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-88524f79356d4db1b390048dfdf898d3 | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(O)cc2)cc1.ClCCOCCCl>>COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1 | OC1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)O.ClCCOCCCl.C([O-])([O-])=O.[K+].[K+].C1COCCOCCOCCOCCOCCO1>>OC1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCOCCCl | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]2[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15][CH2:16][O:17][CH3:18])[cH:19][cH:20][c:21]3[C:22]2([OH:23])[c:24]2[cH:25][cH:26][c:27]([OH:28])[cH:35][cH:36]2)[cH:37][cH:38]1.Cl[CH2:29][CH2:30][O:31][CH2:32][CH2:33][Cl:34]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]... | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(O)cc2)cc1.ClCCOCCCl | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 93.1 | [{"value": 35.0, "product": "OC1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCOCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "OC1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCOCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2.5 | HOUR | 4-Hydroxy-4-(4-hydroxyphenyl)-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman (770 mg, 1.4 mmol), bis-(2-chloroethyl)ether (810 mg, 5.7 mmol), potassium carbonate (782 mg, 5.7 mmol) and 18-crown-6(132 mg, 0.49 mmol) were dissolved in dry N,N-dimethylformamide (10 mL) under argon atmosphere, which was then stirre... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HCl | O.CN(C=O)C | 100 | 2.5 | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(O)cc2)cc1.ClCCOCCCl>O.CN(C=O)C>COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cefa7890e58d49e19ddeeadc3974c41b | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1.[I-]>>COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCI)cc2)cc1 | OC1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCOCCCl.[I-].[Na+]>>ICCOCCOC1=CC=C(C=C1)C1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)O | Cl[CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][c:27]1[cH:26][cH:25][c:24]([C:22]2([OH:23])[CH:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:38][cH:37]3)[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15][CH2:16][O:17][CH3:18])[cH:19][cH:20][c:21]32)[cH:36][cH:35]1.[I-:34]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8... | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1.[I-] | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCI)cc2)cc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CC(CC)=O | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[I-;H0;D0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | 92 | [{"value": 90.0, "product": "ICCOCCOC1=CC=C(C=C1)C1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "ICCOCCOC1=CC=C(C=C1)C1(C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxy-4-{4-[2-(2-chloroethoxy)ethoxy]phenyl}-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman (490 mg, 0.9 mmol) was dissolved in 2-butanone (30 ml) under argon atmosphere. Then, sodium iodide (1.4 g, 9.3 mmol) and tetrabutylammonium iodide (1.6 g, 4.5 mmol) were added thereto, and the mixture was refluxed fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | Other | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CC(CC)=O | null | null | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1.[I-]>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CC(CC)=O>COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCI)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-387e02a14d2d4adaad47adce56c50edc | C#CCCCCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Cl-].[NH4+].COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)=O.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#C.C(CCC)[Li]>>[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O | [CH:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[C:19]2=[O:20])[cH:38][cH:39]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5... | C#CCCCCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | af22e63626241b7ef7b156ca9e8464011387cb2140508f9d238feb5631c67f1a | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc(C2CSc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#16:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | 99.5 | [{"value": 99.5, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 1 | HOUR | To a solution of 9-(t-butyldimethylsilyloxy)-1-nonyne (12 g, 47.15 mmol) in dry tetrahydrofuran (150 ml) was added dropwise n-butyl lithium (25.5ml, 42.43 mmol, 1.66 mole/l in tetrahydrofuran) at −78° C., which was then stirred at −20° C. for 1 hour. Then, to this reaction mixture was added 7-methoxy-3-(4-methoxyphenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | null | O1CCCC1 | -20 | 1 | C#CCCCCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>O1CCCC1>COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-633ebe28f90a49ec92db8c9daf1faa33 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O.C(#N)[BH3-].[Na+].O>>[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | O[C:19]1([C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:38][cH:37]2)([CH3:8])[CH2:9][S:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | [I-].[Zn+2].[I-] | ClCCCl | Reduction | OtherReaction | 32c18b8f01f6265a398b8df4f5d0033739d3c8e378cd915941473fb5993b3ae4 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2CSc3ccccc3C2)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]#[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[#16:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12]>>[C:4]-[C:3]#[C:2]-[CH;D3;+0:1]1-[c:5](:[c:6]):[c:7]-[#16:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12] | 50.3 | [{"value": 50.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (5.40 g, 9.49 mmol) in 1,2-dichloroethane (150 ml) were added zinc iodide (4.54 g, 14.23 mmol) and sodium cyanoborohydride (4.47 g, 71.17 mmol), which was then stirred at room temperature for 12 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | [I-].[Zn+2].[I-].ClCCCl | null | 12 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>[I-].[Zn+2].[I-].ClCCCl>COc1ccc(C2(C)CSc3cc(OC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc445b9509554072b27770c6869fa92f | COc1ccc(C2(C)CSc3cc(OC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.O1CCCC1.C(C)(=O)OCC>>[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[CH:19]2[C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37][cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | [Pd] | CO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(C2CSc3ccccc3C2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5](-[C:6])-[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](-[C:6])-[c:7] | 83 | [{"value": 83.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (2.64 g, 4.77 mmol) in methanol (150 ml) and tetrahydrofuran (15 mg) was added 10% Pd-C (850 mg), which was then stirred at room temperature under hydrogen (atmospheric pressure) for 1 day. Ethyl acetate was add... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | null | [Pd].CO | null | 24 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>[Pd].CO>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7dd4a40101104f60b8d867ff5233fcb8 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.Cl.O>>OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | CC(C)(C)[Si](C)(C)[O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][cH:30]2)([CH3:8])[CH2:9][S:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO)cc1 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(C2CSc3ccccc3C2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 92.1 | [{"value": 92.0, "product": "OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 140 | MINUTE | 4-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (2.2 g, 3.95 mmol) was dissolved in tetrahydrofuran (150 ml), and 3N-HCl (11 ml) was added thereto. The reaction mixture was stirred at room temperature for 140 minutes. After the reaction was completed, water was added to the reacti... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | O1CCCC1 | null | 2.333333 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>O1CCCC1>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb0b22fe5c8946d9a78a55221bd2d761 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 | O.C(C)N(CC)CC.CS(=O)(=O)Cl.OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC>>CS(=O)(=O)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[cH:34][cH:35]1.Cl[S:30]([CH3:31])(=[O:32])=[O:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2CSc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 72 | [{"value": 72.0, "product": "CS(=O)(=O)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "CS(=O)(=O)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | 4-(9-Hydroxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methyl thiochroman (882 mg, 1.99 mmol) was dissolved in dichloromethane (60 ml) and triethylamine (1.38 ml, 9.96 mmol), to which was added methanesulfonylchloride (0.77 ml, 9.96 mmol). The reaction mixture was stirred at room temperature for 40 minutes. After the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | HCl | ClCCl | null | 0.666667 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl>ClCCl>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af50e64518f243c5af0707691d2b4dd0 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCN(C)C)cc1>>CN(C)CCCSCCCCCCCCCC1c2ccc(O)cc2SCC1(C)c1ccc(O)cc1 | COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCCCCCSCCCN(C)C.Br.C(C)(=O)O>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCCN(C)C | C[O:22][c:21]1[cH:20][cH:19][c:18]2[c:24]([cH:23]1)[S:25][CH2:26][C:27]([CH3:28])([c:29]1[cH:30][cH:31][c:32]([O:33]C)[cH:34][cH:35]1)[CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][S:7][CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCN(C)C)cc1 | CN(C)CCCSCCCCCCCCCC1c2ccc(O)cc2SCC1(C)c1ccc(O)cc1 | null | null | O | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(C2CSc3ccccc3C2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | A mixture of 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[9-(3-dimethylaminopropylthio)nonyl]thiochroman (50 mg, 0.09 mmol), hydrobromic acid (0.13 ml, 48% aqueous solution) and acetic acid (0.15 ml) was heated for 8 hours. After the reaction was completed, water was added to the reaction solution, and the resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccc2c(c1)CCCS2.c1ccccc1 | Other | O | null | null | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCN(C)C)cc1>O>CN(C)CCCSCCCCCCCCCC1c2ccc(O)cc2SCC1(C)c1ccc(O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-434dffa6d95946b5aedc86a980a81a6f | C#CCCCCCCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCC#C.C(CCC)[Li].COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)=O>>[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O | [CH:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][Si:35]([CH3:36])([CH3:37])[C:38]([CH3:39])([CH3:40])[CH3:41].[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[C:23]2=[O:24])[cH:42][cH:43]1>>[... | C#CCCCCCCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 32c43bb8c46f4cb5536ede6cee58ac07810f00f75e5d5068c9f1bf838a1ce5f8 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc(C2COc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#8:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#8:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | 99 | [{"value": 99.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | -20 | CELSIUS | 80 | MINUTE | 9-(t-Butyl dimethylsilyloxy)-1-nonyne (7.1 g, 27.9 mmol) was dissolved in dry tetrahydrofuran (70 mL) under argon atmosphere, which was then cooled down to −78° C. n-Butyllithium (15.1 ml, 25.1 mmol, 1.66 mol/l solution in tetrahydrofuran) was slowly added dropwise thereto, and the mixture was stirred at −20° C. for 80... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | null | O1CCCC1 | -20 | 1.333333 | C#CCCCCCCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1>O1CCCC1>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9d1a179e0a541f8bfbcd308542cc988 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O.C(#N)[BH3-].[Na+].O>>[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | O[C:23]1([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:42][cH:41]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | [I-].[Zn+2].[I-] | ClCCCl | Reduction | OtherReaction | d9ad9de0a2df8f543d454c115f7a58d9a012b1cbcc0f40fa0bf7cc7b376ca1e8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc3C2)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]#[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12]>>[C:4]-[C:3]#[C:2]-[CH;D3;+0:1]1-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12] | 50 | [{"value": 50.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.7, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | 8 | HOUR | To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (3.10 g, 5.06 mmol) in 1,2-dichloroethane (200 ml) were added zinc iodide (2.42 g, 7.59 mmol) and sodium cyanoborohydride (2.23 g, 35.42 mmol), which was then stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | [I-].[Zn+2].[I-].ClCCCl | null | 8 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>[I-].[Zn+2].[I-].ClCCCl>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9f09e6b4c28d42718313d4fe165cf405 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.C(C)(=O)OCC>>[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[cH:41][cH:42]1>>[CH3:1][O... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | [Pd] | O1CCCC1.CO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(C2COc3ccccc3C2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5](-[C:6])-[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](-[C:6])-[c:7] | 8,884.4 | [{"value": 89.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8884.4, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | 1 | DAY | To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (150 g, 2.51 mmol) in methanol (100 ml) and tetrahydrofuran (10 ml) was added 10% Pd—C (570 mg), which was then stirred at room temperature under hydrogen (atmospheric pressure) for 1 day. Ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | null | [Pd].O1CCCC1.CO | null | 24 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>[Pd].O1CCCC1.CO>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c5ff6d47c4741639e7e9582c711852a | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.[NH+]1=CC=CC=C1.O>>OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | CC(C)(C)[Si](C)(C)[O:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:35][cH:34]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 | null | null | C(C)O | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(C2COc3ccccc3C2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 77 | [{"value": 77.0, "product": "OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | 4-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxymet hoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (1.34 g, 2.23 mmol) was dissolved in ethanol (70 ml), and pyridinium ptoluenesulfonate (426 mg, 1.70 mmol) was added thereto. The reaction mixture was stirred at room temperature for 10 hours, water was added, and the resu... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | C(C)O | null | 10 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>C(C)O>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85f1800f7cce4a2c8e4ab87e8d876810 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 | O.C(C)N(CC)CC.CS(=O)(=O)Cl.OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC>>CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[cH:38][cH:39]1.Cl[S:34]([CH3:35])(=[O:36])=[O:37]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2COc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 97.5 | [{"value": 97.0, "product": "CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-(9-Hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (435 mg, 0.89 mmol) was dissolved in dichloromethane (30 ml), to which were added triethylamine (0.62 ml, 4.47 mmol) and methanesulfonyl chloride (0.34 ml, 4.47 mmol). The reaction mixture was stirred at room temperature for 30 minutes. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HCl | ClCCl | null | 0.5 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl>ClCCl>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3767a57b129b4c1b8e3765f731eeb162 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN=[N+]=[N-])cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1 | N(=[N+]=[N-])CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC>>NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [N-]=[N+]=[N:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:35][cH:34]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2(... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN=[N+]=[N-])cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1 | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(C2COc3ccccc3C2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 100.6 | [{"value": 100.6, "product": "NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-(9-azidononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (411 mg, 0.80 mmol) in methanol (100 ml) was added 10% Pd—C (100 mg), which was then stirred overnight at room temperature under hydrogen (atmospheric pressure). The resulting mixture was filtered through cellite and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | [Pd].CO | null | 8 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN=[N+]=[N-])cc1>[Pd].CO>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e1303aa57d08490ab4c08a11e97e8579 | CC(C)(C)O.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1.O=C=NS(=O)(=O)Cl>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNS(=O)(=O)NC(=O)OC(C)(C)C)cc1 | ClS(=O)(=O)N=C=O.C(C)(C)(C)O.NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.C(C)N(CC)CC.[Cl-].[NH4+]>>C(C)(C)(C)OC(=O)NS(=O)(=O)NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [OH:40][C:41]([CH3:42])([CH3:43])[CH3:44].[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[cH:45][cH:46]1.Cl[S:34](=[O:35])(=[O:36... | CC(C)(C)O.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1.O=C=NS(=O)(=O)Cl | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNS(=O)(=O)NC(=O)OC(C)(C)C)cc1 | null | null | ClCCl | Protection | OtherReaction | 0bbc4c233da03715176630400b22a686884663e77f16d0b01344c4d7e649e5db | ff2b36e0771fa61d21c4f0bb7dcf5b81e9b00ebe8b3641ed7401a76124e01378 | c1ccc(C2COc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:11]-[C:8](-[C;D1... | 36 | [{"value": 36.0, "product": "C(C)(C)(C)OC(=O)NS(=O)(=O)NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.3, "product": "C(C)(C)(C)OC(=O)NS(=O)(=O)NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desir... | -78 | CELSIUS | 2.5 | HOUR | To a solution of chlorosulfonylisocyanate (25 μl, 0.292 mmol) in dichloromethane (1 ml) was added t-butanol (27 μl, 0.292 mmol) at −38° C. for 10 minutes, which was then stirred for 2.5 hours. Then, the reaction mixture was cooled down to −78° C., 4-(9-aminononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Primary amine | Sulfonamide.Sulfonamide.Carbamic ester | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HCl | ClCCl | -78 | 2.5 | CC(C)(C)O.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1.O=C=NS(=O)(=O)Cl>ClCCl>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNS(=O)(=O)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93bee10c868143f38eb6769bca14ba9a | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNS(=O)(=O)NC(=O)OC(C)(C)C)cc1.OCCCC(F)(F)C(F)(F)F>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN(C(=O)OC(C)(C)C)S(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 | N(=NC(=O)OCC)C(=O)OCC.ClCCl.C(C)(C)(C)OC(=O)NS(=O)(=O)NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.FC(CCCO)(C(F)(F)F)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ClCCl>>C(C)(C)(C)OC(=O)N(S(=O)(=O)NCCCC(C(F)(F)F)(F)F)CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][S:41](=[O:42])(=[O:43])[NH:44][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:4... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNS(=O)(=O)NC(=O)OC(C)(C)C)cc1.OCCCC(F)(F)C(F)(F)F | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN(C(=O)OC(C)(C)C)S(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Protection | OtherReaction | f01eeeafebac738e97d0171795d25ca932f618a26ea08d906aa555da993bf86f | 31cd65a6d9e31d39b41c3278908b5361af416faf87517e00e13daf8b64653fab | c1ccc(C2COc3ccccc3C2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[NH;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])-[#16:7](=... | 67 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)N(S(=O)(=O)NCCCC(C(F)(F)F)(F)F)CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-[9-(N-t-butyloxycarbonylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (5 7 mg, 0.088 mmol) in dichloromethane (2 ml) were added 4,4,5,5,5-pentafluoropentyl alcohol (15.6 mg, 0.088 mmol) and triphenylphosphine (23 mg, 0.088 mmol) at room temperature. Diethyl azo... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonamide.Carbamic ester.Ether.Primary alcohol | Sulfonamide.Carbamic ester.Ether.Boc | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HO- | CCCCCC.C(C)(=O)OCC | null | 8 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNS(=O)(=O)NC(=O)OC(C)(C)C)cc1.OCCCC(F)(F)C(F)(F)F>CCCCCC.C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN(C(=O)OC(C)(C)C)S(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c8a90937fc941d6aa4e1f527bfdf07d | COCCOCCO.Cc1ccc(S(=O)(=O)Cl)cc1>>COCCOCCOS(=O)(=O)c1ccc(C)cc1 | O.COCCOCCO.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)OCCOCCOC)C | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][cH:18]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][cH:18]1 | COCCOCCO.Cc1ccc(S(=O)(=O)Cl)cc1 | COCCOCCOS(=O)(=O)c1ccc(C)cc1 | null | null | N1=CC=CC=C1 | 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] | 98.4 | [{"value": 98.4, "product": "C1(=CC=C(C=C1)S(=O)(=O)OCCOCCOC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of diethylene glycol monomethylether (12 g, 100 mmol) in pyridine (70 ml) was added p-toluenesulfonyl chloride (22.8 g, 120 mmol) at 0° C., which was then stirred at room temperature for 2 hours. Water was added thereto, and the mixture was extracted with diethyl ether. The extracted organic layer was was... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | null | 2 | COCCOCCO.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>COCCOCCOS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fa491b162164f098d0ec14018659b67 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1=O | COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)=O.Br>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)=O | C[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][S:11][c:12]3[cH:13][c:14]([O:15]C)[cH:16][cH:17][c:18]3[C:19]2=[O:20])[cH:9][cH:8]1>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]2)[CH2:10][S:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]2[C:19]1=[O:20] | COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1=O | null | null | C(C)(=O)O | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C1c2ccccc2SCC1c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 92.9 | [{"value": 92.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (2.27 g, 7.22 mmol) in acetic acid (75 ml) was added 48% aqueous HBr solution (75 mg), which was then heated under reflux for 1 day. The reaction mixture was extracted with diethyl ether. The organic layer was washed with saturated sodium bicarbon... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | C(C)(=O)O | null | null | COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>C(C)(=O)O>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ebda4027a69c42b3933bf0b65468a55e | CC(C)=O.CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1=O.COCCl>>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2=O)cc1 | O.OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)=O.C([O-])([O-])=O.[K+].