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-27586a11f84249d2aead91f87b678a79 | O=[N+]([O-])c1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1>>Nc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)[N+](=O)[O-]>>S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([S:6][C@@H:7]2[S:8][CH2:9][C@@H:10]([OH:11])[C@H:12]([OH:13])[C@H:14]2[OH:15])[cH:16][cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([S:6][C@@H:7]2[S:8][CH2:9][C@@H:10]([OH:11])[C@H:12]([OH:13])[C@H:14]2[OH:15])[cH:16][cH:17]1 | O=[N+]([O-])c1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | Nc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | [Pd].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(S[C@H]2CCCCS2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.7, "product": "S([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 170 mg of 10% palladium-on-charcoal are added to a solution of 1.7 g (5.61.10-3 mol) of 4-nitrophenyl 1,5-dithio-β-D-xylopyranoside in 150 ml of methanol. The reaction medium is kept under hydrogen pressure (3.5.105Pa) at room temperature for 3 days. Repeat amounts of 170 mg of 10% palladium-on-charcoal are added after... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCSCC1 | Other | [Pd].[Pd].CO | null | 24 | O=[N+]([O-])c1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1>[Pd].[Pd].CO>Nc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2f66ead790264f6bbe1372504f543aaf | CC(=O)Nc1ccc(S)cc1.CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O>>CC(=O)Nc1ccc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 | SC1=CC=C(C=C1)NC(C)=O.C(C)(=O)O[C@H]1C(SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)NC(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([SH:9])[cH:28][cH:29]1.Br[CH:10]1[S:11][CH2:12][C@@H:13]([O:14][C:15]([CH3:16])=[O:17])[C@H:18]([O:19][C:20]([CH3:21])=[O:22])[C@H:23]1[O:24][C:25]([CH3:26])=[O:27]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][C@@H:10]2[S:11][CH2:12][C@@H:13]([O:14][C:15]([C... | CC(=O)Nc1ccc(S)cc1.CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O | CC(=O)Nc1ccc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 | null | [O-2].[Zn+2] | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 41eb4169cc1c426d43dc569580dd0ec8565a8304594e4280ca11b9ad92e50932 | ae759e6442d3a6ef2ad31108cf75640407a35bdd782f9ee6223a83f3ea914aca | c1ccc(S[C@H]2CCCCS2)cc1 | Br-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 25 | [{"value": 25.0, "product": "C(C)(=O)O[C@H]1[C@H](SC2=CC=C(C=C2)NC(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation IV is followed starting from 4.5 g (27.10-3 mol) of N-(4-mercaptophenyl)acetamide, 11.43 g (32.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide and 2.16 g (27.10-3 mol) of zinc oxide (ZnO), 3 g (yield: 25%) of the expected product are obtained after recrystallizat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic thiol | Monosulfide.Monosulfide | C1CCSCC1 | C1CCSCC1 | c1ccccc1.C1CCSCC1 | HBr | [O-2].[Zn+2] | null | null | CC(=O)Nc1ccc(S)cc1.CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O>[O-2].[Zn+2]>CC(=O)Nc1ccc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4b2ec04873ae4d519d8ca8b0c0b1965c | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(O)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.C(C)O.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.OC1=CC=C(C#N)C=C1>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16]... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(O)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | null | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 112.5 | [{"value": 41.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 112.5, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 24 | HOUR | A suspension of 6.5 g (12.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6 g (50.4.10-3 mol) of 4-hydroxybenzonitrile, 6.9 g (50.5.10-3 mol) of zinc chloride and 4.4 g (25.1.10-3 mol) of silver imidazolate in 200 ml of anhydrous methylene chloride is stirred at 40° C., under an inert atmosphere, in... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(Cl)Cl | 40 | 24 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccc(O)cc1>[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-826a99c45042499d9978bfa9b6772ca8 | Br.CC(=O)OC1SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Br | Br.C(C)(=O)OC1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1>>C(C)(=O)O[C@H]1[C@@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br | [BrH:19].CC(=O)O[CH:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17][C@H:18]1[Br:19] | Br.CC(=O)OC1SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Br | null | null | C(C)(=O)O.ClC(C)Cl | Miscellaneous | OtherReaction | 085265934c9ef15b3d142dfe0968fcbc9f20210fa5f6b87db3345c06eb723ae8 | 7fd221d6bc550fece57899922371ca9708c83eef2486437d767760c6ef7433d1 | C1CCSCC1 | C-C(=O)-O-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[BrH;D0;+0:10]>>[Br;H0;D1;+0:10]-[C@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 39 | [{"value": 39.0, "product": "C(C)(=O)O[C@H]1[C@@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 3.50 ml of a 30% solution of hydrobromic acid in glacial acetic acid are added at 10° C. to a solution of 2.10 g (6.3.10-3 mol) of 1,2,3,4-tetra-O-acetyl-5-thio-D-xylopyranose in 10 cm3 of dichloroethane. After 2 to 3 h, the reaction medium is hydrolyzed, washed with a solution of sodium bicarbonate and dried over sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Monosulfide | Secondary halide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1 | HO- | C(C)(=O)O.ClC(C)Cl | null | 2.5 | Br.CC(=O)OC1SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O>C(C)(=O)O.ClC(C)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Br |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e7b03201d99f4d3da974587d2d9e325c | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1ccc(O)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | C(C)(=O)O[C@H]1C(SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.OC1=CC=C(C#N)C=C1>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[CH:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S... | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1ccc(O)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | null | [O-2].[Zn+2] | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 35 | [{"value": 35.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 48 | HOUR | A suspension of 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 4-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile is stirred at 50° C., under an inert atmosphere, in the presence of a molecular si... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2].C(C)#N.C1(=CC=CC=C1)C | 50 | 48 | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1ccc(O)cc1>[O-2].[Zn+2].C(C)#N.C1(=CC=CC=C1)C>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e496953e1a8048e29a65351a07d1384b | CC(=O)OC1SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](O)SC[C@H]1OC(C)=O | C(C1=CC=CC=C1)N.C(C)(=O)OC1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1>>C(C)(=O)O[C@H]1[C@@H](O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | CC(=O)[O:12][CH:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:15]([O:16][C:17]([CH3:18])=[O:19])[CH2:14][S:13]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:11]([OH:12])[S:13][CH2:14][C@H:15]1[O:16][C:17]([CH3:18])=[O:19] | CC(=O)OC1SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](O)SC[C@H]1OC(C)=O | null | null | CCOCC | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | C1CCSCC1 | C-C(=O)-[O;H0;D2;+0:1]-[CH;D3;+0:2](-[#16:3]-[C:4])-[C:5](-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[C:10]>>[C:4]-[#16:3]-[C@H;D3;+0:2](-[OH;D1;+0:1])-[C:5](-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[C:10] | 47.3 | [{"value": 47.0, "product": "C(C)(=O)O[C@H]1[C@@H](O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "C(C)(=O)O[C@H]1[C@@H](O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | 22 ml (0.2 mol) of benzylamine are added under an inert atmosphere to a solution of 15 g (44.8.10-3 mol) of 1,2,3,4-tetra-O-acetyl-5-thio-D-xylopyranose in 450 ml of ether. After 7 hours at room temperature (15°-25° C.), the reaction mixture is concentrated under reduced pressure and the residue is dissolved in methyle... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1CCSCC1 | HO- | CCOCC | null | 7 | CC(=O)OC1SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O>CCOCC>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](O)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aa359b71c3c249e1a1f6ac726e50d826 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](O)SC[C@H]1OC(C)=O.N#CC(Cl)(Cl)Cl>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O | ClC(C#N)(Cl)Cl.[H-].[Na+].C(C)(=O)O[C@H]1[C@@H](O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O>>ClC(C(O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1)=N)(Cl)Cl | [CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:11]([OH:12])[S:19][CH2:20][C@H:21]1[O:22][C:23]([CH3:24])=[O:25].[C:13](#[N:14])[C:15]([Cl:16])([Cl:17])[Cl:18]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:11]([O:12][C:13](=[NH:14])[C:15]([Cl:16])([Cl:17])[Cl:1... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](O)SC[C@H]1OC(C)=O.N#CC(Cl)(Cl)Cl | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O | null | null | C(Cl)Cl | Acylation | OtherReaction | 8045d30783d505e653fcb6064f74ac59e775d4240e5a26759512143eefde6598 | 2554d984b82cd13e50d59270df17cf414095f213aef52eb5729ce2a3821b08e4 | C1CCSCC1 | [C:1]-[#16:2]-[C:3](-[OH;D1;+0:4])-[C:5].[Cl;D1;H0:6]-[C:7](-[Cl;D1;H0:8])(-[Cl;D1;H0:9])-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]>>[C:1]-[#16:2]-[C:3](-[O;H0;D2;+0:4]-[C;H0;D3;+0:10](=[NH;D1;+0:11])-[C:7](-[Cl;D1;H0:6])(-[Cl;D1;H0:8])-[Cl;D1;H0:9])-[C:5] | 53 | [{"value": 53.0, "product": "ClC(C(O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1)=N)(Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1.5 ml (15.10-3 mol) of trichloroacetonitrile and 70 mg of NaH (2.3.10-3 mol of NaH in 80% dispersion) are added to a solution of 1 g (3.42.10-3 mol) of 2, 3, 4 -tri-O-acetyl-5-thio-α-D-xylopyranose in 10 ml of methylene chloride. After 4 h at room temperature, the reaction medium is filtered on silica in methylene chl... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary alcohol | Ether | null | null | C1CCSCC1 | null | C(Cl)Cl | null | 4 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](O)SC[C@H]1OC(C)=O.N#CC(Cl)(Cl)Cl>C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-418881fc22e24d458e9e207dc7692320 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.N#Cc1ccc(O)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | B(F)(F)F.CCOCC.ClC(C(O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1)=N)(Cl)Cl.OC1=CC=C(C#N)C=C1.C([O-])(O)=O.[Na+]>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | N=C(O[C@@H:18]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1)C(Cl)(Cl)Cl.[OH:19][c:20]1[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.N#Cc1ccc(O)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 124e7afba9b8d52fc6cf9e24391e7453a9dcf1dc136e30648f2cbe02023e495c | e2efce9d8711506057c2be6924214b8e9da82840eace9ffb369b9491121b942c | c1ccc(O[C@H]2CCCCS2)cc1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[C@H;D3;+0:1]1-[#16:2]-[C:3]-[C@@H;D3;+0:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C@H;D3;+0:9](-[#8:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C@H;D3;+0:14]-1-[#8:15]-[C:16](-[C;D1;H3:17])=[O;D1;H0:18].[OH;D1;+0:19]-[c:20](:[c:21]):[c:22]>>[C;D1;H3:7]-[C:6](=[O;D1;H0:8])-[#8:5]-[C@@H;D3;+0:4]1-... | 80 | [{"value": 80.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1 ml of a 0.1M solution of boron trifluoride etherate in methylene chloride is added at -15° C., under an inert atmosphere, to a suspension of 250 mg (0.57.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 57 mg (0.48.10-3 mol) of 4-hydroxybenzonitrile and a molecular sieve (1 nm) in 10 ml ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ester.Ester.Ester.Ether.Aromatic alcohol.Monosulfide | Ester.Ester.Ester.Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.N#Cc1ccc(O)cc1>C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-13743bab816c42d08511bed55df6ab1e | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1>>N#Cc1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | C[O-].[Na+].C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C#N | CC(=O)[O:12][C@@H:11]1[CH2:10][S:9][C@@H:8]([O:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]2)[C@H:15]([O:16]C(C)=O)[C@H:13]1[O:14]C(C)=O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][C@@H:8]2[S:9][CH2:10][C@@H:11]([OH:12])[C@H:13]([OH:14])[C@H:15]2[OH:16])[cH:17][cH:18]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1 | N#Cc1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 129.5 | [{"value": 73.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 129.5, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1.5 ml of a solution of sodium methylate in methanol (8% w/v of Na) are added under an inert atmosphere to a suspension of 10 g (25.4.10-3 mol) of 4-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in 200 ml of methanol. The reaction mixture is stirred at room temperature for 30 min, neutralized by the addition... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | 0.5 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C#N)cc1>CO>N#Cc1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b9a267834ffc4d2eb782eaa76b1e6127 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(O)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1 | C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.[N+](=O)([O-])C1=CC=C(C=C1)O>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:18]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(O)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1 | null | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+] | CCOCC.C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 87220374342126504d844a864c6a0b0615525a951864d2f2be70950a0d07a062 | fed42e8fc071443976795469c55fd4c60d2f3610547317310572a82f86f5f128 | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[C@H;D3;+0:1]1-[#16:2]-[C:3]-[C@@H;D3;+0:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C@H;D3;+0:9](-[#8:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C@H;D3;+0:14]-1-[#8:15]-[C:16](-[C;D1;H3:17])=[O;D1;H0:18].[OH;D1;+0:19]-[c:20](:[c:21]):[c:22]>>[C;D1;H3:7]-[C:6](=[O;D1;H0:8])-[#8:5]-[C@@H;D3;+0:4]1-[C:3]-[#16:2]-[C@@H;... | 25.2 | [{"value": 25.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.2, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 50 | CELSIUS | 48 | HOUR | A suspension of 5.6 g (15.8.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 2 g (14.3.10-3 mol) of 4-nitrophenol, 4 g (29.3.10-3 mol) of zinc chloride and 3.8 g (21.7.10-3 mol) of silver imidazolate in 80 ml of anhydrous methylene chloride is stirred at 50° C., under an inert atmosphere, in the absenc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Ester.Aromatic alcohol | Ester.Ester.Ester.Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].CCOCC.C(Cl)Cl | 50 | 48 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccc(O)cc1>[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].CCOCC.C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-14c101d07d4f4ec98d6975cff8caa0ec | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1>>O=[N+]([O-])c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | C[O-].[Na+].C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)[N+](=O)[O-] | CC(=O)[O:13][C@@H:12]1[CH2:11][S:10][C@@H:9]([O:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:19][cH:18]2)[C@H:16]([O:17]C(C)=O)[C@H:14]1[O:15]C(C)=O>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][C@@H:9]2[S:10][CH2:11][C@@H:12]([OH:13])[C@H:14]([OH:15])[C@H:16]2[OH:17])[cH:18][cH:19]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1 | O=[N+]([O-])c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 81.1 | [{"value": 79.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na) is added under an inert atmosphere to a suspension of 1.1 g (2.6.10-3 mol) of 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in 30 ml of methanol. After complete solubilization (2 h), the reaction mixture is neutralized by the addition of A... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1>CO>O=[N+]([O-])c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e92d2415ae14a2c94e457a5f31e7891 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 | OC1=CC=C(C=C1)C(C)=O.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][c:23]([C:24]([CH3:25])=[O:26])[cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.CC(=O)c1ccc(O)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 | null | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 18 | [{"value": 18.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIII is followed starting from 2 g (14.7.10-3 mol) of 1-(4-hydroxyphenyl)ethanone, 2.8 g (16.10-3 mol) of silver imidazolate, 5.74 g (16.1.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4 g (29.3.10-3 mol) of zinc chloride in 100 ml of methylene chlorid... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.CC(=O)c1ccc(O)cc1>[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-16997713f3d246619c9ee28f3feb0f62 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.CC(=O)c1ccc(O)cc1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 | B(F)(F)F.CCOCC.ClC(C(O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)CS1)=N)(Cl)Cl.OC1=CC=C(C=C1)C(C)=O>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | N=C(C(Cl)(Cl)Cl)[O:19][C@@H:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.O[c:20]1[cH:21][cH:22][c:23]([C:24]([CH3:25])=[O:26])[cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.CC(=O)c1ccc(O)cc1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | dc649d20eef2927edf81c95a955f14dfc8a1ac720f998fc6a553c232b1280c37 | ba4fde0d1cd80111aa55e2bc2dbd9b8f2f4ebccbc46388273591dfed5b7f9a67 | c1ccc(O[C@H]2CCCCS2)cc1 | Cl-C(-Cl)(-Cl)-C(=N)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[#16:4]-[C:5].O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[C:5]-[#16:4]-[C:2](-[O;H0;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-[C:3] | 47 | [{"value": 47.