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-c3a75813d0b24864aa4f7cd526efd6aa | ord-0838bc27829a48ddb77a3ea2f05dfa4b | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.Fc1ccc(CS)c(F)c1>>CCOC(=O)C1=CCCCC1SCc1ccc(F)cc1F | FC1=C(C=CC(=C1)F)NS(=O)(=O)C1CCCC=C1C(=O)OCC.FC1=C(C=CC(=C1)F)CS>>FC1=C(CSC2CCCC=C2C(=O)OCC)C=CC(=C1)F | O=S(=O)(Nc1ccc(F)cc1F)[CH:11]1[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH2:8][CH2:9][CH2:10]1.[SH:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][c:20]1[F:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][CH2:8][CH2:9][CH2:10][CH:11]1[S:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][c:20]1[F:21] | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.Fc1ccc(CS)c(F)c1 | CCOC(=O)C1=CCCCC1SCc1ccc(F)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e004b55701497d7f887b0985a65eca3bb4adb702fb3d6e33c5b8a4e402b31ab3 | cfa39748e584de8627741a4eb08a3e46f3d1f6ce86fafef224e3e259ec2309d6 | C1=CC(SCc2ccccc2)CCC1 | F-c1:c:c:c(-N-S(=O)(=O)-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]=[C:6]-2-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):c(-F):c:1.[SH;D1;+0:11]-[C:12]-[c:13]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]1=[C:5]-[C:4]-[C:3]-[C:2]-[CH;D3;+0:1]-1-[S;H0;D2;+0:11]-[C:12]-[c:13] | 45 | [{"value": 45.0, "product": "FC1=C(CSC2CCCC=C2C(=O)OCC)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Reference Example 1, ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (455 mg) and (2,4-difluorophenyl)-methanethiol (421 mg) were reacted to give ethyl 6-[(2,4-difluorobenzyl)sulfanyl]-1-cyclohexene-1-carboxylate (185 mg) as a colorless oil.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Aromatic halide.Aliphatic thiol | Monosulfide | c1ccccc1.C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HF | null | null | null | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.Fc1ccc(CS)c(F)c1>>CCOC(=O)C1=CCCCC1SCc1ccc(F)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3feff6d5a39d4247b999e4775af002e6 | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.Fc1ccc(CS)c(Cl)c1>>CCOC(=O)C1=CCCCC1SCc1ccc(F)cc1Cl | FC1=C(C=CC(=C1)F)NS(=O)(=O)C1CCCC=C1C(=O)OCC.ClC1=C(C=CC(=C1)F)CS>>ClC1=C(CSC2CCCC=C2C(=O)OCC)C=CC(=C1)F | O=S(=O)(Nc1ccc(F)cc1F)[CH:11]1[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH2:8][CH2:9][CH2:10]1.[SH:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][c:20]1[Cl:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][CH2:8][CH2:9][CH2:10][CH:11]1[S:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][c:20]1[Cl:21] | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.Fc1ccc(CS)c(Cl)c1 | CCOC(=O)C1=CCCCC1SCc1ccc(F)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e004b55701497d7f887b0985a65eca3bb4adb702fb3d6e33c5b8a4e402b31ab3 | cfa39748e584de8627741a4eb08a3e46f3d1f6ce86fafef224e3e259ec2309d6 | C1=CC(SCc2ccccc2)CCC1 | F-c1:c:c:c(-N-S(=O)(=O)-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]=[C:6]-2-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):c(-F):c:1.[SH;D1;+0:11]-[C:12]-[c:13]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]1=[C:5]-[C:4]-[C:3]-[C:2]-[CH;D3;+0:1]-1-[S;H0;D2;+0:11]-[C:12]-[c:13] | 78.6 | [{"value": 78.6, "product": "ClC1=C(CSC2CCCC=C2C(=O)OCC)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Reference Example 1, ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (835 mg) and (2-chloro-4-fluorophenyl)-methanethiol (853 mg) were reacted to give ethyl 6-[(2-chloro-4-fluorobenzyl)sulfanyl]-1-cyclohexene-1-carboxylate (625 mg) as a colorless oil.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Aromatic halide.Aliphatic thiol | Monosulfide | c1ccccc1.C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HF | null | null | null | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.Fc1ccc(CS)c(Cl)c1>>CCOC(=O)C1=CCCCC1SCc1ccc(F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b62278c274db46dcb1e9e75703cc9117 | CCOC(=O)C1=C(S)COCC1.O.[O-]B1OO1>>CCOC(=O)C1=C(S(=O)(=O)O)COCC1 | B1(OO1)[O-].O.O.O.O.[Na+].SC1=C(CCOC1)C(=O)OCC>>C(C)OC(=O)C1=C(COCC1)S(=O)(=O)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([SH:8])[CH2:12][O:13][CH2:14][CH2:15]1.[OH2:10].O1B([O-:9])[O:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([S:8](=[O:9])(=[O:10])[OH:11])[CH2:12][O:13][CH2:14][CH2:15]1 | CCOC(=O)C1=C(S)COCC1.O.[O-]B1OO1 | CCOC(=O)C1=C(S(=O)(=O)O)COCC1 | null | null | C(C)(=O)O | Oxidation | OtherReaction | 758743a35c9f016e87fe2fb3df23bd0cb8d344cfb036e3d974e04ecd9b5c862b | aff842b1e0544720c37b2e5de00aad8b4ddf1a80763bf6e57aac3b66d41b30f2 | C1=CCOCC1 | [#8:1]-[C:2]-[C:3](-[SH;D1;+0:4])=[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9].[O-;H0;D1:10]-B1-O-[O;H0;D2;+0:11]-1.[OH2;D0;+0:12]>>[#8:1]-[C:2]-[C:3](-[S;H0;D4;+0:4](=[O;H0;D1;+0:12])(=[O;H0;D1;+0:10])-[OH;D1;+0:11])=[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9] | 219.9 | [{"value": 219.9, "product": "C(C)OC(=O)C1=C(COCC1)S(=O)(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Sodium perborate tetrahydrate (24.5 g) was added to acetic acid (130 ml) and the mixture was heated to 50–55° C. Thereto was added dropwise a solution of ethyl 5-sulfanyl-3,6-dihydro-2H-pyran-4-carboxylate (10.0 g) in acetic acid (30 ml) over 2 h. The mixture was stirred at 50–55° C. for 3 h, and the reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Sulfonic acid | B1OO1 | null | C1=CCOCC1 | HO-.B | C(C)(=O)O | null | 3 | CCOC(=O)C1=C(S)COCC1.O.[O-]B1OO1>C(C)(=O)O>CCOC(=O)C1=C(S(=O)(=O)O)COCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56f544069272408e88280cef3c65fcbf | CCOC(=O)C1=C(S(=O)(=O)O)COCC1.O=S(Cl)Cl>>CCOC(=O)C1=C(S(=O)(=O)Cl)COCC1 | C(C)OC(=O)C1=C(COCC1)S(=O)(=O)O.S(=O)(Cl)Cl>>ClS(=O)(=O)C1=C(CCOC1)C(=O)OCC | O[S:8]([C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:15][CH2:14][O:13][CH2:12]1)(=[O:9])=[O:10].O=S(Cl)[Cl:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([S:8](=[O:9])(=[O:10])[Cl:11])[CH2:12][O:13][CH2:14][CH2:15]1 | CCOC(=O)C1=C(S(=O)(=O)O)COCC1.O=S(Cl)Cl | CCOC(=O)C1=C(S(=O)(=O)Cl)COCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | C1=CCOCC1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[C:5](=[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10])-[C:11]-[#8:12]>>[#8:12]-[C:11]-[C:5](-[S;H0;D4;+0:2](-[Cl;H0;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4])=[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10] | null | [] | 85 | CELSIUS | 3 | HOUR | 4-(Ethoxycarbonyl)-5,6-dihydro-2H-pyran-3-sulfonic acid (27.5 g) was dissolved in thionyl chloride (82.6 ml) and the mixture was stirred at room temperature →85° C. for 3 h. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in ethyl acetate (100 ml). The obtained solu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | C1=CCOCC1 | HCl | null | 85 | 3 | CCOC(=O)C1=C(S(=O)(=O)O)COCC1.O=S(Cl)Cl>>CCOC(=O)C1=C(S(=O)(=O)Cl)COCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2ba31c2284e4a64a1f0849c2bdeeb97 | Cc1c(O)ccc(OCC(=O)c2ccccc2)c1C>>Cc1c(O)cc2c(-c3ccccc3)coc2c1C | OC1=C(C(=C(OCC(=O)C2=CC=CC=C2)C=C1)C)C.O>>CC1=C(C2=C(C(=CO2)C2=CC=CC=C2)C=C1O)C | O=[C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[CH2:14][O:15][c:16]1[cH:6][cH:5][c:3]([OH:4])[c:2]([CH3:1])[c:17]1[CH3:18]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][c:6]2[c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][o:15][c:16]2[c:17]1[CH3:18] | Cc1c(O)ccc(OCC(=O)c2ccccc2)c1C | Cc1c(O)cc2c(-c3ccccc3)coc2c1C | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | 41440ef63bdcad0549de493ff63648d9e9e6255c65e521389e251312ab757f94 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(-c2coc3ccccc23)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:13]:[c:12]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[o;H0;D2;+0:3]:[c:4](:[c:5]):[c;H0;D3;+0:6]:1:[c:7]:[c:8]):[c:10]:[c:11] | 50 | [{"value": 50.0, "product": "CC1=C(C2=C(C(=CO2)C2=CC=CC=C2)C=C1O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 5 | HOUR | A mixture of 2-(4-hydroxy-2,3-dimethyl-phenoxy)-1-phenyl-ethanone (1.2 g, 4.70 mmol) and polyphosphoric acid (ca. 100 mg) in xylene (10 mL) was stirred at 150° C. for 5 h. The mixture was poured into water, extracted with ethylacetate, washed and dried to give 6,7-dimethyl-3-phenyl-benzofuran-5-ol (560 mg) as a light b... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccccc1 | c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | HO- | C=1(C(=CC=CC1)C)C | 150 | 5 | Cc1c(O)ccc(OCC(=O)c2ccccc2)c1C>C=1(C(=CC=CC1)C)C>Cc1c(O)cc2c(-c3ccccc3)coc2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d619a21ed5a948189dcf96e79df7704d | CC(=O)Oc1cc(C(C)=O)c(O)c(C)c1C>>CC(=O)c1cc(O)c(C)c(C)c1O | O.OC1=C(C=C(C(=C1C)C)OC(C)=O)C(C)=O.C([O-])([O-])=O.[K+].[K+].Cl.O>>OC1=C(C=C(C(=C1C)C)O)C(C)=O | CC(=O)[O:7][c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:12]([OH:13])[c:10]([CH3:11])[c:8]1[CH3:9]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([OH:7])[c:8]([CH3:9])[c:10]([CH3:11])[c:12]1[OH:13] | CC(=O)Oc1cc(C(C)=O)c(O)c(C)c1C | CC(=O)c1cc(O)c(C)c(C)c1O | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 86.3 | [{"value": 86.3, "product": "OC1=C(C=C(C(=C1C)C)O)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The phenylethanone of Step 2 (500 mg) was dissolved in MeOH (20 mL), and potassium carbonate (1 eq.) was added followed by water (1 mL). The mixture was stirred at room temperature for 1 h, and then was poured into water. The solution was acidified with HCl and a precipitate was formed. The precipitate was collected an... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccccc1 | HO- | CO | null | 1 | CC(=O)Oc1cc(C(C)=O)c(O)c(C)c1C>CO>CC(=O)c1cc(O)c(C)c(C)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0dedfd9308af4bb791ec2fa3e6564c11 | C1=COCCC1.CC(=O)c1cc(O)c(C)c(C)c1O>>CC(=O)c1cc(OC2CCCCO2)c(C)c(C)c1O | OC1=C(C=C(C(=C1C)C)O)C(C)=O.O1CCCC=C1.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>OC1=C(C=C(C(=C1C)C)OC1OCCCC1)C(C)=O | [CH:8]1=[CH:9][CH2:10][CH2:11][CH2:12][O:13]1.[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([OH:7])[c:14]([CH3:15])[c:16]([CH3:17])[c:18]1[OH:19]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[c:14]([CH3:15])[c:16]([CH3:17])[c:18]1[OH:19] | C1=COCCC1.CC(=O)c1cc(O)c(C)c(C)c1O | CC(=O)c1cc(OC2CCCCO2)c(C)c(C)c1O | null | null | ClCCl | Heteroatom Alkylation and Arylation | oxa-Michael addition | 1c7c788bec8addec628516b12629525fab255984248a4af23c71106a7726e25d | da6d2e768f263ce18da31b53a21ee41abe25d00717257e942f83f912a04f86d8 | c1ccc(OC2CCCCO2)cc1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1):[c:10] | null | [] | null | null | 4 | HOUR | 1-(2,5-Dihydroxy-3,4-dimethyl-phenyl)-ethanone of Step 3 (275 mg) was dissolved in dichloromethane (20 mL) and 3,4-dihydro-2H-pyran (0.2 mL) was added followed by pyridinium p-toluenesulfonate (PPTS) (30 mg). The mixture was stirred at room temperature for 4 h. The mixture was dried over MgSO4 and purified on silica ge... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | c1ccccc1.C1CCOCC1 | null | ClCCl | null | 4 | C1=COCCC1.CC(=O)c1cc(O)c(C)c(C)c1O>ClCCl>CC(=O)c1cc(OC2CCCCO2)c(C)c(C)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6cf1ac37f0c3467b85144d07fc359468 | CC(=O)c1cc2cc(OC3CCCCO3)c(C)c(C)c2o1>>CC(=O)c1cc2cc(O)c(C)c(C)c2o1 | OC1=C(C=O)C=C(C(=C1C)C)O.CC1=C(C2=C(C=C(O2)C(C)=O)C=C1OC1OCCCC1)C.O>>OC=1C(=C(C2=C(C=C(O2)C(C)=O)C1)C)C | C1CCC([O:9][c:8]2[cH:7][c:6]3[cH:5][c:4]([C:2]([CH3:1])=[O:3])[o:15][c:14]3[c:12]([CH3:13])[c:10]2[CH3:11])OC1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[cH:7][c:8]([OH:9])[c:10]([CH3:11])[c:12]([CH3:13])[c:14]2[o:15]1 | CC(=O)c1cc2cc(OC3CCCCO3)c(C)c(C)c2o1 | CC(=O)c1cc2cc(O)c(C)c(C)c2o1 | null | Cl | CO | Reduction | OtherReaction | b5ceb9e953399e2a3f2f3d503c3846f04ccb158d8f8d4f3b209561e13fedc821 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1ccc2occc2c1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 62.9 | [{"value": 62.9, "product": "OC=1C(=C(C2=C(C=C(O2)C(C)=O)C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1-[6,7-dimethyl-5-(tetrahydro-pyran-2-yloxy)-benzofuran-2-yl]-ethanone (1.1 g) (prepared from 2,5-dihydroxy-3,4-dimethyl-benzaldehyde following the procedure of Steps 3, 4 and 5 of Example 13) and conc. HCl (10 drops) in MeOH (20 mL) was stirred at room temperature for 2 h. Water was poured into the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | C1CCOCC1 | null | c1ccc2occc2c1 | HO- | Cl.CO | null | 2 | CC(=O)c1cc2cc(OC3CCCCO3)c(C)c(C)c2o1>Cl.CO>CC(=O)c1cc2cc(O)c(C)c(C)c2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d4f7692cf52494abd0a18c6db39fe8c | BrBr.CC(=O)c1cc2cc(OC3CCCCO3)c(C)c(C)c2o1>>CC(=O)c1oc2c(C)c(C)c(O)cc2c1Br | CC1=C(C2=C(C=C(O2)C(C)=O)C=C1OC1OCCCC1)C.BrBr>>BrC1=C(OC2=C1C=C(C(=C2C)C)O)C(C)=O | Br[Br:16].C1CCC([O:12][c:11]2[c:9]([CH3:10])[c:7]([CH3:8])[c:6]3[o:5][c:4]([C:2]([CH3:1])=[O:3])[cH:15][c:14]3[cH:13]2)OC1>>[CH3:1][C:2](=[O:3])[c:4]1[o:5][c:6]2[c:7]([CH3:8])[c:9]([CH3:10])[c:11]([OH:12])[cH:13][c:14]2[c:15]1[Br:16] | BrBr.CC(=O)c1cc2cc(OC3CCCCO3)c(C)c(C)c2o1 | CC(=O)c1oc2c(C)c(C)c(O)cc2c1Br | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 2c6f0975c32686d0299e1e32358c3adcdf96823c5abe80aa310f5798e47d19f7 | ff4dd98a50e7cd80a36487c4e40275cd61e3a78460a3a8623820553c89f26f44 | c1ccc2occc2c1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#8;a:6]:[c:7]2:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-C3-C-C-C-C-O-3):[c:12]:[c:13]:2:[cH;D2;+0:14]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:14]1:[c:13]2:[c:12]:[c:10](-[OH;D1;+0:11]):[c:9]:[c:8]:[c:7]:2:[#8;a:6]:[c:5]:1-[C:3](-[C;D1;H3:2])=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | To a solution of 1-[6,7-dimethyl-5-(tetrahydro-pyran-2-yloxy)-benzofuran-2-yl]-ethanone (200 mg) in chloroform (20 mL) was added bromine (120 mg). After 1 h, the solution was washed with water and dried over MgSO4 and concentrated. The residue was purified by silica gel column eluting with 10% hexane in DCM to give 1-(... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic halide.Aromatic alcohol | C1CCOCC1.c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1 | HBr | C(Cl)(Cl)Cl | null | 1 | BrBr.CC(=O)c1cc2cc(OC3CCCCO3)c(C)c(C)c2o1>C(Cl)(Cl)Cl>CC(=O)c1oc2c(C)c(C)c(O)cc2c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f20c4532687d4372ba7b7e28df96a7db | BrBr.CC(=O)Oc1cc2cc(C(C)=O)oc2c(C)c1C>>CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C | C(C)(=O)OC=1C(=C(C2=C(C=C(O2)C(C)=O)C1)C)C.BrBr.BrBr>>BrCC(=O)C=1OC2=C(C1)C=C(C(=C2C)C)OC(C)=O | Br[Br:13].[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[CH3:12])[o:14][c:15]2[c:16]([CH3:17])[c:18]1[CH3:19]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[CH2:12][Br:13])[o:14][c:15]2[c:16]([CH3:17])[c:18]1[CH3:19] | BrBr.CC(=O)Oc1cc2cc(C(C)=O)oc2c(C)c1C | CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc2occc2c1 | Br-[Br;H0;D1;+0:1].[#8;a:2]:[c:3]-[C:4](-[CH3;D1;+0:5])=[O;D1;H0:6]>>[#8;a:2]:[c:3]-[C:4](=[O;D1;H0:6])-[CH2;D2;+0:5]-[Br;H0;D1;+0:1] | 83.6 | [{"value": 83.6, "product": "BrCC(=O)C=1OC2=C(C1)C=C(C(=C2C)C)OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 10 | MINUTE | 1-(5-Acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone (83 mg) (prepared from 1-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-ethanone from Example 14 with acetanhydride and pyridine), was dissolved in chloroform (10 mL). Bromine (50 mg) was added and the solution was stirred at 70° C. for 10 min. When the color of bromine dis... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccc2occc2c1 | HBr | C(Cl)(Cl)Cl | 70 | 0.166667 | BrBr.CC(=O)Oc1cc2cc(C(C)=O)oc2c(C)c1C>C(Cl)(Cl)Cl>CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b060b3d71c424ba2bba7ef8e1ba232ce | C1COCCN1.CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C>>CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C | BrCC(=O)C=1OC2=C(C1)C=C(C(=C2C)C)OC(C)=O.N1CCOCC1.C([O-])([O-])=O.[K+].[K+]>>CC1=C(C2=C(C=C(O2)C(CN2CCOCC2)=O)C=C1OC(C)=O)C | [NH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.Br[CH2:12][C:10]([c:9]1[cH:8][c:7]2[cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[c:23]([CH3:24])[c:21]([CH3:22])[c:20]2[o:19]1)=[O:11]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[CH2:12][N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[o:19][c:20]2[c:21... | C1COCCN1.CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 505036e350a62516c632060eeae05d8239108a346b706af40653d2560d91da48 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCOCC1)c1cc2ccccc2o1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1 | 89.8 | [{"value": 89.8, "product": "CC1=C(C2=C(C=C(O2)C(CN2CCOCC2)=O)C=C1OC(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone (47 mg) from Example 16, morpholine (15 mg), and potassium carbonate (25 mg) in acetone (10 mL) was stirred at room temperature for 30 min. It was then evaporated to dryness, and the residue was purified by silica gel column eluting with 5% MeOH ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccc2occc2c1.C1COCC[NH]1 | HBr | CC(=O)C | null | null | C1COCCN1.CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C>CC(=O)C>CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b842ae5328c45729c573b6344de6cb9 | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C>>Cc1c(O)cc2cc(C(=O)CN3CCOCC3)oc2c1C | CC1=C(C2=C(C=C(O2)C(CN2CCOCC2)=O)C=C1OC(C)=O)C.C([O-])(O)=O.[Na+]>>OC=1C(=C(C2=C(C=C(O2)C(CN2CCOCC2)=O)C1)C)C | CC(=O)[O:4][c:3]1[c:2]([CH3:1])[c:20]([CH3:21])[c:19]2[c:6]([cH:5]1)[cH:7][c:8]([C:9](=[O:10])[CH2:11][N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[o:18]2>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][c:6]2[cH:7][c:8]([C:9](=[O:10])[CH2:11][N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[o:18][c:19]2[c:20]1[CH3:21] | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C | Cc1c(O)cc2cc(C(=O)CN3CCOCC3)oc2c1C | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | O=C(CN1CCOCC1)c1cc2ccccc2o1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 54.8 | [{"value": 54.8, "product": "OC=1C(=C(C2=C(C=C(O2)C(CN2CCOCC2)=O)C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester (23 mg), prepared as in Example 17, in MeOH (10 mL) was stirred while sodium bicarbonate (10 mg) was added. Then the mixture was stirred at RT overnight, followed by evaporation to dryness. The residue was purified by silica gel co... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccc2occc2c1.C1COCC[NH]1 | HO- | CO | null | 8 | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C>CO>Cc1c(O)cc2cc(C(=O)CN3CCOCC3)oc2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8069000183dc4965a4d2ca5ec8fc21cf | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C>>Cc1c(O)cc2cc(C(O)CN3CCOCC3)oc2c1C | [BH4-].[Na+].CC1=C(C2=C(C=C(O2)C(CN2CCOCC2)=O)C=C1OC(C)=O)C.O>>OC(CN1CCOCC1)C=1OC2=C(C1)C=C(C(=C2C)C)O | CC(=O)[O:4][c:3]1[c:2]([CH3:1])[c:20]([CH3:21])[c:19]2[c:6]([cH:5]1)[cH:7][c:8]([C:9](=[O:10])[CH2:11][N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[o:18]2>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][c:6]2[cH:7][c:8]([CH:9]([OH:10])[CH2:11][N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[o:18][c:19]2[c:20]1[CH3:21] | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C | Cc1c(O)cc2cc(C(O)CN3CCOCC3)oc2c1C | null | null | CO | Reduction | OtherReaction | ba270c4e4c66c0ca4c384010b56cde71211c1d0a42b18d125d377e517b054cad | 0ceccbeb1a171407aae4661a0628d0d4c1bc76338bade38dd330e39814e68322 | c1ccc2oc(CCN3CCOCC3)cc2c1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[#8;a:11]:[c:12]>>[#7:5]-[C:6]-[CH;D3;+0:7](-[OH;D1;+0:8])-[c:9](:[c:10]):[#8;a:11]:[c:12].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 68.2 | [{"value": 68.2, "product": "OC(CN1CCOCC1)C=1OC2=C(C1)C=C(C(=C2C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester (35 mg), prepared as in Example 17, in MeOH (10 mL) was stirred while NaBH4 (40 mg) was added, and the mixture was stirred at room temperature for an additional 4 h. The mixture was poured into water, and extracted with ethylacetat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Secondary alcohol.Aromatic alcohol | null | null | c1ccc2occc2c1.C1COCC[NH]1 | Other | CO | null | 4 | CC(=O)Oc1cc2cc(C(=O)CN3CCOCC3)oc2c(C)c1C>CO>Cc1c(O)cc2cc(C(O)CN3CCOCC3)oc2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e0bcad1b034343be927c12c829b6cd8e | CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C.CNC(C)O>>Cc1c(O)cc2cc(C3(O)CN(C)CCO3)oc2c1C | O.BrCC(=O)C=1OC2=C(C1)C=C(C(=C2C)C)OC(C)=O.CNC(C)O.C([O-])([O-])=O.