7f32afead5a272e9f9c3376384617cf46d1f41528c07c62a0 | 24a9dd2a1f5258889ba19b94426efe6fc90f5f9d7c761574387c6d65581f3783 | C1COCOC1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | 8 | HOUR | To a solution of (±)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 0.6 g (3 mmol), in acetonitrile, 2 mL, is added 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU), 0.45 mL (3 mmol), and 2-iodopropane, 0.33 mL (3.3 mmol). The solution is stirred overnight at room temperature, diluted with diethyl ether, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carboxylic acid | Ester | null | null | C1COCOC1 | HI | C(C)#N.C(C)OCC | null | 8 | CC(C)I.CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1>C(C)#N.C(C)OCC>CC(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1a331950e4dd4997b61684a90a5e772a | CC(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1>>CC(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 | C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)C>>NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)C | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C@H:8]1[CH2:9][C@@H:10]([CH2:11][C:12]#[N:13])[O:14][C:15]([CH3:16])([CH3:17])[O:18]1>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C@H:8]1[CH2:9][C@@H:10]([CH2:11][CH2:12][NH2:13])[O:14][C:15]([CH3:16])([CH3:17])[O:18]1 | CC(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | CC(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 | null | [Pt](=O)=O | C(C)(=O)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1COCOC1 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | null | null | A mixture of (±)-cis-1-methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetate, 0.55 g, in glacial acetic acid is hydrogenated with platinum dioxide at 50 pounds per square inch (PSI). Concentration, dilution with ethyl acetate and bicarbonate wash, followed by washing with brine and drying provides 250 mg of (±... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1COCOC1 | null | [Pt](=O)=O.C(C)(=O)O | null | null | CC(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1>[Pt](=O)=O.C(C)(=O)O>CC(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37e8689612b643c69b9ba6881e96180a | CC(C)C(=O)CC(=O)Nc1ccccc1.O=Cc1ccccc1>>CC(C)C(=O)C(=Cc1ccccc1)C(=O)Nc1ccccc1 | CC(C(CC(=O)NC1=CC=CC=C1)=O)C.NCCC(=O)O.C(C1=CC=CC=C1)=O>>CC(C(C(C(=O)NC1=CC=CC=C1)=CC1=CC=CC=C1)=O)C | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[CH2:6][C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[C:6](=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(C)C(=O)CC(=O)Nc1ccccc1.O=Cc1ccccc1 | CC(C)C(=O)C(=Cc1ccccc1)C(=O)Nc1ccccc1 | null | null | C(C)(=O)O.O | C-C Coupling | Aldol condensation | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1ccccc1)Nc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[c:12]>>[C:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#7:11]-[c:12] | 84.7 | [{"value": 84.7, "product": "CC(C(C(C(=O)NC1=CC=CC=C1)=CC1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 100 kg of 4-methyl-3-oxo-N-phenyl-pentanamide (Example B) in 660 kg of hexanes is treated with agitation under nitrogen with 8 kg of β-alanine, 47 kg of benzaldehyde, and 13 kg of glacial acetic acid. The resulting suspension is heated to reflux with removal of water for 20 hours. An additional 396 kg o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.O | null | null | CC(C)C(=O)CC(=O)Nc1ccccc1.O=Cc1ccccc1>C(C)(=O)O.O>CC(C)C(=O)C(=Cc1ccccc1)C(=O)Nc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bc325b8893574d99b132a5fdc2ef0766 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.CCOC(CCN)OCC>>CCOC(CCn1c(-c2ccc(F)cc2)c(-c2ccccc2)c(C(=O)Nc2ccccc2)c1C(C)C)OCC | FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.NCCC(OCC)OCC.C(C(C)(C)C)(=O)O>>C(C)OC(CCN1C(=C(C(=C1C1=CC=C(C=C1)F)C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)OCC | O=[C:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[CH:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:23]([C:24](=[O:25])[NH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[C:33](=O)[CH:34]([CH3:35])[CH3:36].[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][NH2:7])[O:37][CH2:38][CH3:39]>>[CH3:1][CH2:2][O:3][CH:4]([C... | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.CCOC(CCN)OCC | CCOC(CCn1c(-c2ccc(F)cc2)c(-c2ccccc2)c(C(=O)Nc2ccccc2)c1C(C)C)OCC | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Paal-Knorr pyrrole synthesis | 0cb7b72300a2af7a2e4398a0e1226bb84c0d31edad76ec86c7b51828dc8686b6 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | O=C(Nc1ccccc1)c1c[nH]c(-c2ccccc2)c1-c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[CH;D3;+0:5](-[C:6](=[O;D1;H0:7])-[#7:8]-[c:9])-[CH;D3;+0:10](-[C;H0;D3;+0:11](=O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16])-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21].[C:22]-[C:23]-[NH2;D1;+0:24]>>[C:22]-[C:23]-[n;H0;D3;+0:24]1:[c;H0;D3;+0:1](-[C:2](-[C;D1;H3:... | 81.2 | [{"value": 81.2, "product": "C(C)OC(CCN1C(=C(C(=C1C1=CC=C(C=C1)F)C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22.5 | CELSIUS | null | null | To a nitrogen purged flask equipped with a mechanical stirrer is added 130 kg (311 mol) of (±)4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers, 540 L of heptanes and 60 L of toluene, 59 kg (400 mol) of 3-amino-1,1-diethoxypro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 22.5 | null | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.CCOC(CCN)OCC>C1(=CC=CC=C1)C>CCOC(CCn1c(-c2ccc(F)cc2)c(-c2ccccc2)c(C(=O)Nc2ccccc2)c1C(C)C)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-51298362f8764f68810a8c2258e4294c | CCOC(CCn1c(-c2ccc(F)cc2)c(-c2ccccc2)c(C(=O)Nc2ccccc2)c1C(C)C)OCC>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CCC=O | C(C)OC(CCN1C(=C(C(=C1C1=CC=C(C=C1)F)C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)OCC.Cl>>FC1=CC=C(C=C1)C1=C(C(=C(N1CCC=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | CCO[CH:33]([CH2:32][CH2:31][n:30]1[c:4]([CH:2]([CH3:1])[CH3:3])[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1-[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[O:34]CC>>[CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][c... | CCOC(CCn1c(-c2ccc(F)cc2)c(-c2ccccc2)c(C(=O)Nc2ccccc2)c1C(C)C)OCC | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CCC=O | null | null | CC(=O)C | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C(Nc1ccccc1)c1c[nH]c(-c2ccccc2)c1-c1ccccc1 | C-C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 94.3 | [{"value": 94.3, "product": "FC1=CC=C(C=C1)C1=C(C(=C(N1CCC=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a nitrogen purged flask fitted with an overhead stirrer, a thermometer, and a condenser is added 20 kg (37.8 mol) of 1-(3,3-diethoxypropyl)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl- 1 H-pyrrole-3-carboxamide along with 200 L of