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXI is followed starting from 380 mg (0.882.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 100 mg (73.5.10-3 mol) of 1-(4-hydroxyphenyl)ethanone and 1.47 ml of a 0.1M solution of boron trifluoride etherate in methylene chloride, 140 mg (yield: ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | C1CCSCC1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(=N)C(Cl)(Cl)Cl)SC[C@H]1OC(C)=O.CC(=O)c1ccc(O)cc1>C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-91a405a4a3ab4efe98cbffeacbb1c9de | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1>>CC(=O)c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C(C)=O | CC(=O)[O:13][C@@H:12]1[CH2:11][S:10][C@@H:9]([O:8][c:7]2[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:19][cH:18]2)[C@H:16]([O:17]C(C)=O)[C@H:14]1[O:15]C(C)=O>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][C@@H:9]2[S:10][CH2:11][C@@H:12]([OH:13])[C@H:14]([OH:15])[C@H:16]2[OH:17])[cH:18][cH:19]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1 | CC(=O)c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 88.2 | [{"value": 88.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 0.9 g (2.2.10-3 mol) of 4-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.8 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 50 ml of methanol for 1 h, 0.55 g (yield: 88%) of the expected product is obt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc(C(C)=O)cc1>CO>CC(=O)c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fe312a64789d4aa28cb765688102371f | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.CC(=O)c1cccc(O)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1 | OC=1C=C(C=CC1)C(C)=O.C(C)(=O)O[C@H]1C(SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[CH:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([C:25]([CH3:26])=[O:27])[cH:28]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])... | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.CC(=O)c1cccc(O)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1 | null | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+] | C(C)#N.C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 14 | [{"value": 14.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.8, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIII is followed starting from 3.45 g (25.3.10-3 mol) of 1-(3-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(C)#N.C(Cl)Cl | null | null | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.CC(=O)c1cccc(O)c1>[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(C)#N.C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f98c4cda947409292d44698476dcbc5 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1>>CC(=O)c1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1 | C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC(=CC=C1)C(C)=O | CC(=O)[O:14][C@@H:13]1[CH2:12][S:11][C@@H:10]([O:9][c:8]2[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:19]2)[C@H:17]([O:18]C(C)=O)[C@H:15]1[O:16]C(C)=O>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][C@@H:10]2[S:11][CH2:12][C@@H:13]([OH:14])[C@H:15]([OH:16])[C@H:17]2[OH:18])[cH:19]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1 | CC(=O)c1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 85 | [{"value": 85.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC(=CC=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC(=CC=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 1.36 g (3.3.10-3 mol) of 3-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 50 ml of methanol for 30 min, 0.8 g (yield: 85%) of the expected product is ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1>CO>CC(=O)c1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-231454abe7284d98adfcccdd34ddb1a5 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1O>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N | OC1=C(C#N)C=CC=C1.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:18]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26]#[N:27]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1O | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N | null | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 87220374342126504d844a864c6a0b0615525a951864d2f2be70950a0d07a062 | fed42e8fc071443976795469c55fd4c60d2f3610547317310572a82f86f5f128 | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[C@H;D3;+0:1]1-[#16:2]-[C:3]-[C@@H;D3;+0:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C@H;D3;+0:9](-[#8:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C@H;D3;+0:14]-1-[#8:15]-[C:16](-[C;D1;H3:17])=[O;D1;H0:18].[OH;D1;+0:19]-[c:20](:[c:21]):[c:22]>>[C;D1;H3:7]-[C:6](=[O;D1;H0:8])-[#8:5]-[C@@H;D3;+0:4]1-[C:3]-[#16:2]-[C@@H;... | 20 | [{"value": 20.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIII is followed starting from 2 g (16.8.10-3 mol) of 2-hydroxybenzonitrile, 4.4 g (25.1.10-3 mol) of silver imidazolate, 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4.6 g (33.6.10-3 mol) of zinc chloride in 80 ml of methylene chloride, 1... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Ester.Aromatic alcohol | Ester.Ester.Ester.Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1ccccc1O>[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-77ee1249bab045feb3c459539c7d4d4c | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N>>N#Cc1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O | C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)C#N | CC(=O)[O:14][C@@H:13]1[CH2:12][S:11][C@@H:10]([O:9][c:8]2[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][cH:7]2)[C@H:17]([O:18]C(C)=O)[C@H:15]1[O:16]C(C)=O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][C@@H:10]1[S:11][CH2:12][C@@H:13]([OH:14])[C@H:15]([OH:16])[C@H:17]1[OH:18] | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N | N#Cc1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 88 | [{"value": 88.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 1.26 g (3.2.10-3 mol) of 2-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 70 ml of methanol for 30 min, 0.75 g (yield: 88%) of the expected product is ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N>CO>N#Cc1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9094a061a11242d6a707afb2325720a6 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(O)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 | OC=1C=C(C#N)C=CC1.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([C:25]#[N:26])[cH:27]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16]... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(O)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 | null | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[C@@H;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 33.3 | [{"value": 33.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.3, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIII is followed starting from 2 g (16.8.10-3 mol) of 3-hydroxybenzonitrile, 2.9 mg (16.5.10-3 mol) of silver imidazolate, 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4.6 g (33.6.10-3 mol) of zinc chloride in 80 ml of methylene chloride, ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.N#Cc1cccc(O)c1>[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-de6b93c29d3a4007a7f8a9a45c1c7379 | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1cccc(O)c1>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 | C(C)(=O)O[C@H]1C(SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br.OC=1C=C(C#N)C=CC1>>C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[CH:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([C:25]#[N:26])[cH:27]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S... | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1cccc(O)c1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 | null | [O-2].[Zn+2] | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 25 | [{"value": 25.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.9, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXVIII is followed starting from 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 3-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile, 138 mg (yield: 25%) o... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [O-2].[Zn+2].C(C)#N.C1(=CC=CC=C1)C | null | null | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.N#Cc1cccc(O)c1>[O-2].[Zn+2].C(C)#N.C1(=CC=CC=C1)C>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d279cfea5adb4eb4852a26d5438186a3 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1>>N#Cc1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1 | C(C)(=O)O[C@H]1[C@H](OC2=CC(=CC=C2)C#N)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC(=CC=C1)C#N | CC(=O)[O:13][C@@H:12]1[CH2:11][S:10][C@@H:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18]2)[C@H:16]([O:17]C(C)=O)[C@H:14]1[O:15]C(C)=O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][C@@H:9]2[S:10][CH2:11][C@@H:12]([OH:13])[C@H:14]([OH:15])[C@H:16]2[OH:17])[cH:18]1 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1 | N#Cc1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 85 | [{"value": 85.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC(=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC(=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 2.12 g (5.4.10-3 mol) of 3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 60 ml of methanol for 30 min, 1.22 g (yield: 85%) of the expected product are... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1>CO>N#Cc1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-06ef2526ca4b4e82962cc682dc5f8a8a | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1O>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC=C1)O.C(C)(=O)O[C@H]1[C@H](SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[C@@H:11]1[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:18]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[N+:26](=[O:27])[O-:28]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])... | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1O | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-] | null | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | efa8f35bda4476325bb3535cfd8fe78cdfb6d0688653fd2327c43441d9dc9381 | bfdd22690603596f7afca35a25168a5e45780ded8b67efe2d5aeb4048e6634ec | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[C@H;D3;+0:1]1-[S;H0;D2;+0:2]-[CH2;D2;+0:3]-[C@@H;D3;+0:4](-[O;H0;D2;+0:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9](-[#8:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C:14]-1-[#8:15]-[C:16](-[C;D1;H3:17])=[O;D1;H0:18].[OH;D1;+0:19]-[c:20](:[c:21]):[c:22]>>[C;D1;H3:7]-[C:6](=[O;D1;H0:8])-[O;H0;D2;+0:5]-[C@@H;D3;+0:1]1-[CH2;... | 15.3 | [{"value": 15.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | If the procedure described in Preparation LXXXIII is followed starting from 2 g (14.4.10-3 mol) of 2-nitrophenol, 2.5 g (14.2.10-3 mol) of silver imidazolate, 6 g (15.7.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4 g (29.3.10-3 mol) of zinc chloride in 80 ml of methylene chloride, 0.91 g (yield... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol.Monosulfide | Ester.Ether.Monosulfide | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O.O=[N+]([O-])c1ccccc1O>[N-]1C=NC=C1.[Ag+].[Cl-].[Zn+2].[Cl-].C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3dad95ee87aa442ca66bdccf28072882 | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-]>>O=[N+]([O-])c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O | C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)[N+](=O)[O-] | CC(=O)[O:15][C@@H:14]1[CH2:13][S:12][C@@H:11]([O:10][c:9]2[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]2)[C@H:18]([O:19]C(C)=O)[C@H:16]1[O:17]C(C)=O>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][C@@H:11]1[S:12][CH2:13][C@@H:14]([OH:15])[C@H:16]([OH:17])[C@H:18]1[OH:19] | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-] | O=[N+]([O-])c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 68 | [{"value": 68.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 0.85 g (2.05.10-3 mol) of 2-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.1 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 50 ml of methanol for 30 min, 0.4 g (yield: 68%) of the expected product is ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-]>CO>O=[N+]([O-])c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f67d5b7de822472492c840983cb533d4 | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.CC(=O)c1ccccc1O>>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O | OC1=C(C=CC=C1)C(C)=O.C(C)(=O)O[C@H]1C(SC[C@H]([C@@H]1OC(C)=O)OC(C)=O)Br>>C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | Br[CH:18]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[CH2:16][S:17]1.[OH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26]([CH3:27])=[O:28]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[C@@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@H:11]([O:12][C:13]([CH3:14])=[O:15])[C... | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.CC(=O)c1ccccc1O | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O | null | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+] | C(C)#N.C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3c49bc43fe6079339f39c9429da6d5ccfe2ce56b99deb4c8c20e73bf9d688a42 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(O[C@H]2CCCCS2)cc1 | Br-[CH;D3;+0:1](-[#16:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[c:13]:[c:14](-[OH;D1;+0:15]):[c:16]>>[C:3]-[#16:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:15]-[c:14](:[c:16]):[c:13]-[C:11](-[C;D1;H3:10])=[O;D1;H0:12])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9] | 13.5 | [{"value": 13.5, "product": "C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.3, "product": "C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIII is followed starting from 3.45 g (25.3.10-3 mol) of 1-(2-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCSCC1 | C1CCSCC1 | C1CCSCC1.c1ccccc1 | HBr | [Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(C)#N.C(Cl)Cl | null | null | CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O.CC(=O)c1ccccc1O>[Cl-].[Zn+2].[Cl-].[N-]1C=NC=C1.[Ag+].C(C)#N.C(Cl)Cl>CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-10114c1b82204ff0a3cd5529f1b818ad | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O>>CC(=O)c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O | C(C)(=O)O[C@H]1[C@H](OC2=C(C=CC=C2)C(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)C(C)=O | CC(=O)[O:15][C@@H:14]1[CH2:13][S:12][C@@H:11]([O:10][c:9]2[c:4]([C:2]([CH3:1])=[O:3])[cH:5][cH:6][cH:7][cH:8]2)[C@H:18]([O:19]C(C)=O)[C@H:16]1[O:17]C(C)=O>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][C@@H:11]1[S:12][CH2:13][C@@H:14]([OH:15])[C@H:16]([OH:17])[C@H:18]1[OH:19] | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O | CC(=O)c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 84 | [{"value": 84.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=C(C=CC=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 0.88 g (2.1.10-3 mol) of 2-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.1 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 50 ml of methanol for 30 min, 0.51 g (yield: 84%) of the expected product is... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O>CO>CC(=O)c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a861c83a05a249d8b29e8cc1b67b61a7 | CC(=O)OC(C)=O.CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1>>CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 | C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)[N+](=O)[O-])SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C(C)(=O)OC(C)=O>>C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)NC(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].O=[N+:4]([O-])[c:5]1[cH:6][cH:7][c:8]([O:9][C@@H:10]2[S:11][CH2:12][C@@H:13]([O:14][C:15]([CH3:16])=[O:17])[C@H:18]([O:19][C:20]([CH3:21])=[O:22])[C@H:23]2[O:24][C:25]([CH3:26])=[O:27])[cH:28][cH:29]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C@@H:10]2[S:11][CH2:12][C@@H:13]([... | CC(=O)OC(C)=O.CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1 | CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 | null | [Pd] | null | Acylation | OtherReaction | e42a085282c3a07a051d4fb8d2fca17494e60eb1125ef7dc723a241b4f07d443 | f3ba867686f6df7397dc4715602a55649ceb24345966ae3ca69ac9bcc38b3956 | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O=[N+;H0;D3:4](-[O-])-[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] | 51 | [{"value": 51.0, "product": "C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)NC(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 30 mg of 10% palladium-on-charcoal are added to a solution of 150 mg (0.36.10-3 mol) of 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in acetic anhydride, under a nitrogen atmosphere, and the reaction mixture obtained is then kept under hydrogen pressure (3.5.105Pa) at 50° C. for 15 hours. After filtration... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Nitro group | Secondary amide | null | null | c1ccccc1.C1CCSCC1 | HO- | [Pd] | null | null | CC(=O)OC(C)=O.CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1>[Pd]>CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-35470696234d4b8197beaf8e865c2a32 | CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1>>CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | C(C)(=O)O[C@H]1[C@H](OC2=CC=C(C=C2)NC(C)=O)SC[C@H]([C@@H]1OC(C)=O)OC(C)=O.C[O-].[Na+]>>O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)NC(C)=O | CC(=O)[O:14][C@@H:13]1[CH2:12][S:11][C@@H:10]([O:9][c:8]2[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:20][cH:19]2)[C@H:17]([O:18]C(C)=O)[C@H:15]1[O:16]C(C)=O>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C@@H:10]2[S:11][CH2:12][C@@H:13]([OH:14])[C@H:15]([OH:16])[C@H:17]2[OH:18])[cH:19][cH:20]1 | CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1 | CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | null | CO | Reduction | OtherReaction | 9f424ad7f135049f3c8d93f2a53a0b1989dca890eeca4f2b7f1c9a5ebac8c1d6 | 686e1cba4ec2306fea5356e180d738af5e7014418eb9d90530fa6033ee4812fa | c1ccc(O[C@H]2CCCCS2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]1-[C:3]-[#16:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 83 | [{"value": 83.0, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "O([C@H]1[C@H](O)[C@@H](O)[C@H](O)CS1)C1=CC=C(C=C1)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | If the procedure described in Preparation LXXXIV is followed starting from 1.2 g (2.8.10-3 mol) of 4-acetamidophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 70 μl of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 100 cm3 of methanol, 0.7 g (yield: 83%) of the expected product is obtained... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCSCC1 | HO- | CO | null | null | CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1>CO>CC(=O)Nc1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-879d85c422674bbdb657f5a7f9e3d453 | C=CCCC(=O)O.CCCCCCCCCCCC(CC=O)OC1CCCCO1>>C=CCC(C(=O)O)C(O)CC(CCCCCCCCCCC)OC1CCCCO1 | O1C(CCCC1)OC(CC=O)CCCCCCCCCCC.C(C)(C)NC(C)C.C(CCC)[Li].Cl.C(CCC=C)(=O)O>>C(C=C)C(C(=O)O)C(CC(CCCCCCCCCCC)OC1OCCCC1)O | [CH2:1]=[CH:2][CH2:3][CH2:4][C:5](=[O:6])[OH:7].[CH:8](=[O:9])[CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[O:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:29]1>>[CH2:1]=[CH:2][CH2:3][CH:4]([C:5](=[O:6])[OH:7])[CH:8]([OH:9])[CH2:10][CH:11]([CH2:12][CH2:13][CH2... | C=CCCC(=O)O.CCCCCCCCCCCC(CC=O)OC1CCCCO1 | C=CCC(C(=O)O)C(O)CC(CCCCCCCCCCC)OC1CCCCO1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 995c7a5cbf37230035b00de18cd91aae550f6b3916b2678b4c13427cfa9d9370 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | C1CCOCC1 | [C;D1;H2:1]=[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[C:8]-[C:9]-[CH;D2;+0:10]=[O;H0;D1;+0:11]>>[C:8]-[C:9]-[CH;D3;+0:10](-[OH;D1;+0:11])-[CH;D3;+0:4](-[C:3]-[C:2]=[C;D1;H2:1])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | -50 | CELSIUS | 15 | MINUTE | C)a) 2 ml of diisopropylamine in 30 ml of dry THF were cooled to -20° C. and thereupon 9.68 ml of butyl lithium (1.6M/hexane) were added dropwise in such a manner that the temperature did not exceed -20° C. The mixture was subsequently stirred for 15 minutes and then cooled to -50° C. Thereafter, 0.720 ml of 4-pentenoi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | C1CCOCC1 | null | C1CCOC1 | -50 | 0.25 | C=CCCC(=O)O.CCCCCCCCCCCC(CC=O)OC1CCCCO1>C1CCOC1>C=CCC(C(=O)O)C(O)CC(CCCCCCCCCCC)OC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ce478d5428574cabb9ca865e818520be | CCCCCCCCCCCC(CC(=O)C(CCCCCC)C(=O)OC)OC1CCCCO1>>CCCCCCCCCCCC(CC(O)C(CCCCCC)C(=O)OC)OC1CCCCO1 | [BH4-].[Na+].CO.C(CCCCC)C(C(=O)OC)C(CC(CCCCCCCCCCC)OC1OCCCC1)=O.[BH4-].[Na+]>>C(CCCCC)C(C(=O)OC)C(CC(CCCCCCCCCCC)OC1OCCCC1)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][C:14](=[O:15])[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:23](=[O:24])[O:25][CH3:26])[O:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][O:33]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:... | CCCCCCCCCCCC(CC(=O)C(CCCCCC)C(=O)OC)OC1CCCCO1 | CCCCCCCCCCCC(CC(O)C(CCCCCC)C(=O)OC)OC1CCCCO1 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1CCOCC1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5](-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5](-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10] | 96.3 | [{"value": 96.3, "product": "C(CCCCC)C(C(=O)OC)C(CC(CCCCCCCCCCC)OC1OCCCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 7.76 g of methyl 2-hexyl-3-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate (0.017 mol) were dissolved in 500 ml of THF while gassing with argon, treated with 20 ml of MeOH and cooled to -5° C. 5.3 g of sodium borohydride (0.14 mol) were added portionwise while stirring in such a manner that the temperature did not e... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1CCOCC1 | null | C1CCOC1 | -5 | null | CCCCCCCCCCCC(CC(=O)C(CCCCCC)C(=O)OC)OC1CCCCO1>C1CCOC1>CCCCCCCCCCCC(CC(O)C(CCCCCC)C(=O)OC)OC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c04649af83bc427ba93579ecd97a2120 | CCCCCCCCCCC[C@H](CC=O)OC1CCCCO1.Cc1ccc([S@@](=O)CC(=O)OC(C)(C)C)cc1>>CCCCCCCCCCCC(CC(O)[C@H](C(=O)OC(C)(C)C)[S@](=O)c1ccc(C)cc1)OC1CCCCO1 | Cl.C1(=CC=C(C=C1)[S@@](=O)CC(=O)OC(C)(C)C)C.C(C)(C)(C)[Mg]Br.O1C(CCCC1)O[C@@H](CC=O)CCCCCCCCCCC>>OC([C@H](C(=O)OC(C)(C)C)[S@](=O)C1=CC=C(C=C1)C)CC(CCCCCCCCCCC)OC1OCCCC1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:13][CH:14]=[O:15])[O:33][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][O:39]1.[CH2:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[S@:24](=[O:25])[c:26]1[cH:27][cH:28][c:29]([CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][CH2:3... | CCCCCCCCCCC[C@H](CC=O)OC1CCCCO1.Cc1ccc([S@@](=O)CC(=O)OC(C)(C)C)cc1 | CCCCCCCCCCCC(CC(O)[C@H](C(=O)OC(C)(C)C)[S@](=O)c1ccc(C)cc1)OC1CCCCO1 | null | null | CCOCC.C1CCOC1 | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | O=[S@@](CCCCOC1CCCCO1)c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[#16:9](=[O;D1;H0:10])-[c:11].[C:12]-[C:13]-[CH;D2;+0:14]=[O;H0;D1;+0:15]>>[C:12]-[C:13]-[CH;D3;+0:14](-[OH;D1;+0:15])-[C@@H;D3;+0:8](-[#16:9](=[O;D1;H0:10])-[c:11])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:2](-[C;D1;H3:1])(-[C;D1;H3:3])-[C;D1;... | 67 | [{"value": 67.0, "product": "OC([C@H](C(=O)OC(C)(C)C)[S@](=O)C1=CC=C(C=C1)C)CC(CCCCCCCCCCC)OC1OCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.3, "product": "OC([C@H](C(=O)OC(C)(C)C)[S@](=O)C1=CC=C(C=C1)C)CC(CCCCCCCCCCC)OC1OCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | G)a) 16.5 g of t-butyl [(S)-p-tolylsulfinyl]acetate were dissolved in a mixture of 600 ml of ether and 60 ml of THF and cooled to -78° C. 43 ml of t-butylmagnesium bromide were then added dropwise in such a manner that the temperature remained below -70° C. After stirring at -78° C. for 1 hour 13.4 g of (R)-3-[(tetrahy... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1.C1CCOCC1 | null | CCOCC.C1CCOC1 | -78 | null | CCCCCCCCCCC[C@H](CC=O)OC1CCCCO1.Cc1ccc([S@@](=O)CC(=O)OC(C)(C)C)cc1>CCOCC.C1CCOC1>CCCCCCCCCCCC(CC(O)[C@H](C(=O)OC(C)(C)C)[S@](=O)c1ccc(C)cc1)OC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3076d3da99f84c1fb207661fe9054400 | CCCCCCCCCCC[C@H](CC(=O)OC(C)(C)C)OC1CCCCO1>>CCCCCCCCCCC[C@H](CC=O)OC1CCCCO1 | [H-].C(C(C)C)[Al+]CC(C)C.O1C(CCCC1)O[C@@H](CC(=O)OC(C)(C)C)CCCCCCCCCCC.[Cl-].[NH4+].Cl>>O1C(CCCC1)O[C@@H](CC=O)CCCCCCCCCCC | CC(C)(C)O[C:14]([CH2:13][C@@H:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:22]1)=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:13][CH:14]=[O:15])[O:16][CH:17]1[CH2:18][CH2:19][C... | CCCCCCCCCCC[C@H](CC(=O)OC(C)(C)C)OC1CCCCO1 | CCCCCCCCCCC[C@H](CC=O)OC1CCCCO1 | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | b1296420569009c052ad4c7016568f90672030772406ba8ff8471efe57ef3191 | c76b8c70819551adc022d514db26b6763680199f8eb4cf7151247cfc099be223 | C1CCOCC1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | -75 | CELSIUS | 1 | HOUR | I)a) 9.2 g of t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate were dissolved in 115 ml of toluene while gassing with argon and with the exclusion of moisture and cooled to -75° C. 26.5 ml of a 1.2M solution of diisobutylaluminum hydride in toluene were then added dropwise in such a manner that the temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Aldehyde | null | null | C1CCOCC1 | HO- | C1(=CC=CC=C1)C | -75 | 1 | CCCCCCCCCCC[C@H](CC(=O)OC(C)(C)C)OC1CCCCO1>C1(=CC=CC=C1)C>CCCCCCCCCCC[C@H](CC=O)OC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1961c38b3bfe41e9850737dd3646a122 | C=CCC[C@H](CC(=O)OC)OC1CCCCO1>>COC(=O)CC[C@@H](CCC=O)OC1CCCCO1 | [H][H].O1C(CCCC1)O[C@@H](CC(=O)OC)CCC=C.O=[O+][O-].C(C)(=O)OCC>>C(=O)CC[C@H](CCC(=O)OC)OC1OCCCC1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:7]([CH2:6][CH2:9][CH:10]=[CH2:8])[O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C@@H:7]([CH2:8][CH2:9][CH:10]=[O:11])[O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1 | C=CCC[C@H](CC(=O)OC)OC1CCCCO1 | COC(=O)CC[C@@H](CCC=O)OC1CCCCO1 | null | null | null | Oxidation | OtherReaction | a709adf97241c850e428c2e169f4bfa24e154979857c6cfc7cf80f8e2b7b8b94 | ce4dfe29da175b4be2970f5874e6d804f166e676de169f194bc28c7d63538310 | C1CCOCC1 | [#8:1]-[C:2]-[#8:3]-[C@@H;D3;+0:4](-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH;D2;+0:12]=[CH2;D1;+0:13]>>[#8:1]-[C:2]-[#8:3]-[C@@H;D3;+0:4](-[CH2;D2;+0:10]-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9])-[CH2;D2;+0:13]-[CH2;D2;+0:11]-[CH;D2;+0:12]=[O;D1;H0:14] | null | [] | null | null | null | null | A solution of 2.56 g of methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoate in 40 ml of ethyl acetate was treated with ozone at -75° C. After completion of the reaction 0.1 g of Pd-on-carbon was added thereto and the mixture was hydrogenated at room temperature. After the hydrogen uptake was finished the catalyst... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Allyl | Aldehyde.Ester.Ether | null | null | C1CCOCC1 | Other | null | null | null | C=CCC[C@H](CC(=O)OC)OC1CCCCO1>>COC(=O)CC[C@@H](CCC=O)OC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-79667b592cd94ca2943c996933ceac25 | CCCCCCCCCCCC(CC(O)[C@@H](CCCCCC)C(=O)O)OC1CCCCO1>>CCCCCCCCCCCC1CC[C@@H](O)C(=O)O1 | C(CCCCC)[C@@H](C(=O)O)C(CC(CCCCCCCCCCC)OC1OCCCC1)O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O[C@H]1C(OC(CC1)CCCCCCCCCCC)=O | CCCCCC[C@H:15]([CH:14](O)[CH2:13][CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:16]C1CCCCO1)[C:17](=[O:18])[OH:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][C@@H:15]([OH:16])[C:17](=[O:18])[O:19]1 | CCCCCCCCCCCC(CC(O)[C@@H](CCCCCC)C(=O)O)OC1CCCCO1 | CCCCCCCCCCCC1CC[C@@H](O)C(=O)O1 | null | null | C(C)O | Miscellaneous | OtherReaction | caf1a3475a88b9f500d6b53e83c2a3f83571f46b9786084fd1b0293b2cdff362 | 4beeef97bf689da98d365baede373100109f312304138bcf9ec3e62abdba53eb | O=C1CCCCO1 | C-C-C-C-C-C-[C@@H;D3;+0:1](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[CH;D3;+0:5](-O)-[C:6]-[CH;D3;+0:7](-[C:8]-[C:9])-[O;H0;D2;+0:10]-C1-C-C-C-C-O-1>>[C:9]-[C:8]-[CH;D3;+0:7]1-[C:6]-[CH2;D2;+0:5]-[C@@H;D3;+0:1](-[OH;D1;+0:10])-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-1 | null | [] | null | null | 1 | HOUR | M)a) 15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid were dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulfonic acid monohydrate were added. The reaction mixture was heated to 55°-60° C. until the reaction was finished. The solvent was removed in va... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Secondary alcohol | Ester.Secondary alcohol | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HO- | C(C)O | null | 1 | CCCCCCCCCCCC(CC(O)[C@@H](CCCCCC)C(=O)O)OC1CCCCO1>C(C)O>CCCCCCCCCCCC1CC[C@@H](O)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-518a16e34f3943a5b14400a699394dc9 | CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1>>CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1 | O.C(CCCCC)[C@H]1C(OC(CC1O)CCCCCCCCCCC)=O.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>C(CCCCC)[C@H]1C(OC(CC1=O)CCCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH:14]([OH:15])[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:23](=[O:24])[O:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][C:14](=[O:15])[C@@H:16]([CH2:1... | CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1 | CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1 | null | null | CC(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 52800a55078129c9d27eb3a0d105b5e4e9c8b534c2b3da640d60eb3dbe57f55d | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCOC(=O)C1 | [C:1]-[C:2]1-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]-[CH;D3;+0:8]-1-[OH;D1;+0:9]>>[C:1]-[C:2]1-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9] | null | [] | null | null | null | null | M)b) 3 g of a diastereomer mixture of tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one were dissolved in 300 ml of acetone. 3 ml of Jones' reagent were added dropwise while stirring in such a manner that the temperature did not exceed 25° C. After 3 hours the reaction mixture was poured into 700 ml of H2O. The... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | null | CC(=O)C | null | null | CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1>CC(=O)C>CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ec56bca52c65474f938fae5cfb0fea03 | CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1>>CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1 | C(CCCCC)[C@H]1C(OC(CC1=O)CCCCCCCCCCC)=O>>C(CCCCC)[C@@H]1C(O[C@@H](C[C@@H]1O)CCCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][C:14](=[O:15])[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:23](=[O:24])[O:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:13][C@H:14]([OH:15])[C@H:16]([CH2... | CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1 | CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1 | null | O=[Pt]=O | C(C)(=O)OCC | Reduction | Reduction of ketone to secondary alcohol | 0d65dfaf3667114951b0c26d66f3cae6706fb649a24a9851bb9f5559348721c6 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C1CCCCO1 | [C:1]-[C:2]1-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[C:2]1-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]-[C@@H;D3;+0:8]-1-[OH;D1;+0:9] | null | [] | null | null | 12 | HOUR | M)c) 8 g of an isomer mixture of tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one were dissolved in 2 l of ethyl acetate and 3 g of PtO2 were added. The mixture was then hydrogenated (50 bar) for 12 hours. The catalyst was filtered off and the solution was evaporated. After recrystallization there were obtained 7 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | null | O=[Pt]=O.C(C)(=O)OCC | null | 12 | CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1>O=[Pt]=O.C(C)(=O)OCC>CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-22f7dc4741844f499aa6a903ab0faa86 | CC(C)(C)[Si](C)(C)Cl.CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1>>CCCCCCCCCCC[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)O1 | C(CCCCC)[C@@H]1C(O[C@@H](C[C@@H]1O)CCCCCCCCCCC)=O.C(C)(C)(C)[Si](Cl)(C)C.CCOCC>>C(CCCCC)[C@@H]1C(O[C@@H](C[C@@H]1O[Si](C)(C)C(C)(C)C)CCCCCCCCCCC)=O | Cl[Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:13][C@H:14]([OH:15])[C@H:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:30](=[O:31])[O:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2... | CC(C)(C)[Si](C)(C)Cl.CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1 | CCCCCCCCCCC[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)O1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | O=C1CCCCO1 | 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].[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[OH;D1;+0:13])-[C:14]>>[#8:8]-[C:9](=[O;D1;H0:10])-[C: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])-[C:14] | 63.5 | [{"value": 63.5, "product": "C(CCCCC)[C@@H]1C(O[C@@H](C[C@@H]1O[Si](C)(C)C(C)(C)C)CCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | M)d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one were dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF were then added dropwise. The mixture was stirred for 48 hours. The reaction mixtures was poured in to 100 ml of ether and washed with 1N hydrochloric acid. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | C1CCOCC1 | HCl | CN(C)C=O | null | 48 | CC(C)(C)[Si](C)(C)Cl.CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1>CN(C)C=O>CCCCCCCCCCC[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d4da2a89a30143c9af8c5932f42a6311 | CCCCCCCCCCC[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1>>CCCCCCCCCCC[C@H](C[C@H](O)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1 | C(CCCCC)[C@H](C(=O)OCC1=CC=CC=C1)[C@H](C[C@@H](CCCCCCCCCCC)OC1OCCCC1)O[Si](C)(C)C(C)(C)C.O.O.O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(CCCCC)[C@H](C(=O)OCC1=CC=CC=C1)[C@H](C[C@@H](CCCCCCCCCCC)OC1OCCCC1)O | CC(C)(C)[Si](C)(C)[O:15][C@@H:14]([CH2:13][C@@H:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:33][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][O:39]1)[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[C... | CCCCCCCCCCC[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1 | CCCCCCCCCCC[C@H](C[C@H](O)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1 | null | null | C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | O=C(CCCCOC1CCCCO1)OCc1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](-[C:3])-[OH;D1;+0:1] | 60.4 | [{"value": 60.4, "product": "C(CCCCC)[C@H](C(=O)OCC1=CC=CC=C1)[C@H](C[C@@H](CCCCCCCCCCC)OC1OCCCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | M)g) 480 mg benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate and 350 mg of tetrabutylammonium fluoride trihydrate were dissolved in 8 ml of THF and stirred for 12 hours. After evaporation the residue was dissolved in 50 ml of ether and washed with water. The etherea... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | c1ccccc1.C1CCOCC1 | Other | C1CCOC1 | null | 12 | CCCCCCCCCCC[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1>C1CCOC1>CCCCCCCCCCC[C@H](C[C@H](O)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f2832b5fb09b4e59ad1cd227ee44f57d | C=CCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC.CC(C)C[C@H](NC=O)C(=O)O>>C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O | C(CCCCC)[C@@H]1C(O[C@H]1C[C@@H](CCC=C)O)=O.C(=O)N[C@@H](CC(C)C)C(=O)O>>C(CCCCC)[C@H]1[C@@H](OC1=O)CC(CCC=C)OC([C@@H](NC=O)CC(C)C)=O | [CH2:1]=[CH:2][CH2:3][CH2:4][C@H:5]([CH2:6][C@@H:7]1[O:8][C:9](=[O:10])[C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[OH:18].O[C:19](=[O:20])[C@H:21]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH:26][CH:27]=[O:28]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([CH2:6][C@@H:7]1[O:8][C:9](=[O:10])[C@H:11]1[CH2:12][CH2:13][CH2:1... | C=CCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC.CC(C)C[C@H](NC=O)C(=O)O | C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O | null | null | null | Protection | Esterification of Carboxylic Acids | 624bf219458ba212c982344d7c3d6088244bf818423b8912fbf03efe5373c5bf | 547c73c17c71bc10d21cd3cdbafe9d7a279f866fe729eea28fdc1be18f1a2791 | O=C1CCO1 | 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:10]-[C@H;D3;+0:11](-[OH;D1;+0:12])-[C:13]-[C:14]-[C:15]=[C;D1;H2:16]>>[#8:8]-[C:9]-[C:10]-[CH;D3;+0:11](-[C:13]-[C:14]-[C:15]=[C;D1;H2:16])-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | null | null | by esterifying (S)-3-hexyl-(S)-4-[(R)-2-hydroxy-5-hexenyl)-2-oxetanone with N-formyl-L-leucine there was obtained
Conditions: See reaction.notes.procedure_details.