[K+].COCCl.CC(=O)C>>COCOC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OCOC)=O | CC(=O)[CH3:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][S:12][c:13]3[cH:14][c:15]([OH:16])[cH:20][cH:21][c:22]3[C:23]2=[O:24])[cH:25][cH:26]1.Cl[CH2:17][O:18][CH3:19]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][S:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:... | CC(C)=O.CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1=O.COCCl | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2=O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e97d515ea7a1ec81347c0558820156b6554bc9323cfb7a752fc7803ef3cff770 | a54bb1c3134c641688f716ebcda0194133ec382426b0eb737466094cc4bbd7fa | O=C1c2ccccc2SCC1c1ccccc1 | C-C(=O)-[CH3;D1;+0:1].Cl-[CH2;D2;+0:2]-[#8:3]-[C;D1;H3:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:4]-[#8:3]-[CH2;D2;+0:2]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[CH3;D1;+0:1]-[#8:13]-[C:14]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 99 | [{"value": 99.0, "product": "COCOC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OCOC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-one (1.92 g, 6.7 mmol) in dry acetone (200 ml) were added potassium carbonate (8.34 g, 60.42 mmol) and methoxymethyl chloride (3.04 ml, 40.28 mmol), which was then heated for 8 hours. Water was added thereto, and the resulting solution was extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ether.Aromatic alcohol.Aromatic alcohol | Ether.Ether.Ether.Ether | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | HCl | null | null | null | CC(C)=O.CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1=O.COCCl>>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f286ed6f9e9461fb83980ce87cae00e | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 | O.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.[OH-].[Na+].COCCl>>OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | CC(C)(C)[Si](C)(C)[O:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:25]#[C:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:35][cH:34]2)([CH3:10])[CH2:11][S:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C... | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)O | Deprotection | OtherReaction | fd1cc0ec6ce8d5db2ebcfd08db7a899b0b21aaef3813e6715d25aac004d879c3 | 105c33985510e634b0dac4f9ce95a6e9f913aa74441ff940c1b9352a2a1cab8d | c1ccc(C2CSc3ccccc3C2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[C;H0;D2;+0:6]#[C;H0;D2;+0:7]-[C:8](-[C:9])-[c:10]>>[C:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8](-[C:9])-[c:10].[C:3]-[C:2]-[OH;D1;+0:1] | 75 | [{"value": 75.0, "product": "OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.9, "product": "OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | 4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman (1.43 g, 2.27 mmol) was dissolved in ethanol (100 ml) and tetrahydrofuran (10 ml), and 20% palladium hydroxide on carbon (500 mg) which had been washed with ethanol was added thereto. The reaction solution was stir... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)O | null | 24 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)O>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-80c17f7a2bde4c4eb9e2b31ac6f0ab0f | COCCOCCSCCCCCCCCCC1c2ccc(OCOC)cc2SCC1(C)c1ccc(OCOC)cc1>>COCCOCCSCCCCCCCCCC1c2ccc(O)cc2SCC1(C)c1ccc(O)cc1 | COCOC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCSCCOCCOC.Cl.O>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCOCCOC | COC[O:23][c:22]1[cH:21][cH:20][c:19]2[c:25]([cH:24]1)[S:26][CH2:27][C:28]([CH3:29])([c:30]1[cH:31][cH:32][c:33]([O:34]COC)[cH:35][cH:36]1)[CH:18]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][S:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][S:8][... | COCCOCCSCCCCCCCCCC1c2ccc(OCOC)cc2SCC1(C)c1ccc(OCOC)cc1 | COCCOCCSCCCCCCCCCC1c2ccc(O)cc2SCC1(C)c1ccc(O)cc1 | null | null | O1CCCC1.C(C)(C)O | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2CSc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 74 | [{"value": 74.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCOCCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCOCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a solution of 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{9-[2-(2-methoxyethoxy)ethylthio]nonyl}thiochroman (68 mg, 0.109 mmol) in isopropanol (5.5 ml) and tetrahydrofuran (0.9 ml) was added 5N-HCl (1.47 ml) at room temperature, which was stirred for 2 days. Water was added thereto, and the resulting sol... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccc2c(c1)CCCS2.c1ccccc1 | HO- | O1CCCC1.C(C)(C)O | null | 48 | COCCOCCSCCCCCCCCCC1c2ccc(OCOC)cc2SCC1(C)c1ccc(OCOC)cc1>O1CCCC1.C(C)(C)O>COCCOCCSCCCCCCCCCC1c2ccc(O)cc2SCC1(C)c1ccc(O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ffdd5cd198f44aaf81452252372484d6 | CC(C)(C)[Si](C)(C)Cl.OCCOCCCl>>CC(C)(C)[Si](C)(C)OCCOCCCl | ClCCOCCO.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>[Si](C)(C)(C(C)(C)C)OCCOCCCl | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][Cl:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][Cl:14] | CC(C)(C)[Si](C)(C)Cl.OCCOCCCl | CC(C)(C)[Si](C)(C)OCCOCCCl | null | null | C(C)#N | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 92.1 | [{"value": 92.0, "product": "[Si](C)(C)(C(C)(C)C)OCCOCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "[Si](C)(C)(C(C)(C)C)OCCOCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of ethylene glycol mono-2-chloroethyl ether (6.2 g, 50 mmol) in acetonitrile (150 mg) were added imidazole (6.77 g, 99.54 mmol) and t-butyldimethylsilyl chloride (11.25 g, 74.65 mmol) at room temperature. The reaction mixture was stirred overnight at the same temperature. After the reaction was completed,... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | C(C)#N | null | 8 | CC(C)(C)[Si](C)(C)Cl.OCCOCCCl>C(C)#N>CC(C)(C)[Si](C)(C)OCCOCCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a619bff754cd4f39b2201f36aedd1f84 | COC1(C(O)C(=O)c2ccccc2)C=CN=CC1>>COc1ccc2c(c1)OCC(c1ccncc1)C2=O | C(=O)(O)[O-].[Na+].[NH4+].[Cl-].C(C)(=O)[O-].OC(C(=O)C1=CC=CC=C1)C1(CC=NC=C1)OC>>COC1=CC=C2C(C(COC2=C1)C1=CC=NC=C1)=O | [CH3:1][O:2][C:3]1([CH:10]([OH:9])[C:18]([c:11]2[cH:8][cH:7][cH:6][cH:5][cH:12]2)=[O:19])[CH:13]=[CH:14][N:15]=[CH:16][CH2:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][CH:11]([c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1)[C:18]2=[O:19] | COC1(C(O)C(=O)c2ccccc2)C=CN=CC1 | COc1ccc2c(c1)OCC(c1ccncc1)C2=O | null | null | O1CCCC1.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | dd024ae7e97c6cd4992b0e6810279dc49ac723997401fb844d0cb2ba0c94d36e | e26216450dbc3dd01629bc51d6162489c247b28b1aa88683a5b210151b74ca39 | O=C1c2ccccc2OCC1c1ccncc1 | [C;D1;H3:1]-[#8:2]-[C;H0;D4;+0:3]1(-[CH;D3;+0:4](-[OH;D1;+0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:2)-[CH2;D2;+0:14]-[CH;D2;+0:15]=[N;H0;D2;+0:16]-[CH;D2;+0:17]=[CH;D2;+0:18]-1>>[C;D1;H3:1]-[#8:2]-[c;H0;D3;+0:3]1:[c:19]:[cH;D2;+0:10]:[c;H0;D... | 55 | [{"value": 55.0, "product": "COC1=CC=C2C(C(COC2=C1)C1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-hydroxy-4-methoxy-2-(4-pyridyl)acetophenone (3.51 g, 14.4 mmol) in tetrahydrofuran (30 ml) were added under ice-cooling dry acetate (2.72 ml, 28.8 mmol) and a solution of N,N,N′,N′-tetramethyl-diaminomethane (1.96 ml, 14.4 mmol) in DMF (10 ml), which was then stirred for 30 minutes. After the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Substituted imine.Secondary alcohol | Ketone.Ether.Ether | c1ccccc1.C1=CN=CCC1 | c1ccc2c(c1)CCCO2.c1ccncc1 | c1ccc2c(c1)CCCO2.c1ccncc1 | Other | O1CCCC1.CN(C)C=O | null | 1 | COC1(C(O)C(=O)c2ccccc2)C=CN=CC1>O1CCCC1.CN(C)C=O>COc1ccc2c(c1)OCC(c1ccncc1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58583feedb6c454f8356542d931ad6ea | CI.COc1ccc2c(c1)OCC(c1ccncc1)C2=O>>COc1ccc2c(c1)OCC(C)(c1ccncc1)C2=O | [NH4+].[Cl-].