[K+].[K+]>>OC=1C(=C(C2=C(C=C(O2)C2(CN(CCO2)C)O)C1)C)C | CC(=O)[O:4][c:3]1[c:2]([CH3:1])[c:19]([CH3:20])[c:18]2[c:6]([cH:5]1)[cH:7][c:8]([C:9](=[O:10])[CH2:11]Br)[o:17]2.[NH:12]([CH3:13])[CH:14]([CH3:15])[OH:16]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][c:6]2[cH:7][c:8]([C:9]3([OH:10])[CH2:11][N:12]([CH3:13])[CH2:14][CH2:15][O:16]3)[o:17][c:18]2[c:19]1[CH3:20] | CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C.CNC(C)O | Cc1c(O)cc2cc(C3(O)CN(C)CCO3)oc2c1C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 702b157a86a56e76aa494318df7090c3c53371fc4fa7e2c29c8f72ab027fdc87 | 7e3331757dd2f750754139bc304381506c0f2b6dafa5e616dfc0c9fb97b7c4df | c1ccc2oc(C3CNCCO3)cc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[#8;a:6]:[c:7].C-C(=O)-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[C;D1;H3:12]-[NH;D2;+0:13]-[CH;D3;+0:14](-[CH3;D1;+0:15])-[OH;D1;+0:16]>>[C;D1;H3:12]-[N;H0;D3;+0:13]1-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[OH;D1;+0:3])(-[c:4](:[c:5]):[#8;a:6]:[c:7])-[O;H0;D2;+0:16]-[CH... | 78.2 | [{"value": 78.2, "product": "OC=1C(=C(C2=C(C=C(O2)C2(CN(CCO2)C)O)C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2-bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone (30 mg), methylaminoethanol (7 mg), and potassium carbonate (20 mg) in acetone (10 mL) was stirred at RT for 1 h. The mixture was poured into water and extracted with ethylacetate. The organic layer was dried and evaporated followed by purificatio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Secondary alcohol.Secondary amine | Ether.Tertiary alcohol.Aromatic alcohol.Tertiary amine | null | C1COCC[NH]1 | c1ccc2occc2c1.C1COCC[NH]1 | HBr | CC(=O)C | null | 1 | CC(=O)Oc1cc2cc(C(=O)CBr)oc2c(C)c1C.CNC(C)O>CC(=O)C>Cc1c(O)cc2cc(C3(O)CN(C)CCO3)oc2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7de22d0f2eb54aa7921a13c19744900f | C1=COCCC1.Cc1c(O)cc(C=O)c(O)c1C>>Cc1c(OC2CCCCO2)cc(C=O)c(O)c1C | OC1=C(C=O)C=C(C(=C1C)C)O.O1CCCC=C1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>OC1=C(C=O)C=C(C(=C1C)C)OC1OCCCC1 | [CH:5]1=[CH:6][CH2:7][CH2:8][CH2:9][O:10]1.[CH3:1][c:2]1[c:3]([OH:4])[cH:11][c:12]([CH:13]=[O:14])[c:15]([OH:16])[c:17]1[CH3:18]>>[CH3:1][c:2]1[c:3]([O:4][CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10]2)[cH:11][c:12]([CH:13]=[O:14])[c:15]([OH:16])[c:17]1[CH3:18] | C1=COCCC1.Cc1c(O)cc(C=O)c(O)c1C | Cc1c(OC2CCCCO2)cc(C=O)c(O)c1C | null | null | ClCCl | Heteroatom Alkylation and Arylation | oxa-Michael addition | 1c7c788bec8addec628516b12629525fab255984248a4af23c71106a7726e25d | da6d2e768f263ce18da31b53a21ee41abe25d00717257e942f83f912a04f86d8 | c1ccc(OC2CCCCO2)cc1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1):[c:10] | 49.8 | [{"value": 49.8, "product": "OC1=C(C=O)C=C(C(=C1C)C)OC1OCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2,5-Dihydroxy-3,4-dimethyl-benzaldehyde (2.0 g) was dissolved in dichloromethane (50 mL) and 3,4-dihydro-2H-pyran (1.5 g) was added followed by addition of p-toluenesulfonic acid monohydrate (200 mg). The solution was stirred at room temperature for 1 hour and quenched by adding sodium bicarbonate solution (1 mL). Then... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | c1ccccc1.C1CCOCC1 | null | ClCCl | null | 1 | C1=COCCC1.Cc1c(O)cc(C=O)c(O)c1C>ClCCl>Cc1c(OC2CCCCO2)cc(C=O)c(O)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4343c0c6effe4c3a9e64392e14908cdb | COC(=O)CBr.Cc1c(OC2CCCCO2)cc(C=O)c(O)c1C>>COC(=O)COc1c(C=O)cc(OC2CCCCO2)c(C)c1C | O.OC1=C(C=O)C=C(C(=C1C)C)OC1OCCCC1.BrCC(=O)OC.C([O-])([O-])=O.[K+].[K+]>>COC(COC1=C(C(=C(C=C1C=O)OC1OCCCC1)C)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[c:8]([CH:9]=[O:10])[cH:11][c:12]([O:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:19]2)[c:20]([CH3:21])[c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8]([CH:9]=[O:10])[cH:11][c:12]([O:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:19]2)[c:20]([CH3:21])[c:22... | COC(=O)CBr.Cc1c(OC2CCCCO2)cc(C=O)c(O)c1C | COC(=O)COc1c(C=O)cc(OC2CCCCO2)c(C)c1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(OC2CCCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]-[C:7]=[O;D1;H0:6] | 51.8 | [{"value": 51.8, "product": "COC(COC1=C(C(=C(C=C1C=O)OC1OCCCC1)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 2-hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-benzaldehyde (150 mg) from Step 1, methyl bromoacetate (180 mg) and potassium carbonate (200 mg) in DMF (10 mL) was stirred at room temperature for 2 hours. Then the solution was poured into water and extracted with ethylacetate. The ethyl acetate was was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.C1CCOCC1 | HBr | CN(C)C=O | null | 2 | COC(=O)CBr.Cc1c(OC2CCCCO2)cc(C=O)c(O)c1C>CN(C)C=O>COC(=O)COc1c(C=O)cc(OC2CCCCO2)c(C)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85a2f5e267c84706804a0fc80444029f | COC(=O)c1cc2cc(O)c(C)c(C)c2o1>>Cc1c(O)cc2cc(CO)oc2c1C | COC(=O)C=1OC2=C(C1)C=C(C(=C2C)C)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>OCC=1OC2=C(C1)C=C(C(=C2C)C)O | CO[C:9]([c:8]1[cH:7][c:6]2[cH:5][c:3]([OH:4])[c:2]([CH3:1])[c:13]([CH3:14])[c:12]2[o:11]1)=[O:10]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][c:6]2[cH:7][c:8]([CH2:9][OH:10])[o:11][c:12]2[c:13]1[CH3:14] | COC(=O)c1cc2cc(O)c(C)c(C)c2o1 | Cc1c(O)cc2cc(CO)oc2c1C | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2occc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#8;a:5]:[c:6] | 44.1 | [{"value": 44.1, "product": "OCC=1OC2=C(C1)C=C(C(=C2C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid methyl ester (231 mg) prepared as in Example 2, was dissolved in THF and lithium aluminum hydride (93 mg) was added. The mixture was stirred at room temperature for 4 h. Then the solution was poured into water and extracted with ethylacetate. The ethyl acetate was was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2occc2c1 | Other | C1CCOC1 | null | 4 | COC(=O)c1cc2cc(O)c(C)c(C)c2o1>C1CCOC1>Cc1c(O)cc2cc(CO)oc2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e258e6a24542474ba0381f930f986120 | CC(C)N(C(C)C)P(N)(=O)Cl.O=P([O-])(OCc1ccccc1)OCc1ccccc1>>CCOP(=O)(C#N)OCC | [O-]P([O-])(=O)OP(=O)([O-])[O-].P(OC(C)(C)C)(OC(C)(C)C)[O-].C(C1=CC=CC=C1)OP(=O)(OCC1=CC=CC=C1)[O-].C(C)(C)N(P(=O)(N)Cl)C(C)C>>C(C)OP(OCC)(=O)C#N | CC(N(P(=O)(Cl)[NH2:7])[CH:9]([CH3:1])[CH3:10])[CH3:6].[O-][P:4]([O:3][CH2:2]c1ccccc1)(=[O:5])[O:8]Cc1ccccc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([C:6]#[N:7])[O:8][CH2:9][CH3:10] | CC(C)N(C(C)C)P(N)(=O)Cl.O=P([O-])(OCc1ccccc1)OCc1ccccc1 | CCOP(=O)(C#N)OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 44945b48395c0ab715d6891c1001b38acdb76a09553e58c9b624fd3237cd5516 | 690ee693a3915ef015ee0ffe4e5bdd5a8963af32bdddfda193db21e9d178f8b9 | null | C-C(-[CH3;D1;+0:1])-N(-[CH;D3;+0:2](-[C;D1;H3:3])-[CH3;D1;+0:4])-P(-Cl)(=O)-[NH2;D1;+0:5].[O-]-[P;H0;D4;+0:6](=[O;D1;H0:7])(-[#8:8]-[CH2;D2;+0:9]-c1:c:c:c:c:c:1)-[O;H0;D2;+0:10]-C-c1:c:c:c:c:c:1>>[C;D1;H3:3]-[CH2;D2;+0:2]-[O;H0;D2;+0:10]-[P;H0;D4;+0:6](=[O;D1;H0:7])(-[#8:8]-[CH2;D2;+0:9]-[CH3;D1;+0:4])-[C;H0;D2;+0:1]#[... | null | [] | null | null | null | null | In order to try different protecting groups on the phosphate, several other methods of phosphorylation were attempted. These included the use of alkylamidophosphines, which have been shown to readily phosphorylate alcohols and phenols in high yield. For example, di-tert-butyloxy (N,N-diisopropylamido)phosphine, prepare... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Nitrile | c1ccccc1.c1ccccc1 | null | null | HCl | null | null | null | CC(C)N(C(C)C)P(N)(=O)Cl.O=P([O-])(OCc1ccccc1)OCc1ccccc1>>CCOP(=O)(C#N)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-553c413765554627bebc5f8dec940306 | COc1ccc(C=O)c(OC)c1OC>>COc1ccc(C=O)c(O)c1O | Cl.B(Cl)(Cl)Cl.C([O-])(O)=O.[Na+].COC1=C(C=O)C=CC(=C1OC)OC.B(Cl)(Cl)Cl>>OC1=C(C=O)C=CC(=C1O)OC | C[O:10][c:9]1[c:6]([CH:7]=[O:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[O:12]C>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([OH:10])[c:11]1[OH:12] | COc1ccc(C=O)c(OC)c1OC | COc1ccc(C=O)c(O)c1O | null | null | ClCCl.CCCCCC.C(C)(=O)OCC | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[O;H0;D2;+0:7]-C):[c:8]>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2](-[OH;D1;+0:1]):[c:6](-[OH;D1;+0:7]):[c:8] | null | [] | null | null | 2 | HOUR | An anhydrous dichloromethane (500 mL) solution of 2,3,4-trimethoxy-benzaldehyde (6a, 19.6 g, 100 mmol) under argon at ambient temperature was stirred for 10 min and boron trichloride (100 mL, 100 mmol, 1 eq, 1.0 M soln in dichloromethane) was added. After 2 hours, the second equivalent of boron trichloride (100 mL, 100... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl.CCCCCC.C(C)(=O)OCC | null | 2 | COc1ccc(C=O)c(OC)c1OC>ClCCl.CCCCCC.C(C)(=O)OCC>COc1ccc(C=O)c(O)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9af51249e6348399a70185518c0bc2d | CCCCCC1=CCCC1=O.COC(=O)CC(=O)OC>>CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC | C(CCCC)C=1C(CCC1)=O.C(CC(=O)OC)(=O)OC.C[O-].[Na+]>>C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[CH:11][CH2:10][CH2:9][C:7]1=[O:8].[CH2:12]([C:13](=[O:14])[O:15][CH3:16])[C:17](=[O:18])[O:19][CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH:12]([C:13](=[O:14])[O:15][CH3:16])[C:17](=[O:18])[O:19][CH3:20] | CCCCCC1=CCCC1=O.COC(=O)CC(=O)OC | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC | null | null | null | C-C Coupling | OtherReaction | fd506cf634d55bf99e34f898f8d1975a1f72a9379fefd16d2e5845f9cf3c8814 | 898e66379ea5c9946b068a7796ddcf4c38fd80e0571f55d1ac4ead7978c7ea75 | O=C1CCCC1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].[C:10]-[C:11]-[C;H0;D3;+0:12]1=[CH;D2;+0:13]-[C:14]-[C:15]-[C:16]-1=[O;D1;H0:17]>>[C:10]-[C:11]-[CH;D3;+0:12]1-[C:16](=[O;D1;H0:17])-[C:15]-[C:14]-[CH;D3;+0:13]-1-[CH;D3;+0:5](-[C:3](=[O;D1;H0:4])-[#8:2]-[C;D1;H3:1])-[C:6](=[O;D... | 93.8 | [{"value": 93.8, "product": "C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | The reaction product was refined to obtain 95 g (0.6 mol) of 2-pentyl-2-cyclopentenone. Moreover, 95 g (0.6 mol) of 2-pentyl-2-cyclopentenone was dropped to a solution, prepared by dissolving 118 g (0.9 mol) of dimethyl malonate in 38 g of methanol anhydride in a nitrogen atmosphere, cooling the mixture to 0° C. and ad... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone.Ester.Ester | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | null | 0 | 2 | CCCCCC1=CCCC1=O.COC(=O)CC(=O)OC>>CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b77438f2ab34e7bb8042f94df2cf5a7 | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC.CCCCCC1C(=O)CCC1CC(=O)O>>CCCCCC1C(=O)CCC1CC(=O)OC | C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC.C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC.C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC.C(CCCC)C1C(CCC1=O)CC(=O)O>>C(CCCC)C1C(CCC1=O)CC(=O)OC | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)O[CH3:16].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH2:12][C:13](=[O:14])[OH:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC.CCCCCC1C(=O)CCC1CC(=O)O | CCCCCC1C(=O)CCC1CC(=O)OC | null | null | O | Heteroatom Alkylation and Arylation | O-methylation | 584c206b70fd291cdfaa6a3fc8fb3b571f5864638d82543702ab3d931c144f86 | 43fdfffe15a01c77924b1c923a99c979d5ae5cf13440224e510e701641bf99be | O=C1CCCC1 | C-C-C-C-C-C1-C(-C(-C(=O)-O-C)-C(=O)-O-[CH3;D1;+0:1])-C-C-C-1=O.[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 97.4 | [{"value": 97.3, "product": "C(CCCC)C1C(CCC1=O)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "C(CCCC)C1C(CCC1=O)CC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A 1 L four-neck flask equipped with a stirrer, a supply unit, a thermometer and a rectifier was charged with 600 g of raw material containing 545 g (1.92 mol) of dimethyl 2-pentyl-3-oxo-cyclopentylmalonate produced in the same manner as in Production Example 1 and the raw material was heated to 180° C. with stirring un... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ester.Ester | Ester | C1CCCC1 | null | C1CCCC1 | HO- | O | null | 16 | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC.CCCCCC1C(=O)CCC1CC(=O)O>O>CCCCCC1C(=O)CCC1CC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-adb75d18fb8c449a94b5109ee5f32ae9 | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC>>CCCCCC1C(=O)CCC1CC(=O)OC | C(CCCC)C1C(CCC1=O)CC(=O)O.C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC>>C(CCCC)C1C(CCC1=O)CC(=O)OC | COC(=O)[CH:12]([CH:11]1[CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:7](=[O:8])[CH2:9][CH2:10]1)[C:13](=[O:14])[O:15][CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC | CCCCCC1C(=O)CCC1CC(=O)OC | null | null | O | Reduction | Decarboxylation | 33f176f6ce02426b2726e71e3c19f64673952a2b50dd48518b89a08efe25965b | b45711df98eaf2a3f54e3027da3f1b57580ab2f6d54e9ac2a56731961e64969a | O=C1CCCC1 | C-O-C(=O)-[CH;D3;+0:1](-[C:2](-[C:3])-[C:4]-[C:5]=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[C:4]-[C:5]=[O;D1;H0:6] | 90.8 | [{"value": 90.7, "product": "C(CCCC)C1C(CCC1=O)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "C(CCCC)C1C(CCC1=O)CC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 9 | HOUR | The same 1 L four-neck flask that was used in Example 1 was charged with 600 g of raw material containing 557 g (1.96 mol) of dimethyl 2-pentyl-3-oxo-cyclopentylmalonate produced in the same manner as in Production Example 1 and the raw material was heated to 180° C. with stirring under normal pressure. Then, the suppl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | null | C1CCCC1 | HO- | O | null | 9 | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC>O>CCCCCC1C(=O)CCC1CC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-442cb6effe204e93a42b49768d720102 | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC.CCCCCC1C(=O)CCC1CC(=O)O>>CCCCCC1C(=O)CCC1CC(=O)OC | C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC.C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC.C(CCCC)C1C(CCC1=O)C(C(=O)OC)C(=O)OC.C(CCCC)C1C(CCC1=O)CC(=O)O>>C(CCCC)C1C(CCC1=O)CC(=O)OC | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)O[CH3:16].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH2:12][C:13](=[O:14])[OH:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC.CCCCCC1C(=O)CCC1CC(=O)O | CCCCCC1C(=O)CCC1CC(=O)OC | null | null | O | Heteroatom Alkylation and Arylation | O-methylation | 584c206b70fd291cdfaa6a3fc8fb3b571f5864638d82543702ab3d931c144f86 | 43fdfffe15a01c77924b1c923a99c979d5ae5cf13440224e510e701641bf99be | O=C1CCCC1 | C-C-C-C-C-C1-C(-C(-C(=O)-O-C)-C(=O)-O-[CH3;D1;+0:1])-C-C-C-1=O.[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 96 | [{"value": 96.0, "product": "C(CCCC)C1C(CCC1=O)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.9, "product": "C(CCCC)C1C(CCC1=O)CC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The same 1 L four-neck flask that was used in Example 1 was charged with 600 g of raw material containing 550 g (1.94 mol) of dimethyl 2-pentyl-3-oxo-cyclopentylmalonate produced in the same manner as in Production Example 1 and the raw material was heated to 215° C. with stirring under normal pressure. Then, the suppl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ester.Ester | Ester | C1CCCC1 | null | C1CCCC1 | HO- | O | null | 4 | CCCCCC1C(=O)CCC1C(C(=O)OC)C(=O)OC.CCCCCC1C(=O)CCC1CC(=O)O>O>CCCCCC1C(=O)CCC1CC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8793196be2554b07b1b776d773339178 | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC>>CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC | C(CCCCCCC)(=O)Cl.N#N.SCCC[Si](OCC)(OCC)OCC.[SiH4]>>C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC | Cl[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:9].[SH:10][CH2:11][CH2:12][CH2:13][Si:14]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[S:10][CH2:11][CH2:12][CH2:13][Si:14]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20... | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC | CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC | null | null | CCCCCC.C(C)N(CC)CC | Acylation | thioether_nucl_sub | 774e8f449f87493fdbd93fdbbfef7c7bc086966dfce8806abcb487630046ef59 | cf70b55890699bc889b230d5ae9783daf8be8d20d1ad4c06197ffaf659088f4e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 87 | [{"value": 87.0, "product": "C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet, and temperature controller were charged 1,021 grams of 3-mercaptopropyltriethoxysilane (SILQUEST® A-1891 silane from OSi Specialties, Inc., a subsidiary of Crompton Corp. of Greenw... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aliphatic thiol | Carbo-thioester | null | null | null | HCl | CCCCCC.C(C)N(CC)CC | null | null | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC>CCCCCC.C(C)N(CC)CC>CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2cdc9ab8298469c92bf748bc8239564 | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1>>CCO[Si](CCCSC(C)=O)(OCC)OCC | S1C(=CC=C1)CC(=O)O.[O-]CC.[Na+].ClCCC[Si](OCC)(OCC)OCC>>C(C)(=O)SCCC[Si](OCC)(OCC)OCC | Cl[CH2:7][CH2:6][CH2:5][Si:4]([O:3][CH2:2][CH3:1])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17].O[C:9]([CH2:10]c1ccc[s:8]1)=[O:11]>>[CH3:1][CH2:2][O:3][Si:4]([CH2:5][CH2:6][CH2:7][S:8][C:9]([CH3:10])=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17] | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1 | CCO[Si](CCCSC(C)=O)(OCC)OCC | null | null | S1C(=CC=C1)C(=O)O.C(C)O | Acylation | OtherReaction | 63c844c1ec474495593d771b062be3364adf503c0822f2fd1bfb69f229709474 | dfe9fe1a6355f40a3f716cb9a21cc73ccd389fac1a8bf4766414c46a9aa66845 | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-c1:[s;H0;D2;+0:7]:c:c:c:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[C;H0;D3;+0:4](-[CH3;D1;+0:6])=[O;D1;H0:5] | 78 | [{"value": 78.0, "product": "C(C)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using as a solvent the alcohol corresponding to the silane alkoxy group. Into a 250 ml, three-neck round bottomed flask equipped with magnetic stir bar, temperature probe/controller, heating mantle, addition... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Carbo-thioester | c1ccsc1 | null | null | HCl | S1C(=CC=C1)C(=O)O.C(C)O | null | null | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1>S1C(=CC=C1)C(=O)O.C(C)O>CCO[Si](CCCSC(C)=O)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e50976b1d03a405c8b69ff3c747f0580 | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1>>CCO[Si](CSC(C)=O)(OCC)OCC | N#N.S1C(=CC=C1)CC(=O)O.ClC[Si](OCC)(OCC)OCC.S1C(=CC=C1)C(=O)O.[O-]CC.[Na+]>>C(C)(=O)SC[Si](OCC)(OCC)OCC | Cl[CH2:5][Si:4]([O:3][CH2:2][CH3:1])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15].O[C:7]([CH2:8]c1ccc[s:6]1)=[O:9]>>[CH3:1][CH2:2][O:3][Si:4]([CH2:5][S:6][C:7]([CH3:8])=[O:9])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15] | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1 | CCO[Si](CSC(C)=O)(OCC)OCC | null | null | COCCOCCOC | Acylation | OtherReaction | 63c844c1ec474495593d771b062be3364adf503c0822f2fd1bfb69f229709474 | dfe9fe1a6355f40a3f716cb9a21cc73ccd389fac1a8bf4766414c46a9aa66845 | null | Cl-[CH2;D2;+0:1]-[#14:2](-[#8:3]-[C:4]-[C;D1;H3:5])(-[#8:6]-[C:7]-[C;D1;H3:8])-[#8:9]-[C:10]-[C;D1;H3:11].O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-c1:[s;H0;D2;+0:15]:c:c:c:1>>[C;D1;H3:5]-[C:4]-[#8:3]-[#14:2](-[#8:6]-[C:7]-[C;D1;H3:8])(-[#8:9]-[C:10]-[C;D1;H3:11])-[CH2;D2;+0:1]-[S;H0;D2;+0:15]-[C;H0;D3;+0:12](-[C... | 55 | [{"value": 55.0, "product": "C(C)(=O)SC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 8 | CELSIUS | null | null | This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using a nonprotic solvent. 88 grams of powdered sodium ethoxide and 600 ml diglyme were charged into a one-liter, three-neck round-bottomed flask equipped with magnetic stir bar, temperature probe/controller... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Carbo-thioester | c1ccsc1 | null | null | HCl | COCCOCCOC | 8 | null | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1>COCCOCCOC>CCO[Si](CSC(C)=O)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eda0b50d30a844b4a41d341f4fdb9a14 | O=C1c2ccccc2C(=O)c2c1cc(S(=O)(=O)[O-])c(O)c2O.O=S(=O)(O)Cl>>O=C1c2ccccc2C(=O)c2c1cc(S(=O)(=O)Cl)c(O)c2O | ClS(=O)(=O)O.[Na+].OC=1C(=CC=2C(C3=CC=CC=C3C(C2C1O)=O)=O)S(=O)(=O)[O-]>>OC=1C(=CC=2C(C3=CC=CC=C3C(C2C1O)=O)=O)S(=O)(=O)Cl | [O-][S:15]([c:14]1[cH:13][c:12]2[c:11]([c:21]([OH:22])[c:19]1[OH:20])[C:9](=[O:10])[c:8]1[c:3]([cH:4][cH:5][cH:6][cH:7]1)[C:2]2=[O:1])(=[O:16])=[O:17].O=S(=O)(O)[Cl:18]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[c:11]2[c:12]1[cH:13][c:14]([S:15](=[O:16])(=[O:17])[Cl:18])[c:19]([OH:20])[c:21]2[OH:22... | O=C1c2ccccc2C(=O)c2c1cc(S(=O)(=O)[O-])c(O)c2O.O=S(=O)(O)Cl | O=C1c2ccccc2C(=O)c2c1cc(S(=O)(=O)Cl)c(O)c2O | null | null | null | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | O=C1c2ccccc2C(=O)c2ccccc21 | O-S(=O)(=O)-[Cl;H0;D1;+0:1].[O-]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]1:[c:6]:[c:7](:[c:8](:[c:9](-[O;D1;H1:10]):[c:11]:1-[O;D1;H1:12])-[C:13](=[O;D1;H0:14])-[c:15])-[C:16]=[O;D1;H0:17]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]1:[c:6]:[c:7](:[c:8](:[c:9](-[O;D1;H1:10]):[c:11]:1-[O;D1;... | 66 | [{"value": 66.0, "product": "OC=1C(=CC=2C(C3=CC=CC=C3C(C2C1O)=O)=O)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 3,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid sodium salt (1.4 g, 3.9 mmoles) was combined with 30 mL of chlorosulfonic acid and heated to 90° C. for 5 hours, after which the solution was cooled to 0° C. and poured into 100 g of ice. After the ice melted the solution was extracted with CH2Cl2 (3×100 mL), methylene... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccc2c(c1)Cc1ccccc1C2 | HO- | null | 90 | null | O=C1c2ccccc2C(=O)c2c1cc(S(=O)(=O)[O-])c(O)c2O.O=S(=O)(O)Cl>>O=C1c2ccccc2C(=O)c2c1cc(S(=O)(=O)Cl)c(O)c2O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b6db5d76b7944ff18a499f9e72331b8a | CC(C)=CCCl.Cc1cccc(C)c1O>>CC(C)=CCC1(C)CCC=C(C)C1=O | C(C=C(C)C)Cl.[H-].[Na+].CC1=C(C(=CC=C1)C)O.CO>>CC=1C(C(CCC1)(CC=C(C)C)C)=O | Cl[CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3].[c:6]1([CH3:7])[cH:8][cH:9][cH:10][c:11]([CH3:12])[c:13]1[OH:14]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[C:13]1=[O:14] | CC(C)=CCCl.Cc1cccc(C)c1O | CC(C)=CCC1(C)CCC=C(C)C1=O | null | [Pd] | C1(=CC=CC=C1)C | Acylation | OtherReaction | 6fffa0d222ffb075bcbc34d9c48f49de1c39007f8ab248d00542f709b46ecf62 | 42da64ec40e29427a46e8ef6b6ff47f2a7e2f11a2072895485933fd72aabade3 | O=C1C=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C;D1;H3:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[C;D1;H3:12]):[c;H0;D3;+0:13]:1-[OH;D1;+0:14]>>[C;D1;H3:6]-[C;H0;D3;+0:7]1=[CH;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C;H0;D4;+0:11](-[C;D1;H3:12])(-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D... | null | [] | 50 | CELSIUS | 45 | MINUTE | Sodium hydride (60%, 85 g, 2.13 mol) was added portionwise to a solution of 2,6-dimethylphenol (250 g, 2.05 mol) in 2 L of toluene at 10-15° C. The resulting suspension was stirred for 45 min. The mixture was cooled to 50° C., and prenyl chloride (262 g, 2.13 mol, 85%) was added during 1.5 h keeping the temperature at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ketone | c1ccccc1 | C1=CCCCC1 | C1=CCCCC1 | Other | [Pd].C1(=CC=CC=C1)C | 50 | 0.75 | CC(C)=CCCl.Cc1cccc(C)c1O>[Pd].C1(=CC=CC=C1)C>CC(C)=CCC1(C)CCC=C(C)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00827ff276b54f969f5cbc888a5ba452 | CC(C)=CCC1(C)CCC=C(C)C1=O>>CC(C)=CCC1(C)CCC2CC2(C)C1=O | CC=1C(C(CCC1)(CC=C(C)C)C)=O.[H-].[Na+].[I-].C[S+](=O)(C)C.[H][H]>>CC12C(C(CCC2C1)(CC=C(C)C)C)=O | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:12]([CH3:13])[C:14]1=[O:15]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]2[CH2:11][C:12]2([CH3:13])[C:14]1=[O:15] | CC(C)=CCC1(C)CCC=C(C)C1=O | CC(C)=CCC1(C)CCC2CC2(C)C1=O | null | null | O.CS(=O)C | C-C Coupling | OtherReaction | 6383c24477e07121e04e7644483ae404183a2aa5a3feed555f1b575b70ffe352 | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1CCCC2CC12 | [C;D1;H3:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[C:5]-[C:6]-[C:7]-1=[O;D1;H0:8]>>[C;D1;H3:1]-[C;H0;D4;+0:2]12-[C:9]-[CH;D3;+0:3]-1-[C:4]-[C:5]-[C:6]-[C:7]-2=[O;D1;H0:8] | 83 | [{"value": 83.0, "product": "CC12C(C(CCC2C1)(CC=C(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium hydride (60%, 2.11 g, 52.8 mmol) was added to a suspension of trimethylsulfoxonium iodide (11.6 g, 52.8 mmol) in 60 ml of dimethyl sulfoxide. The mixture was stirred for 30 min until hydrogen evolution stopped. 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone was added and the mixture was stirred over night... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=CCCCC1 | C1CCC2CC2C1 | C1CCC2CC2C1 | Other | O.CS(=O)C | null | null | CC(C)=CCC1(C)CCC=C(C)C1=O>O.CS(=O)C>CC(C)=CCC1(C)CCC2CC2(C)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9f153e8525b4067966b861eb0782cb3 | CC(C)=CCC1(C)CCC=C(C)C1=O.CI>>CC(C)=CCC1(C)CC=CC(C)(C)C1=O | CC=1C(C(CCC1)(CC=C(C)C)C)=O.[Li+].CC(C)[N-]C(C)C.CI>>CC1(C(C(CC=C1)(CC=C(C)C)C)=O)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[C:14]1=[O:15].I[CH3:13]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH:9]=[CH:10][C:11]([CH3:12])([CH3:13])[C:14]1=[O:15] | CC(C)=CCC1(C)CCC=C(C)C1=O.CI | CC(C)=CCC1(C)CC=CC(C)(C)C1=O | null | null | CC(C)(C)OC.C1CCOC1 | C-C Coupling | OtherReaction | a5ed2f3bda8728aa6eb383f8aa7578c4b8c5323291d56fb502a1a0736d1e049b | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1CC=CCC1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[CH2;D2;+0:5]-[C:6]-[C:7]-[C:8]-1=[O;D1;H0:9]>>[C;D1;H3:2]-[C;H0;D4;+0:3]1(-[CH3;D1;+0:1])-[CH;D2;+0:4]=[CH;D2;+0:5]-[C:6]-[C:7]-[C:8]-1=[O;D1;H0:9] | null | [] | -78 | CELSIUS | 1 | HOUR | 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone (5.00 g, 26 mmol) was added to a solution of LDA (prepared from diisopropylamine (3.15 g, 31.2 mmol) and n-BuLi (1.6M in hexane, 19.5 ml, 31.2 mmol)) in THF (50 ml) at −78° C. The mixture was stirred for 1 h at −78° C. Methyl iodide (5.54 g, 39 mmol) was added and t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1 | HI | CC(C)(C)OC.C1CCOC1 | -78 | 1 | CC(C)=CCC1(C)CCC=C(C)C1=O.CI>CC(C)(C)OC.C1CCOC1>CC(C)=CCC1(C)CC=CC(C)(C)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f340efd2e2d0433dbd255d55b8ae8bf5 | CC(C)=CCC1(C)CCC=C(C)C1=O>>CC(C)=CCC1(C)CCCC(C)C1=O | CC=1C(C(CCC1)(CC=C(C)C)C)=O.[O-]S(=O)S(=O)[O-].[Na+].[Na+]>>CC1(C(C(CCC1)C)=O)CC=C(C)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[C:13]1=[O:14]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:12])[C:13]1=[O:14] | CC(C)=CCC1(C)CCC=C(C)C1=O | CC(C)=CCC1(C)CCCC(C)C1=O | null | null | null | Reduction | Hydrogenation (double to single) | 36c089d27e46ae7bb4df3563f4ed1e4684984208b1f092ae42b91f9c5627fd64 | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1CCCCC1 | [C;D1;H3:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[C:5]-[C:6]-[C:7]-1=[O;D1;H0:8]>>[C;D1;H3:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[C:4]-[C:5]-[C:6]-[C:7]-1=[O;D1;H0:8] | null | [] | null | null | null | null | This compound was prepared as a mixture of 2 isomers by reduction of 2,6-dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone with Na2S2O4. 1H-NMR (400 MHz, CDCl3): 5.15-5.12, 4.94-4.89 (2m, 1H, 2′-H), 2.69-1.26 (m, 9H), 1.70, 1.68 (2s, 3H, 3′-CH3), 1.61, 1.60 (2s, 3H, 4′-H), 1.47, 0.98 (2s, 3H, 6-CH3), 1.00, 0.99 (2d, J=... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1 | null | null | null | null | CC(C)=CCC1(C)CCC=C(C)C1=O>>CC(C)=CCC1(C)CCCC(C)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6dd357ae782d47b2bc25946eb45b099c | CC(C)=CCC1(C)CCC=C(C)C1=O>>CC(C)=CCC1(C)CCC=C(C)C1(C)O | CC=1C(C(CCC1)(CC=C(C)C)C)=O.C[Mg]Cl>>CC1(C(=CCCC1(CC=C(C)C)C)C)O | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[C:13]1=[O:15]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[C:13]1([CH3:14])[OH:15] | CC(C)=CCC1(C)CCC=C(C)C1=O | CC(C)=CCC1(C)CCC=C(C)C1(C)O | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Miscellaneous | OtherReaction | 82f307c2771f24472352179bfdcbd50ca1b6a8d7cf7b2748b565724a523407a8 | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | C1=CCCCC1 | [C:1]=[C:2]-[C:3]-[C:4]1(-[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9](-[C;D1;H3:10])-[C;H0;D3;+0:11]-1=[O;H0;D1;+0:12]>>[C:1]=[C:2]-[C:3]-[C:4]1(-[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9](-[C;D1;H3:10])-[C;H0;D4;+0:11]-1(-[C;D1;H3:13])-[OH;D1;+0:12] | 78 | [{"value": 78.0, "product": "CC1(C(=CCCC1(CC=C(C)C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "CC1(C(=CCCC1(CC=C(C)C)C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 45 | MINUTE | 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohexenone (245 g, 1.28 mol) was added dropwise to a solution of methyl magnesium chloride (105 g, 1.41 mol) in THF (400 ml) and toluene (1.5 L) at room temperature. The temperature rose to 50° C. The mixture was stirred for additional 45 min, was then cooled to 15° C. and poured... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1 | Other | C1(=CC=CC=C1)C.C1CCOC1 | 15 | 0.75 | CC(C)=CCC1(C)CCC=C(C)C1=O>C1(=CC=CC=C1)C.C1CCOC1>CC(C)=CCC1(C)CCC=C(C)C1(C)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd44bcdd9c8945a98b0da8058f632e23 | CC(C)=CCC1(C)CCC=C(C)C1(C)O.CI>>COC1(C)C(C)=CCCC1(C)CC=C(C)C | CI.CC1(C(=CCCC1(CC=C(C)C)C)C)O.[Li]CCCC>>COC1(C(CCC=C1C)(CC=C(C)C)C)C | [OH:2][C:3]1([CH3:4])[C:5]([CH3:6])=[CH:7][CH2:8][CH2:9][C:10]1([CH3:11])[CH2:12][CH:13]=[C:14]([CH3:15])[CH3:16].I[CH3:1]>>[CH3:1][O:2][C:3]1([CH3:4])[C:5]([CH3:6])=[CH:7][CH2:8][CH2:9][C:10]1([CH3:11])[CH2:12][CH:13]=[C:14]([CH3:15])[CH3:16] | CC(C)=CCC1(C)CCC=C(C)C1(C)O.CI | COC1(C)C(C)=CCCC1(C)CC=C(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | cd10a9010f842ab825b304bd2965f17f9c39c4c64e5fc6cd91306ae51817de0d | 9271b713ded6954f3329c61a211042ac37c82b3aff1b62cb455035e69339dd27 | C1=CCCCC1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[C;D1;H3:4])(-[OH;D1;+0:5])-[C:6](-[C;D1;H3:7])=[C:8]-[C:9]>>[C:2]-[C:3](-[C;D1;H3:4])(-[O;H0;D2;+0:5]-[CH3;D1;+0:1])-[C:6](-[C;D1;H3:7])=[C:8]-[C:9] | 93.7 | [{"value": 93.0, "product": "COC1(C(CCC=C1C)(CC=C(C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "COC1(C(CCC=C1C)(CC=C(C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1,2,6-trimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enol (5.00 g, 24.0 mmol) in THF (80 ml) was added n-BuLi (1.6M in hexane, 16.5 ml, 26.4 mmol) at 0° C. After the mixture was stirred for 30 min, methyl iodide (5.18 g, 36.5 mmol) was added. The mixture was stirred at room temperature over night and the... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | C1=CCCCC1 | HI | C1CCOC1 | null | 0.5 | CC(C)=CCC1(C)CCC=C(C)C1(C)O.CI>C1CCOC1>COC1(C)C(C)=CCCC1(C)CC=C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a4703e3c2844eb2a6fea95691c7e22c | CC(C)=CCC1(C)CCC=C(C)C1=O>>CC(C)=CCC1(C)CCC=C(C)C1O | CC=1C(C(CCC1)(CC=C(C)C)C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC=1C(C(CCC1)(CC=C(C)C)C)O | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[C:13]1=[O:14]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[CH:13]1[OH:14] | CC(C)=CCC1(C)CCC=C(C)C1=O | CC(C)=CCC1(C)CCC=C(C)C1O | null | null | C(C)OCC | Reduction | Reduction of ketone to secondary alcohol | 363d5f69f20636c0e94be5dd25ac73c01a81378640b68ce139612b5190f90ea7 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CCCCC1 | [C:1]=[C:2]-[C:3]-[C:4]1(-[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9](-[C;D1;H3:10])-[C;H0;D3;+0:11]-1=[O;H0;D1;+0:12]>>[C:1]=[C:2]-[C:3]-[C:4]1(-[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9](-[C;D1;H3:10])-[CH;D3;+0:11]-1-[OH;D1;+0:12] | 98 | [{"value": 98.0, "product": "CC=1C(C(CCC1)(CC=C(C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "CC=1C(C(CCC1)(CC=C(C)C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone (5.00 g, 26.04 mmol) was added dropwise to a suspension of lithium aluminium hydride (0.73 g, 18.2 mmol) in diethyl ether at 0° C. The mixture was stirred at room temperature for 1 h. The resulting suspension was quenched with water, aqueous sodium hydroxide solutio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1 | null | C(C)OCC | null | 1 | CC(C)=CCC1(C)CCC=C(C)C1=O>C(C)OCC>CC(C)=CCC1(C)CCC=C(C)C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7d02303c56544f8ad2d461477c161c2 | CC(C)=CCCl.Cc1cccc(C)c1O>>CC(C)=CCC1(C)C=CC=C(C)C1=O | CC1=C(C(=CC=C1)C)O.[OH-].[K+].C(C=C(C)C)Cl>>CC=1C(C(C=CC1)(CC=C(C)C)C)=O | Cl[CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3].[c:6]1([CH3:7])[cH:8][cH:9][cH:10][c:11]([CH3:12])[c:13]1[OH:14]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][C:6]1([CH3:7])[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:13]1=[O:14] | CC(C)=CCCl.Cc1cccc(C)c1O | CC(C)=CCC1(C)C=CC=C(C)C1=O | null | null | C1=CC=CC=C1 | Acylation | OtherReaction | 88fb5000ae461b24cd74d7407af653ba3d3fc4b2d1217911456ffd00ec357618 | b4f30537787923ba4feee7b56623cd7e4096609819c2bebbb8bd88243f26f603 | O=C1C=CC=CC1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C;D1;H3:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[C;D1;H3:12]):[c;H0;D3;+0:13]:1-[OH;D1;+0:14]>>[C;D1;H3:6]-[C;H0;D3;+0:7]1=[CH;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-[C;H0;D4;+0:11](-[C;D1;H3:12])(-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;... | null | [] | 0 | CELSIUS | 3 | HOUR | A mixture of 2,6-dimethylphenol (5.00 g, 41.0 mmol), powdered KOH (85%, 1.5 eq., 4.05 g, 61.5 mmol), prenyl chloride (85%, 1.2 eq., 6.05 g, 49.2 mmol) and (NBu4)HSO4 (50 mg) in benzene (50 ml) was stirred at 0° C. for 3 h. The green suspension was then poured on ice and extracted with pentane. The organic phase was was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ketone.Conjugated diene | c1ccccc1 | C1=CCCC=C1 | C1=CCCC=C1 | HCl | C1=CC=CC=C1 | 0 | 3 | CC(C)=CCCl.Cc1cccc(C)c1O>C1=CC=CC=C1>CC(C)=CCC1(C)C=CC=C(C)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-265cf475ddee42328a84105d9d35affc | CC(C)(C#N)c1ccccc1.O>>CC(C)(C=O)c1ccccc1 | Cl.O.CC(C#N)(C)C1=CC=CC=C1.[H-].C(C(C)C)[Al+]CC(C)C>>CC(C=O)(C)C1=CC=CC=C1 | N#[C:4][C:2]([CH3:1])([CH3:3])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[OH2:5]>>[CH3:1][C:2]([CH3:3])([CH:4]=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | CC(C)(C#N)c1ccccc1.O | CC(C)(C=O)c1ccccc1 | null | null | CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | c1ccccc1 | N#[C;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5].[OH2;D0;+0:6]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[c:5])-[CH;D2;+0:1]=[O;H0;D1;+0:6] | 92.8 | [{"value": 92.8, "product": "CC(C=O)(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 2-methyl-2-phenylpropanenitrile (290 g, 2.00 mol) in hexane (2000 mL) at 0° C. under N2 is added diisobutylaluminum hydride (DIBAL-H) (2600 mL, 1M in hexane) over a period of 80 minutes. The reaction mixture is stirred at 6–14° C. for 15 minutes, then allowed to warm to room temperature and stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1ccccc1 | Other | CCCCCC | null | 0.25 | CC(C)(C#N)c1ccccc1.O>CCCCCC>CC(C)(C=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dba42e243a1e4925a377154a69991339 | CC(C)(C=O)c1ccccc1.CN.[C-]#N>>CNC(C#N)C(C)(C)c1ccccc1 | [C-]#N.[K+].Cl.CN.CC(C=O)(C)C1=CC=CC=C1>>CC(C(C#N)NC)(C)C1=CC=CC=C1 | O=[CH:3][C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][NH2:2].[C-:4]#[N:5]>>[CH3:1][NH:2][CH:3]([C:4]#[N:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | CC(C)(C=O)c1ccccc1.CN.[C-]#N | CNC(C#N)C(C)(C)c1ccccc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 67834ce29ee7faed9c771a892a45df3a078cc52972b167e999c188543c3ef065 | 8743950731596ea1e685ccc6d45d1ba830801fe94588e1dd93bbf1291f95e93b | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5].[C-;H0;D1:6]#[N;D1;H0:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[C;D1;H3:8]-[NH;D2;+0:9]-[CH;D3;+0:1](-[C;H0;D2;+0:6]#[N;D1;H0:7])-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5] | 95 | [{"value": 95.0, "product": "CC(C(C#N)NC)(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 25 | HOUR | To a solution of potassium cyanide (103 g, 1.56 mol) and methylamine hydrochloride (106 g, 1.56 mol) in water (1000 mL) is added a solution of 2-methyl-2-phenylpropanal (222 g, 1.50 mol) in methanol (1000 mL) over a period of 30 minutes. An ice-water bath is used occasionally to maintain the reaction temperature betwee... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile.Secondary amine | null | null | c1ccccc1 | HO- | O.CO | null | 25 | CC(C)(C=O)c1ccccc1.CN.[C-]#N>O.CO>CNC(C#N)C(C)(C)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02dcb73ac3424272a81fdd4037603a1a | CC(C)(C=O)c1ccccc1.Cc1ccc([S@@](N)=O)cc1>>Cc1ccc([S@](=O)N=CC(C)(C)c2ccccc2)cc1 | CC1(OC1C1=CC=CC=C1)C.CC(C=O)(C)C1=CC=CC=C1.C1(=CC=C(C=C1)[S@](=O)N)C>>CC(C=N[S@@](=O)C1=CC=C(C=C1)C)(C)C1=CC=CC=C1 | O=[CH:9][C:10]([CH3:11])([CH3:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([S@:6](=[O:7])[NH2:8])[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S@:6](=[O:7])[N:8]=[CH:9][C:10]([CH3:11])([CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | CC(C)(C=O)c1ccccc1.Cc1ccc([S@@](N)=O)cc1 | Cc1ccc([S@](=O)N=CC(C)(C)c2ccccc2)cc1 | null | [O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.FC1=C(C(=C(C(=C1B(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | O=[S@](N=CCc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5].[NH2;D1;+0:6]-[#16:7](=[O;D1;H0:8])-[c:9]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[c:5])-[CH;D2;+0:1]=[N;H0;D2;+0:6]-[#16:7](=[O;D1;H0:8])-[c:9] | 81 | [{"value": 81.0, "product": "CC(C=N[S@@](=O)C1=CC=C(C=C1)C)(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 19 | HOUR | To a stirred solution of 2.5 g of 2,2-dimethyl-3-phenyloxirane (16 mmol) in 85 mL of anhydrous benzene is added 0.415 g (0.362 mmol, 5 mol %) of tris(pentafluorophenyl) borane. The light yellow solution is stirred at 25° C. for 19 hours. The reaction mixture containing the 2-methyl-2-phenylpropanal is then treated with... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | c1ccccc1.c1ccccc1 | HO- | [O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.FC1=C(C(=C(C(=C1B(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.C1=CC=CC=C1 | 25 | 19 | CC(C)(C=O)c1ccccc1.Cc1ccc([S@@](N)=O)cc1>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.FC1=C(C(=C(C(=C1B(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.C1=CC=CC=C1>Cc1ccc([S@](=O)N=CC(C)(C)c2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26e67c3358a347cdbaf3b4613a22bfa4 | CC(C)(C(=O)O)c1ccccc1.COc1ccc(CN)cc1OC>>COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1OC | COC=1C=C(CN)C=CC1OC.CC(C(=O)O)(C)C1=CC=CC=C1.C(C)(C)N(C(C)C)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C>>COC=1C=C(CNC(C(C)(C)C2=CC=CC=C2)=O)C=CC1OC | O[C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:20][c:21]1[O:22][CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[O:22][... | CC(C)(C(=O)O)c1ccccc1.COc1ccc(CN)cc1OC | COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1OC | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)NCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[c:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:8]-[c:9] | 95 | [{"value": 95.0, "product": "COC=1C=C(CNC(C(C)(C)C2=CC=CC=C2)=O)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "COC=1C=C(CNC(C(C)(C)C2=CC=CC=C2)=O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methyl-2-phenylpropionic acid (3.28 g, 20 mmol) in DMF (50 ml) was treated sequentially with N,N-diisopropylethylamine (8.09 g, 80 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (7.60 g, 20 mmol) then 3,4-dimethoxybenzylamine (3.34 g, 20 mmol) and then stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.CCOC(=O)C | null | null | CC(C)(C(=O)O)c1ccccc1.COc1ccc(CN)cc1OC>CN(C)C=O.CCOC(=O)C>COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f446c5c1f2ca4b21879adc68a053ceb4 | CO.COc1ccc(C#N)cc1Br>>CONCc1cccc(Br)c1 | CO.BrC=1C=C(C#N)C=CC1OC.B.C1CCOC1>>BrC=1C=C(CNOC)C=CC1 | [CH3:1][OH:2].CO[c:8]1[cH:7][cH:6][c:5]([C:4]#[N:3])[cH:11][c:9]1[Br:10]>>[CH3:1][O:2][NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1 | CO.COc1ccc(C#N)cc1Br | CONCc1cccc(Br)c1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 06e3b738e36a3fb3b92f84d0fa24f3a2fe570200e0b8cfa7863114ff98d06671 | 44d286b4cdb5308a16d5fd2584ba1c21eb94ef264b5d325ba52275eb8bc4678b | c1ccccc1 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c:7]:[c:8]:1-[Br;D1;H0:9].