Workup: there was obtained | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | C1COC1 | HO- | null | null | null | C=CCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC.CC(C)C[C@H](NC=O)C(=O)O>>C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-47909ec221c7454fbe9eb8bd39f16bc3 | CC(C)C[C@H](NC=O)C(=O)O.CCCCCCC/C=C\CC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC>>C=CCC[C@H](OC(=O)[C@H](C)NC=O)[C@H]1OC(=O)[C@H]1CCCCCC | C(CCCCC)[C@@H]1C(O[C@H]1C[C@@H](CC\C=C/CCCCCCC)O)=O.C(=O)N[C@@H](CC(C)C)C(=O)O>>C(CCCCC)[C@H]1[C@H](OC1=O)[C@H](CCC=C)OC([C@@H](NC=O)C)=O | CC(C)[CH2:10][C@@H:9]([C:7](O)=[O:8])[NH:11][CH:12]=[O:13].CCCCCCC/[CH:1]=[CH:2]\[CH2:3][CH2:4][C@H:5](C[C@@H:14]1[O:15][C:16](=[O:17])[C@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[OH:6]>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@H:5]([O:6][C:7](=[O:8])[C@H:9]([CH3:10])[NH:11][CH:12]=[O:13])[C@H:14]1[O:15][C:16](=[O:... | CC(C)C[C@H](NC=O)C(=O)O.CCCCCCC/C=C\CC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC | C=CCC[C@H](OC(=O)[C@H](C)NC=O)[C@H]1OC(=O)[C@H]1CCCCCC | null | null | null | C-C Coupling | OtherReaction | ee78f13b36a3f7f86df9c0b30421861a1d18e43adf16264be9f8884bb75896f9 | 132f33a64e1d471821b9d9580ec15a1f090b5c961a68bbebb608be4c65d66e1b | O=C1CCO1 | C-C(-C)-[CH2;D2;+0:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].C-C-C-C-C-C-C/[CH;D2;+0:8]=[C:9]\[C:10]-[C:11]-[C@@H;D3;+0:12](-[OH;D1;+0:13])-C-[C@@H;D3;+0:14]1-[#8:15]-[C:16](=[O;D1;H0:17])-[C:18]-1-[C:19]>>[C:19]-[C:18]1-[C:16](=[O;D1;H0:17])-[#8:15]-[C@@H;D3;+0:14]-1-[C@H;D3;+0:12](-[C:11]-[C:... | null | [] | null | null | null | null | by esterifying (S)-3-hexyl-(S)-4-[(R,Z)-2-hydroxy-5-tridecenyl)-2oxetanone with N-formyl-L-leucine there was obtained
Conditions: See reaction.notes.procedure_details.
Workup: there was obtained | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Secondary alcohol | Ester.Ester.Allyl | C1COC1 | C1COC1 | C1COC1 | HO- | null | null | null | CC(C)C[C@H](NC=O)C(=O)O.CCCCCCC/C=C\CC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC>>C=CCC[C@H](OC(=O)[C@H](C)NC=O)[C@H]1OC(=O)[C@H]1CCCCCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-33bd20993ae242758a05ade7c8cf3ad4 | C=CCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCCCCCC.CC(C)C[C@H](NC=O)C(=O)O>>CCCCCCC/C=C\CC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O | C(CCCCCCCCC)[C@@H]1C(O[C@H]1C[C@@H](CCC=C)O)=O.C(=O)N[C@@H](CC(C)C)C(=O)O>>C(CCCCC)[C@H]1[C@@H](OC1=O)C[C@H](CC\C=C/CCCCCCC)OC([C@@H](NC=O)CC(C)C)=O | [CH2:1]([CH2:5][CH2:6][CH2:7][CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C@H:14]([CH2:13][C@@H:12]([CH2:11][CH2:10][CH:9]=[CH2:8])[OH:25])[O:15][C:16]1=[O:17])[CH2:23][CH3:24].O[C:26](=[O:27])[C@H:28]([CH2:29][CH:30]([CH3:31])[CH3:32])[NH:33][CH:34]=[O:35]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\... | C=CCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCCCCCC.CC(C)C[C@H](NC=O)C(=O)O | CCCCCCC/C=C\CC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O | null | null | null | C-C Coupling | OtherReaction | 3067e0e4d4c824c6787b52c0f595f6432710d6ee3d6ad162f1773c7e967a4e48 | 4c1bc2004969fb4e182ec0fef943a01fc4dfc7ef38d5785ed702d7c7fb97c85d | O=C1CCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]-[C:12]-[C:13]=[CH2;D1;+0:14].[C:15]-[C:16]-[CH2;D2;+0:17]-[CH2;D2;+0:18]-[C:19]-[CH2;D2;+0:20]-[CH2;D2;+0:21]-[CH2;D2;+0:22]-[C;D1;H3:23]>>[C:8]-[C:9](-[C:11]-[C:12]/[C:13]=[CH;D2;+0:14]\[CH2;D2;+0:18]-[C:19]-[CH2;D... | null | [] | null | null | null | null | by esterifying (S)-3-decyl-(S)-4-[(R)-2-hydroxy-5-hexenyl)-2-oxetanone with N-formyl-L-leucine there was obtained
Conditions: See reaction.notes.procedure_details.
Workup: there was obtained | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Allyl | Ester | null | null | C1COC1 | null | null | null | null | C=CCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCCCCCC.CC(C)C[C@H](NC=O)C(=O)O>>CCCCCCC/C=C\CC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0de16def84324b30a9beac0de74809f8 | CC(C)C[C@@H](C(=O)O)N(C)C=O.CCCCC/C=C\C/C=C\CCCCCCCC(O)CC1OC(=O)C1CC>>C=CCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCCCCCC)OC(=O)[C@H](CC(C)C)NC=O | C(C)C1C(OC1CC(CCCCCCC\C=C/C\C=C/CCCCC)O)=O.C(=O)N([C@@H](CC(C)C)C(=O)O)C>>C(CCCCCCCCC)[C@H]1[C@@H](OC1=O)C[C@H](CCC=C)OC([C@@H](NC=O)CC(C)C)=O | C[N:30]([C@H:25]([C:23](O)=[O:24])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH:31]=[O:32].C(=C\[CH2:1]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])\CCC[CH2:14][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH:7]1[O:8][C:9](=[O:10])[CH:11]1[CH2:12][CH3:13])[OH:22]>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH2:6][C@@H:7]1[O:8][C... | CC(C)C[C@@H](C(=O)O)N(C)C=O.CCCCC/C=C\C/C=C\CCCCCCCC(O)CC1OC(=O)C1CC | C=CCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCCCCCC)OC(=O)[C@H](CC(C)C)NC=O | null | null | null | Acylation | OtherReaction | 5aac3367a87de90921b630083cdedd8c9cec41e9b582cd58bb1233767a2f871e | 0f81133497d0c8b3d40f7c7c6812da07decc743dd2bdc81a7d75ee18ea0b9342 | O=C1CCO1 | C-[N;H0;D3;+0:1](-[C:2]=[O;D1;H0:3])-[C:4](-[C:5])-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[C:8]-[C:9]/[CH;D2;+0:10]=[CH;D2;+0:11]\[CH2;D2;+0:12]/C=C\C-C-C-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[C:15]-[C:16]-[CH;D3;+0:17](-[OH;D1;+0:18])-[C:19]-[C:20]1-[#8:21]-[C:22](=[O;D1;H0:23])-[C:24]-1-[C:25]-[CH3;D1;+0:26]>>[C:8]-[C:9]-[CH2;D2;+0... | null | [] | null | null | null | null | by esterifying 3-ethyl-4-[(10Z,13Z)-2-hydroxy-10,13-nonadecadienyl)-2-oxetanone with N-formyl-N-methyl-L-leucine there was obtained
Conditions: See reaction.notes.procedure_details.