acetone. The solution is stirred and 100 L of 2N hydrochloric acid solution is a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CC(=O)C | null | null | CCOC(CCn1c(-c2ccc(F)cc2)c(-c2ccccc2)c(C(=O)Nc2ccccc2)c1C(C)C)OCC>CC(=O)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CCC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-806b44f4b9cd4b5184ff969fcae41bdf | CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1>>CC1(C)O[C@H](CCN)C[C@H](CC(=O)O)O1 | [H][H].O.C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)O.N>>NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)O | [CH3:1][C:2]1([CH3:3])[O:4][C@H:5]([CH2:6][C:7]#[N:8])[CH2:9][C@H:10]([CH2:11][C:12](=[O:13])[OH:14])[O:15]1>>[CH3:1][C:2]1([CH3:3])[O:4][C@H:5]([CH2:6][CH2:7][NH2:8])[CH2:9][C@H:10]([CH2:11][C:12](=[O:13])[OH:14])[O:15]1 | CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1 | CC1(C)O[C@H](CCN)C[C@H](CC(=O)O)O1 | null | null | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1COCOC1 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | 52.8 | [{"value": 52.8, "product": "NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | A solution of 1.04 g (4.88 mmol) of (±)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid in 100 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.53 g of water wet Raney nickel #30. The solution is heated at 45° C. and 50 psig hydrogen pressure for 17 hours. The sus... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1COCOC1 | null | CO | 45 | null | CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1>CO>CC1(C)O[C@H](CCN)C[C@H](CC(=O)O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e9af0c16de3b42cea332fbbddd9d1440 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.CC1(C)O[C@H](CCN)C[C@H](CC(=O)O)O1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)O.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.C(C)OCC.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1.CC1(C)[O:36][C@@H:35]([CH2:37][C:38](O)=[O:39])[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]1>>[CH3:1][... | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.CC1(C)O[C@H](CCN)C[C@H](CC(=O)O)O1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | null | null | CS(=O)C.O | Aromatic Heterocycle Formation | OtherReaction | 88b1c3309521478299f2506a30fb0da7d9f074c0185ed180ecebc70534d06648 | ace646bda34ee0b7f86eba46d7406afcd515b387b9aae1bd99ad77336c2c1802 | O=C1CCC[C@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3]-[C;H0;D3;+0:4](-O)=[O;D1;H0:5])-[C:6]-[C:7](-[C:8]-[C:9]-[NH2;D1;+0:10])-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26]:[c:27])-[c... | 24.7 | [{"value": 24.7, "product": "FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 18 | HOUR | A solution of 0.26 g (1.21 mmol) of (±)-cis-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid and 0.504 g (1.20 mmol) of (±)4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers in 5 mL of dimethyl sulfoxide is heated at 105... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone.Ether.Ether.Primary amine | Ester.Secondary alcohol | C1COCOC1 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | CS(=O)C.O | 105 | 18 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.CC1(C)O[C@H](CCN)C[C@H](CC(=O)O)O1>CS(=O)C.O>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d15cd1699d9c4e79a33d560421fd6908 | C=CC[C@@H]1C[C@H](CC#N)OC2(CCCC2)O1>>N#CC[C@H]1C[C@@H](CC=O)OC2(CCCC2)O1 | C(C=C)[C@@H]1C[C@@H](OC2(CCCC2)O1)CC#N.O=[O+][O-].O=[O+][O-]>>O=CC[C@@H]1C[C@@H](OC2(CCCC2)O1)CC#N | C=[CH:8][CH2:7][C@@H:6]1[CH2:5][C@H:4]([CH2:3][C:2]#[N:1])[O:16][C:11]2([O:10]1)[CH2:12][CH2:13][CH2:14][CH2:15]2>>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][C@@H:6]([CH2:7][CH:8]=[O:9])[O:10][C:11]2([CH2:12][CH2:13][CH2:14][CH2:15]2)[O:16]1 | C=CC[C@@H]1C[C@H](CC#N)OC2(CCCC2)O1 | N#CC[C@H]1C[C@@H](CC=O)OC2(CCCC2)O1 | null | null | ClCCl | Oxidation | Alkene oxidation to aldehyde | bba9eb9a112fc7573e22f83c2d00d38db23db9bd0c71632ed02baac3559c409c | 32819d6b5381845ad0bcd88c90cc74f19ec27991c6c1ce562774976396f3fe8e | C1COC2(CCCC2)OC1 | C=[CH;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[CH;D2;+0:1]=[O;D1;H0:5] | null | [] | null | null | null | null | A solution of (±)-cis-9-(2-propenyl)-6,10-dioxaspiro[4.5]decane-7-acetonitrile, 3.4 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsbach generator, flow rate 0.1, voltage=90 V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone ap... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Aldehyde | null | null | C1COC2(CCCC2)OC1 | null | ClCCl | null | null | C=CC[C@@H]1C[C@H](CC#N)OC2(CCCC2)O1>ClCCl>N#CC[C@H]1C[C@@H](CC=O)OC2(CCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b50b1d60512843a3837a65020aad8c77 | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1>>NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 | [H][H].O.C(#N)C[C@@H]1C[C@@H](OC2(CCCC2)O1)CC(=O)O.N>>NCC[C@@H]1C[C@@H](OC2(CCCC2)O1)CC(=O)O | [N:1]#[C:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][C:12]2([CH2:13][CH2:14][CH2:15][CH2:16]2)[O:17]1>>[NH2:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][C:12]2([CH2:13][CH2:14][CH2:15][CH2:16]2)[O:17]1 | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 | NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 | null | null | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1COC2(CCCC2)OC1 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | 47.2 | [{"value": 47.2, "product": "NCC[C@@H]1C[C@@H](OC2(CCCC2)O1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | A solution of 1.17 g (4.88 mmol) of (±)-cis-9-(cyanomethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid in 100 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.53 g of water wet Raney nickel #30. The solution is heated at 45° C. and 50 pounds per square inch gage (psig) hydroge... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1COC2(CCCC2)OC1 | null | CO | 45 | null | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1>CO>NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6f25c4a0dd794e09a3182580f1de7326 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OC2(CCCC2)O1)CC(=O)O.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.C(C)OCC.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1.O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]C2(CCCC2)[O:36]1)=[O:39]>>[CH3:1]... | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | null | null | CS(=O)C.O | Aromatic Heterocycle Formation | OtherReaction | be140d0447bff97f3d0e9a2a60dc4fa87a6c1365f48aa4d58a6357efba451fc6 | ace646bda34ee0b7f86eba46d7406afcd515b387b9aae1bd99ad77336c2c1802 | O=C1CCC[C@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7]-[C:8]-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-C2(-C-C-C-C-2)-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26]:[c:27... | 24.7 | [{"value": 24.7, "product": "FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 3 | HOUR | A solution of 0.295 g (1.21 mmol) of (±)-cis-9-(2-aminoethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid and 0.504 g (1.20 mmol) of (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers in 5 mL of dimethyl sulfoxide is heated at... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone.Ether.Ether.Primary amine | Ester.Secondary alcohol | C1COC2(CCCC2)OC1 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | CS(=O)C.O | 105 | 3 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCC2)O1>CS(=O)C.O>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f5b0f028a854ac0a60d81cd2b219033 | C=CC[C@@H]1C[C@H](CC#N)OC2(CCCCC2)O1>>N#CC[C@H]1C[C@@H](CC=O)OC2(CCCCC2)O1 | C(C=C)[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC#N.O=[O+][O-].O=[O+][O-]>>O=CC[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC#N | C=[CH:8][CH2:7][C@@H:6]1[CH2:5][C@H:4]([CH2:3][C:2]#[N:1])[O:17][C:11]2([O:10]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2>>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][C@@H:6]([CH2:7][CH:8]=[O:9])[O:10][C:11]2([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[O:17]1 | C=CC[C@@H]1C[C@H](CC#N)OC2(CCCCC2)O1 | N#CC[C@H]1C[C@@H](CC=O)OC2(CCCCC2)O1 | null | null | ClCCl | Oxidation | Alkene oxidation to aldehyde | bba9eb9a112fc7573e22f83c2d00d38db23db9bd0c71632ed02baac3559c409c | 32819d6b5381845ad0bcd88c90cc74f19ec27991c6c1ce562774976396f3fe8e | C1CCC2(CC1)OCCCO2 | C=[CH;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[CH;D2;+0:1]=[O;D1;H0:5] | null | [] | null | null | null | null | A solution of (±)-cis-4-(2-propenyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile 4.26 g (19.42 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsbach generator, flow rate 0.1, voltage=90 V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone a... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Aldehyde | null | null | C1CCC2(CC1)OCCCO2 | null | ClCCl | null | null | C=CC[C@@H]1C[C@H](CC#N)OC2(CCCCC2)O1>ClCCl>N#CC[C@H]1C[C@@H](CC=O)OC2(CCCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3d84a1c79e4c48b59df80afeab5d15aa | N#CC[C@H]1C[C@@H](CC=O)OC2(CCCCC2)O1>>N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O.O=CC[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC#N.C(C)OCC>>C(#N)C[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)O | [N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][C@@H:6]([CH2:7][CH:8]=[O:9])[O:11][C:12]2([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[O:18]1>>[N:1]#[C:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][C:12]2([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[O:18]1 | N#CC[C@H]1C[C@@H](CC=O)OC2(CCCCC2)O1 | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | null | null | CC(=O)C | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | C1CCC2(CC1)OCCCO2 | [#8:1]-[C:2]-[C:3]-[CH;D2;+0:4]=[O;D1;H0:5]>>[#8:1]-[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | 15 | MINUTE | Jones reagent (chromium trioxide-sulfuric acid-water), 4.4 mL (8.85 mmol), is added dropwise to a 0° C. solution of (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile, 3.62 g (12.6 mmol), dissolved in 30 mL of acetone until the orange color is not discharged. After stirring a further 15 minutes, the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | C1CCC2(CC1)OCCCO2 | Other | CC(=O)C | null | 0.25 | N#CC[C@H]1C[C@@H](CC=O)OC2(CCCCC2)O1>CC(=O)C>N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8789da92b4ea432e916d981dc13d4073 | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1>>NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | [H][H].O.C(#N)C[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)O.N>>NCC[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)O | [N:1]#[C:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][C:12]2([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[O:18]1>>[NH2:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][C:12]2([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[O:18]1 | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | null | null | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1CCC2(CC1)OCCCO2 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | 40 | CELSIUS | null | null | A solution of 0.13 g of (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid in 20 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.2 g of water wet Raney nickel #30. The solution is heated at 40° C. and 50 pounds per square inch gage (psig) hydrogen pressure fo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CCC2(CC1)OCCCO2 | null | CO | 40 | null | N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1>CO>NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d79d449b7efe4df5a170b24db9b08aad | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)O.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.CS(=O)C.C(C)OCC.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1.O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]C2(CCCCC2)[O:36]1)=[O:39]>>[CH3:1... | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 7d01b623edaf1c3d7cd7c69ac8d3ee9743a084246dd99d36b63801a27961305b | ace646bda34ee0b7f86eba46d7406afcd515b387b9aae1bd99ad77336c2c1802 | O=C1CCC[C@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7]-[C:8]-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-C2(-C-C-C-C-C-2)-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26]:[c:... | null | [] | 105 | CELSIUS | 3 | HOUR | A solution of 0.31 g (1.21 mmol) of (±)-cis-4-(2-aminoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid and 0.504 g (1.20 mmol) of (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers in 5 mL of dimethyl sulfoxide is heated at... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone.Ether.Ether.Primary amine | Ester.Secondary alcohol | C1CCC2(CC1)OCCCO2 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | O | 105 | 3 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1>O>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-148fb88f54bc47f586ea0de1d06b0d0a | C=CC[C@@H](O)C[C@@H]1CO1.CC(C)O.[C-]#N>>C=CC[C@@H]1C[C@H](CC#N)OCO1 | C(C)(C)O.[C-]#N.[K+].C(C=C)[C@H](C[C@H]1OC1)O.O>>C(C=C)[C@@H]1C[C@@H](OCO1)CC#N | [CH2:1]=[CH:2][CH2:3][C@H:4]([CH2:5][C@H:6]1[O:10][CH2:11]1)[OH:12].CC(O)[CH3:7].[C-:8]#[N:9]>>[CH2:1]=[CH:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8]#[N:9])[O:10][CH2:11][O:12]1 | C=CC[C@@H](O)C[C@@H]1CO1.CC(C)O.[C-]#N | C=CC[C@@H]1C[C@H](CC#N)OCO1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4c15f157a12f53c42684a56c8c1dc0ee43b25d3db1e9bf3482f1a71033594b9c | b2727f0507fdca4a006da10729db27fe4375933b6c39a949f86c89c9d12de99b | C1COCOC1 | C-C(-O)-[CH3;D1;+0:1].[C-;H0;D1:2]#[N;D1;H0:3].