[C;D1;H3:10]-[OH;D1;+0:11]>>[Br;D1;H0:9]-[c:8]1:[c:7]:[c:4](-[CH2;D2;+0:5]-[NH;D2;+0:6]-[O;H0;D2;+0:11]-[C;D1;H3:10]):[c:3]:[c:2]:[cH;D2;+0:1]:1 | 64 | [{"value": 64.0, "product": "BrC=1C=C(CNOC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirring solution of 3-bromo-4-methoxy-benzonitrile (1.00 g, 4.7 mmol) in THF (30 ml) was treated drop-wise with borane-THF (14.2 ml, 1M solution in THF, 14.2 mmol). The mixture was heated at reflux, under argon for 5 h. To the cooled reaction mixture was cautiously added MeOH (20 ml). The volatiles were removed in v... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile.Methanol | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1 | null | null | CO.COc1ccc(C#N)cc1Br>C1CCOC1>CONCc1cccc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-271befcf31bf4de5be010ffc3ee4aa19 | COc1ccc(C=O)cc1OC.C[C@H](N)Cc1ccccc1>>COc1ccc(CN[C@@H](C)Cc2ccccc2)cc1OC | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COC=1C=C(C=O)C=CC1OC.S(=O)(=O)(O)O.C[C@@H](CC1=CC=CC=C1)N.C(C)N(CC)CC>>COC=1C=C(CN[C@H](CC2=CC=CC=C2)C)C=CC1OC | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18]1.[NH2:8][C@@H:9]([CH3:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][C@@H:9]([CH3:10])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]1[O:20][CH3:21] | COc1ccc(C=O)cc1OC.C[C@H](N)Cc1ccccc1 | COc1ccc(CN[C@@H](C)Cc2ccccc2)cc1OC | null | null | ClCCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CCNCc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[C;D1;H3:7])-[NH2;D1;+0:8]>>[C:5]-[C:6](-[C;D1;H3:7])-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 67 | [{"value": 67.0, "product": "COC=1C=C(CN[C@H](CC2=CC=CC=C2)C)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "COC=1C=C(CN[C@H](CC2=CC=CC=C2)C)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 3,4-dimethoxybenzaldehyde (1.06 g, 6.4 mmol), (S)-1-methyl-2-phenylethylamine sulfate (1.18 g, 6.4 mmol) and triethylamine (0.89 ml, 6.4 mmol) in 1,2-dichloroethane (50 ml) was stirred at room temperature under argon for 15 min. Sodium triacetoxyborohydride (2.97 g, 14 mmol) was added over 5 min. then sti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | ClCCCl | null | 16 | COc1ccc(C=O)cc1OC.C[C@H](N)Cc1ccccc1>ClCCCl>COc1ccc(CN[C@@H](C)Cc2ccccc2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87b5f8a346014a829528bbadfc81e446 | COc1ccc(CCN[C@@H](C)Cc2ccccc2)cc1OC.O=C(Cl)c1cccc(Br)c1>>COc1ccc(CCN(C(=O)c2cccc(Br)c2)[C@@H](C)Cc2ccccc2)cc1OC | BrC=1C=C(C(=O)Cl)C=CC1.COC=1C=C(C=CC1OC)CCN[C@H](CC1=CC=CC=C1)C>>BrC=1C=C(C(=O)N([C@H](CC2=CC=CC=C2)C)CCC2=CC(=C(C=C2)OC)OC)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C@@H:19]([CH3:20])[CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][c:29]1[O:30][CH3:31].Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c... | COc1ccc(CCN[C@@H](C)Cc2ccccc2)cc1OC.O=C(Cl)c1cccc(Br)c1 | COc1ccc(CCN(C(=O)c2cccc(Br)c2)[C@@H](C)Cc2ccccc2)cc1OC | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N(CCc1ccccc1)CCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:6]-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The title compound was prepared from 3-bromobenzoyl chloride and (S)-[2-(3,4 dimethoxyphenyl)ethyl]-(1-methyl-2-phenylethyl)amine D8 according to a procedure similar to that for Example 76.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccc(CCN[C@@H](C)Cc2ccccc2)cc1OC.O=C(Cl)c1cccc(Br)c1>>COc1ccc(CCN(C(=O)c2cccc(Br)c2)[C@@H](C)Cc2ccccc2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b6c9c55b1b4432a92c1ab271f086e9c | COc1ccc(CCNC[C@H](C)c2ccccc2)cc1OC.O=C(Cl)c1ccc2c(c1)OCO2>>COc1ccc(CCN(C[C@H](C)c2ccccc2)C(=O)c2ccc3c(c2)OCO3)cc1OC | O1COC2=C1C=CC(=C2)C(=O)Cl.COC=1C=C(C=CC1OC)CCNC[C@H](C)C1=CC=CC=C1>>COC=1C=C(C=CC1OC)CCN(C(=O)C1=CC2=C(OCO2)C=C1)C[C@H](C)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][CH2:10][C@H:11]([CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:30][c:31]1[O:32][CH3:33].Cl[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]2[c:25]([cH:26]1)[O:27][CH2:28][O:29]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]([CH2:10][C@H:11]([CH3:12]... | COc1ccc(CCNC[C@H](C)c2ccccc2)cc1OC.O=C(Cl)c1ccc2c(c1)OCO2 | COc1ccc(CCN(C[C@H](C)c2ccccc2)C(=O)c2ccc3c(c2)OCO3)cc1OC | null | null | C(C)N(CC)CC | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccc2c(c1)OCO2)N(CCc1ccccc1)CCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 74.5 | [{"value": 68.0, "product": "COC=1C=C(C=CC1OC)CCN(C(=O)C1=CC2=C(OCO2)C=C1)C[C@H](C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "COC=1C=C(C=CC1OC)CCN(C(=O)C1=CC2=C(OCO2)C=C1)C[C@H](C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | A stirring solution of benzo[1,3]dioxole-5-carbonyl chloride (151 mg, 0.82 mmol) in MDC (5 ml) was treated with a pre-mixed solution of (R)-[2-(3,4-dimethoxy-phenyl)-ethyl]-(2-phenyl-propyl)-amine (D12, 245 mg, 0.75 mmol) and triethylamine (0.17 ml) in MDC (2 ml). After stirring under argon at room temperature for 72 h... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)OCO2 | HCl | C(C)N(CC)CC | null | 72 | COc1ccc(CCNC[C@H](C)c2ccccc2)cc1OC.O=C(Cl)c1ccc2c(c1)OCO2>C(C)N(CC)CC>COc1ccc(CCN(C[C@H](C)c2ccccc2)C(=O)c2ccc3c(c2)OCO3)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-198625e865c349d6bf36a744738e8613 | C1C2CC3CC1CC(C2)C3.O=CO.O=S(=O)(O)O>>O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 | C12CC3CC(CC(C1)C3)C2.OC12CC3(CC(CC(C1)C3)C2)O.ClCCCl.S(O)(O)(=O)=O.C(=O)O>>OC12CC3(CC(CC(C1)C3)C2)O.C12(CC3(CC(CC(C1)C3)C2)C(=O)O)C(=O)O | [CH:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9]1)[CH2:10][CH:11]([CH2:15]3)[CH2:16]2.[CH:12](=[O:13])[OH:14].O=S(=O)([OH:1])[OH:3]>>[O:1]=[C:2]([OH:3])[C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9]1)[CH2:10][C:11]([C:12](=[O:13])[OH:14])([CH2:15]3)[CH2:16]2 | C1C2CC3CC1CC(C2)C3.O=CO.O=S(=O)(O)O | O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 | null | null | null | Acylation | OtherReaction | 3e8c4b9d86edd07c04e618791abcbd8dbe11208be45d91e4f36d3bce3521dc9a | 05b1e9e4110bc86f2bd7cbdf6b80dcc179cd6fe787ce74ddba60fa77e8ec4cfa | C1C2CC3CC1CC(C2)C3 | O=S(=O)(-[OH;D1;+0:1])-[OH;D1;+0:2].[C:3]1-[C:4]-[C:5]-[CH;D3;+0:6]2-[C:7]-[CH;D3;+0:8]-1-[C:9]-[C:10]-[C:11]-2.[O;D1;H0:12]=[CH;D2;+0:13]-[O;D1;H1:14]>>[O;D1;H0:12]=[C;H0;D3;+0:13](-[O;D1;H1:14])-[C;H0;D4;+0:8]12-[C:3]-[C:4]-[C:5]-[C;H0;D4;+0:6](-[C:15](=[O;H0;D1;+0:1])-[OH;D1;+0:2])(-[C:7]-1)-[C:11]-[C:10]-[C:9]-2 | null | [] | null | null | null | null | The synthesis of 2-methacryloyloxy-2-(3-(2-hydroxy-2-propyl)1-1-adamantyl)propane was performed by the following method. First, according to the method described in Japanese Patent Application Laid-open No. 2002-167342, 1000 g of 1,3-dihydroxyadamantane was synthesized from adamantane. Next, a four-necked flask equippe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Carboxylic acid.Carboxylic acid | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | HO- | null | null | null | C1C2CC3CC1CC(C2)C3.O=CO.O=S(=O)(O)O>>O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-946f03b2dca0420599ed66931098e182 | C=C(C)C(=O)OC(C)(C)C12CC3CC(C1)CC(C(C)(C)OC(=O)C(=C)C)(C3)C2>>O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 | C(C(=C)C)(=O)OC(C)(C)C12CC3(CC(CC(C1)C3)C2)C(C)(C)OC(C(=C)C)=O.C12CC3CC(CC(C1)C3)C2.OC12CC3(CC(CC(C1)C3)C2)O.S(O)(O)(=O)=O>>OC12CC3(CC(CC(C1)C3)C2)O.C12(CC3(CC(CC(C1)C3)C2)C(=O)O)C(=O)O | C=C(C)C(=[O:13])[O:14]C(C)(C)[C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9]1)[CH2:10][C:11]([C:12](C)(C)[O:3][C:2](C(=C)C)=[O:1])([CH2:15]3)[CH2:16]2>>[O:1]=[C:2]([OH:3])[C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9]1)[CH2:10][C:11]([C:12](=[O:13])[OH:14])([CH2:15]3)[CH2:16]2 | C=C(C)C(=O)OC(C)(C)C12CC3CC(C1)CC(C(C)(C)OC(=O)C(=C)C)(C3)C2 | O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 | null | null | C(=O)O.ClCCCl | Miscellaneous | OtherReaction | 9351ea7ce4c16b15d2a92bf25854d47b2fdd561705737f42f9bde07f336c30fd | f23d9e9523698ee811d52b830189892076b3f889e1772926d6055086cb6cc8cf | C1C2CC3CC1CC(C2)C3 | C-C(=C)-C(=[O;H0;D1;+0:1])-[O;H0;D2;+0:2]-C(-C)(-C)-[C;H0;D4;+0:3]12-[C:4]-[C:5](-[C;H0;D4;+0:6](-C)(-C)-[O;H0;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-C(-C)=C)(-[C:10]-[C:11]-[C:12]-1)-[C:13]-[C:14]-[C:15]-2>>[O;D1;H0:9]=[C;H0;D3;+0:8](-[OH;D1;+0:7])-[C;H0;D4;+0:3]12-[C:4]-[C:5](-[C;H0;D3;+0:6](=[O;H0;D1;+0:1])-[OH;D1;+0... | null | [] | null | null | null | null | The synthesis of 2-methacryloyloxy-2-(3-(2-methacryloyloxy-2-propyl)-1-adamantyl)propane was performed by the following method. First, according to the method described in Japanese Patent Application Laid-open No. 2002-167342, 100 g of 1,3-dihydroxyadamantane was synthesized from adamantane. Next, a four-necked flask e... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Vinyl.Vinyl | Carboxylic acid.Carboxylic acid | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | Other | C(=O)O.ClCCCl | null | null | C=C(C)C(=O)OC(C)(C)C12CC3CC(C1)CC(C(C)(C)OC(=O)C(=C)C)(C3)C2>C(=O)O.ClCCCl>O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e661ecaad28b4a00931ae197f0f3c7ff | CC(C)(C#N)N=NC(C)(C)C#N.c1ccc2c(c1)CCN2>>CC(C)N1CCc2ccccc21 | N1CCC2=CC=CC=C12.[SnH](CCCC)(CCCC)CCCC.CC(C)(C#N)N=NC(C)(C)C#N>>C(C)(C)N1CCC2=CC=CC=C12 | CC(C)(C#N)N=N[C:1](C)([C:2]#N)[CH3:3].[NH:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CC(C)(C#N)N=NC(C)(C)C#N.c1ccc2c(c1)CCN2 | CC(C)N1CCc2ccccc21 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 6f8aa694c1fea69721deedda2030a76837f3663aafe54b379ef0fdc23d0471db | d99cc8e2c462a957cfb2c9c6cb463a002ac6cab2ca5969133dc779eb1a3a9348 | c1ccc2c(c1)CCN2 | C-C(-C)(-C#N)-N=N-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-[C;H0;D2;+0:3]#N.[c:4]:[c:5]1:[c:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[CH3;D1;+0:1]-[CH;D3;+0:3](-[CH3;D1;+0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[c:6]:[c:5]-1:[c:4] | null | [] | null | null | null | null | A three-hour addition of nBu3SnH (154 μL, 573 μmol) and AIBN (34 mg, 208 μmol) solution in benzene (1 mL) to a refluxing solution of the unpurified ketimine (125 mg, 521 μmol) in benzene (50 mL) delivered, after flash chromatography (30% CH2Cl2/Hexanes) 0.024 g (30%) of the desired indoline as a colorless oil. Rƒ=0.1 (... | 10.6084/m9.figshare.5104873.v1 | null | Diazene.Nitrile.Nitrile.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | C1=CC=CC=C1 | null | null | CC(C)(C#N)N=NC(C)(C)C#N.c1ccc2c(c1)CCN2>C1=CC=CC=C1>CC(C)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4a68867ef8f04e06881a1c8b1485ab02 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Clc1nccc(Oc2ccnc(Cl)n2)n1>>C=Cc1nccc(Oc2ccnc(C=C)n2)n1 | ClC1=NC=CC(=N1)OC1=NC(=NC=C1)Cl.C(=C)[Sn](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>>C(=C)C1=NC=CC(=N1)OC1=NC(=NC=C1)C=C | CCC[CH2][Sn]([CH2]CCC)([CH2]C[CH2:14][CH3:15])[CH:2]=[CH2:1].Cl[c:3]1[n:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][n:12][c:13](Cl)[n:16]2)[n:17]1>>[CH2:1]=[CH:2][c:3]1[n:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][n:12][c:13]([CH:14]=[CH2:15])[n:16]2)[n:17]1 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Clc1nccc(Oc2ccnc(Cl)n2)n1 | C=Cc1nccc(Oc2ccnc(C=C)n2)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CCOC(=O)C | C-C Coupling | OtherReaction | 09a9788678a16cc7a2710b39b4c5c6e4dce07f7dedb3ec29fb75bec0bcda3989 | 20a56244d59ecb15ab496f5cdf3a085b565f2b94a0e0464d13b172a4e17b1d21 | c1cc(Oc2ccncn2)ncn1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-[CH2;D2;+0:1]-[CH3;D1;+0:2])-[CH;D2;+0:3]=[C;D1;H2:4].Cl-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9].Cl-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H2:4]=[CH;D2;+0:3]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14].[CH2;D1;+0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:5](:... | 61 | [{"value": 61.0, "product": "C(=C)C1=NC=CC(=N1)OC1=NC(=NC=C1)C=C", "details": "PERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | null | null | The 2-chloropyrimidinyl ether intermediate (500 mg, 0.896 mmol) (see Example 1), vinyltributyltin (600 mg, 1.89 mmol), BHT (20 mg), and (PPh3)4Pd (50 mg, 0.045 mmol) were suspended in degassed toluene (10 mL) under argon and heated to 115° C. for 3 h. The reaction mixture was cooled, diluted with EtOAc (100 mL), washed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Vinyl.Tin | Vinyl.Vinyl | c1cncnc1.c1cncnc1 | c1cncnc1.c1cncnc1 | c1cncnc1.c1cncnc1 | HCl.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C | 115 | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Clc1nccc(Oc2ccnc(Cl)n2)n1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C>C=Cc1nccc(Oc2ccnc(C=C)n2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-171ce8970ab944cf9a8e13b2499c8ab9 | C1COCCN1.Cc1cc(Cl)ccn1>>Clc1ccnc(CN2CCOCC2)c1 | CC1=NC=CC(=C1)Cl.C1CC(=O)N(C1=O)Br.N1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>>O1CCN(CC1)CC1=NC=CC(=C1)Cl | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH3:7])[cH:14]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14]1 | C1COCCN1.Cc1cc(Cl)ccn1 | Clc1ccnc(CN2CCOCC2)c1 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | CCOC(=O)C.CN(C)C=O.C(Cl)(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a82e7b369befc31fcac88f7fe646a76e64499f9d60ba9b1ff71c1adbcf448387 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(CN2CCOCC2)nc1 | [#8:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[c:9]:[c:8](-[CH2;D2;+0:7]-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#8:1]-[C:2]-[C:3]-1):[#7;a:10]:[c:11] | null | [] | null | null | 8 | HOUR | A mixture of the 2-methyl-4-chloropyridine (1.00 g, 7.84 mmol), NBS (1.42 g, 8.00 mmol) and benzoyl peroxide (˜10 mg) in 10 mL of CCl4 was heated at reflux for 5 h. After cooling down, the reaction mixture was filtered and filtrate was concentrated to give the crude products mixture, which was dissolved in DMF and trea... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.CCOC(=O)C.CN(C)C=O.C(Cl)(Cl)(Cl)Cl | null | 8 | C1COCCN1.Cc1cc(Cl)ccn1>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.CCOC(=O)C.CN(C)C=O.C(Cl)(Cl)(Cl)Cl>Clc1ccnc(CN2CCOCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2646942418ce43359f515379ea575146 | BrCc1ccccc1.CN(C)C=O>>c1ccc(COCc2ccccc2)cc1 | C(C1=CC=CC=C1)Br.[H-].[Na+].CN(C)C=O>>C(C1=CC=CC=C1)OCC1=CC=CC=C1 | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.N([CH3:1])([CH:5]=[O:6])[CH3:15]>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1 | BrCc1ccccc1.CN(C)C=O | c1ccc(COCc2ccccc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 571bca16a08ddaad6e3abed2f99b04fbb2bbe07d2c42b4008d772773a112e55e | 204900b68d487b245252094c4ccbed5a9df699c5195177b38ee4d7a1438c290c | c1ccc(COCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-N(-[CH3;D1;+0:6])-[CH;D2;+0:7]=[O;H0;D1;+0:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[CH2;D2;+0:7]-[c:9]1:[c:10]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:11]:[c:12]:1):[c:4] | null | [] | null | null | 3 | HOUR | To a solution of the above alcohol (430 mg, 3.0 mmol) in DMF (10 mL) was added NaH (144 mg of a 60% dispersion in mineral oil, 3.60 mmol) and the mixture was then cooled in an ice bath. Benzyl bromide (437 uL, 3.60 mmol) was then added and the mixture was stirred at room temperature for 3 h. After normal aqueous work-u... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide | Ether | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | null | null | 3 | BrCc1ccccc1.CN(C)C=O>>c1ccc(COCc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d793debe87e84fa9bb83bfe2b15e1506 | CNC(=O)c1cc(Oc2cccc3cc(C(=O)Nc4cc(C(C)(C)C)cc(NS(C)(=O)=O)c4OC)n(C)c23)ccn1>>CCOCC.c1ccc2[nH]ccc2c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)C=1N(C2=C(C=CC=C2C1)OC1=CC(=NC=C1)C(NC)=O)C)OC)NS(=O)(=O)C>>N1C=CC2=CC=CC=C12.CCOCC | Cn1c([C:11](=O)[NH:10][c:9]2[cH:8][c:7]([C:6](C)(C)C)[cH:14][c:12](NS(C)(=O)=O)[c:13]2O[CH3:1])cc2ccc[c:4](Oc3ccnc(C(=O)N[CH3:2])c3)[c:5]21>>[CH3:1][CH2:2][O:3][CH2:4][CH3:5].[cH:6]1[cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:13]2[cH:14]1 | CNC(=O)c1cc(Oc2cccc3cc(C(=O)Nc4cc(C(C)(C)C)cc(NS(C)(=O)=O)c4OC)n(C)c23)ccn1 | CCOCC.c1ccc2[nH]ccc2c1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | null | Reduction | OtherReaction | 03faa860ef6b466af806e2bc83289cb1f8d4c2ed6d035c283d235098f562adcf | c4bcc1a8ff503468e268147b10e897f21d3383088aede53a5f9aadc76751a156 | c1ccc2[nH]ccc2c1 | C-n1:[c;H0;D3;+0:1]2:[c;H0;D3;+0:2](-O-c3:c:c:n:c(-C(=O)-N-[CH3;D1;+0:3]):c:3):c:c:c:c:2:c:c:1-[C;H0;D3;+0:4](=O)-[NH;D2;+0:5]-[c:6]1:[c:7]:[c;H0;D3;+0:8](-[C;H0;D4;+0:9](-C)(-C)-C):[cH;D2;+0:10]:[c;H0;D3;+0:11](-N-S(-C)(=O)=O):[c;H0;D3;+0:12]:1-O-[CH3;D1;+0:13]>>[CH3;D1;+0:13]-[CH2;D2;+0:3]-[#8:14]-[CH2;D2;+0:2]-[CH3;... | 61 | [{"value": 61.0, "product": "N1C=CC2=CC=CC=C12.CCOCC", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 6 | HOUR | A Schlenk tube was charged with Pd(OAc)2 (16 mg, 0.07 mmol), K3PO4 (525 mg, 2.40 mmol), di-t-butylbiphenylphosphine (42 mg, 0.14 mmol) and the 7-hydroxyindole ester (see Example 6) (307 mg, 1.4 mmol), and capped with a septum and purged with argon. A solution of the benzyl ether from above (270 mg, 1.16 mmol) in 3 mL o... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether.Ether.Secondary amide.Secondary amide | Ether | c1ccccc1.c1cccc2cc[nH]c12.c1ccncc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | CC(=O)[O-].CC(=O)[O-].[Pd+2] | 100 | 6 | CNC(=O)c1cc(Oc2cccc3cc(C(=O)Nc4cc(C(C)(C)C)cc(NS(C)(=O)=O)c4OC)n(C)c23)ccn1>CC(=O)[O-].CC(=O)[O-].[Pd+2]>CCOCC.c1ccc2[nH]ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65517cb8e3c04b42a5dcdb707311818a | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.COc1c(N)cc(C(C)(C)C)cc1NS(C)(=O)=O.O=C(O)c1cc2ccccc2[nH]1.On1nnc2cccnc21>>COc1c(NC(=O)c2cc3cccc(Oc4ccnc(CN(C)C)c4)c3n2C)cc(C(C)(C)C)cc1NS(C)(=O)=O | N1C(=CC2=CC=CC=C12)C(=O)O.CCN(C(C)C)C(C)C.CN(C)C=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C1=CC2=C(N=C1)N(N=N2)O.NC=1C(=C(C=C(C1)C(C)(C)C)NS(=O)(=O)C)OC>>C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)C=1N(C2=C(C=CC=C2C1)OC1=CC(=NC=C1)CN(C)C)C)OC)NS(=O)(=O)C | CN(C(On1nnc2cccnc21)=[N+](C)C)[CH3:28].O=[CH:21][N:22]([CH3:23])[CH3:24].[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:29][c:30]([C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35][c:36]1[NH:37][S:38]([CH3:39])(=[O:40])=[O:41].O[C:6](=[O:7])[c:8]1[cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:26]2[nH:27]1.n1n[c:25]2[cH:16][cH:17][cH:18][n:1... | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.COc1c(N)cc(C(C)(C)C)cc1NS(C)(=O)=O.O=C(O)c1cc2ccccc2[nH]1.On1nnc2cccnc21 | COc1c(NC(=O)c2cc3cccc(Oc4ccnc(CN(C)C)c4)c3n2C)cc(C(C)(C)C)cc1NS(C)(=O)=O | null | null | CCOC(=O)C | Acylation | OtherReaction | d48d9fe12e9c882a2b0abbe0a4725b562d0bb32b760c5865247e93ffe3888a2f | a85f7c688100a96cb1a549bfbfc45d8593b2dbb406198a553b98eabaa1a2d9e2 | O=C(Nc1ccccc1)c1cc2cccc(Oc3ccncc3)c2[nH]1 | C-N(-[CH3;D1;+0:1])-C(-O-n1:n:n:c2:c:c:c:n:c:2:1)=[N+](-C)-C.O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7](:[cH;D2;+0:8]:[c:9]:[c:10]):[nH;D2;+0:11]:1.O=[CH;D2;+0:12]-[#7:13](-[C;D1;H3:14])-[C;D1;H3:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19].[OH;D1;+0:20]-n1:n:n:[c;H0;D3;+0:21]2:[cH;D2;+0:22]:[c:23]:[c:24]:[#7... | null | [] | null | null | 5 | MINUTE | To a solution of the indole carboxylic acid (360 mg, 0.93 mmol) in 4 mL of DMF was added Hunig's base (418 uL, 2.4 mmol). After 5 min, HATU (439 mg, 1.12 mmol) and HOAt (12 mg, 0.09 mmol) were added and then N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (253 mg, 0.93 mmol). The mixture was stirred overni... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Carboxylic acid.Tertiary amide.Primary amine | Ether.Secondary amide | c1cnc2[nH]nnc2c1.c1ccc2[nH]ccc2c1.c1cnc2nn[nH]c2c1 | c1cc2ccccc2[nH]1.c1ccncc1 | c1ccccc1.c1cc2ccccc2[nH]1.c1ccncc1 | HO- | CCOC(=O)C | null | 0.083333 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.COc1c(N)cc(C(C)(C)C)cc1NS(C)(=O)=O.O=C(O)c1cc2ccccc2[nH]1.On1nnc2cccnc21>CCOC(=O)C>COc1c(NC(=O)c2cc3cccc(Oc4ccnc(CN(C)C)c4)c3n2C)cc(C(C)(C)C)cc1NS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-666ad5959a9b4ddc926a44f4999e78fe | COc1cccc([N+](=O)[O-])c1[N+](=O)[O-]>>COc1cccc(N)c1N | O.O.[Sn](Cl)Cl.[N+](=O)([O-])C=1C(=C(C=CC1)OC)[N+](=O)[O-].[OH-].[Na+]>>NC=1C(=C(C=CC1)OC)N | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]1[N+:10](=O)[O-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[c:9]1[NH2:10] | COc1cccc([N+](=O)[O-])c1[N+](=O)[O-] | COc1cccc(N)c1N | null | null | CCOC(=O)C | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6] | 71.1 | [{"value": 52.0, "product": "NC=1C(=C(C=CC1)OC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.1, "product": "NC=1C(=C(C=CC1)OC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tin(II)chloride dihydrate (11.9 g, 52.6 mmol) was added to a solution of the above dinitroanisole (2.21 g, 8.76 mmol) in EtOAc (30 mL). The mixture was heated to reflux for 0.25 h upon which the solution became red in color. The solution was cooled to room temperature and poured onto aqueous 2.0 M NaOH. The aqueous pha... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1 | Other | CCOC(=O)C | null | null | COc1cccc([N+](=O)[O-])c1[N+](=O)[O-]>CCOC(=O)C>COc1cccc(N)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e5746b5c34054a009e87e1018a304f9f | COC(OC)c1cc(Cl)ccn1>>O=C(O)c1cc2ccccc2[nH]1 | ClC1=CC(=NC=C1)C(OC)OC.O[Li].O.C1CCOC1.CO>>N1C(=CC2=CC=CC=C12)C(=O)O | C[O:3][CH:2]([O:1][CH3:8])[c:4]1[cH:5][c:6](Cl)[cH:7][cH:11][n:12]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[nH:12]1 | COC(OC)c1cc(Cl)ccn1 | O=C(O)c1cc2ccccc2[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 4758d7ba060182abc70ff60394fdbf25716cfffb54c039c464771dd27dd9a5f4 | 5dfe87e64357b461f30fd7c81794ec7e48f7637c7ac9c03e71e87d3737bdb306 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[CH;D3;+0:2](-[O;H0;D2;+0:3]-[CH3;D1;+0:4])-[c:5]1:[c:6]:[c;H0;D3;+0:7](-Cl):[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:1>>[O;H0;D1;+0:3]=[C;H0;D3;+0:2](-[OH;D1;+0:1])-[c:5]1:[c:6]:[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[cH;D2;+0:4]:[c:11]:[c:12]:[c;H0;D3;+0:9]:2:[nH;D2;+0:10]:1 | 90.5 | [{"value": 90.5, "product": "N1C(=CC2=CC=CC=C12)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of the above ether (770 mg, 2.1 mmol) in THF/MeOH (25 mL/10 mL) was added LiOH.H2O (218.1 mg, 2.50 eq) dissolved in 3 mL of water. The clear reaction solution was stirred at room temperature for 5 h, then concentrated in vacuo. The residual aqueous solution was diluted with water (15 mL), and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Carboxylic acid | c1ccncc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | null | O | null | 5 | COC(OC)c1cc(Cl)ccn1>O>O=C(O)c1cc2ccccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bf0f83c98cd47049c28a4312f33317e | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O | C(C)(C)(C)[Si](O[C@H]1C[C@@H](O[C@@]1(CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(NCC1=CC=CC=C1)NCC1=CC=CC=C1)N1C(=O)NC(=O)C(C)=C1)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.CO>>C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO | CC(C)(C)[Si](C)(C)[O:8][C@H:7]1[CH2:6][C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:33](=[O:34])[nH:32][c:30]2=[O:31])[O:29][C@@:9]1([CH2:10][O:11][Si](c1ccccc1)(c1ccccc1)C(C)(C)C)[CH:12]([NH:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][c:2]1[cH:3][n:... | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O | null | null | O1CCCC1 | Deprotection | OtherReaction | bd7040a39ad85a2c3bfd998d34ac16e7127d9c4e33a1400049e3f4e51e3ba999 | 48f3bf6b592ef26d22b6b1cdf6554655672438fd529e8208760ff43315f27aa1 | O=c1ccn([C@H]2CCC(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](-[C:5]-[O;H0;D2;+0:6]-[Si](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-C(-C)(-C)-C)-[#8:7]>>[#8:7]-[C:4](-[C:5]-[OH;D1;+0:6])-[C:2](-[OH;D1;+0:1])-[C:3] | 100 | [{"value": 100.0, "product": "C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired"... | null | null | 3 | HOUR | 3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-(1,1′-diphenylmethylaminomethyl)thymidine (2) (1.2 g, 1.5 mmol) was dissolved in tetrahydrofuran (50 mL) at ambient temperature. A solution of tetrabutylammonium fluoride in tetrahydrofuran (4.5 mL) was then added to the solution. The resulting mixtur... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.Silyl protective group | Primary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CCOC1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 3 | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O>O1CCCC1>Cc1cn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc05bdb0f53e4ab480962f2ffcda9a1e | Cc1cn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O | C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO.C(C)(=O)O>>NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO | c1ccc(CN[CH:10]([C@@:9]2([CH2:12][OH:13])[C@@H:7]([OH:8])[CH2:6][C@H:5]([n:4]3[cH:3][c:2]([CH3:1])[c:18](=[O:19])[nH:17][c:15]3=[O:16])[O:14]2)[NH:11]Cc2ccccc2)cc1>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@:9]([CH2:10][NH2:11])([CH2:12][OH:13])[O:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19] | Cc1cn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O | null | [Pd] | C(C)O | Deprotection | OtherReaction | ebcb62b0cee28ac375043d4efcc15ae372e32a8afec9cbfdfea9a3d36c8b53ff | 979bea025e86b23768e3b6416c2b4011b3ba1bc8928a29b90e7c5e231c2241bc | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | [C:1]-[C:2](-[CH;D3;+0:3](-N-C-c1:c:c:c:c:c:1)-[NH;D2;+0:4]-C-c1:c:c:c:c:c:1)(-[C:5])-[#8:6]-[C:7]>>[C:1]-[C:2](-[CH2;D2;+0:3]-[NH2;D1;+0:4])(-[C:5])-[#8:6]-[C:7] | null | [] | null | null | null | null | 4′-C-(1,1′-diphenylmethylaminomethyl)thymidine (3) (0.65 g, 1.5 mmol) was dissolved in absolute ethanol (50 mL). Cyctohexene (12 mL), glacial acetic acid (5 mL) and 5%-palladium on charcoal (0.6 g) were added and the mixture heated under reflux with stirring. The solution was heated for 5 hours and then allowed to cool... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Secondary amine | Primary amine | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CCOC1 | Other | [Pd].C(C)O | null | null | Cc1cn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O>[Pd].C(C)O>Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4786a30f4102434ba01e0ca25365f301 | Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O.O=C(O)CNC(=O)C(F)(F)F>>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O | C(C)(C)N(CC)C(C)C.FC(C(=O)NCC(=O)O)(F)F.NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO>>FC(C(=O)NCC(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO)(F)F | [CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@:9]([CH2:10][OH:11])([CH2:12][NH2:13])[O:24]2)[c:25](=[O:26])[nH:27][c:28]1=[O:29].O[C:14](=[O:15])[CH2:16][NH:17][C:18](=[O:19])[C:20]([F:21])([F:22])[F:23]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@:9]([CH2:10][OH:11])([CH2:12][NH:13][C:14](=[... | Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O.O=C(O)CNC(=O)C(F)(F)F | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[#8:7]-[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | null | null | 4′-C-Aminomethylthymidine (4) (0.14 mmol) was dissolved in anhydrous N,N-dimethylformamide (1 mL). N-Trifluoroacetylglycine (0.036 g, 0.21 mmol) and O-(N-succimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate [TSTU] (0.085, 0.28 mmol) were then added and the solution stirred at ambient temperature. Diisopropylethyl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cncnc1.C1CCOC1 | HO- | CN(C=O)C | null | null | Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O.O=C(O)CNC(=O)C(F)(F)F>CN(C=O)C>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a2225e84c354943a777719f4cd032d4 | CCOC(=O)C(F)(F)F.Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O | NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO.C(C)N(CC)CC.FC(C(=O)OCC)(F)F>>FC(C(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO)(F)F | CCO[C:14](=[O:15])[C:16]([F:17])([F:18])[F:19].[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@:9]([CH2:10][OH:11])([CH2:12][NH2:13])[O:20]2)[c:21](=[O:22])[nH:23][c:24]1=[O:25]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@:9]([CH2:10][OH:11])([CH2:12][NH:13][C:14](=[O:15])[C:16]([F:17])([F:18])... | CCOC(=O)C(F)(F)F.Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O | null | null | CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[#8:7]-[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6] | 66 | [{"value": 66.0, "product": "FC(C(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 4′-C-Aminomethylthymidine (4) (1.5 mmol) was dissolved in methanol (10 mL) and triethylamine (1.5 mL) at ambient temperature. The solution was then treated with neat ethyl trifluoroacetate (1 mL) and the resulting solution stirred for 18 hours at ambient temperature with exclusion of moisture. The solvents and reagents... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1cncnc1.C1CCOC1 | HO- | CO | null | 18 | CCOC(=O)C(F)(F)F.Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O>CO>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8cd46d3c7d05431fb2c0c7f3a7ae3da7 | Cc1cn([C@H]2C[C@H](O)[C@@](CNC(=O)C(F)(F)F)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@](CN)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O | P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CNC(C(F)(F)F)=O>>P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CN | O=C(C(F)(F)F)[NH:11][CH2:10][C@@:9]1([CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([OH:24])[OH:25])[C@@H:7]([OH:8])[CH2:6][C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:30](=[O:31])[nH:29][c:27]2=[O:28])[O:26]1>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@:9]([CH2:10][NH... | Cc1cn([C@H]2C[C@H](O)[C@@](CNC(=O)C(F)(F)F)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@H](O)[C@@](CN)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O | null | null | N | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 18 | HOUR | 4′-C-(N-trifluoroacetylaminomethyl)thymidine triphosphate (8) was dissolved in concentrated aqueous ammonia solution and allowed to stand for 18 hours at ambient temperature. The solution was then lyophilised to give the title compound (9) as a white powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1cncnc1.C1CCOC1 | Other | N | null | 18 | Cc1cn([C@H]2C[C@H](O)[C@@](CNC(=O)C(F)(F)F)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O>N>Cc1cn([C@H]2C[C@H](O)[C@@](CN)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d5e97497e1d41aab531e4ebb94a2526 | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O>>CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@]1(CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(NCc1ccccc1)NCc1ccccc1 | C(C)(C)(C)[Si](O[C@H]1C[C@@H](O[C@@]1(CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(NCC1=CC=CC=C1)NCC1=CC=CC=C1)N1C(=O)NC(=O)C(C)=C1)(C)C.C(C1=CC=CC=C1)(C1=CC=CC=C1)N.C(C)(=O)O.[BH3-]C#N.[Na+]>>C(C)(C)(C)[Si](O[C@H]1C[C@@H](O[C@@]1(CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(NCC1=CC=CC=C1)NCC1=CC=CC=C1)N1C(=O)NC(=O)C=C1)(C... | C[c:14]1[cH:13][n:12]([C@H:11]2[CH2:10][C@H:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[C@:21]([CH2:22][O:23][Si:24]([c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)([c:31]3[cH:32][cH:33][cH:34][cH:35][cH:36]3)[C:37]([CH3:38])([CH3:39])[CH3:40])([CH:41]([NH:42][CH2:43][c:44]3[cH:45][cH:46][cH:47][cH:48]... | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@]1(CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(NCc1ccccc1)NCc1ccccc1 | null | null | C(C)#N | Miscellaneous | OtherReaction | e2b428145bb25f1063aa09bb03912d37079cb743b4732df627cc55fd0c4649a9 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1ccn([C@H]2CC[C@](CO[SiH](c3ccccc3)c3ccccc3)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 | C-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]-[#8:5]):[c:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9]>>[#8:5]-[C:4]-[#7;a:3]1:[c:2]:[cH;D2;+0:1]:[c:8](=[O;D1;H0:9]):[#7;a:7]:[c:6]:1 | 69 | [{"value": 69.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-formyl-2-deoxyuridine (10) (Yang et al; Tetrahedron Letters 1992, 33, 37–40.) (0.15 g, 0.25 mmol) was treated with Ph2CHNH2 (0.07 g, 0.37 mmol, 0.064 mL), glacial acetic acid (0.015 g, 0.26 mmol, 0.015 mL) and NaBH3CN (0.023 g, 0.37 mmol) in acetonitr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cncnc1 | c1ccncn1 | C1CCOC1.c1ccncn1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)#N | null | null | Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]c1=O>C(C)#N>CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@]1(CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(NCc1ccccc1)NCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c5835ed9058457aa9bbc2561f7d57c9 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@]1(CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(NCc1ccccc1)NCc1ccccc1>>O=c1ccn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 | C(C)(C)(C)[Si](O[C@H]1C[C@@H](O[C@@]1(CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(NCC1=CC=CC=C1)NCC1=CC=CC=C1)N1C(=O)NC(=O)C=C1)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO>>C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)C... | CC(C)(C)[Si](C)(C)[O:9][C@H:8]1[CH2:7][C@H:6]([n:5]2[cH:4][cH:3][c:2](=[O:1])[nH:33][c:31]2=[O:32])[O:30][C@@:10]1([CH2:11][O:12][Si](c1ccccc1)(c1ccccc1)C(C)(C)C)[CH:13]([NH:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[NH:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5]([... | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@]1(CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(NCc1ccccc1)NCc1ccccc1 | O=c1ccn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 | null | null | O1CCCC1 | Deprotection | OtherReaction | bd7040a39ad85a2c3bfd998d34ac16e7127d9c4e33a1400049e3f4e51e3ba999 | 48f3bf6b592ef26d22b6b1cdf6554655672438fd529e8208760ff43315f27aa1 | O=c1ccn([C@H]2CCC(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](-[C:5]-[O;H0;D2;+0:6]-[Si](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-C(-C)(-C)-C)-[#8:7]>>[#8:7]-[C:4](-[C:5]-[OH;D1;+0:6])-[C:2](-[OH;D1;+0:1])-[C:3] | 78 | [{"value": 78.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-(1,1′-diphenylmethylaminomethyl)-2′-deoxyuridine (11) (0.13 g, 0.16 mmol) was treated with tetrabutylammonium fluoride solution (0.45 mL) in tetrahydrofuran (5 mL) according to the procedure used for the preparation of compound (3). The title compound... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.Silyl protective group | Primary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1 | null | c1ccncn1.C1CCOC1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | null | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@]1(CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C(NCc1ccccc1)NCc1ccccc1>O1CCCC1>O=c1ccn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5d943e80966940b7bc9cb935cb92d36f | O=c1ccn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1>>NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O | C1(=CC=CC=C1)CNC(NCC1=CC=CC=C1)[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)CO.C1=CCCCC1.C(C)(=O)O.NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO>>NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)CO | c1ccc(CN[CH:2]([NH:1]Cc2ccccc2)[C@:3]2([CH2:4][OH:5])[O:6][C@@H:7]([n:8]3[cH:9][cH:10][c:11](=[O:12])[nH:13][c:14]3=[O:15])[CH2:16][C@@H:17]2[OH:18])cc1>>[NH2:1][CH2:2][C@:3]1([CH2:4][OH:5])[O:6][C@@H:7]([n:8]2[cH:9][cH:10][c:11](=[O:12])[nH:13][c:14]2=[O:15])[CH2:16][C@@H:17]1[OH:18] | O=c1ccn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1 | NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O | null | [Pd] | C(C)O | Deprotection | OtherReaction | ebcb62b0cee28ac375043d4efcc15ae372e32a8afec9cbfdfea9a3d36c8b53ff | 979bea025e86b23768e3b6416c2b4011b3ba1bc8928a29b90e7c5e231c2241bc | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | [C:1]-[C:2](-[C:3])(-[CH;D3;+0:4](-N-C-c1:c:c:c:c:c:1)-[NH;D2;+0:5]-C-c1:c:c:c:c:c:1)-[#8:6]-[C:7]>>[C:1]-[C:2](-[C:3])(-[CH2;D2;+0:4]-[NH2;D1;+0:5])-[#8:6]-[C:7] | 101.7 | [{"value": 100.0, "product": "NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.7, "product": "NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4′-C-(1,1′-diphenylmethylaminomethyl)-2′-deoxyuridine (12) (0.056 g, 0.13 mmol) was treated with cyclohexene (1 mL), glacial acetic acid 0.5 mL) and 5% palladium on charcoal (0.06 g) in ethanol (5 mL) according to the procedure used for the preparation of compound (4). The crude product was purified by dissolving in wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Secondary amine | Primary amine | c1ccccc1.c1ccccc1 | null | C1CCOC1.c1ccncn1 | Other | [Pd].C(C)O | null | null | O=c1ccn([C@H]2C[C@H](O)[C@](CO)(C(NCc3ccccc3)NCc3ccccc3)O2)c(=O)[nH]1>[Pd].C(C)O>NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ed602aad6f84b358ab5d4461855826e | CC(=O)Oc1c(F)c(F)c(F)c(F)c1F.NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O>>CC(=O)NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O | NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)CO.C(C)(=O)OC1=C(C(=C(C(=C1F)F)F)F)F>>C(C)(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)O)CO | Fc1c(F)c(F)c(O[C:2]([CH3:1])=[O:3])c(F)c1F.[NH2:4][CH2:5][C@:6]1([CH2:7][OH:8])[O:9][C@@H:10]([n:11]2[cH:12][cH:13][c:14](=[O:15])[nH:16][c:17]2=[O:18])[CH2:19][C@@H:20]1[OH:21]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@:6]1([CH2:7][OH:8])[O:9][C@@H:10]([n:11]2[cH:12][cH:13][c:14](=[O:15])[nH:16][c:17]2=[O:18])[CH2:19][C@@H... | CC(=O)Oc1c(F)c(F)c(F)c(F)c1F.NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O | CC(=O)NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O | null | null | CN(C=O)C | Acylation | Aminolysis of esters | bee80c17ba750e5b878660daaf03b34b83cc65c10d42a24fde7726a66e741f89 | f21fd5f8c88779686ca0dcd2a6ec464a4e9cd0b9a76d99bbd673ae535081dde3 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):c(-F):c:1-F.[#8:4]-[C:5]-[C:6]-[NH2;D1;+0:7]>>[#8:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 82 | [{"value": 82.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 4′-C-Aminomethyl-2′-deoxyuridine (13) (0.034 g, 0.13 mmol) was dissolved in anhydrous N,N-dimethylformamide (0.5 mL) at ambient temperature. Excess pentafluorophenyl acetate (0.88 g, 0.39 mmol) was then added directly to the reaction mixture as a solid. The resulting solution was stirred for 18 hours at ambient tempera... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Secondary amide | c1ccccc1 | null | C1CCOC1.c1ccncn1 | HF | CN(C=O)C | null | 18 | CC(=O)Oc1c(F)c(F)c(F)c(F)c1F.NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O>CN(C=O)C>CC(=O)NC[C@]1(CO)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb8b2ce4648d484bbd1870054f1bc6c7 | CC(=O)NCC(=O)O.Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O>>CC(=O)NCC(=O)NC[C@]1(CO)O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O | C(C)(C)N(CC)C(C)C.NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO.C(C)(=O)NCC(=O)O.[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O>>C(C)(=O)NCC(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO | O[C:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])=[O:7].[NH2:8][CH2:9][C@:10]1([CH2:11][OH:12])[O:13][C@@H:14]([n:15]2[cH:16][c:17]([CH3:18])[c:19](=[O:20])[nH:21][c:22]2=[O:23])[CH2:24][C@@H:25]1[OH:26]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C:6](=[O:7])[NH:8][CH2:9][C@:10]1([CH2:11][OH:12])[O:13][C@@H:14]([n:15]2[cH:16][c:17]([C... | CC(=O)NCC(=O)O.Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O | CC(=O)NCC(=O)NC[C@]1(CO)O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[#8:8]-[C:9]-[C:10]-[NH2;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7] | null | [] | null | null | 18 | HOUR | 4′-C-(Aminomethyl)thymidine (4) (0.025 g, 0.1 mmol), N-acetylglycine (0.023 g, 0.2 mmol) and TSTU (0.09 g, 0.3 mmol) were dissolved in anhydrous N,N-dimethylformamide (1 mL) at ambient temperature. Diisopropylethylamine (0.065 g, 0.5 mmol, 0.087 mL) was then added and the reaction mixture stirred for 18 hours at ambien... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCOC1.c1cncnc1 | HO- | CN(C=O)C | null | 18 | CC(=O)NCC(=O)O.Cc1cn([C@H]2C[C@H](O)[C@@](CN)(CO)O2)c(=O)[nH]c1=O>CN(C=O)C>CC(=O)NCC(=O)NC[C@]1(CO)O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9949be2671b4e299f745542bda2d702 | CC(=O)NCC(=O)NC[C@]1(CO)O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)[C@H](CC(C)C)NC(=O)OCC3c4ccccc4-c4ccccc43)O2)c(=O)[nH]c1=O | [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O.C(C)(=O)NCC(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO.NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO.C(C)(C)N(CC)C(C)C.C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H](CC(C)C)C(=O)O>>C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H](CC(C)C)C(=O)NC[C@]1([C@H](C[C@@H](O1)N1... | CC(=O)NCC(=O)[NH:13][CH2:12][C@@:9]1([CH2:10][OH:11])[C@@H:7]([OH:8])[CH2:6][C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:43](=[O:44])[nH:42][c:40]2=[O:41])[O:39]1.O[C:14](=[O:15])[C@H:16]([CH2:17][CH:18]([CH3:19])[CH3:20])[NH:21][C:22](=[O:23])[O:24][CH2:25][CH:26]1[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2-[c:33]2[cH:34][cH:3... | CC(=O)NCC(=O)NC[C@]1(CO)O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)[C@H](CC(C)C)NC(=O)OCC3c4ccccc4-c4ccccc43)O2)c(=O)[nH]c1=O | null | null | CN(C)C=O | Acylation | OtherReaction | 4665d7eb1e059fa98b3f12c5adcb8b6eb803a667ac153193dd3326828285173d | bbb043cea476a895a106a81a54aecbe1570485968aab284509e3f5f3d74caae2 | O=C(CNC(=O)OCC1c2ccccc2-c2ccccc21)NCC1CC[C@H](n2ccc(=O)[nH]c2=O)O1 | C-C(=O)-N-C-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[#8:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[C:8])-[#7:9]-[C:10]=[O;D1;H0:11]>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[C:8])-[#7:9]-[C:10]=[O;D1;H0:11] | null | [] | null | null | null | null | 4′-C-(Aminomethyl)thymidine (4) (0.025 g, 0.1 mmol), N-(9-fluorenylmethyloxycarbonyl)leucine (0.071 g, 0.2 mmol), TSTU (0.09 g, 0.3 mmol) and diisopropylethylamine (0.065 g, 0.5 mmol, 0.087 mL) were combined in DMF (1 mL) according to the procedure used to prepare compound (19). The title compound (20) was obtained as ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Secondary amide | Secondary amide | null | null | c1cncnc1.C1CCOC1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=O | null | null | CC(=O)NCC(=O)NC[C@]1(CO)O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>CN(C)C=O>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)[C@H](CC(C)C)NC(=O)OCC3c4ccccc4-c4ccccc43)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e281f1e4429247d3adca645f05b2dcea | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CN)O2)c(=O)[nH]c1=O | FC(C(=O)NCC(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO)(F)F>>NCC(=O)NC[C@]1([C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)CO | O=C(C(F)(F)F)[NH:17][CH2:16][C:14]([NH:13][CH2:12][C@@:9]1([CH2:10][OH:11])[C@@H:7]([OH:8])[CH2:6][C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:22](=[O:23])[nH:21][c:19]2=[O:20])[O:18]1)=[O:15]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@:9]([CH2:10][OH:11])([CH2:12][NH:13][C:14](=[O:15])[CH2:16][NH2:17])[O:18]2)... | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CN)O2)c(=O)[nH]c1=O | null | null | N | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]>>[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1] | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4′-C-(N-trifluoroacetylglycylaminomethyl)thymidine (5) (17 mg, 0.4 mmol) was dissolved in concentrated aqueous ammonia solution (1 mL) and allowed to stand overnight at ambient temperature. The reaction mixture was then lyophilised to give the title compound (22) as a colourless resin (0.0088 g, 67%). δH(300 MHz, D2O) ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1cncnc1.C1CCOC1 | Other | N | null | 8 | Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CNC(=O)C(F)(F)F)O2)c(=O)[nH]c1=O>N>Cc1cn([C@H]2C[C@H](O)[C@](CO)(CNC(=O)CN)O2)c(=O)[nH]c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef2f3557d9a44dbeaeb9c3c384b3664e | NCCc1c[nH]cn1.O=[N+]([O-])c1ccc(F)cc1>>O=[N+]([O-])c1ccc(NCCc2cnc[nH]2)cc1 | CS(=O)C.C(C)N(CC)CC.Cl.Cl.NCCC1=CNC=N1.FC1=CC=C(C=C1)[N+](=O)[O-]>>[N+](=O)([O-])C1=CC=C(C=C1)NCCC1=CN=CN1 | [NH2:8][CH2:9][CH2:10][c:11]1[cH:12][nH:13][cH:14][n:15]1.F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:17][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][c:11]2[cH:12][n:13][cH:14][nH:15]2)[cH:16][cH:17]1 | NCCc1c[nH]cn1.O=[N+]([O-])c1ccc(F)cc1 | O=[N+]([O-])c1ccc(NCCc2cnc[nH]2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCc2cnc[nH]2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[c:9]1:[c:10]:[nH;D2;+0:11]:[c:12]:[n;H0;D2;+0:13]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[C:8]-[c:9]1:[c:10]:[n;H0;D2;+0:11]:[c:12]:[nH;D2;+0:13]:1):[c:4]:[c:5] | 89.6 | [{"value": 89.6, "product": "[N+](=O)([O-])C1=CC=C(C=C1)NCCC1=CN=CN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 10 | HOUR | 100 ml of DMSO were introduced into a 500 ml three-necked flask and treated with 30.9 g of triethylamine, 18.4 g of histamine dihydrochloride and 14.4 g of 1-fluoro-4-nitrobenzene. The mixture was stirred at 80° C. for 10 h, treated with 20 ml of water and stirred at 80° C. for a further 3 h. Following this, the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | HF | O | 80 | 10 | NCCc1c[nH]cn1.O=[N+]([O-])c1ccc(F)cc1>O>O=[N+]([O-])c1ccc(NCCc2cnc[nH]2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f1ef429b3c44887b59ac94f97264e8c | NCCCn1ccnc1.O=[N+]([O-])c1ccc(F)cc1>>O=[N+]([O-])c1ccc(NCCCn2ccnc2)cc1 | NCCCN1C=NC=C1.FC1=CC=C(C=C1)[N+](=O)[O-].CS(=O)C>>[N+](=O)([O-])C1=CC=C(C=C1)NCCCN1C=NC=C1 | [NH2:8][CH2:9][CH2:10][CH2:11][n:12]1[cH:13][cH:14][n:15][cH:16]1.F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][n:12]2[cH:13][cH:14][n:15][cH:16]2)[cH:17][cH:18]1 | NCCCn1ccnc1.O=[N+]([O-])c1ccc(F)cc1 | O=[N+]([O-])c1ccc(NCCCn2ccnc2)cc1 | null | null | C(C)N(CC)CC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCCn2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c: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](:[c:2]:[c:3]):[c:4]:[c:5] | 111.4 | [{"value": 111.4, "product": "[N+](=O)([O-])C1=CC=C(C=C1)NCCCN1C=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | 100 ml of DMSO were introduced into a 500 ml three-necked flask and treated with 10.3 g of triethylamine, 12.8 g of 1-(3-aminopropyl)imidazole and 14.4 g of 1-fluoro-4-nitrobenzene. The mixture was stirred at 80° C. for 12 h, cooled to room temperature and subsequently poured onto 1 l of ice. A sample of the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | HF | C(C)N(CC)CC | 80 | 12 | NCCCn1ccnc1.O=[N+]([O-])c1ccc(F)cc1>C(C)N(CC)CC>O=[N+]([O-])c1ccc(NCCCn2ccnc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6c83fa214378440c89210958526a08e4 | Cc1cc(F)ccc1[N+](=O)[O-].NCCCn1ccnc1>>Cc1cc(NCCCn2ccnc2)ccc1[N+](=O)[O-] | N(CCO)(CCO)CCO.NCCCN1C=NC=C1.FC=1C=CC(=C(C1)C)[N+](=O)[O-]>>[N+](=O)([O-])C1=C(C=C(C=C1)NCCCN1C=NC=C1)C | F[c:4]1[cH:3][c:2]([CH3:1])[c:16]([N+:17](=[O:18])[O-:19])[cH:15][cH:14]1.[NH2:5][CH2:6][CH2:7][CH2:8][n:9]1[cH:10][cH:11][n:12][cH:13]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][CH2:8][n:9]2[cH:10][cH:11][n:12][cH:13]2)[cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19] | Cc1cc(F)ccc1[N+](=O)[O-].NCCCn1ccnc1 | Cc1cc(NCCCn2ccnc2)ccc1[N+](=O)[O-] | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCCn2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c: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](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 17 | HOUR | 150 ml of dimethyl sulfoxide were introduced into a 500 ml three-necked flask and treated with 22.6 g of triethanolamine (99% strength), 28.7 g of 1-(3-amino-propyl)imidazole (98% strength) and 24.2 g of 5-fluoro-2-nitrotoluene (96% strength). The mixture was stirred at 80° C. for 17 h. Following this, the batch was co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | HF | CS(=O)C | 80 | 17 | Cc1cc(F)ccc1[N+](=O)[O-].NCCCn1ccnc1>CS(=O)C>Cc1cc(NCCCn2ccnc2)ccc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00e902becac84755aca74d9f42cf30fb | CCO>>CCO.O.OCC(O)CO | C(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO>>C(C)O.O.OCC(O)CO.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO | [CH3:26][CH2:27][OH:28]>>[CH3:26][CH2:27][OH:28].[OH2:29].[OH:30][CH2:31][CH:32]([OH:33])[CH2:34][OH:35] | CCO | CCO.O.OCC(O)CO | null | null | O.OCC(O)CO | Miscellaneous | OtherReaction | a244f833733718b07f52109095aa98cd5943ebccc6e7556166190ea2fb1e9527 | 3886f50ccf014aba7d974a7f782a7e63fb3f50b880ebcf5701bc7ab1c8a8ad31 | null | null | null | [] | null | null | null | null | 95% ethanol (USP) was diluted with water (USP), glycerin (USP), and glycerol monooleate (Eastman Chemical, Kingsport N.Y.) to provide a final solution at ethanol/water/glycerin/glycerol monooleate percent ratios of 35/59/5/1, respectively. Oxybutynin free base was then dissolved into the above solution to a concentrati... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol.Primary alcohol.Secondary alcohol | null | null | null | Other | O.OCC(O)CO | null | null | CCO>O.OCC(O)CO>CCO.O.OCC(O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-88fa344a52a84607aa162aa511c4c43b | CCO>>CCO.O.OCC(O)CO | C(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO>>C(C)O.O.OCC(O)CO.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO | [CH3:26][CH2:27][OH:28]>>[CH3:26][CH2:27][OH:28].[OH2:29].[OH:30][CH2:31][CH:32]([OH:33])[CH2:34][OH:35] | CCO | CCO.O.OCC(O)CO | null | null | O.OCC(O)CO | Miscellaneous | OtherReaction | a244f833733718b07f52109095aa98cd5943ebccc6e7556166190ea2fb1e9527 | 3886f50ccf014aba7d974a7f782a7e63fb3f50b880ebcf5701bc7ab1c8a8ad31 | null | null | null | [] | null | null | null | null | 95% ethanol (USP) was diluted with water (USP), glycerin (USP), and glycerol monooleate (Eastman Chemical, Kingsport N.Y.) to provide a final solution at ethanol/water/glycerin/glycerol monooleate percent ratios of 35/59/5/1, respectively. Oxybutynin free base was then dissolved into the above solution to a concentrati... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol.Primary alcohol.Secondary alcohol | null | null | null | Other | O.OCC(O)CO | null | null | CCO>O.OCC(O)CO>CCO.O.OCC(O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f07d33de0b8549108bb55562f9fdb65a | CCO>>CCO.O.OCC(O)CO | C(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO>>C(C)O.O.OCC(O)CO.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO | [CH3:26][CH2:27][OH:28]>>[CH3:26][CH2:27][OH:28].[OH2:29].[OH:30][CH2:31][CH:32]([OH:33])[CH2:34][OH:35] | CCO | CCO.O.OCC(O)CO | null | null | O.OCC(O)CO | Miscellaneous | OtherReaction | a244f833733718b07f52109095aa98cd5943ebccc6e7556166190ea2fb1e9527 | 3886f50ccf014aba7d974a7f782a7e63fb3f50b880ebcf5701bc7ab1c8a8ad31 | null | null | null | [] | null | null | null | null | 95% ethanol (USP) was diluted with water (USP), glycerin (USP), and glycerol monooleate (Eastman Chemical, Kingsport NY) to provide a final solution at ethanol/water/glycerin/glycerol monooleate percent ratios of 35/59/5/1, respectively. Oxybutynin free base was then dissolved into the above solution to a concentration... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol.Primary alcohol.Secondary alcohol | null | null | null | Other | O.OCC(O)CO | null | null | CCO>O.OCC(O)CO>CCO.O.OCC(O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-761efd575dc141deb57881de7b02e7ad | CCO>>CCO.O.OCC(O)CO | C(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO>>C(C)O.O.OCC(O)CO.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO | [CH3:26][CH2:27][OH:28]>>[CH3:26][CH2:27][OH:28].[OH2:29].[OH:30][CH2:31][CH:32]([OH:33])[CH2:34][OH:35] | CCO | CCO.O.OCC(O)CO | null | null | O.OCC(O)CO | Miscellaneous | OtherReaction | a244f833733718b07f52109095aa98cd5943ebccc6e7556166190ea2fb1e9527 | 3886f50ccf014aba7d974a7f782a7e63fb3f50b880ebcf5701bc7ab1c8a8ad31 | null | null | null | [] | null | null | null | null | 95% ethanol (USP) was diluted with water (USP), glycerin (USP), and glycerol monooleate (Eastman Chemical, Kingsport N.Y.) to provide a final solution at ethanol/water/glycerin/glycerol monooleate percent ratios of 35/59/5/1, respectively. Oxybutynin free base was then dissolved into the above solution to a concentrati... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol.Primary alcohol.Secondary alcohol | null | null | null | Other | O.OCC(O)CO | null | null | CCO>O.OCC(O)CO>CCO.O.OCC(O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-278ccc5998f54f15ac9cb0e5406b4b9d | CCOc1ccc(C2CCC3(CC2)OCCO3)c(F)c1F>>CCOc1ccc(C2CCC(=O)CC2)c(F)c1F | C1COC2(CCC(CC2)C2=C(C(=C(C=C2)OCC)F)F)O1.C(=O)O>>FC1=C(C=CC(=C1F)OCC)C1CCC(CC1)=O | C1C[O:12][C:11]2(O1)[CH2:10][CH2:9][CH:8]([c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:17]([F:18])[c:15]1[F:16])[CH2:14][CH2:13]2>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:14]2)[c:15]([F:16])[c:17]1[F:18] | CCOc1ccc(C2CCC3(CC2)OCCO3)c(F)c1F | CCOc1ccc(C2CCC(=O)CC2)c(F)c1F | null | null | C1(=CC=CC=C1)C | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(c2ccccc2)CC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | 100 | [{"value": 100.0, "product": "FC1=C(C=CC(=C1F)OCC)C1CCC(CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Crude 4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexanone monoethylene acetal (50.3 mmol) obtained in Step 1 was dissolved in 200 ml of toluene, 87% formic acid (503 mmol) was added, and the solution was heated to reflux for 4 hours. The reaction solution was washed twice with 100 ml of a saturated aqueous solution of sodium... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | C1(=CC=CC=C1)C | null | null | CCOc1ccc(C2CCC3(CC2)OCCO3)c(F)c1F>C1(=CC=CC=C1)C>CCOc1ccc(C2CCC(=O)CC2)c(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ff8dfbed6ca40f0b866cec334ac483f | CCOc1ccc(C2CCC(=O)CC2)c(F)c1F.c1ccc([P+](CCC2OCCCO2)(c2ccccc2)c2ccccc2)cc1>>CCOc1ccc(C2CCC(=CCC3OCCCO3)CC2)c(F)c1F | CC(C)(C)[O-].[K+].[Br-].O1C(OCCC1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.FC1=C(C=CC(=C1F)OCC)C1CCC(CC1)=O>>FC1=C(C=CC(=C1F)OCC)C1CCC(CC1)=CCC1OCCCO1 | O=[C:11]1[CH2:10][CH2:9][CH:8]([c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:24]([F:25])[c:22]2[F:23])[CH2:21][CH2:20]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:12][CH2:13][CH:14]2[O:15][CH2:16][CH2:17][CH2:18][O:19]2)cc1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][C:11](=[CH:12][CH2:13][CH:14]3[O:15]... | CCOc1ccc(C2CCC(=O)CC2)c(F)c1F.c1ccc([P+](CCC2OCCCO2)(c2ccccc2)c2ccccc2)cc1 | CCOc1ccc(C2CCC(=CCC3OCCCO3)CC2)c(F)c1F | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | 4ace91bfe286d7308b684482c14d0e07094c3e16f8d78c7715341add0f69a6d3 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C(CC1OCCCO1)=C1CCC(c2ccccc2)CC1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[#8:6]-[C:7](-[C:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[#8:10]>>[#8:6]-[C:7](-[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-[#8:10] | 73.4 | [{"value": 73.4, "product": "FC1=C(C=CC(=C1F)OCC)C1CCC(CC1)=CCC1OCCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 1 | HOUR | A mixture of 2-(1,3-dioxane-2-yl)-ethyltriphenyl phosphonium bromide (60.4 mmol) and 30 ml of THF was cooled down to −30° C. by use of a refrigerant under a nitrogen flow. To this mixture, t-BuOK (60.4 mmol) was added, and the mixture was stirred for one hour. A solution of the crude 4-(2,3-difluoro-4-ethoxyphenyl)-cyc... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1.C1COCOC1 | HO- | C1CCOC1 | -30 | 1 | CCOc1ccc(C2CCC(=O)CC2)c(F)c1F.c1ccc([P+](CCC2OCCCO2)(c2ccccc2)c2ccccc2)cc1>C1CCOC1>CCOc1ccc(C2CCC(=CCC3OCCCO3)CC2)c(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce76130bc77244d494327549fffb2ce1 | CCOc1ccc(C2CCC(=CCC3OCCCO3)CC2)c(F)c1F>>CCOc1ccc([C@@H]2CC[C@@H](CCC3OCCCO3)CC2)c(F)c1F | FC1=C(C=CC(=C1F)OCC)C1CCC(CC1)=CCC1OCCCO1>>FC1=C(C=CC(=C1F)OCC)[C@@H]1CC[C@H](CC1)CCC1OCCCO1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][C:11](=[CH:12][CH2:13][CH:14]3[O:15][CH2:16][CH2:17][CH2:18][O:19]3)[CH2:20][CH2:21]2)[c:22]([F:23])[c:24]1[F:25]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH2:12][CH2:13][CH:14]3[O:15][CH2:16][CH2:17][CH2:18][O:19]3)[C... | CCOc1ccc(C2CCC(=CCC3OCCCO3)CC2)c(F)c1F | CCOc1ccc([C@@H]2CC[C@@H](CCC3OCCCO3)CC2)c(F)c1F | null | [Pd] | C1(=CC=CC=C1)C.C(C)O | Reduction | Hydrogenation (double to single) | da8a9b0fabf153e7390d0529375b4e7b6b9340230ccf509d4c3ece1ac615e7d0 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc([C@H]2CC[C@H](CCC3OCCCO3)CC2)cc1 | [#8:1]-[C:2](-[C:3]-[CH;D2;+0:4]=[C;H0;D3;+0:5](-[C:6]-[C:7])-[C:8]-[C:9])-[#8:10]>>[#8:1]-[C:2](-[C:3]-[CH2;D2;+0:4]-[C@H;D3;+0:5](-[C:6]-[C:7])-[C:8]-[C:9])-[#8:10] | 100 | [{"value": 100.0, "product": "FC1=C(C=CC(=C1F)OCC)[C@@H]1CC[C@H](CC1)CCC1OCCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | The 2-(2-(4-(2,3-difluoro-4-ethoxyphenyl)cyclohexylidene)-ethyl)-1,3-dioxane (36.9 mmol) obtained by the reaction of Step 3 was dissolved in 100 ml of a mixed solvent of toluene/ethanol (1/1), 4.0 g of 5-wt %-palladium/carbon catalyst was added, and the solution was stirred for 7 hours at room temperature under a hydro... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1.C1COCOC1 | null | [Pd].C1(=CC=CC=C1)C.C(C)O | null | 7 | CCOc1ccc(C2CCC(=CCC3OCCCO3)CC2)c(F)c1F>[Pd].C1(=CC=CC=C1)C.C(C)O>CCOc1ccc([C@@H]2CC[C@@H](CCC3OCCCO3)CC2)c(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5d2a3c98a094bf9b2875bcfff8c573c | CCOc1ccc([C@@H]2CC[C@@H](CCC3OCCCO3)CC2)c(F)c1F>>CCOc1ccc([C@@H]2CC[C@@H](CCC=O)CC2)c(F)c1F | FC1=C(C=CC(=C1F)OCC)[C@@H]1CC[C@H](CC1)CCC1OCCCO1.C(=O)O>>FC1=C(C=CC(=C1F)OCC)[C@@H]1CC[C@H](CC1)CCC=O | C1CO[CH:14]([CH2:13][CH2:12][C@H:11]2[CH2:10][CH2:9][C@H:8]([c:7]3[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:20]([F:21])[c:18]3[F:19])[CH2:17][CH2:16]2)[O:15]C1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH2:12][CH2:13][CH:14]=[O:15])[CH2:16][CH2:17]2)[c:18]([F:19])[c:20]1[F:21] | CCOc1ccc([C@@H]2CC[C@@H](CCC3OCCCO3)CC2)c(F)c1F | CCOc1ccc([C@@H]2CC[C@@H](CCC=O)CC2)c(F)c1F | null | null | C1(=CC=CC=C1)C | Miscellaneous | Acetal hydrolysis to aldehyde | c0e8259a4c04433c939fe17907d7eafe1c52bcb535318030bf0e1cb6f82c0712 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(C2CCCCC2)cc1 | [C:1]-[C:2]-[CH;D3;+0:3]1-O-C-C-C-[O;H0;D2;+0:4]-1>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 100 | [{"value": 100.0, "product": "FC1=C(C=CC(=C1F)OCC)[C@@H]1CC[C@H](CC1)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The 2-(2-(trans-4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexyl)-ethyl)-1,3-dioxane (19.8 mmol) obtained by the reaction of Step 4 was dissolved in 100 ml of toluene, 87% formic acid (198 mmol) was added, and the solution was heated to reflux for 4 hours. The reaction solution was twice washed with 50 ml of a saturated aque... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCOC1 | null | c1ccccc1.C1CCCCC1 | HO- | C1(=CC=CC=C1)C | null | null | CCOc1ccc([C@@H]2CC[C@@H](CCC3OCCCO3)CC2)c(F)c1F>C1(=CC=CC=C1)C>CCOc1ccc([C@@H]2CC[C@@H](CCC=O)CC2)c(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e406312d98c049aa96999117a8c91f3e | C=CC=O>>C=CC=O | CN(C(C=C)=O)C.C(=O)C=C.N(=NC(C#N)(C)C)C(C#N)(C)C>>CN(C(C=C)=O)C.C(=O)C=C | [CH2:8]=[CH:9][CH:10]=[O:11]>>[CH2:8]=[CH:9][CH:10]=[O:11] | C=CC=O | C=CC=O | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | To tetrahydrofuran (300 g) were added N,N-dimethylacrylamide (70 g), acrolein (30 g) and AIBN (2,2′-azobisisobutyronitrile) (5 g). The resulting mixture was reacted at 66° C. for 8 hours. After reaction, the resulting mixture was precipitated in ether, filtered, and dehydrated, thereby obtaining poly(N,N-dimethylacryla... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O1CCCC1 | null | null | C=CC=O>O1CCCC1>C=CC=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12928a2eaec7459589ce187d1ee9646a | C=C(C)C(=O)OCCO>>C=C(C)C(=O)OCCO | COC(C(=C)C)=O.OCCOC(C(=C)C)=O.C(C=C)(=O)O.CC(C)(C#N)N=NC(C)(C)C#N>>COC(C(=C)C)=O.OCCOC(C(=C)C)=O.C(C=C)(=O)O | [CH2:8]=[C:9]([CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH2:15][OH:16]>>[CH2:8]=[C:9]([CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH2:15][OH:16] | C=C(C)C(=O)OCCO | C=C(C)C(=O)OCCO | null | null | CC(=O)CC.O1CCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | To tetrahydrofuran (250 g) and methylethylketone (250 g) were added methylmethacrylate (40 g), 2-hydroxyethylmethacrylate (30 g), acrylic acid (30 g) and AIBN (2.5 g). The resulting mixture was reacted at 66° C. for 8 hours. After reaction, the resulting mixture was precipitated in ether, filtered, and dehydrated, ther... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(=O)CC.O1CCCC1 | null | null | C=C(C)C(=O)OCCO>CC(=O)CC.O1CCCC1>C=C(C)C(=O)OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-750d8ab497db4ebeb91e5d10a9695c1b | C=CC(OC)OC.C=CC=O.COCC(C)OC(C)=O>>C=C(C)C(=O)OC.C=C(C)C(=O)OCCO.C=CC(=O)O | CC(COC)OC(=O)C.COC(C=C)OC.C(=O)C=C>>COC(C(=C)C)=O.OCCOC(C(=C)C)=O.C(C=C)(=O)O | [CH3:14][O:20][CH:19]([O:16][CH3:15])[CH:18]=[CH2:17].[CH:9](=[CH2:10])[CH:11]=[O:12].[CH2:1]([CH:2]([CH3:3])[O:21][C:4](=[O:5])[CH3:8])[O:6][CH3:7]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH3:7].[CH2:8]=[C:9]([CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH2:15][OH:16].[CH2:17]=[CH:18][C:19](=[O:20])[OH:21] | C=CC(OC)OC.C=CC=O.COCC(C)OC(C)=O | C=C(C)C(=O)OC.C=C(C)C(=O)OCCO.C=CC(=O)O | null | null | null | Acylation | OtherReaction | 65460a54a1bf21ae503da0fb81f9b603fc6db58af8e7bac21de01b6e814263bf | 4394e8022841beefad133ac77e7c756c74cc3fec5db8914262dd1070a955fcc5 | null | [C;D1;H2:1]=[C:2]-[CH;D3;+0:3](-[O;H0;D2;+0:4]-[CH3;D1;+0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:7].[C;D1;H3:8]-[CH;D3;+0:9](-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-[C;D1;H3:12])-[O;H0;D2;+0:13]-[C;H0;D3;+0:14](-[CH3;D1;+0:15])=[O;D1;H0:16].[CH2;D1;+0:17]=[CH;D2;+0:18]-[CH;D2;+0:19]=[O;D1;H0:20]>>[C;D1;H2:1]=[C:2]-[C;H0;D3;+0:3](=[O;H0... | null | [] | null | null | null | null | To propyleneglycolmethyletheracetate (PGMEA) (130 g) as an organic solvent were added poly(N,N-dimethylacryladmide/3,3-dimethoxypropene/acrolein) (3 g) obtained from Example 1, poly(methylmethacrylate/2-hydroxyethylmethacrylate/acrylic acid) (7 g) obtained from Example 2 and triphenylsulfonium triflate (0.05 g) as a ph... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ether.Ether.Ether.Vinyl | Carboxylic acid.Ester.Ester.Primary alcohol.Vinyl.Vinyl | null | null | null | Other | null | null | null | C=CC(OC)OC.C=CC=O.COCC(C)OC(C)=O>>C=C(C)C(=O)OC.C=C(C)C(=O)OCCO.C=CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-156955290ae845ef8c4c29c66f5866ca | C=C(C)C(=O)O.CC(C)=O.O=C1OC(=O)[C@@H]2CCCC[C@H]12>>C=C(C)C(=O)OCCOC(=O)C1CCCCC1C(=O)O | CC(=O)C.[C@@H]12[C@@H](CCCC1)C(=O)OC2=O.C(C(=C)C)(=O)O>>C(C(=C)C)(=O)OCCOC(=O)C1C(CCCC1)C(=O)O | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[OH:6].C[C:8]([CH3:7])=[O:9].[C:10]1(=[O:11])[C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]2[C:18](=[O:19])[O:20]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[C:18](=[O:19])[OH:20] | C=C(C)C(=O)O.CC(C)=O.O=C1OC(=O)[C@@H]2CCCC[C@H]12 | C=C(C)C(=O)OCCOC(=O)C1CCCCC1C(=O)O | null | null | O | Protection | OtherReaction | 88e33a1da3a3458d2b82b80e9b8e6d156e5642270cb078fa99f672050dfa2a85 | d08edf875d3a4b403a08ae8fd0cf1342df8502dc704b991940af7ae29f106b2d | C1CCCCC1 | C-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;H0;D1;+0:3].[C;D1;H2:4]=[C:5](-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9].[O;D1;H0:10]=[C;H0;D3;+0:11]1-[O;H0;D2;+0:12]-[C:13](=[O;D1;H0:14])-[C@@H;D3;+0:15]2-[C:16]-[C:17]-[C:18]-[C:19]-[C@H;D3;+0:20]-1-2>>[C;D1;H2:4]=[C:5](-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2... | null | [] | null | null | 1 | HOUR | Into acetone (1,000 ml) were dissolved cis-1,2-cyclohexane dicarboxylic anhydride (308.3 g), methacrylic acid (2-hydroxyethyl) (273.3 g) and 4-(dimethylamine) pyridine (4.9 g), and heated for 5 hours under reflux. After acetone had been distilled off under reduced pressure, 1N hydrochloric acid (500 ml) and ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carboxylic acid.Ketone | Carboxylic acid.Ester.Ester | C1CC[C@H]2COC[C@H]2C1 | null | C1CCCCC1 | Other | O | null | 1 | C=C(C)C(=O)O.CC(C)=O.O=C1OC(=O)[C@@H]2CCCC[C@H]12>O>C=C(C)C(=O)OCCOC(=O)C1CCCCC1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02c0ddb3dd46487290cbe5ee3bbd5d63 | OC[C@@H](O)[C@@H](O)[C@@H](O)CO.OC[C@H](O)C(O)[C@@H](O)CO.O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O>>OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | C([C@H]([C@H]([C@H]([C@H](CO)O)O)O)O)O.C([C@H]([C@@H]([C@@H]([C@H](CO)O)O)O)O)O.OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO.C([C@H](O)[C@H](O)[C@H](O)CO)O.C([C@H](O)[C@@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)O.C([C@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO)O.[C@@H]1([C@@H]([C@@H]([C@@H]([C@H]([C@@H]1O)O)O)O)O)O.C... | O[C@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[C@@H:18]([OH:19])[CH2:20][OH:21].OC([C@@H](O)[CH2:10][OH:11])[C@@H](O)[CH2:22][OH:23].O[C@H]1[C@H:7]([OH:6])[C@H:16]([OH:17])[C@H:14]([OH:15])[C@@H:12]([OH:13])[C@@H:9]1[OH:8]>>[OH:1][CH2:2][C@@H:3]([OH:4])[C@@H:5]([O:6][C@H:7]1[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@H:... | OC[C@@H](O)[C@@H](O)[C@@H](O)CO.OC[C@H](O)C(O)[C@@H](O)CO.O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O | OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34e0a3f88b2f57ed7c4bec6476031bf118be09afc16e8b39b989f686f1540b33 | 7e797b6b8c0c9bab05d231d06fdd9e03052e7f7b88ca619d2e7f6dd67bfb2df8 | C1CCOCC1 | O-C(-[C@@H](-O)-[CH2;D2;+0:1]-[O;D1;H1:2])-[C@@H](-O)-[CH2;D2;+0:3]-[O;D1;H1:4].O-[C@@H]1-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7](-[O;D1;H1:8])-[C:9]-[C:10](-[O;D1;H1:11])-[C@H;D3;+0:12]-1-[OH;D1;+0:13].O-[C@H;D3;+0:14](-[C:15](-[O;D1;H1:16])-[CH2;D2;+0:17]-[O;D1;H1:18])-[C:19](-[C:20])-[O;D1;H1:21]>>[C:20]-[C:19](-[O;D1;H1... | null | [] | null | null | null | null | Examples of the sugar alcohols are D, L-arabitol, ribitol, xylitol, D, L-sorbitol, D, L-mannitol, D, L-iditol, D, L-talitol, meso-inositol, dulcitol, and allodulcitol. Further, maltitol obtained by subjecting disaccharides to hydrogenation and reductants (e.g., reduced starch syrup) obtained by subjecting oligosacchari... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Ether.Ether.Primary alcohol.Primary alcohol.Secondary alcohol | C1CCCCC1 | C1CCOCC1 | C1CCOCC1 | HO- | null | null | null | OC[C@@H](O)[C@@H](O)[C@@H](O)CO.OC[C@H](O)C(O)[C@@H](O)CO.O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O>>OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02e7e21623fd4748b28d74da50786052 | Nc1ccc2nc(O)c(O)nc2c1>>[N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1 | Cl.NC=1C=C2N=C(C(=NC2=CC1)O)O.[N-]=[N+]=[N-].[Na+].N(=O)[O-].[Na+]>>N(=[N+]=[N-])C=1C=C2N=C(C(=NC2=CC1)O)O | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([OH:10])[c:11]([OH:12])[n:13][c:14]2[cH:15]1>>[N-:1]=[N+:2]=[N:3][c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([OH:10])[c:11]([OH:12])[n:13][c:14]2[cH:15]1 | Nc1ccc2nc(O)c(O)nc2c1 | [N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1 | null | null | O.OS(=O)(=O)O | Miscellaneous | Amine to azide | 874c0cf1984ab0c3156493e6524e4a76434860bf4d8c4f6115608f4b54932f2a | 0dcf06f7cec37f2f50b2497bf88be0f43ce4890a2df8b6f4eb18df3f7b6a2a7d | c1ccc2nccnc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[#7;+:7]=[N;-;D1;H0:8]):[c:6] | 67 | [{"value": 67.0, "product": "N(=[N+]=[N-])C=1C=C2N=C(C(=NC2=CC1)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.8, "product": "N(=[N+]=[N-])C=1C=C2N=C(C(=NC2=CC1)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | A solution of 5 g (23.5 mmol) 6-amino-2,3-dihydroxyquinoxaline hydrochloride in 250 ml 0.5 N H2SO4 is cooled to 0° C. and then a solution of 1.65 g (24 mmol) NaNO2 in 50 ml water is added. After stirring at 0° C. for 15 min., a solution of 1.5 g (24 mmol) NaN3 in 100 ml water is added. Stirring at 0° C. for 45 min. giv... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Azide | null | null | c1ccc2nccnc2c1 | Other | O.OS(=O)(=O)O | 0 | 0.25 | Nc1ccc2nc(O)c(O)nc2c1>O.OS(=O)(=O)O>[N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a942e4fd4c9b4307850ab5026494e834 | O=[N+]([O-])O.[N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1>>[N-]=[N+]=Nc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | N(=[N+]=[N-])C=1C=C2N=C(C(=NC2=CC1)O)O.[N+](=O)(O)[O-]>>N(=[N+]=[N-])C=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O | O[N+:16](=[O:17])[O-:18].[N-:1]=[N+:2]=[N:3][c:15]1[cH:4][cH:5][c:6]2[n:7][c:8]([OH:9])[c:10]([OH:11])[n:12][c:13]2[cH:14]1>>[N-:1]=[N+:2]=[N:3][c:4]1[cH:5][c:6]2[n:7][c:8]([OH:9])[c:10]([OH:11])[n:12][c:13]2[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | O=[N+]([O-])O.[N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1 | [N-]=[N+]=Nc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 37bdfc0ed0dc9f813368bd3bc7c72a93dce8c81565853939e7b462c53f39d02d | 5a3824aa005ce892a6e1c787f983b0d27b16b43391fc0c52a724f93c6266a8aa | c1ccc2nccnc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[N;-;D1;H0:4]=[#7;+:5]=[N;H0;D2;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]2:[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:2:[c:15]:[cH;D2;+0:16]:1>>[N;-;D1;H0:4]=[#7;+:5]=[N;H0;D2;+0:6]-[c;H0;D3;+0:16]1:[c:15]:[c:14]2:[#7;a:13]:[c:12]:[c:11]:[#7;a:10]:[c:9]:2:[c:8]:[c;H0;D3;+0:7]:1-[N+;H0;D... | 78 | [{"value": 78.0, "product": "N(=[N+]=[N-])C=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O", "details": "PERCENTYIELD", "is_desired": false}] | 24 | CELSIUS | 4 | HOUR | 2 g 6-azido-2,3-dihydroxyquinoxaline is suspended in 100 ml glacial acetic acid. To the suspension is added 16 ml fuming nitric acid at 24° C. The mixture is stirred at 24° C. for 4 h giving a precipitate of 1.9 g (78%) 6-azido-2,3-dihydroxy-7-nitroquinoxaline. IR: a peak at 2120 cm−1. NMR: two singlets (7.0 and 7.7 pp... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrate | Azide.Nitro group | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | HO- | C(C)(=O)O | 24 | 4 | O=[N+]([O-])O.[N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1>C(C)(=O)O>[N-]=[N+]=Nc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13df26d266a64ad88e30ef4d4128c856 | Oc1nc2ccc(C(F)(F)F)cc2nc1O>>O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1C(F)(F)F | OC1=NC2=CC=C(C=C2N=C1O)C(F)(F)F.[N+](=O)([O-])[O-].[K+].Cl>>OC1=NC2=CC(=C(C=C2N=C1O)[N+](=O)[O-])C(F)(F)F | [cH:4]1[cH:5][c:6]2[n:7][c:8]([OH:9])[c:10]([OH:11])[n:12][c:13]2[cH:14][c:15]1[C:16]([F:17])([F:18])[F:19]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[n:7][c:8]([OH:9])[c:10]([OH:11])[n:12][c:13]2[cH:14][c:15]1[C:16]([F:17])([F:18])[F:19] | Oc1nc2ccc(C(F)(F)F)cc2nc1O | O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1C(F)(F)F | null | null | [OH-].[Na+].OS(=O)(=O)O | Functional Group Addition | OtherReaction | 5bb74314601b8a07868b6724521bd2147502d00fa9938aa4b54a5783d20f96b8 | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccc2nccnc2c1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:2:[c:13]:[cH;D2;+0:14]:1>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:2:[c:13]:[c;H0;D3;+0:14]:1-[#7;+:15](-[O;-;D1;H0:16])=[O;D1;H0:17] | 72 | [{"value": 72.0, "product": "OC1=NC2=CC(=C(C=C2N=C1O)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "OC1=NC2=CC(=C(C=C2N=C1O)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 24 | CELSIUS | 3 | HOUR | A solution of 1 g (4.4 mmol) 2,3-dihydroxy-6-trifluoromethylquinoxaline in 10 ml concentrated H2SO4 is cooled to 0° C. and 438 mg (4.4 mmol) KNO3 is added. The mixture is stirred at 0° C. for 0.5 h and at 24° C. for 3 h. The reaction mixture is poured into ice-water to give 1.02 g crude product. The crude product is di... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | Other | [OH-].[Na+].OS(=O)(=O)O | 24 | 3 | Oc1nc2ccc(C(F)(F)F)cc2nc1O>[OH-].[Na+].OS(=O)(=O)O>O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d389543dfca3403984fc379dfada1957 | Oc1nc2ccc(Cl)cc2nc1O>>O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1Cl | [N+](=O)([O-])[O-].[K+].ClC=1C=C2N=C(C(=NC2=CC1)O)O>>ClC=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O | [cH:4]1[cH:5][c:6]2[n:7][c:8]([OH:9])[c:10]([OH:11])[n:12][c:13]2[cH:14][c:15]1[Cl:16]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[n:7][c:8]([OH:9])[c:10]([OH:11])[n:12][c:13]2[cH:14][c:15]1[Cl:16] | Oc1nc2ccc(Cl)cc2nc1O | O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1Cl | null | null | S(O)(O)(=O)=O | Functional Group Addition | OtherReaction | 5bb74314601b8a07868b6724521bd2147502d00fa9938aa4b54a5783d20f96b8 | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccc2nccnc2c1 | [Cl;D1;H0:1]-[c:2]1:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[cH;D2;+0:11]:1>>[Cl;D1;H0:1]-[c:2]1:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c;H0;D3;+0:11]:1-[#7;+:12](-[O;-;D1;H0:13])=[O;D1;H0:14] | 88 | [{"value": 88.0, "product": "ClC=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "ClC=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Finely powdered potassium nitrate (1.01 g, 10 mmol) is added during 5 min. to a stirred solution of 6-chloro-2,3-dihydroxyquinoxaline (1.97 g, 10 mmol) in 50 ml of concentrated sulfuric acid at 0° C. After 1 h, the ice bath was removed and stirring continued for 2.5 h at room temperature. The mixture is poured into 200... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | Other | S(O)(O)(=O)=O | null | 1 | Oc1nc2ccc(Cl)cc2nc1O>S(O)(O)(=O)=O>O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2b9757f8dd5e40beb81d93fb78750d32 | C#C[Si](C)(C)C.O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1Br>>C[Si](C)(C)C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | BrC=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O.C[Si](C)(C)C#C>>OC1=NC2=CC(=C(C=C2N=C1O)C#C[Si](C)(C)C)[N+](=O)[O-] | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].Br[c:7]1[cH:8][c:9]2[n:10][c:11]([OH:12])[c:13]([OH:14])[n:15][c:16]2[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][c:9]2[n:10][c:11]([OH:12])[c:13]([OH:14])[n:15][c:16]2[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | C#C[Si](C)(C)C.O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1Br | C[Si](C)(C)C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 8917c76131fd1d6c0f73ddeb3eada5a190521ccd8222fe1834ae40371801b863 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2nccnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:[c:10]:1-[#7;+:11].[C;D1;H3:12]-[#14:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C:16]#[CH;D1;+0:17]>>[#7;+:11]-[c:10]1:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:17]#[C:16]-[#14:13](-[C;D1;H3:12])(-[C;D1;H3:14... | 70 | [{"value": 70.0, "product": "OC1=NC2=CC(=C(C=C2N=C1O)C#C[Si](C)(C)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "OC1=NC2=CC(=C(C=C2N=C1O)C#C[Si](C)(C)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 500 mg (1.9 mmol) 6-bromo-2,3-dihydroxy-7-nitroquinoxaline (supra) in 10 ml dry dimethylformamide and 20 ml dry triethylamine is added to 4 mg palladium(II)acetate, 8 mg triphenylphosphine and 600 μl (4.3 mmol) trimethylsilylacetylene. The mixture is refluxed for 2.5 h under nitrogen. After cooling to room... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | null | C#C[Si](C)(C)C.O=[N+]([O-])c1cc2nc(O)c(O)nc2cc1Br>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>C[Si](C)(C)C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ece84acd02d486896ae7513d4434d3f | C[Si](C)(C)C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-]>>C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | OC1=NC2=CC(=C(C=C2N=C1O)C#C[Si](C)(C)C)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+]>>C(#C)C=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]2[n:6][c:7]([OH:8])[c:9]([OH:10])[n:11][c:12]2[cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH:1]#[C:2][c:3]1[cH:4][c:5]2[n:6][c:7]([OH:8])[c:9]([OH:10])[n:11][c:12]2[cH:13][c:14]1[N+:15](=[O:16])[O-:17] | C[Si](C)(C)C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | null | null | CO | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2nccnc2c1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | 88 | [{"value": 88.0, "product": "C(#C)C=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "C(#C)C=1C=C2N=C(C(=NC2=CC1[N+](=O)[O-])O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 300 mg (0.99 mmol) 2,3-dihydroxy-6-trimethylsilylethynyl-7-nitroquinoxaline in 10 ml methanol is added to 200 mg (1.45 mmol) potassium carbonate and then stirred at room temperature for 1 h. The reaction mixture is evaporated in vacuo and 4N hydrochloric acid is added to pH 6. The precipitated product is ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccc2nccnc2c1 | Other | CO | null | 1 | C[Si](C)(C)C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-]>CO>C#Cc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47f59773229d4319a93d7c9cf0becb3a | C=CCC(O)CC=C.O=C(Cl)CCCCBr>>C=CCCC(C=C)OC(=O)CCCCBr | BrCCCCC(=O)Cl.C=CCC(CC=C)O.C(C)N(CC)CC>>BrCCCCC(=O)OC(CCC=C)C=C | [CH2:1]=[CH:7][CH2:6][CH:5]([CH2:4][CH:3]=[CH2:2])[OH:8].Cl[C:9](=[O:10])[CH2:11][CH2:12][CH2:13][CH2:14][Br:15]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([CH:6]=[CH2:7])[O:8][C:9](=[O:10])[CH2:11][CH2:12][CH2:13][CH2:14][Br:15] | C=CCC(O)CC=C.O=C(Cl)CCCCBr | C=CCCC(C=C)OC(=O)CCCCBr | null | null | C(Cl)Cl | Acylation | OtherReaction | eaf7edf95fe1ca81729982649f7a94da84a6028e14bdb80377c73dbda364ed1b | a4c1c928193a4ebe64c0ee17bff0acb7a23b182e790a7ce7aa444a685a0a6aef | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[CH2;D1;+0:5]=[CH;D2;+0:6]-[CH2;D2;+0:7]-[C:8](-[OH;D1;+0:9])-[C:10]-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8](-[C:10]-[CH2;D2;+0:11]-[CH;D2;+0:12]=[CH2;D1;+0:5])-[CH;D2;+0:7]=[CH2;D1;+0:6] | 48 | [{"value": 48.0, "product": "BrCCCCC(=O)OC(CCC=C)C=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.5, "product": "BrCCCCC(=O)OC(CCC=C)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5-Bromopentanoyl chloride (3.0 g, 0.015 mol) was added dropwise to 1,6-heptadien-4-ol (1.5 g, 0.013 mol) and triethylamine (1.4 g, 0.014 mol) in DCM (25 cm3). The mixture was stirred for 2 h and washed with dilute hydrochloric acid (20%, 50 cm3), saturated aqueous potassium carbonate solution (50 cm3), water (50 cm3) t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol.Allyl.Allyl | Ester.Allyl.Vinyl | null | null | null | HCl | C(Cl)Cl | null | 2 | C=CCC(O)CC=C.O=C(Cl)CCCCBr>C(Cl)Cl>C=CCCC(C=C)OC(=O)CCCCBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0a04d58b441a458d8c93e6b0ec9022dc | C=CCN(CC=C)CCCCCCCCO.Cc1ccc(S(=O)(=O)Cl)cc1>>C=CCN(CC=C)CCCCCCCCOS(=O)(=O)c1ccc(C)cc1 | O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C=C)N(CCCCCCCCO)CC=C.N1=CC=CC=C1>>C(C=C)N(CCCCCCCCOS(=O)(=O)C1=CC=C(C=C1)C)CC=C | [CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][S:1... | C=CCN(CC=C)CCCCCCCCO.Cc1ccc(S(=O)(=O)Cl)cc1 | C=CCN(CC=C)CCCCCCCCOS(=O)(=O)c1ccc(C)cc1 | null | null | C(Cl)(Cl)Cl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 40.1 | [{"value": 40.0, "product": "C(C=C)N(CCCCCCCCOS(=O)(=O)C1=CC=C(C=C1)C)CC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.1, "product": "C(C=C)N(CCCCCCCCOS(=O)(=O)C1=CC=C(C=C1)C)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 4-Toluene-sulphonyl chloride (12.5 g, 0.066 mol) was added slowly to a stirred solution of 8-diallylaminooctan-1-ol (10.0 g, 0.044 mol) and pyridine (7.0 g, 0.088 mol) in chloroform (100 cm3) at 0° C. After 24 h, water (100 cm3) was added and the solution washed with dilute hydrochloric acid (20%, 100 cm3), sodium carb... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 24 | C=CCN(CC=C)CCCCCCCCO.Cc1ccc(S(=O)(=O)Cl)cc1>C(Cl)(Cl)Cl>C=CCN(CC=C)CCCCCCCCOS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9baa63cbb81b4f17809fed9662aa572c | CCBr.c1ccc2c(c1)Cc1ccccc1-2>>CCC1c2ccccc2-c2ccccc21 | Cl.C(CCC)[Li].C1=CC=CC=2C3=CC=CC=C3CC12.BrCC>>C(C)C1C2=CC=CC=C2C=2C=CC=CC12 | Br[CH2:2][CH3:1].[CH2:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21>>[CH3:1][CH2:2][CH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21 | CCBr.c1ccc2c(c1)Cc1ccccc1-2 | CCC1c2ccccc2-c2ccccc21 | null | null | O.C1CCOC1 | C-C Coupling | OtherReaction | 2ec7afc7a563c192c7d2e68bbaec52523c841fcdc0b50693c5649c4cfbd5acf0 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc2c(c1)Cc1ccccc1-2 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[c:3]:[c:4]1:[c:5]-[c:6]:[c:7](:[c:8])-[CH2;D2;+0:9]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[CH;D3;+0:9]1-[c:4](:[c:3]):[c:5]-[c:6]:[c:7]-1:[c:8] | null | [] | -75 | CELSIUS | 1 | HOUR | A solution of n-butyllithium (79.52 cm3, 0.2168 mol, 2.5M in hexane) was added slowly to a solution of fluorene (30.00 g, 0.1807 mol) in THF (300 cm3) at −70° C. The solution was stirred for 1 hour at −75° C. and 1-bromoethane (17.59 cm3, 0.2349 mol) was added slowly. The solution was allowed to warm to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HBr | O.C1CCOC1 | -75 | 1 | CCBr.c1ccc2c(c1)Cc1ccccc1-2>O.C1CCOC1>CCC1c2ccccc2-c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3d1dca7d64040ff9adba958a4a4f430 | CCBr.CCC1c2ccccc2-c2ccccc21>>CCC1(CC)c2ccccc2-c2ccccc21 | Cl.C(CCC)[Li].C(C)C1C2=CC=CC=C2C=2C=CC=CC12.BrCC>>C(C)C1(C2=CC=CC=C2C=2C=CC=CC12)CC | Br[CH2:2][CH3:1].[CH:3]1([CH2:4][CH3:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | CCBr.CCC1c2ccccc2-c2ccccc21 | CCC1(CC)c2ccccc2-c2ccccc21 | null | null | O.C1CCOC1 | C-C Coupling | OtherReaction | 2ec7afc7a563c192c7d2e68bbaec52523c841fcdc0b50693c5649c4cfbd5acf0 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc2c(c1)Cc1ccccc1-2 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C:4]-[CH;D3;+0:5]1-[c:6](:[c:7]):[c:8]-[c:9]:[c:10]-1:[c:11]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:5]1(-[C:4]-[C;D1;H3:3])-[c:6](:[c:7]):[c:8]-[c:9]:[c:10]-1:[c:11] | 68 | [{"value": 68.0, "product": "C(C)C1(C2=CC=CC=C2C=2C=CC=CC12)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "C(C)C1(C2=CC=CC=C2C=2C=CC=CC12)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -75 | CELSIUS | 1 | HOUR | A solution of n-butyllithium (77.34 cm3, 0.1934 mol, 2.5M in hexane) was added slowly to a solution of 9-ethylfluorene (25.00 g, 0.1289 mol) in THF (250 cm3) at −70° C. The solution was stirred for 1 hour at −75° C. and 1-bromoethane (17.59 cm3, 0.1934 mol) was added slowly. The solution was allowed to warm to room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HBr | O.C1CCOC1 | -75 | 1 | CCBr.CCC1c2ccccc2-c2ccccc21>O.C1CCOC1>CCC1(CC)c2ccccc2-c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ad25c02e6ed4dac9bd0fc0cd79b7aae | CCCCCCCCBr.Oc1ccc(-c2ccc(Br)cc2)cc1>>CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1 | BrC1=CC=C(C=C1)C1=CC=C(C=C1)O.BrCCCCCCCC.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]2)[cH:21][cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | CCCCCCCCBr.Oc1ccc(-c2ccc(Br)cc2)cc1 | CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccc2)cc1 | 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] | 66 | [{"value": 66.0, "product": "BrC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "BrC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-bromo-4′-hydroxybiphenyl (50.00 g, 0.2008 mol), 1-bromooctane (50.38 g, 0.2610 mol), potassium carbonate (47.11 g, 0.3414 mol) and butanone (500 cm3) was heated under reflux overnight. The cooled mixture was filtered and the solvent removed on a rotary evaporator. The crude solid was recrystallised from ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(CC)=O | null | null | CCCCCCCCBr.Oc1ccc(-c2ccc(Br)cc2)cc1>CC(CC)=O>CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec27e8507aed4b5fb3044aa9e9651662 | CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1>>CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1 | BrC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC.B(OC)(OC)OC.Cl>>C(CCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)B(O)O | Br[c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:24][cH:23]2)[cH:22][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([B:18]([OH:19])[OH:20])[cH:21][cH:22]2)[cH:23][c... | CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1 | CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1 | null | null | CCCCCC.C1CCOC1 | Functional Group Interconversion | Preparation of boronic acids without boronic ether | ea18136a2a812ba75d88f0154de74a11e900f53593099ed5cfbdc7bb208ca0bd | 3c67ef5cce82b121a680ae296eb1f6d78abe8f9494b62ca3b872477b7553bcfd | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[O;D1;H1:6]-[#5:7](-[O;D1;H1:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 73 | [{"value": 73.0, "product": "C(CCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)B(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "C(CCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | A solution of n-butylithium (50.97 cm3, 0.1274 mol, 2.5M in hexane) was added dropwise to a cooled (−78° C.) stirred solution of 4-bromo-4′-octyloxybiphenyl (40.00 g, 0.1108 mol) in THF (400 cm3). After 1 h, trimethyl borate (23.05 g, 0.2216 mol) was added dropwise to the reaction mixture maintaining a temperature of −... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | CCCCCC.C1CCOC1 | -78 | 1 | CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1>CCCCCC.C1CCOC1>CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e45de571a67c4461b310445d255b6fe5 | CCC1(CC)c2cc(Br)ccc2-c2ccc(Br)cc21.CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1.COCCOC>>CCCCCCCCOc1ccc(-c2ccc(-c3ccc4c(c3)C(CC)(CC)c3cc(-c5ccc(-c6ccc(OCCCCCCCC)cc6)cc5)ccc3-4)cc2)cc1 | BrC1=CC=2C(C3=CC(=CC=C3C2C=C1)Br)(CC)CC.C(CCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].COCCOC>>C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC)CC | Br[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[C:24]([CH2:25][CH3:33])([CH2:27][CH3:28])[c:29]1[cH:30][c:31](Br)[cH:53][cH:54][c:55]1-2.OB(O)[c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:59][cH:58]2)[cH:57][cH:56]1.O([CH2:26][CH2:49][O:40][CH3... | CCC1(CC)c2cc(Br)ccc2-c2ccc(Br)cc21.CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1.COCCOC | CCCCCCCCOc1ccc(-c2ccc(-c3ccc4c(c3)C(CC)(CC)c3cc(-c5ccc(-c6ccc(OCCCCCCCC)cc6)cc5)ccc3-4)cc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | Aromatic Heterocycle Formation | OtherReaction | a7eb521df5414e3505fc0f7fadecba333485ca367552f4fca79f10fe1c5ef724 | 17a93ecb1d3a04979b265b277453639fdd52f96192a54e63bd73e5cfb4be6f7c | c1ccc(-c2ccc(-c3ccc4c(c3)Cc3cc(-c5ccc(-c6ccccc6)cc5)ccc3-4)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[C:7])(-[CH2;D2;+0:8]-[CH3;D1;+0:9])-[c:10]:[c:11]:[c;H0;D3;+0:12](-Br):[c:13]:[c:14].O-B(-O)-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19].[CH3;D1;+0:20]-[O;H0;D2;+0:21]-[CH2;D2;+0:22]-[CH2;D2;+0:23]-O-[CH3;D1;+0:24]>>[C:7]-[C:6](-[CH2;D2;+0:8]-[CH3;D1;+0:23])(-[c:5]:... | 65 | [{"value": 65.0, "product": "C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetrakis(triphenylphosphine)palladium(0) (0.70 g, 0.0006 mol) was added to a stirred solution of 2,7-dibromo-9,9-diethylfluorene (4) (2.33 g, 0.0061 mol), 4-octyloxybiphenyl-4′-yl boronic acid (5.00 g, 0.0153 mol), 20% sodium carbonate solution (100 cm3) and 1,2-dimethoxyethane (150 cm3). The reaction mixture was heate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Boronic acid | Ether | c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12.c1ccccc1.c1ccccc1 | Br-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | null | null | CCC1(CC)c2cc(Br)ccc2-c2ccc(Br)cc21.CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1.COCCOC>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>CCCCCCCCOc1ccc(-c2ccc(-c3ccc4c(c3)C(CC)(CC)c3cc(-c5ccc(-c6ccc(OCCCCCC... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-01ec93ef06ae422da47bd4a3dd215994 | CCCCCCCCOc1ccc(-c2ccc(-c3ccc4c(c3)C(CC)(CC)c3cc(-c5ccc(-c6ccc(OCCCCCCCC)cc6)cc5)ccc3-4)cc2)cc1>>CCC1(CC)c2cc(-c3ccc(-c4ccc(O)cc4)cc3)ccc2-c2ccc(-c3ccc(-c4ccc(O)cc4)cc3)cc21 | B(Br)(Br)Br.C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC)CC>>C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(C=C1)C1=CC=C(C=C1)O)C1=CC=C(C=C1)C1=CC=C(C=C1)O)CC | CCCCCCCC[O:17][c:16]1[cH:15][cH:34][c:33](-[c:32]2[cH:31][cH:30][c:29](-[c:28]3[cH:27][cH:26][c:25]4[c:43]([cH:42]3)[C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[c:6]3[cH:7][c:8](-[c:9]5[cH:10][cH:11][c:12](-[c:13]6[cH:14][cH:35][c:36]([O:37]CCCCCCCC)[cH:38][cH:19]6)[cH:20][cH:21]5)[cH:22][cH:23][c:24]3-4)[cH:41][cH:40]2)[cH:3... | CCCCCCCCOc1ccc(-c2ccc(-c3ccc4c(c3)C(CC)(CC)c3cc(-c5ccc(-c6ccc(OCCCCCCCC)cc6)cc5)ccc3-4)cc2)cc1 | CCC1(CC)c2cc(-c3ccc(-c4ccc(O)cc4)cc3)ccc2-c2ccc(-c3ccc(-c4ccc(O)cc4)cc3)cc21 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | b6f69d716d502b64d6179a2edef13b917c16c52b1906f6d68ae629bc33b79b9d | 736e5be0c4313f69ce19fa28727a9da18e7a37db0f912ae36fd9ca7a66469bc3 | c1ccc(-c2ccc(-c3ccc4c(c3)Cc3cc(-c5ccc(-c6ccccc6)cc5)ccc3-4)cc2)cc1 | C-C-C-C-C-C-C-C-[O;H0;D2;+0:1]-[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](-[c:6]):[cH;D2;+0:7]:[cH;D2;+0:8]:1.C-C-C-C-C-C-C-C-[O;H0;D2;+0:9]-[c:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13](-[c:14]):[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[OH;D1;+0:1]-[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:12]:[c:13](-[c:14]):[cH;D2;+0:15]:[cH;D2;+0:8]:1.[OH;D1;+... | 40.2 | [{"value": 40.0, "product": "C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(C=C1)C1=CC=C(C=C1)O)C1=CC=C(C=C1)C1=CC=C(C=C1)O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.2, "product": "C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(C=C1)C1=CC=C(C=C1)O)C1=CC=C(C=C1)C1=CC=C(C=C1)O)CC", "details": "CALCULATEDPERC... | 0 | CELSIUS | 8 | HOUR | Boron tribromide (99.9%, 1.05 cm3, 0.0111 mol) in DCM (10 ml) was added dropwise to a cooled (0° C.) stirred solution of 9,9-diethyl-2,7-bis(4-octyloxybiphenyl-4′-yl)fluorene (2.90 g, 0.0037 mol) in DCM (100 cm3). The reaction mixture was stirred at room temperature overnight, then poured onto an ice/water mixture (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | 0 | 8 | CCCCCCCCOc1ccc(-c2ccc(-c3ccc4c(c3)C(CC)(CC)c3cc(-c5ccc(-c6ccc(OCCCCCCCC)cc6)cc5)ccc3-4)cc2)cc1>C(Cl)Cl>CCC1(CC)c2cc(-c3ccc(-c4ccc(O)cc4)cc3)ccc2-c2ccc(-c3ccc(-c4ccc(O)cc4)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cd38cd31acaa413aa640bf639ad33f0a | CC(C)=CCC[C@H](C)CCBr.Oc1ccc(Br)cc1>>CC(C)=CCC[C@H](C)CCOc1ccc(Br)cc1 | BrC1=CC=C(C=C1)O.C(C[C@@H](C)CCC=C(C)C)Br.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC=C(C=C1)OCC[C@H](CCC=C(C)C)C | Br[CH2:10][CH2:9][C@H:7]([CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8].[OH:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C@H:7]([CH3:8])[CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1 | CC(C)=CCC[C@H](C)CCBr.Oc1ccc(Br)cc1 | CC(C)=CCC[C@H](C)CCOc1ccc(Br)cc1 | null | null | CC(CC)=O | 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] | 590.9 | [{"value": 68.2, "product": "BrC1=CC=C(C=C1)OCC[C@H](CCC=C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 590.9, "product": "BrC1=CC=C(C=C1)OCC[C@H](CCC=C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-bromophenol (34.6 g, 0.20 mol), (S)-(+)-citronellyl bromide (50 g, 0.023 mol) and potassium carbonate (45 g, 0.33 mol) in butanone (500 cm3) was heated under reflux overnight. The cooled reaction mixture was filtered and the filtrate concentrated under reduced pressure. The crude product was purified by ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(CC)=O | null | null | CC(C)=CCC[C@H](C)CCBr.Oc1ccc(Br)cc1>CC(CC)=O>CC(C)=CCC[C@H](C)CCOc1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0bf40c95fe842e4ad5746ef10d8c610 | CC(C)=CCC[C@H](C)CCOc1ccc(Br)cc1>>CC(C)=CCC[C@H](C)CCOc1ccc(B(O)O)cc1 | B(OC)(OC)OC.BrC1=CC=C(C=C1)OCC[C@H](CCC=C(C)C)C.Cl>>C[C@H](CCOC1=CC=C(C=C1)B(O)O)CCC=C(C)C | Br[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][C@H:7]([CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8])[cH:20][cH:19]1>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][C@H:7]([CH3:8])[CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([B:16]([OH:17])[OH:18])[cH:19][cH:20]1 | CC(C)=CCC[C@H](C)CCOc1ccc(Br)cc1 | CC(C)=CCC[C@H](C)CCOc1ccc(B(O)O)cc1 | null | null | O1CCCC1 | Functional Group Interconversion | Preparation of boronic acids without boronic ether | ea18136a2a812ba75d88f0154de74a11e900f53593099ed5cfbdc7bb208ca0bd | 3c67ef5cce82b121a680ae296eb1f6d78abe8f9494b62ca3b872477b7553bcfd | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[O;D1;H1:6]-[#5:7](-[O;D1;H1:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 67 | [{"value": 65.0, "product": "C[C@H](CCOC1=CC=C(C=C1)B(O)O)CCC=C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "C[C@H](CCOC1=CC=C(C=C1)B(O)O)CCC=C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 2.5M n-Butylithium in hexanes (49.3 cm3, 0.12 mol) was added dropwise to a cooled (−78° C.) solution of 1-bromo-4-[(S)-3,7-dimethyloct-6-enyloxy]benzene (35 g, 0.11 mol) in tetrahydrofuran (350 cm3). The resultant solution was stirred at this temperature for 1 h and then trimethyl borate (23.8 g, 0.23 mol) was added dr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | O1CCCC1 | -78 | null | CC(C)=CCC[C@H](C)CCOc1ccc(Br)cc1>O1CCCC1>CC(C)=CCC[C@H](C)CCOc1ccc(B(O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fe3f07cdc4946e3899738f226f57903 | CC(=O)O.CO[C@@H]1OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1>>CC(=O)O[C@@H]1OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | S(O)(O)(=O)=O.CO[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](OC(C2=CC=CC=C2)=O)C(O1)(COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O.C(C)(=O)O>>C(C)(=O)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](OC(C2=CC=CC=C2)=O)C(O1)(COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O | [CH3:1][C:2](=[O:3])[OH:4].CO[C@@H:5]1[O:6][C:7]([CH2:8][O:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)([CH2:18][O:19][C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[C@@H:28]([O:29][C:30](=[O:31])[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[C@H:38]1[O:39][C:40](=[O:41])[c:42]1[cH:43][cH:44]... | CC(=O)O.CO[C@@H]1OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | CC(=O)O[C@@H]1OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | null | null | O.C(C)(=O)OC(C)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | f97cf69d0b7f69a19fc4ee79e45dfa20e2de9ec7fbaa3c85f72b970a508cfd4f | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(OCC1(COC(=O)c2ccccc2)OC[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | C-O-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6]-[C:7]=[O;D1;H0:8].[C;D1;H3:9]-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C;D1;H3:9]-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6]-[C:7]=[O;D1;H0:8] | null | [] | 25 | CELSIUS | 15 | HOUR | Sulfuric acid (97%, 75 mL) was added to a solution of 1-O-methyl-2,3,5-tri-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-ribofuranose (1.7 g, 2.8 mmoles) in a mixture of acetic acid (6.7 mL) and acetic anhydride (0.67 mL) at 0° C. The reaction mixture was stirred at 25° C. for 15 h and diluted with ethyl acetate (50 mL) and wat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | C1CCOC1 | C1CCOC1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O.C(C)(=O)OC(C)=O.C(C)(=O)OCC | 25 | 15 | CC(=O)O.CO[C@@H]1OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1>O.C(C)(=O)OC(C)=O.C(C)(=O)OCC>CC(=O)O[C@@H]1OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d337e890f4ac46aea5a533793e1357af | CC(=O)O.CO[C@@H]1O[C@](C)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1>>CC(=O)O[C@@H]1O[C@](C)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | S(O)(O)(=O)=O.C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OC)O[C@@]([C@H]1OC(C1=CC=CC=C1)=O)(COC(C1=CC=CC=C1)=O)C.C(C)(=O)O>>C(C)(=O)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](OC(C2=CC=CC=C2)=O)[C@](O1)(COC(C1=CC=CC=C1)=O)C | O[C:2]([CH3:1])=[O:3].C[O:4][C@@H:5]1[O:6][C@:7]([CH3:8])([CH2:9][O:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C@@H:19]([O:20][C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[C@H:29]1[O:30][C:31](=[O:32])[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[O:6][... | CC(=O)O.CO[C@@H]1O[C@](C)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | CC(=O)O[C@@H]1O[C@](C)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | null | null | C(C)(=O)OC(C)=O.[Cl-].[Na+].O.C(C)(=O)OCC | Acylation | OtherReaction | d7652b37cfea6f861e95f72916116d0fb1ed41637e20224471cfc7dab29585ba | 5d96d8cabdf7480c9ca6f9372e2eba1f4c54ba44bff87c469521888d79df5495 | O=C(OCC1OC[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5].O-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;D1;H0:8]>>[C:3]-[C:2](-[O;H0;D2;+0:1]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;D1;H0:8])-[#8:4]-[C:5] | 56 | [{"value": 56.0, "product": "C(C)(=O)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](OC(C2=CC=CC=C2)=O)[C@](O1)(COC(C1=CC=CC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 16 | HOUR | Concentrated sulfuric acid (97%, 99 mL) was added to a solution of 2,3,5-tri-O-benzoyl-1-O-methyl-4-C-methyl-β-D-ribofuranose (1.8 g, 3.6 mmoles) in a mixture of acetic acid (9.0 mL) and acetic anhydride (0.90 mL) at 0° C. The reaction mixture was stirred at 25° C. for 16 h and diluted with ethyl acetate (50 mL) and br... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)OC(C)=O.[Cl-].[Na+].O.C(C)(=O)OCC | 25 | 16 | CC(=O)O.CO[C@@H]1O[C@](C)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1>C(C)(=O)OC(C)=O.[Cl-].[Na+].O.C(C)(=O)OCC>CC(=O)O[C@@H]1O[C@](C)(COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-379b0ec7c95d4c418e88f52f69f88941 | Nc1ncnc2c1c(=O)ccn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>c1cnc2ncncc2c1 | NC=1C2=C(N=CN1)N(C=CC2=O)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO.Cl[Si](O[Si](C(C)C)(C(C)C)Cl)(C(C)C)C(C)C.O>>N1=CN=CC2=C1N=CC=C2 | N[c:8]1[n:7][cH:6][n:5][c:4]2[n:3]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[cH:2][cH:1][c:10](=O)[c:9]21>>[cH:1]1[cH:2][n:3][c:4]2[n:5][cH:6][n:7][cH:8][c:9]2[cH:10]1 | Nc1ncnc2c1c(=O)ccn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | c1cnc2ncncc2c1 | null | null | N1=CC=CC=C1 | Reduction | OtherReaction | 183772bfc4c94fd9be16c7dc4d9cbfc8516c790e592c9b5261f5b9663a8d090d | 52812dd970894bd2b93cad2e096e0c03648dd649df9f4a3211853c4ae28652a7 | c1cnc2ncncc2c1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c;H0;D3;+0:7](=O):[c:8]:[c:9]:[n;H0;D3;+0:10]:2-[C@H]1-O-[C@H](-C-O)-[C@@H](-O)-[C@@H]-1-O>>[#7;a:4]1:[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c:6]2:[cH;D2;+0:7]:[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:5]:1:2 | null | [] | null | null | 20 | HOUR | A reaction mixture of 4-amino-5-oxo-8-(β-D-ribofuranosyl)pyrido[2,3-d]pyrimidine (1.8 g, 6.20 mmol) and 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (2.15 mL, 6.73 mmol) in anhydrous pyridine (25 mL) was stirred at room temperature for 20 h and cooled with ice. Water (0.5 mL) was added, and the mixture stirred at ambi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Primary amine | null | C1CCOC1.c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | HO- | N1=CC=CC=C1 | null | 20 | Nc1ncnc2c1c(=O)ccn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>N1=CC=CC=C1>c1cnc2ncncc2c1 |
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