Workup: there was obtained | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Secondary alcohol | Ester.Secondary amide.Allyl | null | null | C1COC1 | HO- | null | null | null | CC(C)C[C@@H](C(=O)O)N(C)C=O.CCCCC/C=C\C/C=C\CCCCCCCC(O)CC1OC(=O)C1CC>>C=CCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCCCCCC)OC(=O)[C@H](CC(C)C)NC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07a20e79c2184112a21669dbf5ac6d48 | C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O>>CCCCCC[C@@H]1C(=O)O[C@H]1CC(CCCC)OC(=O)[C@H](CC(C)C)NC=O | C(CCCCC)[C@H]1[C@@H](OC1=O)CC(CCC=C)OC([C@@H](NC=O)CC(C)C)=O.[H][H]>>C(CCCCC)[C@H]1[C@@H](OC1=O)CC(CCCC)OC([C@@H](NC=O)CC(C)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[C:8](=[O:9])[O:10][C@H:11]1[CH2:12][CH:13]([CH2:14][CH2:15][CH:16]=[CH2:17])[O:18][C:19](=[O:20])[C@H:21]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH:26][CH:27]=[O:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[C:8](=[O:9])[O:10][C@H:11]1[CH2:12][CH:13]([CH2:14][C... | C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O | CCCCCC[C@@H]1C(=O)O[C@H]1CC(CCCC)OC(=O)[C@H](CC(C)C)NC=O | null | [Pd] | C1CCOC1 | Reduction | Hydrogenation (double to single) | bc16a674f12262641e5cd54edc2026446c884c0ddcda2374dddc2ac4d3dae2ab | 6afc5b4ad7d0f8b85f89bd805881fd9206fc3da38639abfb1c97bb82ede31c54 | O=C1CCO1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH3;D1;+0:4] | null | [] | null | null | null | null | A solution of 10 mg of N-formyl-L-leucine 1-[(trans-3-hexyl-4-oxo-2-oxetanyl)methyl]-4-pentenyl ester in 0.5 ml of THF was treated with 2.5 mg of 5% Pd/C and hydrogenated. After the hydrogen uptake was finished the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was chromatographed over ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | C1COC1 | null | [Pd].C1CCOC1 | null | null | C=CCCC(C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O>[Pd].C1CCOC1>CCCCCC[C@@H]1C(=O)O[C@H]1CC(CCCC)OC(=O)[C@H](CC(C)C)NC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6723282d0299441895895ea4c527a4b9 | CCCCCCCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CC)OC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1>>CCCCCCCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CC)OC(=O)[C@H](CC(C)C)NC=O | C(C)[C@H]1[C@@H](OC1=O)C[C@H](CCCCCCCCCCCCCCCCC)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC(C)C)=O>>C(C)[C@H]1[C@@H](OC1=O)C[C@H](CCCCCCCCCCCCCCCCC)OC([C@@H](NC=O)CC(C)C)=O | c1ccc(CO[C:36]([NH:35][C@H:30]([C:28]([O:27][C@@H: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])[CH2:19][C@@H:20]2[O:21][C:22](=[O:23])[C@H:24]2[CH2:25][CH3:26])=[O:29])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:37])cc1>>[CH3:1][CH2:2][CH2... | CCCCCCCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CC)OC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1 | CCCCCCCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CC)OC(=O)[C@H](CC(C)C)NC=O | null | [Pd] | C1CCOC1 | Reduction | OtherReaction | 24f92a888b3ce678fa1dbe6df499353d3da6cc731d442199241c9e816083f5cd | e008818bdf7f47f5da9e6389d221612ea068a411dbe12c223f0891630c962ab5 | O=C1CCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-O-C-c1:c:c:c:c:c:1>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[CH;D2;+0:6]=[O;D1;H0:7] | null | [] | null | null | null | null | 565 mg of N-[(benzyloxy)carbonyl]-L-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester were dissolved in 12 ml of THF. The mixture was hydrogenated at room temperature in the presence of 40 mg of 10% Pd/C. After the reaction was finished the catalyst was filtered off and the filtrate was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amide | c1ccccc1 | null | C1COC1 | HO- | [Pd].C1CCOC1 | null | null | CCCCCCCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CC)OC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1>[Pd].C1CCOC1>CCCCCCCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CC)OC(=O)[C@H](CC(C)C)NC=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-47bbd098cb2a4725a243aeb6e8e75282 | ClCCCCCBr.N#Cc1ccc(O)cc1>>N#Cc1ccc(OCCCCCCl)cc1 | [H-].[Na+].C(#N)C1=CC=C(C=C1)O.BrCCCCCCl.[H][H]>>ClCCCCCOC1=CC=C(C#N)C=C1 | Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:14][cH:15]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1 | ClCCCCCBr.N#Cc1ccc(O)cc1 | N#Cc1ccc(OCCCCCCl)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | To a solution of 16.9 g (135 mmol) p-cyanophenol in 169 mL of dimethylformamide (DMF), cooled in an ice-bath is added in portions 6.5 g (135 mmol) sodium hydride (50% dispersion in oil). The reaction is stirred and allowed to warm-up to room temperature until no further hydrogen evolution is observed. The solution is t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | null | ClCCCCCBr.N#Cc1ccc(O)cc1>CN(C=O)C>N#Cc1ccc(OCCCCCCl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-adbf3dc1a5cb462d9cbba9a96dc56869 | N#Cc1ccc(OCCCCCCl)cc1.[I-]>>N#Cc1ccc(OCCCCCI)cc1 | ClCCCCCOC1=CC=C(C#N)C=C1.[I-].[Na+]>>ICCCCCOC1=CC=C(C#N)C=C1 | Cl[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:15][cH:14]1.[I-:13]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][I:13])[cH:14][cH:15]1 | N#Cc1ccc(OCCCCCCl)cc1.[I-] | N#Cc1ccc(OCCCCCI)cc1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | null | [] | null | null | 8 | HOUR | To a solution of 32.7 g (146 mmol) of 4-(5-chloropentoxy) benzonitrile in 350 mL acetone is added 38.3 g (150 mmol) of sodium iodide in 230 mL of acetone. The reaction is heated to reflux and stirred overnight. The acetone is removed under reduced pressure and the residue partitioned between water and ether. The ethere... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C | null | 8 | N#Cc1ccc(OCCCCCCl)cc1.[I-]>CC(=O)C>N#Cc1ccc(OCCCCCI)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fdd2eb38b67e4d6b8e06115e859cab46 | COc1ccccc1O.N#Cc1ccc(OCCCCCI)cc1>>COc1ccccc1OCCCCCOc1ccc(C#N)cc1 | [H-].[Na+].C=1(C(O)=CC=CC1)OC.ICCCCCOC1=CC=C(C#N)C=C1.[H][H]>>COC1=C(OCCCCCOC2=CC=C(C#N)C=C2)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].I[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]1 | COc1ccccc1O.N#Cc1ccc(OCCCCCI)cc1 | COc1ccccc1OCCCCCOc1ccc(C#N)cc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCCCOc2ccccc2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 18 | HOUR | To a solution of 5.1 g (41 mmol) of guaiacol in 41 mL of DMF, cooled in an icebath, is added in portions, 20 g (41 mmole) of sodium hydride (50% dispersion in oil). The reaction is allowed to warm up to room temperature and stirred until no further hydrogen evolution is observed. The solution is then again cooled in an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HI | CN(C)C=O.O | null | 18 | COc1ccccc1O.N#Cc1ccc(OCCCCCI)cc1>CN(C)C=O.O>COc1ccccc1OCCCCCOc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-185e1d513d024f29aeed40745a08febf | CCO.N#Cc1ccc(O)cc1>>CCOC(=N)c1ccc(O)cc1 | OC1=CC=C(C#N)C=C1.Cl.C(C)O>>OC1=CC=C(C=C1)C(OCC)=N | [CH3:1][CH2:2][OH:3].[C:4](#[N:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[NH:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1 | CCO.N#Cc1ccc(O)cc1 | CCOC(=N)c1ccc(O)cc1 | null | null | ClCCl | Acylation | OtherReaction | e564e96d7d2f965b49edf364feccacb527e51024ce8a97adfccc27d77cbffea1 | 515b5097d48e8822f99e612a636ab28d5c6d3dcc515412839570278fb17e2efd | c1ccccc1 | [C;D1;H3:1]-[C:2]-[OH;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:5](=[NH;D1;+0:4])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 64 | HOUR | A stirred, 0° C. solution of 4-hydroxybenzonitrile (50.7 g, 426 mmol) in 1400 mL of dichloromethane and 75 mL anhydrous ethanol is treated with anhydrous hydrogen chloride gas (110 g) over 1.5 hours. This solution is stirred at room temperature for 64 hours and the resulting solids collected and washed with 500 mL diet... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Ether | null | null | c1ccccc1 | null | ClCCl | null | 64 | CCO.N#Cc1ccc(O)cc1>ClCCl>CCOC(=N)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-47447b95a1bf45f4834161d3ef59f534 | CCO.COc1ccccc1OCCCCCOc1ccc(C#N)cc1>>CCOC(=N)c1ccc(OCCCCCOc2ccccc2OC)cc1 | Cl.C(C)O.Cl.COC1=C(OCCCCCOC2=CC=C(C#N)C=C2)C=CC=C1>>Cl.COC1=C(OCCCCCOC2=CC=C(C=C2)C(OCC)=N)C=CC=C1 | [CH3:1][CH2:2][OH:3].[C:4](#[N:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[O:23][CH3:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[NH:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20... | CCO.COc1ccccc1OCCCCCOc1ccc(C#N)cc1 | CCOC(=N)c1ccc(OCCCCCOc2ccccc2OC)cc1 | null | null | C(C)OCC | Acylation | OtherReaction | e564e96d7d2f965b49edf364feccacb527e51024ce8a97adfccc27d77cbffea1 | 515b5097d48e8822f99e612a636ab28d5c6d3dcc515412839570278fb17e2efd | c1ccc(OCCCCCOc2ccccc2)cc1 | [C;D1;H3:1]-[C:2]-[OH;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:5](=[NH;D1;+0:4])-[c:6](:[c:7]):[c:8] | null | [] | 5 | CELSIUS | 84 | HOUR | Ethanol (2 B anhydrous, 16.5 L) is cooled with an ice-salt bath to 0° C. Anhydrous hydrogen chloride is introduced until the solution is saturated (~8 hours). At this time the internal temperature is 5° C. To this is added 4-[5-(2-methoxyphenoxy)pentoxy]benzonitrile (1.64 kg, 5.26 mol) as a solid within a period of 10 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | null | C(C)OCC | 5 | 84 | CCO.COc1ccccc1OCCCCCOc1ccc(C#N)cc1>C(C)OCC>CCOC(=N)c1ccc(OCCCCCOc2ccccc2OC)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9bddb73241f64221b25cad0cce98deec | COc1ccccc1OCCCCCCl.N#Cc1ccc(O)cc1>>COc1ccccc1OCCCCCOc1ccc(C#N)cc1 | ClCCCCCOC1=C(C=CC=C1)OC.C([O-])([O-])=O.[K+].[K+].C(#N)C1=CC=C(C=C1)O.[I-].[K+]>>COC1=C(OCCCCCOC2=CC=C(C#N)C=C2)C=CC=C1 | Cl[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.[OH:15][c:16]1[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]1 | COc1ccccc1OCCCCCCl.N#Cc1ccc(O)cc1 | COc1ccccc1OCCCCCOc1ccc(C#N)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCCCOc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | 4-Cyanophenol (742 g, 6.23 mol) is dissolved in dimethyl sulfoxide (7.30 L) and to this solution is added powdered anhydrous potassium carbonate (883 g, 6.30 mol), potassium iodide (1.05 kg, 6.30 mol) and finally 1-(5-chloropentoxy)-2-methoxybenzene (1.44 kg, 6.29 mol). This suspension is heated at 80°-82° C. for 7 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | CS(=O)C | null | 8 | COc1ccccc1OCCCCCCl.N#Cc1ccc(O)cc1>CS(=O)C>COc1ccccc1OCCCCCOc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f556ac80422c467dab5bec5fa4cf8285 | O=C(O)/C=C\C(=O)O>>O=C(O)/C=C\C(=O)O | COC1=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=CC=C1.C(\C=C/C(=O)O)(=O)O>>C(\C=C/C(=O)O)(=O)O.COC1=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=CC=C1 | [O:25]=[C:26]([OH:27])/[CH:28]=[CH:29]\[C:30](=[O:31])[OH:32]>>[O:25]=[C:26]([OH:27])/[CH:28]=[CH:29]\[C:30](=[O:31])[OH:32] | O=C(O)/C=C\C(=O)O | O=C(O)/C=C\C(=O)O | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 55 | CELSIUS | null | null | 4-[5-(2-Methoxyphenoxy)pentoxy]benzenecarboximidamide is dissolved in ethanol (2 B anhydrous, 9.6 L) with warming to 55° C. and this solution is filtered into a 10 gallon resin flask. The filtrate whose temperature is now 50° C. is admixed with a warm (~45° C.), filtered solution of maleic acid (0.488 kg, 4.20 mol) in ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | 55 | null | O=C(O)/C=C\C(=O)O>C(C)O>O=C(O)/C=C\C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0892ced2a4104a93b742dbf72a8cc112 | C=C[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C.CC(C)[Si](Cl)(C(C)C)C(C)C>>C=C[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | N1C=NC=C1.Cl[Si](C(C)C)(C(C)C)C(C)C.O.C(C)(C)(C)OC(=O)N[C@H]([C@H](C=C)O)CC1=CC=CC=C1>>C(C)(C)(C)OC(=O)N[C@H]([C@H](C=C)O[Si](C(C)C)(C(C)C)C(C)C)CC1=CC=CC=C1 | [CH2:1]=[CH:2][C@H:3]([OH:4])[C@H:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].Cl[Si:5]([CH:6]([CH3:7])[CH3:8])([CH:9]([CH3:10])[CH3:11])[CH:12]([CH3:13])[CH3:14]>>[CH2:1]=[CH:2][C@H:3]([O:4][Si:5]([CH:6]([CH3:7])[CH3:8])([CH:9]([CH3:10])[CH3:11]... | C=C[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C.CC(C)[Si](Cl)(C(C)C)C(C)C | C=C[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[C:11]-[C:12](-[OH;D1;+0:13])-[C:14]=[C;D1;H2:15]>>[C:11]-[C:12](-[C:14]=[C;D1;H2:15])-[O;H0;D2;+0:13]-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;... | 82 | [{"value": 82.0, "product": "C(C)(C)(C)OC(=O)N[C@H]([C@H](C=C)O[Si](C(C)C)(C(C)C)C(C)C)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (3S,4S)-N-[(tertbutyloxy)carbonyl]-4-amino-3-hydroxy-5-phenyl pentene [prepared by the method of Hanson et al, J. Org. Chem., 50, 5399 (1985)] (10.0 g, 64.5 mmol), imidazole (9.14g, 13 mmol), and chlorotriisopropylsilane (12.44 g, 43.3 mmol) in anhydrous DMF (40 mL) was stirred for 5 days at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccccc1 | HCl | CN(C)C=O | null | null | C=C[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C.CC(C)[Si](Cl)(C(C)C)C(C)C>CN(C)C=O>C=C[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d2fd2c20c66545699c81e6c81df4e199 | CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C>>CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | C(C)(C)(C)OC(=O)N[C@H]([C@H](CO)O[Si](C(C)C)(C(C)C)C(C)C)CC1=CC=CC=C1>>C(C)(C)(C)OC(=O)N[C@H]([C@H](CO)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1 | [CH3:1][CH:2]([CH3:3])[Si:4]([O:5][C@@H:6]([CH2:7][OH:8])[C@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])([CH:25]([CH3:26])[CH3:27])[CH:28]([CH3:29])[CH3:30]>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][C@@H:6]([CH2:7][OH:8])[C@H:9]([CH2:10][CH:11]1[CH2:... | CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | null | null | CO.[Rh] | Reduction | Arene hydrogenation | cfd1f3b98f7cd3ca3735c14f302dc0acdc6f0d4501cd6920cbb5c1a3d892ff3a | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCCC1 | [C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:1>>[C:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1 | 67 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)N[C@H]([C@H](CO)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.9, "product": "C(C)(C)(C)OC(=O)N[C@H]([C@H](CO)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The alcohol of Step 2 (12.8 g, 29.3 mmol) was dissolved in MeOH (135 mL) and hydrogenated with 5% Rh/C at 60 psi and 60° C. for 30 hours. The filtrate was concentrated and purified by medium pressure column chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound as a white solid (8.70 g, 67%... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | C1CCCCC1 | C1CCCCC1 | null | CO.[Rh] | null | null | CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C>CO.[Rh]>CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b9708d88f0e34657b4a47075b890a3ba | CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C>>CC(C)[Si](O[C@@H](C=O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | C(C)N(CC)CC.CS(=O)C.C(C(=O)Cl)(=O)Cl.C(C)(C)(C)OC(=O)N[C@H]([C@H](CO)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1>>C(C)(C)(C)OC(=O)N[C@H]([C@H](C=O)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1 | [CH3:1][CH:2]([CH3:3])[Si:4]([O:5][C@@H:6]([CH2:7][OH:8])[C@H:9]([CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])([CH:25]([CH3:26])[CH3:27])[CH:28]([CH3:29])[CH3:30]>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][C@@H:6]([CH:7]=[O:8])[C@H:9]([CH2:10][CH:11]1... | CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | CC(C)[Si](O[C@@H](C=O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | null | null | C1CCOC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCCCC1 | [#8:1]-[C:2](-[C:3])-[CH2;D2;+0:4]-[OH;D1;+0:5]>>[#8:1]-[C:2](-[C:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5] | null | [] | null | null | 10 | MINUTE | Freshly distilled dimethyl sulfoxide (0.85 g, 10.8 mmol) was added by syringe to a -78° C. solution of oxalyl chloride (0.69 g, 5.41 mmol) in anhydrous THF (22.6 mL). After 10 minutes, the alcohol of Step 3 (2 g, 4.51 mmol) in anhydrous THF (2.3 mL) was added over a period of 1.2 minutes to the -78° C. solution. The so... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCCCC1 | null | C1CCOC1 | null | 0.166667 | CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C>C1CCOC1>CC(C)[Si](O[C@@H](C=O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-abe21c6608d5455caae2107140a7bbdf | C#CCBr.CC(C)[Si](O[C@@H](C=O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C>>C#CC[C@H](O)[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C | [NH4+].