[C;D1;H2:4]=[C:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]-[C@H;D3;+0:10]1-[#8:11]-[CH2;D2;+0:12]-1>>[C;D1;H2:4]=[C:5]-[C:6]-[C:7]1-[C:9]-[C@H;D3;+0:10](-[CH2;D2;+0:1]-[C;H0;D2;+0:2]#[N;D1;H0:3])-[#8:11]-[CH2;D2;+0:12]-[O;H0;D2;+0:8]-1 | null | [] | null | null | 20 | HOUR | Potassium cyanide, 1.3 g (20 mmol) is added to a room temperature solution of (R*,R*)-α-2-propenyloxiraneethanol, 2.56 g (20 mmol), in 25 mL of 4:1 isopropanol:water. The solution is stirred for 20 hours at ambient temperature, concentrated, and partitioned between ethyl acetate and brine. The aqueous layer is extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Secondary alcohol | Ether.Ether.Nitrile | C1CO1 | C1COCOC1 | C1COCOC1 | HO- | null | null | 20 | C=CC[C@@H](O)C[C@@H]1CO1.CC(C)O.[C-]#N>>C=CC[C@@H]1C[C@H](CC#N)OCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fd5a9b495e42491992d07ec5b729edec | C=CC[C@@H]1C[C@H](CC#N)OCO1>>N#CC[C@H]1C[C@@H](CC=O)OCO1 | C(C=C)[C@@H]1C[C@@H](OCO1)CC#N.O=[O+][O-].O=[O+][O-]>>O=CC[C@@H]1C[C@@H](OCO1)CC#N | C=[CH:8][CH2:7][C@@H:6]1[CH2:5][C@H:4]([CH2:3][C:2]#[N:1])[O:12][CH2:11][O:10]1>>[N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][C@@H:6]([CH2:7][CH:8]=[O:9])[O:10][CH2:11][O:12]1 | C=CC[C@@H]1C[C@H](CC#N)OCO1 | N#CC[C@H]1C[C@@H](CC=O)OCO1 | null | null | ClCCl | Oxidation | Alkene oxidation to aldehyde | bba9eb9a112fc7573e22f83c2d00d38db23db9bd0c71632ed02baac3559c409c | 32819d6b5381845ad0bcd88c90cc74f19ec27991c6c1ce562774976396f3fe8e | C1COCOC1 | C=[CH;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[CH;D2;+0:1]=[O;D1;H0:5] | null | [] | null | null | null | null | A solution of (±)-cis-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 2.57 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsback generator, flow rate 0.1, voltage=90V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone appears. The curr... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Aldehyde | null | null | C1COCOC1 | null | ClCCl | null | null | C=CC[C@@H]1C[C@H](CC#N)OCO1>ClCCl>N#CC[C@H]1C[C@@H](CC=O)OCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bb6410a0138c4ef592942e2835802a42 | N#CC[C@H]1C[C@@H](CC=O)OCO1>>N#CC[C@@H]1C[C@H](CC(=O)O)OCO1 | CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O.O=CC[C@@H]1C[C@@H](OCO1)CC#N.C(C)OCC>>C(#N)C[C@@H]1C[C@@H](OCO1)CC(=O)O | [N:1]#[C:2][CH2:3][C@H:4]1[CH2:5][C@@H:6]([CH2:7][CH:8]=[O:9])[O:11][CH2:12][O:13]1>>[N:1]#[C:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][CH2:12][O:13]1 | N#CC[C@H]1C[C@@H](CC=O)OCO1 | N#CC[C@@H]1C[C@H](CC(=O)O)OCO1 | null | null | CC(=O)C | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | C1COCOC1 | [#8:1]-[C:2]-[C:3]-[CH;D2;+0:4]=[O;D1;H0:5]>>[#8:1]-[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | 15 | MINUTE | Jones reagent (chromium trioxide-sulfuric acid-water), 3.8 mL (97.6 mmol), is added dropwise to a 0° C. solution of (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile, 1.29 g of (7.6 mmol), dissolved in 50 mL of acetone until the orange color is not discharged. After stirring a further 15 minutes, the mixture is poured ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | C1COCOC1 | Other | CC(=O)C | null | 0.25 | N#CC[C@H]1C[C@@H](CC=O)OCO1>CC(=O)C>N#CC[C@@H]1C[C@H](CC(=O)O)OCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8db5abab39714d1d91dcd9473866b68a | N#CC[C@@H]1C[C@H](CC(=O)O)OCO1>>NCC[C@@H]1C[C@H](CC(=O)O)OCO1 | [H][H].O.C(#N)C[C@@H]1C[C@@H](OCO1)CC(=O)O.N>>NCC[C@@H]1C[C@@H](OCO1)CC(=O)O | [N:1]#[C:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][CH2:12][O:13]1>>[NH2:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[O:11][CH2:12][O:13]1 | N#CC[C@@H]1C[C@H](CC(=O)O)OCO1 | NCC[C@@H]1C[C@H](CC(=O)O)OCO1 | null | null | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1COCOC1 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | 60.6 | [{"value": 60.6, "product": "NCC[C@@H]1C[C@@H](OCO1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | A solution of 1.04 g (4.88 mmol) of (±)-cis-6-(cyanomethyl)-1,3-dioxane-4-acetic acid in 100 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.53 g of water wet Raney nickel #30. The solution is heated at 45° C. and 50 pounds per square inch gage (psig) hydrogen pressure for ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1COCOC1 | null | CO | 45 | null | N#CC[C@@H]1C[C@H](CC(=O)O)OCO1>CO>NCC[C@@H]1C[C@H](CC(=O)O)OCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-43c757fdd37f476192371222c5749f23 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OCO1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OCO1)CC(=O)O.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.C(C)OCC.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1.O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]C[O:36]1)=[O:39]>>[CH3:1][CH:2]([... | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OCO1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | null | null | CS(=O)C.O | Aromatic Heterocycle Formation | OtherReaction | 88b1c3309521478299f2506a30fb0da7d9f074c0185ed180ecebc70534d06648 | ace646bda34ee0b7f86eba46d7406afcd515b387b9aae1bd99ad77336c2c1802 | O=C1CCC[C@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7]-[C:8]-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-C-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26]:[c:27])-[c;H0;D3;+... | 23.1 | [{"value": 23.1, "product": "FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 0.26 g (1.21 mmol) of (±)-cis-6-(2-aminoethyl)-1,3-dioxane-4-acetic acid and 0.504 g (1.20 mmol) of (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide in 5 mL of dimethyl sulfoxide is heated at 105° C. for 15 hours. The solution is cooled and poured into 100 mL of diethyl ether and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone.Ether.Ether.Primary amine | Ester.Secondary alcohol | C1COCOC1 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | CS(=O)C.O | null | 18 | CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1.NCC[C@@H]1C[C@H](CC(=O)O)OCO1>CS(=O)C.O>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eebe7f54970b4c3a9ecf4c7b08834f14 | CC(C)(C)O.CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | C(C)OCC.C(C)(C)(C)O.C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].O[C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]([CH3:17])([CH3:18])[O:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]([CH3:17])([CH3:18])[O:19]1 | CC(C)(C)O.CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | null | CN(C1=CC=NC=C1)C | ClCCl | Protection | Esterification of Carboxylic Acids | 4fc51e99c8d41e062b04286df301b17a66d11ed324f4ef1ad52af450df5a149f | 851ee0305feb435b96f77460f854d4a90e8c7d0255370fbd7595161a6919e7ab | C1COCOC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#8:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[OH;D1;+0:10]>>[#8:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:7](-[C;D1;H3:6])(-[C;D1;H3:8])-[C;D1;H3:9] | null | [] | 0 | CELSIUS | 1 | HOUR | (±)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid (3.72 g, 17.44 mmol) is dissolved in 20 mL of dichloromethane, cooled to 0° C. and 0.2 g of 4-dimethylaminopyridine (DMAP) is added, followed by t-butyl alcohol and followed by 4.32 g of dicyclohexylcarbodiimide (DCC). This solution is allowed to slowly war... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary alcohol | Ester | null | null | C1COCOC1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | 0 | 1 | CC(C)(C)O.CC1(C)O[C@H](CC#N)C[C@H](CC(=O)O)O1>CN(C1=CC=NC=C1)C.ClCCl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f47ec550a0f7471890c1276e6075351f | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.O1CCCC1.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@@H]1OC(C[C@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]C(C)(C)[O:36]1)=[O:39].O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 | null | null | O.CCCCCCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8e30b51508dc6a589cdd4f06c85afddd9a01bb1823227fed405ef8a23d32c02e | c5a8056bd33aab4597438c284a5d6d5fc73a7560d573a9ac4f0b77bcc8496ccc | O=C1CCC[C@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7]-[C:8]-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-C(-C)(-C)-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26... | null | [] | null | null | 15 | HOUR | A solution of 0.79 g (2.89 mmol) of (±)-cis-1,1-dimethylethyl 6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate and 100 g (2.41 mmol) of (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers in 15 mL of heptane:toluene (9:1)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Ether.Ether.Primary amine.Boc | Ester.Secondary alcohol | C1COCOC1 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | O.CCCCCCC.C1(=CC=CC=C1)C | null | 15 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>O.CCCCCCC.C1(=CC=CC=C1)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@H]1C[C@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4ca0d4ef21294daea3aab12bdb2f1584 | CC(C)(C)O.N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC2(CCCCC2)O1 | C(C)OCC.C(C)(C)(C)O.C(#N)C[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(#N)C[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)OC(C)(C)C | O[C:2]([CH3:1])([CH3:3])[CH3:4].[OH:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]2([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[O:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]2([CH2:17][CH2:18][CH2:19][CH2:20]... | CC(C)(C)O.N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC2(CCCCC2)O1 | null | CN(C1=CC=NC=C1)C | ClCCl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 8c7399ec7a66a3c3bd9f1d9ceec3ee066db60bfce981481cf69ec04cfba2490f | aef5ffd27f68a20e12653ba553f9902f02d63b7472857a6b9f2a20b4df464cc1 | C1CCC2(CC1)OCCCO2 | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4] | null | [] | 0 | CELSIUS | null | null | (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]-undecane-2-acetic acid 3.32 g (13.12 mmol), is dissolved in 15 mL of dichloromethane, cooled to 0° C. and 0.1 g of 4-dimethylaminopyridine (DMAP) added, followed y t-butyl alcohol, and followed by 3.25 g of dicyclohexylcarbodiimide (DCC). This solution is stirred and allowed ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary alcohol | Ester | null | null | C1CCC2(CC1)OCCCO2 | HO- | CN(C1=CC=NC=C1)C.ClCCl | 0 | null | CC(C)(C)O.N#CC[C@@H]1C[C@H](CC(=O)O)OC2(CCCCC2)O1>CN(C1=CC=NC=C1)C.ClCCl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC2(CCCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-59c9df81cc2c43c7970479ad5cc29ef6 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC2(CCCCC2)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC2(CCCCC2)O1 | C(#N)C[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)OC(C)(C)C.N.[H][H]>>NCC[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]2([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[O:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][CH2:13][NH2:14])[O:15][C:16]2([CH2:17][CH2:18][CH2:19][CH2:20]... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC2(CCCCC2)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC2(CCCCC2)O1 | null | O | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1CCC2(CC1)OCCCO2 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | 97.9 | [{"value": 97.9, "product": "NCC[C@@H]1C[C@@H](OC2(O1)CCCCC2)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | A solution of 1.19 g of (±)-cis-1,1-dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate in 30 mL of methanol saturated with gaseous ammonia is treated with 0.3 g of Raney nickel #30 and hydrogen gas in a shaker at 50 pounds per square inch gage (psig) and 40° C. After 22 hours, thin layer chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CCC2(CC1)OCCCO2 | null | O.CO | null | 22 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC2(CCCCC2)O1>O.CO>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC2(CCCCC2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a9e5e1fe7109474dbd63453d82efc8ef | CC(C)(C)OC(=O)CC(=O)C[C@@H](CC#N)O[Si](C)(C)C(C)(C)C>>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CC#N | O.C(C)OCC.C(#N)C[C@H](CC(CC(=O)OC(C)(C)C)=O)O[Si](C)(C)C(C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(#N)C[C@H](CC(CC(=O)OC(C)(C)C)=O)O | CC(C)(C)[Si](C)(C)[O:13][C@@H:12]([CH2:11][C:9]([CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:10])[CH2:14][C:15]#[N:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][C:15]#[N:16] | CC(C)(C)OC(=O)CC(=O)C[C@@H](CC#N)O[Si](C)(C)C(C)(C)C | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CC#N | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | null | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5]=[O;D1;H0:6]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]=[O;D1;H0:6] | null | [] | 25 | CELSIUS | 5 | HOUR | A solution of crude (R)-1,1-dimethylethyl 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-oxohexanoate, 43 g (0.126 mol) in 350 mL of tetrahydrofuran is treated with 213 mL of tetrabutylammonium fluoride solution (1.0M in hexane). The resulting mixture is stirred for five hours, at 25° C. The mixture is treated wit... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | null | Other | O1CCCC1 | 25 | 5 | CC(C)(C)OC(=O)CC(=O)C[C@@H](CC#N)O[Si](C)(C)C(C)(C)C>O1CCCC1>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CC#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-865eace85c9646cbaf31c08ce3644c8c | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 | C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.N.