[Cl-].C(C)(C)(C)OC(=O)N[C@H]([C@H](C=O)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1.C(C#C)Br.C1(=CC=CC=C1)C>>C(C)(C)(C)OC(=O)N[C@H]([C@H]([C@H](CC#C)O)O[Si](C(C)C)(C(C)C)C(C)C)CC1CCCCC1 | Br[CH2:3][C:2]#[CH:1].[CH:4](=[O:5])[C@H:6]([O:7][Si:8]([CH:9]([CH3:10])[CH3:11])([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:16])[CH3:17])[C@H:18]([CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>>[CH:1]#[C:2][CH2:3][C@H:4]([OH:5])[C@H:6]([O:7][Si:8]([... | C#CCBr.CC(C)[Si](O[C@@H](C=O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C | C#CC[C@H](O)[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C | null | Cl[Hg]Cl | C(C)OCC | C-C Coupling | Grignard_alcohol | 983d8b8e9b89ba290d93feeffe843caf411eba49bd1aefb21a784058d86f3a30 | 3e80fe0b4a87df3724831714de4ab23fef101254d00d9b3074e300e6e8f4b9ea | C1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[#8:4]-[C:5](-[C:6])-[CH;D2;+0:7]=[O;H0;D1;+0:8]>>[#8:4]-[C:5](-[C:6])-[C@@H;D3;+0:7](-[OH;D1;+0:8])-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 45 | MINUTE | To a dry flask under an N2 atmosphere was added Mg (0.40 g, 6.4 mmol), HgCl2 (0.03 g) and anhydrous diethyl ether (4 mL). A solution of 80% propargyl bromide in toluene (1.83 mL, 16.4 mmol) was added to an addition funnel and several drops were added to the reaction mixture. After the reaction was initiated, anhydrous ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | Secondary alcohol | null | null | C1CCCCC1 | Br- | Cl[Hg]Cl.C(C)OCC | 10 | 0.75 | C#CCBr.CC(C)[Si](O[C@@H](C=O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C>Cl[Hg]Cl.C(C)OCC>C#CC[C@H](O)[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e0171f7df0ec444092af546b5b14249f | C#CC[C@H](O)[C@H](O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C>>C#CC[C@H](O)[C@H](O)[C@@H](N)CC1CCCCC1 | C(C)(C)(C)OC(=O)N[C@H]([C@H]([C@H](CC#C)O)O)CC1CCCCC1.FC(C(=O)O)(F)F>>N[C@H]([C@H]([C@H](CC#C)O)O)CC1CCCCC1 | CC(C)(C)OC(=O)[NH:9][C@H:8]([C@H:6]([C@H:4]([CH2:3][C:2]#[CH:1])[OH:5])[OH:7])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH:1]#[C:2][CH2:3][C@H:4]([OH:5])[C@H:6]([OH:7])[C@@H:8]([NH2:9])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | C#CC[C@H](O)[C@H](O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C | C#CC[C@H](O)[C@H](O)[C@@H](N)CC1CCCCC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | C1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | 104.3 | [{"value": 100.0, "product": "N[C@H]([C@H]([C@H](CC#C)O)O)CC1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.3, "product": "N[C@H]([C@H]([C@H](CC#C)O)O)CC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of compound of Step 6 (0.926 g, 2.85 mmol) and trifluoroacetic acid (5.49 mL, 71.3 mmol) in CH2Cl12 (5.49 mL) was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was dissolved in 1.0N KOH (7 mL) and extracted with ethyl acetate (4×10 mL). The combined organic layers wer... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1 | HO- | null | null | null | C#CC[C@H](O)[C@H](O)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C>>C#CC[C@H](O)[C@H](O)[C@@H](N)CC1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-87cf19ff99b24841930e842d4ab30e9b | CCOC(=O)C(Cc1ccccc1)C(=O)OCC>>C=C(Cc1ccccc1)C(=O)OCC | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC1=CC=CC=C1)=O>>C(C)OC(C(=C)CC1=CC=CC=C1)=O | CCO[C:1](=O)[CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[O:12][CH2:13][CH3:14]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[O:12][CH2:13][CH3:14] | CCOC(=O)C(Cc1ccccc1)C(=O)OCC | C=C(Cc1ccccc1)C(=O)OCC | null | null | C(C)O | Miscellaneous | OtherReaction | 87c843d16b5f7d1c0a15b5f02b3c06a8845584571c4987daf92afed6275a224a | c836eb2f68060f44ea0d03ffb318e6493d54422f9dc702608ab5573b0d333994 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3]-[c:4] | 85 | [{"value": 85.0, "product": "C(C)OC(C(=C)CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4.0 g of KOH in 50 ml of ethanol was added at room temperature to 20 g of benzylmalonic acid diethyl ester in 40 ml of ethanol. The mixture was stirred overnight at room temperature, then concentrated by evaporation, thereafter 7.1 ml of water was added and then the mixture was acidified in an ice bath wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester.Vinyl | null | null | c1ccccc1 | HO- | C(C)O | null | 8 | CCOC(=O)C(Cc1ccccc1)C(=O)OCC>C(C)O>C=C(Cc1ccccc1)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-27edfb5bfda24dc2817ffeeee268dc01 | CCOC(=S)C(Cc1ccccc1)CC(C)(C)C>>CC(C)(C)CC(Cc1ccccc1)C(O)=S | C(C)OC(C(CC(C)(C)C)CC1=CC=CC=C1)=S.[OH-].[K+]>>C(C1=CC=CC=C1)C(C(=S)O)CC(C)(C)C | CC[O:15][C:14]([CH:6]([CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[S:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14]([OH:15])=[S:16] | CCOC(=S)C(Cc1ccccc1)CC(C)(C)C | CC(C)(C)CC(Cc1ccccc1)C(O)=S | null | null | CO | Deprotection | OtherReaction | 65c01082ec6254926609c8ce3d388338e51acb862ab958fb28659738e366fdad | 6a00535cbd1c6b0a3a91788e21576cc4d0faa02f2346e8f35105ed8723abcf83 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[S;D1;H0:4]>>[C:3]-[C:2](-[OH;D1;+0:1])=[S;D1;H0:4] | 78.3 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)C(C(=S)O)CC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "C(C1=CC=CC=C1)C(C(=S)O)CC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 400 mg of 2-benzyl-3-tert.-butylthiopropionic acid ethyl ester was dissolved in 1.5 ml of methanol and then reacted with 5 ml of 2N potassium hydroxide solution. The mixture was stirred overnight at room temperature and concentrated by evaporation. The residue was diluted with water and washed with ether. The aqueous l... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Thiocarbonyl | Thiocarbonyl | null | null | c1ccccc1 | Other | CO | null | 8 | CCOC(=S)C(Cc1ccccc1)CC(C)(C)C>CO>CC(C)(C)CC(Cc1ccccc1)C(O)=S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aa19428af98a44e881b7ee2b0e2130c2 | CC(C)(C)CC(Cc1ccccc1)C(O)=S.O=S(=O)([O-])O[O-]>>CC(C)(C)S(=O)(=O)CC(Cc1ccccc1)C(=O)O | O.S(=O)(=O)(O[O-])[O-].[K+].[K+].O.C(C1=CC=CC=C1)C(C(=S)O)CC(C)(C)C>>C(C1=CC=CC=C1)C(C(=O)O)CS(=O)(=O)C(C)(C)C | S=[C:17]([CH:9]([CH2:8][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[OH:19].[O-][S:5](=[O:6])([O:7][O-])=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])(=[O:7])[CH2:8][CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[OH:19] | CC(C)(C)CC(Cc1ccccc1)C(O)=S.O=S(=O)([O-])O[O-] | CC(C)(C)S(=O)(=O)CC(Cc1ccccc1)C(=O)O | null | null | CO | Protection | OtherReaction | be808f854d065ff2860de7fd72a00b8d92257e309dec93323d344bc75daa77d0 | 3e3308bf1189a5d31ee2d3bbd21dd059e0f7bb60b4336696270c402a4e5475cc | c1ccccc1 | S=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[CH2;D2;+0:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9].[O-]-[O;H0;D2;+0:10]-[S;H0;D4;+0:11](-[O-])(=[O;D1;H0:12])=[O;H0;D1;+0:13]>>[C:4]-[C:3](-[CH2;D2;+0:5]-[S;H0;D4;+0:11](=[O;D1;H0:12])(=[O;H0;D1;+0:10])-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9]... | 82 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)C(C(=O)O)CS(=O)(=O)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 280 mg of 2-benzyl-3-tert.-butylthiopropionic acid was dissolved in 5 ml of methanol and, while cooling with ice, 1 g of potassium peroxomonosulfate in 4 ml of water was added and the whole was stirred overnight at room temperature. The solution was diluted with water and extracted with methylene chloride, and the extr... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Carboxylic acid.Sulfone | null | null | c1ccccc1 | Other | CO | null | 8 | CC(C)(C)CC(Cc1ccccc1)C(O)=S.O=S(=O)([O-])O[O-]>CO>CC(C)(C)S(=O)(=O)CC(Cc1ccccc1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7d66cc75a8fd414a9155bf2f7fa6be3b | CC=C[SiH](Cl)Cl.CNC(C)=O>>CC=C[SiH](N(C)C(C)=O)N(C)C(C)=O | [Na].CNC(C)=O.CC=C[SiH](Cl)Cl>>CC=C[SiH](N(C(C)=O)C)N(C(C)=O)C | Cl[SiH:4](Cl)[CH:3]=[CH:2][CH3:1].[NH:5]([CH3:6])[C:7]([CH3:8])=[O:9]>>[CH3:1][CH:2]=[CH:3][SiH:4]([N:5]([CH3:6])[C:7]([CH3:8])=[O:9])[N:10]([CH3:11])[C:12]([CH3:13])=[O:14] | CC=C[SiH](Cl)Cl.CNC(C)=O | CC=C[SiH](N(C)C(C)=O)N(C)C(C)=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 6482004f960159a60220f7dedde45ce2f11df822d4051b6c8b47178acfade35f | b8bd2b628ea83e4e50775cb0b7d3a29a9bc2c9a08504372482f2931f19558245 | null | Cl-[SiH;D3;+0:1](-Cl)-[C:2]=[C:3]-[C;D1;H3:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[C:10]-[#7:11](-[C;D1;H3:12])-[SiH;D3;+0:1](-[C:2]=[C:3]-[C;D1;H3:4])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | null | [] | null | null | null | null | The amidosilanes can be prepared as by the following illustration: mixing a sodium salt of N-methylacetamide with methylvinyldichlorosilane in an inert organic solvent such as toluene, filtering the by-produced sodium chloride from the toluene-product solution, and thereafter removing the toluene by vacuum distillation... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide.Tertiary amide | null | null | null | null | C1(=CC=CC=C1)C | null | null | CC=C[SiH](Cl)Cl.CNC(C)=O>C1(=CC=CC=C1)C>CC=C[SiH](N(C)C(C)=O)N(C)C(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-515189e1fb57456dae58a0ec857392d2 | O=C1c2ccccc2C(=O)N1CCBr.Sc1ccccn1>>O=C1c2ccccc2C(=O)N1CCSc1ccccn1 | C(C)N(CC)CC.SC1=NC=CC=C1.BrCCN1C(C=2C(C1=O)=CC=CC2)=O>>C1(C=2C(C(N1CCSC1=NC=CC=C1)=O)=CC=CC2)=O | Br[CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1 | O=C1c2ccccc2C(=O)N1CCBr.Sc1ccccn1 | O=C1c2ccccc2C(=O)N1CCSc1ccccn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2C(=O)N1CCSc1ccccn1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[SH;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[O;D1;H0:7]=[C:6]-[#7:3](-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C:4]=[O;D1;H0:5] | 46.9 | [{"value": 46.9, "product": "C1(C=2C(C(N1CCSC1=NC=CC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.9, "product": "C1(C=2C(C(N1CCSC1=NC=CC=C1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Triethylamine [12.54 ml (90 mmol)] was added to a suspension of 6.67 g (60 mmol) of 2-mercaptopyridine and 15.24 g (60 mmol) of N-(2-bromoethyl)phthalimide in 200 ml of ethanol and stirred at room temperature for 24 hours. The mixture was heated under reflux for 2 hours. The solvent was distilled off, chloroform was ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HBr | C(C)O | null | 24 | O=C1c2ccccc2C(=O)N1CCBr.Sc1ccccn1>C(C)O>O=C1c2ccccc2C(=O)N1CCSc1ccccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e0b0ae522e9643ab8c80504bb00eddd7 | CCCCCCCC(=O)NCCCCCO.CS(=O)(=O)Cl>>CCCCCCCC(=O)NCCCCCOS(C)(=O)=O | OCCCCCNC(CCCCCCC)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCCNC(CCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].Cl[S:17]([CH3:18])(=[O:19])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][S:17]([CH3:18])(=[O:19])=[O:20] | CCCCCCCC(=O)NCCCCCO.CS(=O)(=O)Cl | CCCCCCCC(=O)NCCCCCOS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 81.6 | [{"value": 74.8, "product": "CS(=O)(=O)OCCCCCNC(CCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "CS(=O)(=O)OCCCCCNC(CCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.00 g (7.77 mmol) of N-(5-hydroxypentyl)caprylamide and 1.30 ml (9.32 mmol) of triethylamine in 50 ml of methylene chloride was added 0.72 ml (9.32 mmol) of methanesulfonyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(Cl)Cl | null | null | CCCCCCCC(=O)NCCCCCO.CS(=O)(=O)Cl>C(Cl)Cl>CCCCCCCC(=O)NCCCCCOS(C)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6f778d0c3e1b4a7f994618527a890c86 | CCCCCCCC(=O)NCCCCCCO.CS(=O)(=O)Cl>>CCCCCCCC(=O)NCCCCCCOS(C)(=O)=O | OCCCCCCNC(CCCCCCC)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>S(=O)(=O)(C)OCCCCCCNC(CCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].Cl[S:18]([CH3:19])(=[O:20])=[O:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][S:18]([CH3:19])(=[O:20])=[O:21] | CCCCCCCC(=O)NCCCCCCO.CS(=O)(=O)Cl | CCCCCCCC(=O)NCCCCCCOS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 107.2 | [{"value": 98.6, "product": "S(=O)(=O)(C)OCCCCCCNC(CCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.2, "product": "S(=O)(=O)(C)OCCCCCCNC(CCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.00 g (7.37 mmol) of N-(6-hydroxyhexyl)caprylamide and 1.23 ml of triethylamine in 50 ml of methylene chloride was added 0.68 ml (8.84 mmol) of methanesulfonyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(Cl)Cl | null | null | CCCCCCCC(=O)NCCCCCCO.CS(=O)(=O)Cl>C(Cl)Cl>CCCCCCCC(=O)NCCCCCCOS(C)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7030c1fd7e86451f857a9e61a4bc804b | CC(C)(C)OC(=O)N1CCC(O)CC1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)(C)(C)OC(=O)N1CCC(CC1)OS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:17][CH2:18]1.Cl[S:13]([CH3:14])(=[O:15])=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17][CH2:18]1 | CC(C)(C)OC(=O)N1CCC(O)CC1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8] | 98.7 | [{"value": 98.6, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.97 mmol) of N-t-butoxycarbonyl-4-hydroxypiperidine and 0.83 ml (5.96 mmol) of triethylamine in 50 ml of methylene chloride was added 0.46 ml (5.96 mmol) of methanesulfonylchloride under ice-cooling and stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1 | HCl | C(Cl)Cl | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e94fd6bfa01d4f6e8f7a35095695cdbe | CN(C)NC(=O)Sc1cccnc1.O=C1c2ccccc2C(=O)N1CCCCBr>>O=C1c2ccccc2C(=O)N1CCCCSc1cccnc1 | BrCCCCN1C(C=2C(C1=O)=CC=CC2)=O.CN(C)NC(=O)SC=1C=NC=CC1.[OH-].[Na+]>>C1(C=2C(C(N1CCCCSC=1C=NC=CC1)=O)=CC=CC2)=O | CN(C)NC(=O)[S:16][c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1.Br[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1 | CN(C)NC(=O)Sc1cccnc1.O=C1c2ccccc2C(=O)N1CCCCBr | O=C1c2ccccc2C(=O)N1CCCCSc1cccnc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | bff53194bc36a65102836e4c5e9a1c5830f50f4b01719183e321ee1ae403e0e4 | 5ed6fe1b068fcdb227c62a05fb4f278fa2a75d69092e65dd59bc906dc5d27d03 | O=C1c2ccccc2C(=O)N1CCCCSc1cccnc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-N(-C)-N-C(=O)-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 4.5 | [{"value": 4.5, "product": "C1(C=2C(C(N1CCCCSC=1C=NC=CC1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.5, "product": "C1(C=2C(C(N1CCCCSC=1C=NC=CC1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3.64 g (20 mmol) of 3-dimethylaminocarbamoylthiopyridine in 100 ml of methanol was added 1.6 g (40 mmol) of sodium hydroxide. The mixture was heated and refluxed for 3 hours under nitrogen atmosphere. After cooling, 5.64 g (20 mmol) of N-(4-bromobutyl)phthalimide was added. The mixture was heated and r... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide.Monosulfide | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HBr | CO | null | null | CN(C)NC(=O)Sc1cccnc1.O=C1c2ccccc2C(=O)N1CCCCBr>CO>O=C1c2ccccc2C(=O)N1CCCCSc1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-017420df954a447280015c49a6216cca | CCC(=O)Cl.NCCCSc1ccncc1>>CCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CC)(=O)Cl>>C(CC)(=O)NCCCSC1=CC=NC=C1 | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1 | CCC(=O)Cl.NCCCSc1ccncc1 | CCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4] | 74.2 | [{"value": 74.2, "product": "C(CC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.2, "product": "C(CC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 0.30 ml (3.48 mmol) of propionyl chloride and the mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with an aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | 0.5 | CCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4a1694bb3df64335856b4b663a854296 | CCCC(=O)Cl.NCCCSc1ccncc1>>CCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCC)(=O)Cl>>C(CCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1 | CCCC(=O)Cl.NCCCSc1ccncc1 | CCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 91.1 | [{"value": 91.1, "product": "C(CCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "C(CCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 0.36 ml (3.48 mmol) of butyryl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-efc045dc445b4acca9722be49a0b70c5 | CCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCC)(=O)Cl>>C(CCCCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[NH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | CCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 81.7 | [{"value": 81.7, "product": "C(CCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "C(CCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 600 mg (2.49 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.39 ml (9.96 mmol) of triethylamine in 25 ml of methylene chloride was added 0.42 ml (2.99 mmol) of hexanoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aa20bcca352d4d548b56b70515a1c325 | CCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCC)(=O)Cl>>C(CCCCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[NH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | CCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 93.1 | [{"value": 84.2, "product": "C(CCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "C(CCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.21 g (5.00 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.79 ml (20.0 mmol) of triethylamine in 50 ml of methylene chloride was added 1.02 ml (6.00 mmol) of caproyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-abb47b82de57402780d9b7b5e758e651 | CCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCCCCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13].[NH2:14][CH2:15][CH2:16][CH2:17][S:18][c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][S:18][c:19]1[cH... | CCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCCCCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 72.2 | [{"value": 72.2, "product": "C(CCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.2, "product": "C(CCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 1.15 ml (4.96 mmol) of lauroyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCCCCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5b872cfa47a4410ab987265db03498d | CCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C: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:15].[NH2:16][CH2:17][CH2:18][CH2:19][S:20][c:21]1[cH:22][cH:23][n:24][cH:25][cH:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[NH:16][CH2:17]... | CCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 74.5 | [{"value": 74.5, "product": "C(CCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "C(CCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 1.22 ml (4.96 mmol) of myristoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-78df409f57be4493824f38128845a8fb | CCCCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C: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:17].[NH2:18][CH2:19][CH2:20][CH2:21][S:22][c:23]1[cH:24][cH:25][n:26][cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:1... | CCCCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 73.8 | [{"value": 73.8, "product": "C(CCCCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "C(CCCCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.21 g (5.00 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.79 ml (20.0 mmol) of triethylamine in 50 ml of methylene chloride was added 1.65 ml (6.00 mmol) of palmitoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-261e2c93070c48fda350af3bbf232b00 | CCCCCCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1 | 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].[NH2:20][CH2:21][CH2:22][CH2:23][S:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:1... | CCCCCCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 95.2 | [{"value": 95.2, "product": "C(CCCCCCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "C(CCCCCCCCCCCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 1.18 ml (3.48 mmol) of stearoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCCCCCCCCCCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCCCCCCCCCCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86b8088d362943dc94d0eaba8b78404c | CCCCCCCC/C=C\CCCCCCCC(=O)Cl.NCCCSc1ccncc1>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCCCC\C=C/CCCCCCCC)(=O)Cl>>C(CCCCCCC\C=C/CCCCCCCC)(=O)NCCCSC1=CC=NC=C1 | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[NH2:20][CH2:21][CH2:22][CH2:23][S:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2... | CCCCCCCC/C=C\CCCCCCCC(=O)Cl.NCCCSc1ccncc1 | CCCCCCCC/C=C\CCCCCCCC(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 83.7 | [{"value": 83.7, "product": "C(CCCCCCC\\C=C/CCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "C(CCCCCCC\\C=C/CCCCCCCC)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 1.55 ml (3.48 mmol) of oleoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCCCCC/C=C\CCCCCCCC(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCCCCC/C=C\CCCCCCCC(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-98d9895ba86346508f59e97bf0b9a4d2 | CCCCC(CC)C(=O)Cl.NCCCSc1ccncc1>>CCCCC(CC)C(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C)C(C(=O)Cl)CCCC>>Cl.C(C)C(C(=O)NCCCSC1=CC=NC=C1)CCCC | Cl[C:8]([CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH3:7])=[O:9].[NH2:10][CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1 | CCCCC(CC)C(=O)Cl.NCCCSc1ccncc1 | CCCCC(CC)C(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5] | 92.8 | [{"value": 92.8, "product": "Cl.C(C)C(C(=O)NCCCSC1=CC=NC=C1)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 800 mg (3.32 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.22 ml (15.9 mmol) of triethylamine in 30 ml of methylene chloride was added 0.69 ml (3.98 mmol) of 2-ethylhexanoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCC(CC)C(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CCCCC(CC)C(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-66499d5214ef4835a72c18c45b45c2ab | NCCCSc1ccncc1.O=C(Cl)C1CCCCC1>>O=C(NCCCSc1ccncc1)C1CCCCC1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C1(CCCCC1)C(=O)Cl>>Cl.C1(CCCCC1)C(=O)NCCCSC1=CC=NC=C1 | [NH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.Cl[C:3](=[O:2])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>>[O:2]=[C:3]([NH:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | NCCCSc1ccncc1.O=C(Cl)C1CCCCC1 | O=C(NCCCSc1ccncc1)C1CCCCC1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6])-[C:5] | 77 | [{"value": 77.0, "product": "Cl.C1(CCCCC1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "Cl.C1(CCCCC1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.66 ml (4.96 mmol) of cyclohexanoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.C1CCCCC1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)C1CCCCC1>C(Cl)Cl>O=C(NCCCSc1ccncc1)C1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ddf096337738401cbb2a49419e14ead6 | CC(C)(C)C(=O)Cl.NCCCSc1ccncc1>>CC(C)(C)C(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C(C)(C)C)(=O)Cl>>Cl.C(C(C)(C)C)(=O)NCCCSC1=CC=NC=C1 | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][CH2:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | CC(C)(C)C(=O)Cl.NCCCSc1ccncc1 | CC(C)(C)C(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6] | 96.4 | [{"value": 96.4, "product": "Cl.C(C(C)(C)C)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.3, "product": "Cl.C(C(C)(C)C)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.61 ml (4.96 mmol) of pivaloyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CC(C)(C)C(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>CC(C)(C)C(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-657feb5cd33641b8bf5a3da5d5b2469f | NCCCSc1ccncc1.O=C(O)C(F)(F)F>>O=C(NCCCSc1ccncc1)C(F)(F)F | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.FC(C(=O)O)(F)F>>Cl.FC(C(=O)NCCCSC1=CC=NC=C1)(F)F | [NH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.O[C:3](=[O:2])[C:15]([F:16])([F:17])[F:18]>>[O:2]=[C:3]([NH:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[C:15]([F:16])([F:17])[F:18] | NCCCSc1ccncc1.O=C(O)C(F)(F)F | O=C(NCCCSc1ccncc1)C(F)(F)F | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6] | 68.4 | [{"value": 68.4, "product": "Cl.FC(C(=O)NCCCSC1=CC=NC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.1, "product": "Cl.FC(C(=O)NCCCSC1=CC=NC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.70 ml (4.96 mmol) of anhydrous trifluoroacetic acid under ice-cooling with stirring and the mixture was stirred for at room temperature for 30 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(O)C(F)(F)F>C(Cl)Cl>O=C(NCCCSc1ccncc1)C(F)(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ac48039bb18450198abb32f9ba0ec62 | NCCCSc1ccncc1.O=C(Cl)c1cccc2ccccc12>>O=C(NCCCSc1ccncc1)c1cccc2ccccc12 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C1(=CC=CC2=CC=CC=C12)C(=O)Cl>>Cl.C1(=CC=CC2=CC=CC=C12)C(=O)NCCCSC1=CC=NC=C1 | [NH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.Cl[C:3](=[O:2])[c:15]1[cH:16][cH:17][cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[O:2]=[C:3]([NH:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12 | NCCCSc1ccncc1.O=C(Cl)c1cccc2ccccc12 | O=C(NCCCSc1ccncc1)c1cccc2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1cccc2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 74.8 | [{"value": 74.8, "product": "Cl.C1(=CC=CC2=CC=CC=C12)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "Cl.C1(=CC=CC2=CC=CC=C12)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio) pyridine dihydrochloride and 2.78 ml (19.9 mmol) of trietylamine in 40 ml of methylene chloride was added 0.75 ml (4.98 mmol) of 1-naphthoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2ccccc2c1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1cccc2ccccc12>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1cccc2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f15dd3fd1fd04d268953342d248889ee | NCCCSc1ccncc1.O=C(Cl)C=Cc1ccccc1>>O=C(C=Cc1ccccc1)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C=CC1=CC=CC=C1)(=O)Cl>>Cl.C(C=CC1=CC=CC=C1)(=O)NCCCSC1=CC=NC=C1 | [NH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.Cl[C:3](=[O:2])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:2]=[C:3]([CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | NCCCSc1ccncc1.O=C(Cl)C=Cc1ccccc1 | O=C(C=Cc1ccccc1)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(C=Cc1ccccc1)NCCCSc1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5] | 88.8 | [{"value": 88.8, "product": "Cl.C(C=CC1=CC=CC=C1)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "Cl.C(C=CC1=CC=CC=C1)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 830 mg (4.98 mmol) of cinnamoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)C=Cc1ccccc1>C(Cl)Cl>O=C(C=Cc1ccccc1)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ab431e826f8541ac954ed70e60f53a88 | NCCCSc1ccncc1.O=C(Cl)c1ccc(Cl)cc1>>O=C(NCCCSc1ccncc1)c1ccc(Cl)cc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.ClC1=CC=C(C(=O)Cl)C=C1>>Cl.ClC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1 | [NH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.Cl[C:3](=[O:2])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1>>[O:2]=[C:3]([NH:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1 | NCCCSc1ccncc1.O=C(Cl)c1ccc(Cl)cc1 | O=C(NCCCSc1ccncc1)c1ccc(Cl)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 118.6 | [{"value": 79.3, "product": "Cl.ClC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 118.6, "product": "Cl.ClC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.63 ml (4.96 mmol) of 4-chlorobenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1ccc(Cl)cc1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5c3cce7cb3a4ad4bf8f878f0513c956 | COc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>>COc1ccc(C(=O)NCCCSc2ccncc2)cc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C1=CC=C(C=C1)OC)(=O)Cl>>COC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1 | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]1)=[O:8].[NH2:9][CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][S:13][c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[cH:20][cH:21]1 | COc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1 | COc1ccc(C(=O)NCCCSc2ccncc2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78.9 | [{"value": 78.9, "product": "COC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "COC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 846 mg (4.96 mmol) of 4-anisoyl chloride under ice-cooling with stirring and the mixture was stirred for at room temperature for 30 minutes. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | COc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>C(Cl)Cl>COc1ccc(C(=O)NCCCSc2ccncc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f9fba7e62cfc4f3dacab24daff205a17 | Cc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>>Cc1ccc(C(=O)NCCCSc2ccncc2)cc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C1(=CC=C(C=C1)C(=O)Cl)C>>CC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1 | Cl[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)=[O:7].[NH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][S:12][c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][cH:20]1 | Cc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1 | Cc1ccc(C(=O)NCCCSc2ccncc2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 76.6 | [{"value": 76.6, "product": "CC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "CC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.65 ml (4.96 mmol) of 4-toluoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | Cc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>C(Cl)Cl>Cc1ccc(C(=O)NCCCSc2ccncc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-afad64aa4b6845c1aa72f4e04ffcbd0e | CC(C)(C)c1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>>CC(C)(C)c1ccc(C(=O)NCCCSc2ccncc2)cc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C)(C)(C)C1=CC=C(C(=O)Cl)C=C1>>Cl.C(C)(C)(C)C1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1 | Cl[C:9]([c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:23][cH:22]1)=[O:10].[NH2:11][CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][S:15][c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[cH... | CC(C)(C)c1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1 | CC(C)(C)c1ccc(C(=O)NCCCSc2ccncc2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 88 | [{"value": 88.0, "product": "Cl.C(C)(C)(C)C1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "Cl.C(C)(C)(C)C1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.48 ml (4.96 mmol) of 4-t-butylbenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | CC(C)(C)c1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>C(Cl)Cl>CC(C)(C)c1ccc(C(=O)NCCCSc2ccncc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eaa03d3d21724503ab66e842fd29b46d | COc1cc(OC)cc(C(=O)Cl)c1.NCCCSc1ccncc1>>COc1cc(OC)cc(C(=O)NCCCSc2ccncc2)c1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.COC=1C=C(C(=O)Cl)C=C(C1)OC>>COC=1C=C(C(=O)NCCCSC2=CC=NC=C2)C=C(C1)OC | Cl[C:10]([c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:23]1)=[O:11].[NH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][S:16][c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[cH:23... | COc1cc(OC)cc(C(=O)Cl)c1.NCCCSc1ccncc1 | COc1cc(OC)cc(C(=O)NCCCSc2ccncc2)c1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 87.7 | [{"value": 87.7, "product": "COC=1C=C(C(=O)NCCCSC2=CC=NC=C2)C=C(C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "COC=1C=C(C(=O)NCCCSC2=CC=NC=C2)C=C(C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 995 mg (4.96 mmol) of 3,5-dimethoxybenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | COc1cc(OC)cc(C(=O)Cl)c1.NCCCSc1ccncc1>C(Cl)Cl>COc1cc(OC)cc(C(=O)NCCCSc2ccncc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8c4a16f775cb4b12b344b9fa994edf37 | CCCCc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>>CCCCc1ccc(C(=O)NCCCSc2ccncc2)cc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCC)C1=CC=C(C(=O)Cl)C=C1>>Cl.C(CCC)C1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1 | Cl[C:9]([c:8]1[cH:7][cH:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[cH:23][cH:22]1)=[O:10].