[H][H]>>NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]([CH3:17])([CH3:18])[O:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][CH2:13][NH2:14])[O:15][C:16]([CH3:17])([CH3:18])[O:19]1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 | null | O | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1COCOC1 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | 16 | HOUR | A solution of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, 5.63 g (0.048 mol), in 100 mL of methanol saturated with gaseous ammonia is treated with 0.5 g of Raney nickel #30 and hydrogen gas in a shaker at 50 psi and 40° C. After 16 hours, thin layer chromatography indicates no starting ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1COCOC1 | null | O.CO | null | 16 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1>O.CO>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5d1fb43493194994b3fb3fa44d28474b | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 | NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.CC(C)O>>FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)CC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [NH2:30][CH2:31][CH2:32][C@@H:33]1[CH2:34][C@H:35]([CH2:36][C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])[O:44][C:45]([CH3:46])([CH3:47])[O:48]1.O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 | null | null | CCCCCCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Paal-Knorr pyrrole synthesis | 0cb7b72300a2af7a2e4398a0e1226bb84c0d31edad76ec86c7b51828dc8686b6 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | O=C(Nc1ccccc1)c1cn(CC[C@@H]2CCOCO2)c(-c2ccccc2)c1-c1ccccc1 | O=[C;H0;D3;+0:1](-[CH;D3;+0:2](-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7])-[C;H0;D3;+0:8](=O)-[C:9](-[C;D1;H3:10])-[C;D1;H3:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16])-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21].[C:22]-[C:23]-[NH2;D1;+0:24]>>[C:22]-[C:23]-[n;H0;D3;+0:24]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:17](... | null | [] | 25 | CELSIUS | null | null | A solution of (4R-cis)-1,1-dimethylethyl 6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate, 1.36 g (4.97 mol), and (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-R*,S*)] isomers, 1.60 g (3.83 mol), in 50 mL of heptane:toluene (9:1) is... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1COCOC1 | HO- | CCCCCCC.C1(=CC=CC=C1)C | 25 | null | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>CCCCCCC.C1(=CC=CC=C1)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a22068dde3f64fe48a2a34a4a7864cd6 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 | Cl.FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)CC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.O.[OH-].[Na+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@H]1OC(C[C@@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][n:30]2[c:4]([CH:2]([CH3:1])[CH3:3])[c:5]([C:6](=[O:7])[NH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]2-[c:23]2[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]2)[O:40]C(C)(C)[O:36]1)=[O:39]>>[CH3:1][... | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 | null | null | CCCCCC.O1CCCC1 | Miscellaneous | OtherReaction | 331994fd8e639d29fc7a16add5b5f6f47a3c59657b0788aa6b7a1cd453f92f60 | eaf9ff0dd775730c6c8ccf2086d6439c1ce5c44eec4da6accb69dd5bbb357c39 | O=C1CCC[C@@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-C(-C)(-C)-[O;H0;D2;+0:9]-1>>[C:7]-[C:6]1-[C:5]-[C:4](-[OH;D1;+0:9])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-1 | null | [] | null | null | 15 | HOUR | (4R-cis)-1,1-dimethylethyl 6-[2[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate, 4.37 g (6.68 mol), is dissolved in 200 mL of tetrahydrofuran and 15 mL of 10% hydrochloric acid solution is added, and the solution is stirred for 15 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Boc | Ester.Secondary alcohol | C1COCOC1 | C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | CCCCCC.O1CCCC1 | null | 15 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1>CCCCCC.O1CCCC1>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-53fb6f3762fe40c2ae2679984d4a93f8 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.O1CCCC1.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@H]1OC(C[C@@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]C(C)(C)[O:36]1)=[O:39].O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 | null | null | O.CCCCCCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8e30b51508dc6a589cdd4f06c85afddd9a01bb1823227fed405ef8a23d32c02e | c5a8056bd33aab4597438c284a5d6d5fc73a7560d573a9ac4f0b77bcc8496ccc | O=C1CCC[C@@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7]-[C:8]-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-C(-C)(-C)-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26... | null | [] | null | null | 15 | HOUR | A solution of (4R-cis)-1,1-dimethylethyl 6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate, 2.56 g (9.36 mol), and (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers, 3.00 g (7.20 mol), in 60 mL of heptane:toluene (9:1) i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Ether.Ether.Primary amine.Boc | Ester.Secondary alcohol | C1COCOC1 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | O.CCCCCCC.C1(=CC=CC=C1)C | null | 15 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>O.CCCCCCC.C1(=CC=CC=C1)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2c45a2c2970649979f6c2d88874662a4 | C=CC(=O)CC.O=Cc1ccc(F)cc1>>CCC(=O)CCC(=O)c1ccc(F)cc1 | FC1=CC=C(C=O)C=C1.C(=C)C(=O)CC.C(C)N(CC)CC>>FC1=CC=C(C=C1)C(CCC(CC)=O)=O | [CH3:1][CH2:2][C:3](=[O:4])[CH:5]=[CH2:6].[CH:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1 | C=CC(=O)CC.O=Cc1ccc(F)cc1 | CCC(=O)CCC(=O)c1ccc(F)cc1 | null | [Cl-].C(C1=CC=CC=C1)[N+]1=CSC(=C1C)CCO | C(C)OCC | C-C Coupling | Acylation of olefines by aldehydes | c7cfa402c5dba245be96fb0ab888132f858fc0df8133b39d8b17de638426e44f | 7c62a6cffe84f664611abcf0f91a6dfe1822a07a4e9371e0ae14bdfbffbb0037 | c1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[O;D1;H0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[c:8](:[c:9]):[c:10] | 89.5 | [{"value": 89.5, "product": "FC1=CC=C(C=C1)C(CCC(CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of 36.61 g (295 mmol) of 4-fluorobenzaldehyde, 25 g (297.2 mmol) of ethyl vinyl ketone, 29 mL (206.9 mmol) of triethylamine and 11.94 g (44.25 mmol) of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride is stirred and heated at 70° C. for six hours. The cooled solution is diluted with 2 liters of diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Vinyl | Ketone.Ketone | null | null | c1ccccc1 | null | [Cl-].C(C1=CC=CC=C1)[N+]1=CSC(=C1C)CCO.C(C)OCC | 70 | null | C=CC(=O)CC.O=Cc1ccc(F)cc1>[Cl-].C(C1=CC=CC=C1)[N+]1=CSC(=C1C)CCO.C(C)OCC>CCC(=O)CCC(=O)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4d4999f4e3954bdd8280520fa3bb741e | COC(=O)CC(=O)C(C)C.Nc1ccccc1>>CC(C)C(=O)CC(=O)Nc1ccccc1 | NC1=CC=CC=C1.C1(=CC=CC=C1)C.CC(C(CC(=O)OC)=O)C.C(CN)N>>CC(C(CC(=O)NC1=CC=CC=C1)=O)C | CO[C:7]([CH2:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | COC(=O)CC(=O)C(C)C.Nc1ccccc1 | CC(C)C(=O)CC(=O)Nc1ccccc1 | null | null | O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C:5])=[O;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 157.4 | [{"value": 157.4, "product": "CC(C(CC(=O)NC1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A three-necked, 12-L round-bottom flash equipped with a mechanical stirrer, a thermometer and set up for distillation is charged with 2.6 L of toluene, 1.73 kg (12 mol) of methyl 4-methyl-3-oxopentanoate and 72 g (1.18 mol) of ethylene diamine. The mixture is heated to 80° C. and charged with 0.49 kg of aniline. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O | 80 | 16 | COC(=O)CC(=O)C(C)C.Nc1ccccc1>O>CC(C)C(=O)CC(=O)Nc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-12cc04c7756c400ea9f6a684f4b0a26c | O=C(N[C@@H](Cc1cn(C(=O)OCc2ccccc2)cn1)C(=O)O)OCc1ccccc1.c1ccc(N2CCNCC2)cc1>>O=C(N[C@@H](Cc1c[nH]cn1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 | C1(CCCCC1)N=C=NC1CCCCC1.C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CN(C=N1)C(=O)OCC1=CC=CC=C1)C(=O)O.C1(=CC=CC=C1)N1CCNCC1.ON1N=NC2=C1C=CC=C2>>C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CNC=N1)C(=O)N1CCN(CC1)C1=CC=CC=C1 | O=C(OCc1ccccc1)[n:8]1[cH:7][c:6]([CH2:5][C@H:4]([NH:3][C:2](=[O:1])[O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[C:11](O)=[O:12])[n:10][cH:9]1.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][nH:8][cH:9][n:10]1)[C:1... | O=C(N[C@@H](Cc1cn(C(=O)OCc2ccccc2)cn1)C(=O)O)OCc1ccccc1.c1ccc(N2CCNCC2)cc1 | O=C(N[C@@H](Cc1c[nH]cn1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 | null | null | O1CCCC1 | Acylation | OtherReaction | 2d4fa9de67f8516172a8ad5a8040e4b9cd8a899be3dee3e26f3b5bf27603798d | face37508b08df202202ccc41ac58b51abeb084067a6e34d8ef463ce96851537 | O=C(N[C@@H](Cc1c[nH]cn1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C:7]-[c:8]1:[#7;a:9]:[c:10]:[n;H0;D3;+0:11](-C(=O)-O-C-c2:c:c:c:c:c:2):[c:12]:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C:7]-[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1)-[N;H0;D... | 90.6 | [{"value": 90.6, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CNC=N1)C(=O)N1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 7.13 g of N,N'-dibenzyloxycarbonyl histidine, 3.00 g of 4-phenylpiperazine and 16.1 g of N-hydroxybenzotriazole were dissolved in 100 ml of tetrahydrofuran, and to the mixture was added 3.84 g of DCC (dicyclohexylcarbodiimide), and the whole was stirred at a room temperature for three hours. An insoluble matter was fil... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Secondary amine | Tertiary amide | c1ccccc1.c1c[nH]cn1.C1CNCC[NH]1 | c1c[nH]cn1.C1C[NH]CC[NH]1 | c1c[nH]cn1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 3 | O=C(N[C@@H](Cc1cn(C(=O)OCc2ccccc2)cn1)C(=O)O)OCc1ccccc1.c1ccc(N2CCNCC2)cc1>O1CCCC1>O=C(N[C@@H](Cc1c[nH]cn1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2441e4247d98489c8f8cd66875c8b08f | CI.O=S(=O)(NC(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)c1cccc2cnccc12>>CN(C(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)S(=O)(=O)c1cccc2cnccc12 | [Cl-].[Na+].[H-].[Na+].C(C1=CC=CC=C1)OC=1C=C(C=CC1OCC1=CC=CC=C1)CC(CN1CCN(CC1)C1=CC=CC=C1)NS(=O)(=O)C=1C=2C=CN=CC2C=CC1.CI>>C(C1=CC=CC=C1)OC=1C=C(C=CC1OCC1=CC=CC=C1)CC(CN1CCN(CC1)C1=CC=CC=C1)N(S(=O)(=O)C=1C=2C=CN=CC2C=CC1)C | I[CH3:1].[NH:2]([CH:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26]1)[CH2:27][N:28]1[CH2:29][CH2:30][N:31]([c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH2:38][CH2:39]1)[S:40](=[O:41])(=[O:42])[c:43]1[cH:... | CI.O=S(=O)(NC(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)c1cccc2cnccc12 | CN(C(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)S(=O)(=O)c1cccc2cnccc12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | O=S(=O)(NC(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)c1cccc2cnccc12 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[C:4])-[NH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9]>>[C:2]-[C:3](-[C:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9] | null | [] | null | null | 2 | HOUR | 470 mg of the amorphous compound obtained in Example 5 was dissolved in 8 ml of dimethylformamide, and to the solution were sequentially added 30 mg of 60% sodium hydride and 0.1 ml of methyl iodide with ice cooling, and after stirring for two hours with ice cooling was added saturated sodium chloride, and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2cnccc2c1 | HI | CN(C=O)C | null | 2 | CI.O=S(=O)(NC(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)c1cccc2cnccc12>CN(C=O)C>CN(C(Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)CN1CCN(c2ccccc2)CC1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0c1d03dbfb5143ad8ea1cfcb08c5adee | O=S(=O)(c1cccc2cnccc12)N1Cc2cc(OCc3ccccc3)c(OCc3ccccc3)cc2CC1CN1CCN(c2ccccc2)CC1>>O=S(=O)(c1cccc2cnccc12)N1Cc2cc(O)c(O)cc2CC1CN1CCN(c2ccccc2)CC1 | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC=1C=C2CC(N(CC2=CC1OCC1=CC=CC=C1)S(=O)(=O)C=1C=2C=CN=CC2C=CC1)CN1CCN(CC1)C1=CC=CC=C1.C(CS)S.B(F)(F)F.C(C)OCC>>OC=1C=C2CC(N(CC2=CC1O)S(=O)(=O)C=1C=2C=CN=CC2C=CC1)CN1CCN(CC1)C1=CC=CC=C1 | c1ccc(C[O:19][c:18]2[cH:17][c:16]3[c:23]([cH:22][c:20]2[O:21]Cc2ccccc2)[CH2:24][CH:25]([CH2:26][N:27]2[CH2:28][CH2:29][N:30]([c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[CH2:37][CH2:38]2)[N:14]([S:2](=[O:1])(=[O:3])[c:4]2[cH:5][cH:6][cH:7][c:8]4[cH:9][n:10][cH:11][cH:12][c:13]24)[CH2:15]3)cc1>>[O:1]=[S:2](=[O:3])([c:4]... | O=S(=O)(c1cccc2cnccc12)N1Cc2cc(OCc3ccccc3)c(OCc3ccccc3)cc2CC1CN1CCN(c2ccccc2)CC1 | O=S(=O)(c1cccc2cnccc12)N1Cc2cc(O)c(O)cc2CC1CN1CCN(c2ccccc2)CC1 | null | null | null | Deprotection | OtherReaction | f744074d10c724c5b18eb44012443c5df4595a47d8bdf76894f2a5c694f524a1 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=S(=O)(c1cccc2cnccc12)N1Cc2ccccc2CC1CN1CCN(c2ccccc2)CC1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4](-[OH;D1;+0:5]):[c:6] | 90.9 | [{"value": 90.9, "product": "OC=1C=C2CC(N(CC2=CC1O)S(=O)(=O)C=1C=2C=CN=CC2C=CC1)CN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To 314 mg of the amorphous compound obtained in Example 9, were added 2 ml of 1,2-ethanedithiol and 1 ml of boron trifluoride/ethyl ether, and the mixture was stirred at a room temperature for 18 hours. After the addition of saturated sodium bicarbonate aqueous solution, the reaction mixture was extracted twice with a ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1 | null | c1ccc2cnccc2c1.c1ccc2c(c1)CC[NH]C2.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | 18 | O=S(=O)(c1cccc2cnccc12)N1Cc2cc(OCc3ccccc3)c(OCc3ccccc3)cc2CC1CN1CCN(c2ccccc2)CC1>>O=S(=O)(c1cccc2cnccc12)N1Cc2cc(O)c(O)cc2CC1CN1CCN(c2ccccc2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-16583531d898465db747873666a6aa4e | O=C(Cl)OCc1ccccc1.