[NH2:11][CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][S:15][c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[cH:22]... | CCCCc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1 | CCCCc1ccc(C(=O)NCCCSc2ccncc2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 80.7 | [{"value": 80.7, "product": "Cl.C(CCC)C1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "Cl.C(CCC)C1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 0.93 ml (4.96 mmol) of 4-n-butylbenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minute. The react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>C(Cl)Cl>CCCCc1ccc(C(=O)NCCCSc2ccncc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e030ecf13edb4bcca46459c4ab0c5c18 | CCCCOc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>>CCCCOc1ccc(C(=O)NCCCSc2ccncc2)cc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCC)OC1=CC=C(C(=O)Cl)C=C1>>Cl.C(CCC)OC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1 | Cl[C:10]([c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:24][cH:23]1)=[O:11].[NH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][S:16][c:17]2[cH:18][cH:19][n:20][cH:21][cH:... | CCCCOc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1 | CCCCOc1ccc(C(=O)NCCCSc2ccncc2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 76.9 | [{"value": 76.9, "product": "Cl.C(CCC)OC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "Cl.C(CCC)OC1=CC=C(C(=O)NCCCSC2=CC=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 0.94 ml (4.96 mmol) of 4-n-butoxybenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | CCCCOc1ccc(C(=O)Cl)cc1.NCCCSc1ccncc1>C(Cl)Cl>CCCCOc1ccc(C(=O)NCCCSc2ccncc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2c8dc63242cc44cab385e6bb518c6cff | CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1O.NCCCSc1ccncc1>>CC(C)(C)c1cc(C(=O)NCCCSc2ccncc2)cc(C(C)(C)C)c1O | NCCCSC1=CC=NC=C1.C(C)(C)(C)C=1C=C(C(=O)O)C=C(C1O)C(C)(C)C.ON1C(CCC1=O)=O.Cl.C(C)N=C=NCCCN(C)C>>C(C)(C)(C)C=1C=C(C(=O)NCCCSC2=CC=NC=C2)C=C(C1O)C(C)(C)C | O[C:8]([c:7]1[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:27]([OH:28])[c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[cH:21]1)=[O:9].[NH2:10][CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][S:14][c:15]2[cH:... | CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1O.NCCCSc1ccncc1 | CC(C)(C)c1cc(C(=O)NCCCSc2ccncc2)cc(C(C)(C)C)c1O | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCSc1ccncc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 27.3 | [{"value": 27.3, "product": "C(C)(C)(C)C=1C=C(C(=O)NCCCSC2=CC=NC=C2)C=C(C1O)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.3, "product": "C(C)(C)(C)C=1C=C(C(=O)NCCCSC2=CC=NC=C2)C=C(C1O)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.49 g (5.94 mmol) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 889 mg (7.73 mmol) of N-hydroxysuccinimide in 60 ml of methylene chloride was added 1.38 g (7.13 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride under ice-cooling with stirring and the mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | C(Cl)Cl | null | null | CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1O.NCCCSc1ccncc1>C(Cl)Cl>CC(C)(C)c1cc(C(=O)NCCCSc2ccncc2)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c868b3c19e0d4a2d82a6e4b451c62930 | NCCCSc1ccncc1.O=C(O)c1ccccc1C(=O)O>>O=C(O)c1ccccc1C(=O)NCCCSc1ccncc1 | NCCCSC1=CC=NC=C1.C(C=1C(C(=O)O)=CC=CC1)(=O)O>>C(=O)(O)C1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1 | [NH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.O[C:10]([c:9]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][cH:7][cH:8]1)=[O:11]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | NCCCSc1ccncc1.O=C(O)c1ccccc1C(=O)O | O=C(O)c1ccccc1C(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCSc1ccncc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | 92.3 | [{"value": 92.3, "product": "C(=O)(O)C1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "C(=O)(O)C1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 340 mg (2.02 mmol) of 4-(3-aminopropylthio)pyridine and 738 mg (4.98 mmol) of anhydrous phthalic acid in 5 ml of methylene chloride was stirred at room temperature for 30 minutes. The resulting crystals were filtered and dried to obtain 590 mg of the desired compound (92.3%, colorless powder), mp: 151.0°-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(O)c1ccccc1C(=O)O>C(Cl)Cl>O=C(O)c1ccccc1C(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a56f98246b8f496f81cdd9cb617b9400 | NCCCSc1ccncc1.O=C(Cl)c1ccccc1>>O=C(NCCCSc1ccncc1)c1ccccc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | NCCCSc1ccncc1.O=C(Cl)c1ccccc1 | O=C(NCCCSc1ccncc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 84.9 | [{"value": 84.9, "product": "C(C1=CC=CC=C1)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "C(C1=CC=CC=C1)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.58 ml (4.96 mmol) of benzoyl chloride under ice-cooling with stirring and the mixture stirred at room temperature for 30 minutes. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1ccccc1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e39c2dcd2084984895ee85c814023f7 | NCCCSc1ccncc1.O=C(Cl)c1cccnc1>>O=C(NCCCSc1ccncc1)c1cccnc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.Cl.C(C1=CN=CC=C1)(=O)Cl>>C(C1=CN=CC=C1)(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1 | NCCCSc1ccncc1.O=C(Cl)c1cccnc1 | O=C(NCCCSc1ccncc1)c1cccnc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 75.8 | [{"value": 75.8, "product": "C(C1=CN=CC=C1)(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.9, "product": "C(C1=CN=CC=C1)(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.0 g (41.5 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 27.7 ml (200 mmol) of triethylamine in methylene chloride (100 ml), 8.86 g (49.8 mmol) of nicotinoyl chloride hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1cccnc1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a551cb2a1c7144368de100ddce8580d5 | NCCCSc1ccncc1.O=C(Cl)C=Cc1cnc2ccccc2c1>>O=C(C=Cc1cnc2ccccc2c1)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.N1=CC(=CC2=CC=CC=C12)C=CC(=O)Cl>>N1=CC(=CC2=CC=CC=C12)C=CC(=O)NCCCSC1=CC=NC=C1 | [NH2:15][CH2:16][CH2:17][CH2:18][S:19][c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1.Cl[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1)[NH:15][CH2:16][CH2:17][CH2:18][S:19][c:20]1[cH:21][c... | NCCCSc1ccncc1.O=C(Cl)C=Cc1cnc2ccccc2c1 | O=C(C=Cc1cnc2ccccc2c1)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(C=Cc1cnc2ccccc2c1)NCCCSc1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[c:6]:[#7;a:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:7]:[c:6]:[c:5]-[C:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8] | 83.8 | [{"value": 83.8, "product": "N1=CC(=CC2=CC=CC=C12)C=CC(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "N1=CC(=CC2=CC=CC=C12)C=CC(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 396 mg (1.64 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 0.27 ml (1.97 mmol) of triethylamine in 20 ml of methylene chloride, 500 mg (1.96 mmol) of 3-quinolineacryloyl chloride hydrochlride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ncccc2c1.c1ccncc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)C=Cc1cnc2ccccc2c1>C(Cl)Cl>O=C(C=Cc1cnc2ccccc2c1)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-11093efb280540518b66f99ed8c2be55 | NCCCSc1ccncc1.O=C(Cl)c1cccs1>>O=C(NCCCSc1ccncc1)c1cccs1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C1(=CC=CS1)C(=O)Cl>>C1(=CC=CS1)C(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][s:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][s:18]1 | NCCCSc1ccncc1.O=C(Cl)c1cccs1 | O=C(NCCCSc1ccncc1)c1cccs1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 70.5 | [{"value": 70.5, "product": "C1(=CC=CS1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "C1(=CC=CS1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.0 g (41.5 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 27.7 ml (200 mmol) of triethylamine in 100 ml of methylene chloride, 5.35 ml (50.0 mmol) of 2-thenoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccsc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1cccs1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1cccs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9aeedcdb9c5a4914ae3d792adb965e42 | NCCCSc1ccccn1.O=C(Cl)c1cccs1>>O=C(NCCCSc1ccccn1)c1cccs1 | Cl.Cl.NCCCSC1=NC=CC=C1.C(C)N(CC)CC.C1(=CC=CS1)C(=O)Cl>>C1(=CC=CS1)C(=O)NCCCSC1=NC=CC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][s:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1)[c:14]1[cH:15][cH:16][cH:17][s:18]1 | NCCCSc1ccccn1.O=C(Cl)c1cccs1 | O=C(NCCCSc1ccccn1)c1cccs1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccccn1)c1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 85.5 | [{"value": 85.5, "product": "C1(=CC=CS1)C(=O)NCCCSC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.50 g (6.22 mmol) of 2-(3-aminopropylthio)pyridine dihydrochloride and 3.19 ml (22.9 mmol) of triethylamine in 60 ml of methylene chloride, 1.09 ml (7.46 mmol) of.2-thenoyl-chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccsc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccccn1.O=C(Cl)c1cccs1>C(Cl)Cl>O=C(NCCCSc1ccccn1)c1cccs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a90ae34ce8714ddbad0eb996ca1db373 | NCCCSc1cccnc1.O=C(Cl)c1cccs1>>O=C(NCCCSc1cccnc1)c1cccs1 | Cl.Cl.NCCCSC=1C=NC=CC1.C(C)N(CC)CC.C1(=CC=CS1)C(=O)Cl>>C1(=CC=CS1)C(=O)NCCCSC=1C=NC=CC1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][s:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][s:18]1 | NCCCSc1cccnc1.O=C(Cl)c1cccs1 | O=C(NCCCSc1cccnc1)c1cccs1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1cccnc1)c1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 85.4 | [{"value": 85.3, "product": "C1(=CC=CS1)C(=O)NCCCSC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.4, "product": "C1(=CC=CS1)C(=O)NCCCSC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.00 g (8.29 mmol) of 3-(3-aminopropylthio)pyridine dihydrochloride and 4.16 ml (29.9 mmol) of triethylamine in 80 ml of methylene chloride, 1.06 ml (9.95 mmol) of 2-thenoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccsc1 | HCl | C(Cl)Cl | null | null | NCCCSc1cccnc1.O=C(Cl)c1cccs1>C(Cl)Cl>O=C(NCCCSc1cccnc1)c1cccs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e97eadac01b44ac8865f4b6513251185 | OCCCBr.Sc1ccncc1>>OCCCSc1ccncc1 | SC1=CC=NC=C1.C(C)N(CC)CC.BrCCCO>>OCCCSC1=CC=NC=C1 | Br[CH2:4][CH2:3][CH2:2][OH:1].[SH:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[OH:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | OCCCBr.Sc1ccncc1 | OCCCSc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 83.9 | [{"value": 83.9, "product": "OCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.9, "product": "OCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | In 100 ml of methylene chloride were dissolved 11.1 g (100 mmol) of 4-mercaptopyridine and 13.9 ml (100 mmol) of triethylamine, and 9.04 ml (100 mmol) of 3-bromo-1-propanol was added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with a 1N aqueous solution of sodium hydroxide ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1 | HBr | C(Cl)Cl | null | 2 | OCCCBr.Sc1ccncc1>C(Cl)Cl>OCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2a1a95ef38c0417b99080a5543b0a5c5 | NCCCSc1ccncc1.O=C(Cl)c1ccco1>>O=C(NCCCSc1ccncc1)c1ccco1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.O1C(=CC=C1)C(=O)Cl>>O1C(=CC=C1)C(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][o:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][o:18]1 | NCCCSc1ccncc1.O=C(Cl)c1ccco1 | O=C(NCCCSc1ccncc1)c1ccco1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1ccco1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 87.3 | [{"value": 87.3, "product": "O1C(=CC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "O1C(=CC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride, 0.49 ml (4.98 mmol) of 2-furoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccoc1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1ccco1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-98480977321a48fc9c80434e5c786ddb | NCCCSc1ccncc1.O=C(O)c1ccsc1>>O=C(NCCCSc1ccncc1)c1ccsc1 | NCCCSC1=CC=NC=C1.S1C=C(C=C1)C(=O)O.ON1C(CCC1=O)=O.Cl.C(C)N=C=NCCCN(C)C>>S1C=C(C=C1)C(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.O[C:2](=[O:1])[c:14]1[cH:15][cH:16][s:17][cH:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][s:17][cH:18]1 | NCCCSc1ccncc1.O=C(O)c1ccsc1 | O=C(NCCCSc1ccncc1)c1ccsc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCSc1ccncc1)c1ccsc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1 | 76.1 | [{"value": 76.1, "product": "S1C=C(C=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.0, "product": "S1C=C(C=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (7.80 mmol) of thiophene-3-carboxylic acid and 1.08 g (10.1 mmol) of N-hydroxysuccinimide in 70 ml of methylene chloride, 1.80 g (9.36 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccsc1 | HO- | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(O)c1ccsc1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1ccsc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1e860fd9a7364d6a91a5b65f8afc24f0 | NCCCSc1ccncc1.O=C(O)Cc1cccs1>>O=C(Cc1cccs1)NCCCSc1ccncc1 | NCCCSC1=CC=NC=C1.S1C(=CC=C1)CC(=O)O.ON1C(CCC1=O)=O.Cl.C(C)N=C=NCCCN(C)C>>S1C(=CC=C1)CC(=O)NCCCSC1=CC=NC=C1 | [NH2:9][CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][s:8]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][s:8]1)[NH:9][CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | NCCCSc1ccncc1.O=C(O)Cc1cccs1 | O=C(Cc1cccs1)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1cccs1)NCCCSc1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#16;a:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[#16;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6] | 86.3 | [{"value": 86.3, "product": "S1C(=CC=C1)CC(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 913 mg (6.42 mmol) of 2-thienylacetic acid and 961 mg (8.35 mmol) of N-hydroxysuccinimide in 65 ml of methylene chloride, 1.48 g (7.70 mmol) of 1-ethyl-3 (3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1 hour. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccncc1 | HO- | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(O)Cc1cccs1>C(Cl)Cl>O=C(Cc1cccs1)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9f4d0150d86e415cbecb30f8dcefa2d0 | NCCCSc1ccncc1.O=C(O)c1cc(Br)c(Br)s1>>O=C(NCCCSc1ccncc1)c1cc(Br)c(Br)s1 | NCCCSC1=CC=NC=C1.BrC=1C=C(SC1Br)C(=O)O.ON1C(CCC1=O)=O.Cl.C(C)N=C=NCCCN(C)C>>BrC=1C=C(SC1Br)C(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.O[C:2](=[O:1])[c:14]1[cH:15][c:16]([Br:17])[c:18]([Br:19])[s:20]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][c:16]([Br:17])[c:18]([Br:19])[s:20]1 | NCCCSc1ccncc1.O=C(O)c1cc(Br)c(Br)s1 | O=C(NCCCSc1ccncc1)c1cc(Br)c(Br)s1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCSc1ccncc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 71.8 | [{"value": 71.8, "product": "BrC=1C=C(SC1Br)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "BrC=1C=C(SC1Br)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.55 g (8.91 mmol) of 4,5-dibromothiophene-2-carboxylic acid and 1.33 g (11.6 mmol) of N-hydroxysuccinimide in 90 ml of methylene chloride, 2.05 g (10.7 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccsc1 | HO- | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(O)c1cc(Br)c(Br)s1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1cc(Br)c(Br)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dc6dda4f6f4f4e49bffbd2ffd2ad92b8 | Cc1ccc(C(=O)O)s1.NCCCSc1ccncc1>>Cc1ccc(C(=O)NCCCSc2ccncc2)s1 | NCCCSC1=CC=NC=C1.CC1=CC=C(S1)C(=O)O.ON1C(CCC1=O)=O.Cl.C(C)N=C=NCCCN(C)C>>CC1=CC=C(S1)C(=O)NCCCSC1=CC=NC=C1 | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[s:19]1)=[O:7].[NH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][S:12][c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[s:19]1 | Cc1ccc(C(=O)O)s1.NCCCSc1ccncc1 | Cc1ccc(C(=O)NCCCSc2ccncc2)s1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCSc1ccncc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 64.5 | [{"value": 64.5, "product": "CC1=CC=C(S1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.5, "product": "CC1=CC=C(S1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.27 g (8.91 mmol) of 5-methyl-2-thiophenecarboxylic acid and 1.33 g (11.6 mmol) of N-hydroxysuccinimide in 90 ml of methylene chloride, 2.05 g (10.7 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccncc1 | HO- | C(Cl)Cl | null | null | Cc1ccc(C(=O)O)s1.NCCCSc1ccncc1>C(Cl)Cl>Cc1ccc(C(=O)NCCCSc2ccncc2)s1 |
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