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCNCC1>>O=C(OCc1ccccc1)N1CCN(C(=O)[C@H](Cc2ccc(O)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | [OH-].[Na+].C(C1=CC=CC=C1)OC(=O)Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCNCC1.[Cl-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C([C@@H](NS(=O)(=O)C=1C=2C=CN=CC2C=CC1)CC1=CC=C(C=C1)O)=O | Cl[C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O=S(=O)(c1cccc2cnccc12)[O:23][c:22]1[cH:21][cH:20][c:19]([CH2:18][C@@H:17]([C:15]([N:14]2[CH2:13][CH2:12][NH:11][CH2:41][CH2:40]2)=[O:16])[NH:26][S:27](=[O:28])(=[O:29])[c:30]2[cH:31][cH:32][cH:33][c:34]3[cH:35][n:36][cH:37][cH:38][c:39]23)[cH:25][cH:24]... | O=C(Cl)OCc1ccccc1.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCNCC1 | O=C(OCc1ccccc1)N1CCN(C(=O)[C@H](Cc2ccc(O)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | null | null | CO.C(Cl)Cl.C(C)N(CC)CC | Protection | OtherReaction | 74491e7e365d1314990983903fc89d7e6cdc1c09a73539b20abca4de23c0646a | 28ff281c3e3fc46a7dddb8d384a774915d7a6ef6e28045ced9c2e6e6d5a0e8cb | O=C(OCc1ccccc1)N1CCN(C(=O)[C@H](Cc2ccccc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O=S(=O)(-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8])-c1:c:c:c:c2:c:n:c:c:c:1:2.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 620 mg of the crude product obtained in Example 28 was dissolved in 10 ml of methylene chloride, and to the solution were sequentially added 0.29 ml of benzyloxycarbonyl chloride and 3.04 ml of triethylamine with ice cooling. After stirring for two hours with ice cooling, 40 ml of saturated sodium chloride aqueous solu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine.Sulfonate | Carbamic ester.Ether.Aromatic alcohol | c1ccc2cnccc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2cnccc2c1 | HCl | CO.C(Cl)Cl.C(C)N(CC)CC | null | null | O=C(Cl)OCc1ccccc1.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCNCC1>CO.C(Cl)Cl.C(C)N(CC)CC>O=C(OCc1ccccc1)N1CCN(C(=O)[C@H](Cc2ccc(O)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0c3b815bf40646aca5a9b9a17bb5ca53 | BrCCCc1ccccc1.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCNCC1>>O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCNCC1.C1(=CC=CC=C1)CCCBr.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[Cl-].[Na+]>>C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCN(CC1)CCCC1=CC=CC=C1 | Br[CH2:43][CH2:44][CH2:45][c:46]1[cH:47][cH:48][cH:49][cH:50][cH:51]1.[O:1]=[C:2]([C@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH:20][cH:21][c:22]23)[cH:23][cH:24]1)[NH:25][S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][cH:32][c:33]2[cH:34][n:35][cH:... | BrCCCc1ccccc1.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCNCC1 | O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 60.5 | [{"value": 60.5, "product": "C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCN(CC1)CCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 7 | HOUR | 301 mg of the crude product obtained in Example 28 and 95 mg of 3-phenylpropyl bromide were dissolved in 5 ml of dimethylformamide, and to the solution were added 66 mg of potassium carbonate and 72 mg of sodium iodide. After stirring at 80° C. for 7 hours, 30 ml of saturated sodium chloride was added to the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccc2cnccc2c1.c1ccc2cnccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | CN(C=O)C | 80 | 7 | BrCCCc1ccccc1.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCNCC1>CN(C=O)C>O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-80b7e70c04c844d5ac70fc67f35ff99e | O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1>>O=C([C@H](Cc1ccc(O)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCN(CC1)CCCC1=CC=CC=C1.[OH-].[K+].[Cl-].[Na+]>>C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1CCN(CC1)CCCC1=CC=CC=C1 | O=S(=O)(c1cccc2cnccc12)[O:9][c:8]1[cH:7][cH:6][c:5]([CH2:4][C@@H:3]([C:2](=[O:1])[N:26]2[CH2:27][CH2:28][N:29]([CH2:30][CH2:31][CH2:32][c:33]3[cH:34][cH:35][cH:36][cH:37][cH:38]3)[CH2:39][CH2:40]2)[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]3[cH:21][n:22][cH:23][cH:24][c:25]23)[cH:11][cH:10]1>>[O:1... | O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | O=C([C@H](Cc1ccc(O)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | null | null | CO | Reduction | OtherReaction | 8d3501a80697ea4890ac38f15ca267ef68b4b9c0548f46156239e85ec85dc664 | 755d4c7608355ba6558947cede05bc0a8af24b48bc69544e09fcab6bd629384a | O=C([C@H](Cc1ccccc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 | O=S(=O)(-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4])-c1:c:c:c:c2:c:n:c:c:c:1:2>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1CCN(CC1)CCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 216 mg of the amorphous compound obtained in Example 32 was dissolved in 3 ml of methanol, and to the solution was added 0.6 ml of 2N potassium hydroxide aqueous solution. The mixture was refluxed for 10 hours, and after the addition of 30 ml of saturated sodium chloride aqueous solution, extracted twice with 20 ml of ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonate | Aromatic alcohol | c1ccc2cnccc2c1 | null | c1ccccc1.c1ccc2cnccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CO | null | null | O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1>CO>O=C([C@H](Cc1ccc(O)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(CCCc2ccccc2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f41e3820ade4440f8c53eb3a40debdc7 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.c1ccc(N2CCNCC2)cc1>>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCN(c2ccccc2)CC1 | C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O.C1(=CC=CC=C1)N1CCNCC1.ON1N=NC2=C1C=CC=C2.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1CCN(CC1)C1=CC=CC=C1 | O[C:18]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1)=[O:19].[NH:20]1[CH2:21][CH2:22][N:23]([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][... | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.c1ccc(N2CCNCC2)cc1 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCN(c2ccccc2)CC1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCc1ccccc1)N1CCN(c2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:... | 134.2 | [{"value": 134.2, "product": "C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 19.7 g of N-(tert-butoxycarbonyl)tyrosine, 12.5 g of N-phenylpiperazine and 16.1 g of N-hydroxybenzotriazole were dissolved in 100 ml of tetrahydrofuran, and to the solution was added dropwise a solution of 18.7 g of DCC in 50 ml of tetrahydrofuran for 20 minutes with ice cooling, and the mixture was stirred for one ho... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O1CCCC1 | null | 1 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.c1ccc(N2CCNCC2)cc1>O1CCCC1>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCN(c2ccccc2)CC1 |
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