[Li+].CC(C)[N-]C(C)C.COC1=CC=C2C(C(COC2=C1)C1=CC=NC=C1)=O.IC>>COC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)=O | I[CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][CH:11]([c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1)[C:19]2=[O:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C:11]([CH3:12])([c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1)[C:19]2=[O:20] | CI.COc1ccc2c(c1)OCC(c1ccncc1)C2=O | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2=O | null | null | O1CCCC1 | C-C Coupling | Methylation with MeI_tertiary | bf3d68e36f205f944c672efb6b8a859f010ccc3c6201d6e5626395f16df31b6e | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1c2ccccc2OCC1c1ccncc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]1-[c:4]:[c:5]-[#8:6]-[C:7]-[CH;D3;+0:8]-1-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[CH3;D1;+0:1]-[C;H0;D4;+0:8]1(-[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:2)-[C:7]-[#8:6]-[c:5]:[c:4]-[C:3]-1=[O;D1;H0:2] | 56.4 | [{"value": 56.0, "product": "COC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.4, "product": "COC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 30 | MINUTE | To a solution of LDA (2.0 mol/l, 0.863 ml, 1.73 mmol) in tetrahydrofuran (1.5 ml) was added at −78° C. a solution of 7-methoxy-3-(4-pyridyl)chroman-4-one (220 mg, 0.863 mmol) in tetrahydrofuran (2 ml), which was then stirred for 30 minutes. Iodomethane (0.537 ml, 8.63 mmol) was added to -the reaclion solution, which wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1ccncc1 | HI | O1CCCC1 | -10 | 0.5 | CI.COc1ccc2c(c1)OCC(c1ccncc1)C2=O>O1CCCC1>COc1ccc2c(c1)OCC(C)(c1ccncc1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3eb975fd19746b1b04fffaf5e0b855e | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCO.CS(=O)(=O)Cl>>COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCOS(C)(=O)=O | [NH4+].[Cl-].C(C)N(CC)CC.CS(=O)(=O)Cl.OCCCCCCCCCC1C(COC2=CC(=CC=C12)OC)(C1=CC=NC=C1)C>>CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OC)(C1=CC=NC=C1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C:11]([CH3:12])([c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1)[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29].Cl[S:30]([CH3:31])(=[O:32])=[O:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C:11]([CH... | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCO.CS(=O)(=O)Cl | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCOS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2c(c1)CC(c1ccncc1)CO2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 380.3 | [{"value": 38.0, "product": "CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OC)(C1=CC=NC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 380.3, "product": "CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OC)(C1=CC=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-(9-hydroxynonyl)-7-methoxy-3-methyl-3-(4-pyridyl)chroman (108 mg, 0.272 mmol) in methylene chloride (2 mL) were added under ice-cooling triethylamine (0.057 mL, 0.41 mmol) and methanesulfonyl chloride (0.032 ml, 0.41 mmol), which was then stirred for 30 minutes. After the reaction was completed, satu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2c(c1)CCCO2.c1ccncc1 | HCl | C(Cl)Cl | null | 0.5 | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCO.CS(=O)(=O)Cl>C(Cl)Cl>COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCOS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b6f15f1e67548649ee2350a6b7d3ce3 | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F>>CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F | COC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCSCCCC(C(F)(F)F)(F)F.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>>OC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCSCCCC(C(F)(F)F)(F)F | C[O:14][c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][CH2:31][C:32]([F:33])([F:34])[C:35]([F:36])([F:37])[F:38])[C:2]([CH3:1])([c:3]1[cH:4][cH:5][n:6][cH:7][cH:8]1)[CH2:9][O:10]2>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][n:6][cH... | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F | CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)CC(c1ccncc1)CO2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 43 | [{"value": 43.0, "product": "OC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCSCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.5, "product": "OC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCSCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (3RS,4RS)-7-methoxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-3-(4-pyridyl)chroman (15.2 mg, 0.0265 mmol) in methylene chloride (1 ml) was added at −78° C. BBr3 (1.0 mol/l, 0.080 ml), which was then slowly warmed, and stirred for 2 hours under ice-cooling. After the reaction was completed s... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccncc1.c1ccc2c(c1)CCCO2 | Other | C(Cl)Cl | null | 2 | COc1ccc2c(c1)OCC(C)(c1ccncc1)C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F>C(Cl)Cl>CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ba87f94156c4f3bb435ba83a2a70596 | CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F>>CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F | OOS(=O)[O-].[K+].OC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCSCCCC(C(F)(F)F)(F)F>>OC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F | [CH3:1][C:2]1([c:3]2[cH:4][cH:5][n:6][cH:7][cH:8]2)[CH2:9][O:10][c:11]2[cH:12][c:13]([OH:14])[cH:15][cH:16][c:17]2[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:30][CH2:31][CH2:32][C:33]([F:34])([F:35])[C:36]([F:37])([F:38])[F:39]>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][n:6][cH:7][... | CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F | CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F | null | null | O1CCCC1.O | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc2c(c1)CC(c1ccncc1)CO2 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;D1;H0:6])-[C:4]-[C:5] | 81 | [{"value": 81.0, "product": "OC1=CC=C2C(C(COC2=C1)(C1=CC=NC=C1)C)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of (3RS,4RS)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-3-(4-pyridyl)chroman (6.1 mg, 0.011 mmol) in tetrahydrofuran (0.5 ml) was added under ice-cooling a solution of Oxone® (monopersulfate compound; DuPont product) (3.4 mg, 0.0055 mmol) in water (0.5 ml), which was then stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccncc1.c1ccc2c(c1)CCCO2 | null | O1CCCC1.O | null | 5 | CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F>O1CCCC1.O>CC1(c2ccncc2)COc2cc(O)ccc2C1CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89e88c229a15409b8296198e61101a6b | Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1.O=S(Cl)Cl>>O=S(=O)(Cl)CCCC(F)(F)C(F)(F)F | S(=O)(Cl)Cl.FC(C(CCCOS(=O)(=O)C1=CC=C(C=C1)C)(F)F)(F)F.[Li+].[Br-].C(=O)(O)[O-].[Na+].[O-]S(=O)[O-].[Na+].[Na+]>>FC(CCCS(=O)(=O)Cl)(C(F)(F)F)F | Cc1ccc(S(=O)(O[CH2:5][CH2:6][CH2:7][C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14])=[O:3])cc1.Cl[S:2](=[O:1])[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[CH2:5][CH2:6][CH2:7][C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14] | Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1.O=S(Cl)Cl | O=S(=O)(Cl)CCCC(F)(F)C(F)(F)F | null | null | O.CC(=O)C.CN(C)C=O | Functional Group Interconversion | OtherReaction | 8b742556aab3a85f4401a2e3bdc0df90992c3910b3e6552ecaf560b3cdcc8bf8 | 67ff4c463d35213101becf81163b07587eda818e417558d88aaff3bbd42a8828 | null | C-c1:c:c:c(-S(=O)(=[O;H0;D1;+0:1])-O-[CH2;D2;+0:2]-[C:3]-[C:4]):c:c:1.Cl-[S;H0;D3;+0:5](-[Cl;D1;H0:6])=[O;D1;H0:7]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[S;H0;D4;+0:5](-[Cl;D1;H0:6])(=[O;D1;H0:7])=[O;H0;D1;+0:1] | 34.2 | [{"value": 34.0, "product": "FC(CCCS(=O)(=O)Cl)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "FC(CCCS(=O)(=O)Cl)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1,1,1,2,2-pentafluoro-5-p-toluenesulfonyloxypentane (11.0 g, 3.0 mmol) in acetone (10 nm) was added LiBr (523 mg, 6.02 mmol), which was then heated under reflux for 4 hours. After the reaction solution was filtered, the solvent was removed under reduced pressure. The residue thus obtained was dissolved... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate | Sulfonyl halide | c1ccccc1 | null | null | TsOH.HCl | O.CC(=O)C.CN(C)C=O | null | null | Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1.O=S(Cl)Cl>O.CC(=O)C.CN(C)C=O>O=S(=O)(Cl)CCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b65dfbcd877c407d8c2b728ab8996dd2 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCNS(=O)(=O)CCCC(F)(F)C(F)(F)F)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCNS(=O)(=O)CCCC(F)(F)C(F)(F)F | COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCCCCCNS(=O)(=O)CCCC(C(F)(F)F)(F)F.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCNS(=O)(=O)CCCC(C(F)(F)F)(F)F | C[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][S:11][c:12]3[cH:13][c:14]([O:15]C)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][S:30](=[O:31])(=[O:32])[CH2:33][CH2:34][CH2:35][C:36]([F:37])([F:38])[C:39]([F:40])([F:41])[F:42])[cH:9][cH:8]1>>[CH3:1][C:... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCNS(=O)(=O)CCCC(F)(F)C(F)(F)F)cc1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCNS(=O)(=O)CCCC(F)(F)C(F)(F)F | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(C2CSc3ccccc3C2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 72 | [{"value": 72.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCNS(=O)(=O)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.7, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCNS(=O)(=O)CCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfonylamino)nonyl]thiochroman (124 mg, 0.186 mmol) in methylene chloride (1 ml) was added at −78° C. BBr3 (1.0 mol/l, 1.12 ml), which was then slowly warmed over 3 hours. After the reaction was completed, saturated aqueous NaHCO3... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | C(Cl)Cl | null | null | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCNS(=O)(=O)CCCC(F)(F)C(F)(F)F)cc1>C(Cl)Cl>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCNS(=O)(=O)CCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5143708b47c74390a9face0dd7321d0a | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C>>COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C | O.CCCCCC.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)F)O.C(#N)[BH3-].[Na+]>>[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)F | O[C:20]1([C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[S:9][CH2:10][C:11]1([CH3:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([... | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C | null | null | ClCCCl.C(C)(=O)OCC | Reduction | OtherReaction | 32c18b8f01f6265a398b8df4f5d0033739d3c8e378cd915941473fb5993b3ae4 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2CSc3ccccc3C2)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]#[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[#16:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12]>>[C:4]-[C:3]#[C:2]-[CH;D3;+0:1]1-[c:5](:[c:6]):[c:7]-[#16:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12] | 70 | [{"value": 70.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | HOUR | To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-3-(4-fluorophenyl)-4-hydroxy-7-methoxy-3-methylthiochroman (0.55 g, 0.99 mmol) in 1,2-dichloroethane (30 ml) were added zinc iodide(II) (0.35 g) and sodium cyanoborohydride (0.30 g), which was then stirred at 0° C. for 4 hours. After the reaction was completed,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2.c1ccccc1 | Other | ClCCCl.C(C)(=O)OCC | 0 | 4 | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C>ClCCCl.C(C)(=O)OCC>COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf840f5d644249b5ad13bf3fb026acef | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2CCCCCCCCCO.CS(=O)(=O)Cl>>COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2CCCCCCCCCOS(C)(=O)=O | O.CS(=O)(=O)Cl.C(C)N(CC)CC.OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C1(CSC2=CC(=CC=C2C1CCCCCCCCCOS(=O)(=O)C)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[S:9][CH2:10][C:11]([CH3:12])([c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1)[CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].Cl[S:31]([CH3:32])(=[O:33])=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[S:9][CH2:10][C... | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2CCCCCCCCCO.CS(=O)(=O)Cl | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2CCCCCCCCCOS(C)(=O)=O | null | null | ClCCl.CCCCCC.C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2CSc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 99 | [{"value": 99.0, "product": "FC1=CC=C(C=C1)C1(CSC2=CC(=CC=C2C1CCCCCCCCCOS(=O)(=O)C)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-(9-Hydroxynonyl)-3-(4-fluorophenyl)-7-methoxy-3-methylthiochroman (0.41 g, 0.95 mmol) was dissolved in dichloromethane (50 ml), methanesulfonyl chloride (0.44 g) and triethylamine (0.41 g) were added thereto, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was poure... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2c(c1)CCCS2.c1ccccc1 | HCl | ClCCl.CCCCCC.C(C)(=O)OCC | null | 1 | COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2CCCCCCCCCO.CS(=O)(=O)Cl>ClCCl.CCCCCC.C(C)(=O)OCC>COc1ccc2c(c1)SCC(C)(c1ccc(F)cc1)C2CCCCCCCCCOS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a24f98acb4ce4a499920800099682a3f | CC1(c2ccc(F)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F>>CC1(c2ccc(F)cc2)CSc2cc(O)ccc2C1CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F | O.CCCCCC.FC1=CC=C(C=C1)C1(CSC2=CC(=CC=C2C1CCCCCCCCCSCCCC(C(F)(F)F)(F)F)O)C.OOS(=O)[O-].[K+].O>>FC1=CC=C(C=C1)C1(CSC2=CC(=CC=C2C1CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F)O)C | [CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]2)[CH2:10][S:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]2[CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29][CH2:31][CH2:32][CH2:33][C:34]([F:35])([F:36])[C:37]([F:38])([F:39])[F:40]>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6... | CC1(c2ccc(F)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F | CC1(c2ccc(F)cc2)CSc2cc(O)ccc2C1CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F | null | null | O1CCCC1.C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(C2CSc3ccccc3C2)cc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;D1;H0:6])-[C:4]-[C:5] | 66 | [{"value": 66.0, "product": "FC1=CC=C(C=C1)C1(CSC2=CC(=CC=C2C1CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F)O)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | To a solution of (3RS,4RS)-3-(4-fluorophenyl)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]thiochroman (107 mg, 0.18 mmol) in tetrahydrofuran (8 ml) was added Oxone® (monopersulfate compound; DuPont product) (60 mg, 0.1 0 mmol), which was then stirred at 0° C. for 5 minutes. Water (0.5 ml) was added t... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | null | O1CCCC1.C(C)(=O)OCC | 0 | 0.083333 | CC1(c2ccc(F)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F>O1CCCC1.C(C)(=O)OCC>CC1(c2ccc(F)cc2)CSc2cc(O)ccc2C1CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fbdcec5db4e24b20863cebbdbbc14105 | CC([O-])=S.OCCCC(F)(F)C(F)(F)F>>CC(=S)OCCCC(F)(F)C(F)(F)F | FC(CCCO)(C(F)(F)F)F.C(C)N(CC)CC.CS(=O)(=O)Cl.C(C)(=S)[O-].[K+]>>FC(CCCOC(C)=S)(C(F)(F)F)F | [CH3:1][C:2](=[S:3])[O-:4].O[CH2:5][CH2:6][CH2:7][C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14]>>[CH3:1][C:2](=[S:3])[O:4][CH2:5][CH2:6][CH2:7][C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14] | CC([O-])=S.OCCCC(F)(F)C(F)(F)F | CC(=S)OCCCC(F)(F)C(F)(F)F | null | null | ClCCl.CCCCCC.CC(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 7437485e7bbe54fc6c84975e9094c01401f71ace66e81211d9742fbeb8935104 | 2de589ced2803ce8beca9d08c7066f36c2c12f5e3690ba33f9811d04a0e4c7f7 | null | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5](-[O-;H0;D1:6])=[S;D1;H0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5](-[C;D1;H3:4])=[S;D1;H0:7] | 51.5 | [{"value": 51.0, "product": "FC(CCCOC(C)=S)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "FC(CCCOC(C)=S)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 4,4,5,5,5-pentafluoropentanol (23.2 g, 130 mmol) in dry dichloromethane (100 ml) were added dropwise at 0° C. triethylamine (27 g, 267 mmol) and methanesulfonylchloride (30 g, 262 mmol), which was then warmed to room temperature over 12 hours. After the reaction was completed, the mixture was poured in... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Thiocarbonyl | Ether | null | null | null | HO- | ClCCl.CCCCCC.CC(=O)C.C(C)(=O)OCC | null | 12 | CC([O-])=S.OCCCC(F)(F)C(F)(F)F>ClCCl.CCCCCC.CC(=O)C.C(C)(=O)OCC>CC(=S)OCCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-82e944711eb744a3a20c8a0d99ce5d9a | COC(=O)CCCC(OC)OC>>COC(CCCCO)OC | CCCCCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].COC(CCCC(=O)OC)OC.C(C)(=O)OCC>>COC(CCCCO)OC | CO[C:7]([CH2:6][CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:9][CH3:10])=[O:8]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[O:9][CH3:10] | COC(=O)CCCC(OC)OC | COC(CCCCO)OC | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 34.4 | [{"value": 34.0, "product": "COC(CCCCO)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.4, "product": "COC(CCCCO)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of LAH (0.4 g, 11 mmol) in tetrahydrofuran (20 ml) was added dropwise at 0° C. methyl 5,5-dimethoxyvalerate (3.5 g, 20 mmol) dissolved in tetrahydrofuran (30 ml), which was then stirred for 2 hours. After the reaction was completed, the mixture was poured into ice-water (50 ml) and then extracted with e... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | Other | O1CCCC1 | null | 2 | COC(=O)CCCC(OC)OC>O1CCCC1>COC(CCCCO)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5dc346235e4345b39b8312b2a2ad076c | C1CCOC1.CC(=S)OCCCC(F)(F)C(F)(F)F.CS(=O)(=O)Cl.C[O-]>>COC(CCCCSCCCC(F)(F)C(F)(F)F)OC | FC(CCCOC(C)=S)(C(F)(F)F)F.C[O-].[Na+].O1CCCC1.CS(=O)(=O)Cl.C(C)N(CC)CC>>COC(CCCCSCCCC(C(F)(F)F)(F)F)OC | C1[CH2:3][CH2:4]O[CH2:5]1.O([C:7]([CH3:6])=[S:8])[CH2:9][CH2:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18].O=S(Cl)(=[O:19])[CH3:20].[CH3:1][O-:2]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18])[O:19][CH3:20] | C1CCOC1.CC(=S)OCCCC(F)(F)C(F)(F)F.CS(=O)(=O)Cl.C[O-] | COC(CCCCSCCCC(F)(F)C(F)(F)F)OC | null | null | O.C(C)(=O)OCC.CO.ClCCl.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a6d30ae4152f9921627a5e37ffb284e35a77602d6eff09283c4e41a213f04b9d | 1babfd4ee4e1b511e21af8853b709a5e7e19cdaf608c3a80f871daaed50182c9 | null | C1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-O-[CH2;D2;+0:3]-1.Cl-S(=O)(-[CH3;D1;+0:4])=[O;H0;D1;+0:5].[C;D1;H3:6]-[O-;H0;D1:7].[C:8]-[C:9]-[CH2;D2;+0:10]-O-[C;H0;D3;+0:11](-[CH3;D1;+0:12])=[S;H0;D1;+0:13]>>[C:8]-[C:9]-[CH2;D2;+0:10]-[S;H0;D2;+0:13]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[CH;D3;+0:1](-[O;H0;D2;+0:... | null | [] | null | null | 1 | HOUR | To a suspension of LAH (0.4 g, 11 mmol) in tetrahydrofuran (20 ml) was added dropwise at 0° C. methyl 5,5-dimethoxyvalerate (3.5 g, 20 mmol) dissolved in tetrahydrofuran (30 ml), which was then stirred for 2 hours. After the reaction was completed, the mixture was poured into ice-water (50 ml) and then extracted with e... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Thiocarbonyl.Sulfonyl halide | Ether.Ether.Monosulfide | C1CCOC1 | null | null | HCl | O.C(C)(=O)OCC.CO.ClCCl.CCCCCC | null | 1 | C1CCOC1.CC(=S)OCCCC(F)(F)C(F)(F)F.CS(=O)(=O)Cl.C[O-]>O.C(C)(=O)OCC.CO.ClCCl.CCCCCC>COC(CCCCSCCCC(F)(F)C(F)(F)F)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e4a8560b4fb846be894ecde8d8827abe | COC(CCCCSCCCC(F)(F)C(F)(F)F)OC.[O-][I+3]([O-])([O-])[O-]>>COC(CCCCS(=O)CCCC(F)(F)C(F)(F)F)OC | C(C)(=O)OCC.CCCCCC.COC(CCCCSCCCC(C(F)(F)F)(F)F)OC.I(=O)(=O)(=O)[O-].[Na+]>>COC(CCCCS(=O)CCCC(C(F)(F)F)(F)F)OC | [CH3:1][O:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:10][CH2:11][CH2:12][C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19])[O:20][CH3:21].[O-][I+3]([O-])([O-])[O-:9]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][S:8](=[O:9])[CH2:10][CH2:11][CH2:12][C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19])[O:20][CH3:21] | COC(CCCCSCCCC(F)(F)C(F)(F)F)OC.[O-][I+3]([O-])([O-])[O-] | COC(CCCCS(=O)CCCC(F)(F)C(F)(F)F)OC | null | null | O.CO | Oxidation | OtherReaction | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | null | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5].[O-;H0;D1:6]-[I+3](-[O-])(-[O-])-[O-]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:6])-[C:4]-[C:5] | 76.6 | [{"value": 76.0, "product": "COC(CCCCS(=O)CCCC(C(F)(F)F)(F)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "COC(CCCCS(=O)CCCC(C(F)(F)F)(F)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5,5-dimethoxy-1-(4,4,5,5,5-pentafluoropentylthio)pentane (460 mg, 1.4 mmol) in methanol (10 mg) were added sodium periodate (420 mg, 2.0 mmol) dissolved in water (8 ml) and methanol (5 ml), and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reac... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | null | I- | O.CO | null | null | COC(CCCCSCCCC(F)(F)C(F)(F)F)OC.[O-][I+3]([O-])([O-])[O-]>O.CO>COC(CCCCS(=O)CCCC(F)(F)C(F)(F)F)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c82084f26390484a87066af56670b886 | COC(CCCCS(=O)CCCC(F)(F)C(F)(F)F)OC>>O=CCCCCS(=O)CCCC(F)(F)C(F)(F)F | CCCCCC.C(=O)(C(F)(F)F)O.COC(CCCCS(=O)CCCC(C(F)(F)F)(F)F)OC.O>>FC(CCCS(=O)CCCCC=O)(C(F)(F)F)F | CO[CH:2]([O:1]C)[CH2:3][CH2:4][CH2:5][CH2:6][S:7](=[O:8])[CH2:9][CH2:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7](=[O:8])[CH2:9][CH2:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18] | COC(CCCCS(=O)CCCC(F)(F)C(F)(F)F)OC | O=CCCCCS(=O)CCCC(F)(F)C(F)(F)F | null | null | C(Cl)(Cl)Cl.C(C)(=O)OCC | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | null | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 95.1 | [{"value": 93.0, "product": "FC(CCCS(=O)CCCCC=O)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "FC(CCCS(=O)CCCCC=O)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5,5-Dimethoxy-1-(4,4,5,5,5-pentafluoropentylsulfinyl)pentane (355 mg, 0.10 mmol) was dissolved in chloroform (2 ml), 50% TFA aqueous solution (2 ml) was added thereto at room temperature, and the resulting mixture was then stirred for 2 hours. After the reaction was completed, the reaction solution was poured into wate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | null | HO- | C(Cl)(Cl)Cl.C(C)(=O)OCC | null | 2 | COC(CCCCS(=O)CCCC(F)(F)C(F)(F)F)OC>C(Cl)(Cl)Cl.C(C)(=O)OCC>O=CCCCCS(=O)CCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5016be00e95248d5807a0304abc59a13 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCO)cc1.CS(=O)(=O)Cl>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOS(C)(=O)=O)cc1 | O.CS(=O)(=O)Cl.C(C)N(CC)CC.OCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC>>CS(=O)(=O)OCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][OH:27])[cH:32][cH:33]1.Cl[S:28]([CH3:29])(=[O:30])=[O:31]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCO)cc1.CS(=O)(=O)Cl | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOS(C)(=O)=O)cc1 | null | null | ClCCl.CCCCCC.C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2COc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | 4-(3-Hydroxypropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (280 mg, 0.70 mmol) was dissolved in dichloromethane (50 ml), methanesulfonylchloride (0.32 g) and triethylamine (0.30 g) were added thereto, and the mixture was stirred at room temperature for 1 hour After the reaction was completed, the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HCl | ClCCl.CCCCCC.C(C)(=O)OCC | null | 1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCO)cc1.CS(=O)(=O)Cl>ClCCl.CCCCCC.C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOS(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f18d5d1774d4e6f87311fe846750064 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN=[N+]=[N-])cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN)cc1 | N(=[N+]=[N-])CCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.C(Cl)(Cl)Cl.O.N>>NCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [N-]=[N+]=[N:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:29][cH:28]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:1... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN=[N+]=[N-])cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN)cc1 | null | [Pd] | O1CCCC1.CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(C2COc3ccccc3C2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 73 | [{"value": 73.0, "product": "NCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.2, "product": "NCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | (3RS,4RS)-4-(3-Azidopropyl}7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (170 mg, 4.0 mmol) was dissolved in methanol (20 ml) and tetrahydrofuran (5 ml), 10% palladium on carbon (50 mg) was added to this solution, which was then stirred at room temperature under hydrogen for 12 hours. The reaction solutio... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | [Pd].O1CCCC1.CO | null | 12 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN=[N+]=[N-])cc1>[Pd].O1CCCC1.CO>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6920b1e3a81b432baa70093baeedbeea | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN)cc1.O=CCCCCS(=O)CCCC(F)(F)C(F)(F)F>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCNCCCCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 | C(Cl)(Cl)Cl.CO.O.N.NCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.FC(CCCS(=O)CCCCC=O)(C(F)(F)F)F.C(#N)[BH3-].[Na+]>>COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCNCCCCCS(=O)CCCC(C(F)(F)F)(F)F | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][NH2:27])[cH:45][cH:46]1.O=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33](=[O:34])[CH2:35][CH2:36][CH2:37][C:38]([F:39])([F:40])[C:41]([F:42... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN)cc1.O=CCCCCS(=O)CCCC(F)(F)C(F)(F)F | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCNCCCCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(C2COc3ccccc3C2)cc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 29.4 | [{"value": 28.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCNCCCCCS(=O)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.4, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCNCCCCCS(=O)CCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 2 | HOUR | To a solution of (3RS,4RS)-4-(3-aminopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (80 mg, 0.20 mmol) and 5-(4,4,5,5,5-pentafluoropentylsulfinyl)pentanal (80 mg, 0.19 mmol) in methanol (5 ml) was added a solution of sodium cyanoborohydride (12 mg, 0.19 mmol) in methanol (5 ml), which was then stir... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | O.CO | null | 2 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCN)cc1.O=CCCCCS(=O)CCCC(F)(F)C(F)(F)F>O.CO>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCNCCCCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a6cfff8ca16e485880122d3911b38ed1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | O.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O.C(#N)[BH3-].[Na+].CCCCCC>>[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | O[C:23]1([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:42][cH:41]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | ClCCCl.C(C)(=O)OCC | Reduction | OtherReaction | d9ad9de0a2df8f543d454c115f7a58d9a012b1cbcc0f40fa0bf7cc7b376ca1e8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc3C2)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]#[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12]>>[C:4]-[C:3]#[C:2]-[CH;D3;+0:1]1-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12] | 52 | [{"value": 52.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (116 g, 1.9 mmol) in 1,2-dichloroethane (50 ml) were added zinc iodide(II) (0.7 g) and sodium cyanoborohydride (0.6 g), which was then stirred at room temperature for 4 hours. After the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | ClCCCl.C(C)(=O)OCC | null | 4 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>ClCCCl.C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a09ed64c63b94387ac2d265da04ec011 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 | C(C)(=O)OCC.CC1=CC=C(C=C1)S(=O)(=O)[O-].C1=CC=[NH+]C=C1.[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.CCCCCC>>OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | CC(C)(C)[Si](C)(C)[O:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:35][cH:34]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 | null | null | CO | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(C2COc3ccccc3C2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 77 | [{"value": 77.0, "product": "OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 4-[9-(t-Butyldimethylsilyloxy)-nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (0.62 g, 11.0 mmol) was dissolved in methanol (30 ml), PPTS (0.70 g) was added thereto, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, the reaction mixture was concentrated u... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | CO | null | 4 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>CO>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53598c346723420eaeaa22f16cbfcda1 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2C#CCOc2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCO)cc2)cc1 | [Si](C)(C)(C(C)(C)C)OCCOC1=CC=C(OCC#CC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1>>OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1 | CC(C)(C)[Si](C)(C)[O:35][CH2:34][CH2:33][O:32][c:31]1[cH:30][cH:29][c:28]([O:27][CH2:26][C:25]#[C:24][CH:23]2[C:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:39][cH:38]3)([CH3:10])[CH2:11][S:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]32)[cH:37][cH:36]1>>[CH3:1][O:2][CH2:3][O:4][c... | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2C#CCOc2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCO)cc2)cc1 | null | [OH-].[OH-].[Pd+2] | O1CCCC1.C(C)O | Deprotection | OtherReaction | fd1cc0ec6ce8d5db2ebcfd08db7a899b0b21aaef3813e6715d25aac004d879c3 | 105c33985510e634b0dac4f9ce95a6e9f913aa74441ff940c1b9352a2a1cab8d | c1ccc(OCCCC2c3ccccc3SCC2c2ccccc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5]-[C;H0;D2;+0:6]#[C;H0;D2;+0:7]-[C:8](-[C:9])-[c:10]>>[#8:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8](-[C:9])-[c:10].[C:3]-[C:2]-[OH;D1;+0:1] | 71 | [{"value": 71.0, "product": "OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | 4-{3-[4-(2-t-Butyldimethylsilyloxyethoxy)phenoxy]-1-propynyl}-7-methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methylthiochroman (6) prepared in Step 4 (408 mg) was dissolved in a solvent mixture of ethanol (6 ml) and tetrahydrofuran (2 ml), 20% palladium hydroxide/carbon (130 mg) washed with ethanol was added, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | Other | [OH-].[OH-].[Pd+2].O1CCCC1.C(C)O | null | 17 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2C#CCOc2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)cc1>[OH-].[OH-].[Pd+2].O1CCCC1.C(C)O>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCO)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6f4b44fa9634597a85ac14df68e2893 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCO)cc2)cc1.CS(=O)(=O)Cl>>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCOS(C)(=O)=O)cc2)cc1 | [Cl-].[NH4+].C(C)N(CC)CC.CS(=O)(=O)Cl.OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1>>CS(=O)(=O)OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1 | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][S:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][O:27][c:28]2[cH:29][cH:30][c:31]([O:32][CH2:33][CH2:34][OH:35])[cH:40][cH:41]2)[cH:42][cH:43]1.Cl[S:36]([CH3:37])(=[O:38])=[O:39]>>[CH3:1]... | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCO)cc2)cc1.CS(=O)(=O)Cl | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCOS(C)(=O)=O)cc2)cc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(OCCCC2c3ccccc3SCC2c2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 95 | [{"value": 95.0, "product": "CS(=O)(=O)OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "CS(=O)(=O)OCCOC1=CC=C(OCCCC2C(CSC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 0 | CELSIUS | 30 | MINUTE | 4-{3-[4-(2-Hydroxyethoxy)phenoxy]propyl}-7-methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methylthiochroman (7) prepared in Step 5 (45.6 mg, 0.082 mmol) was dissolved in CH2Cl2 (0.4 ml), which was then cooled down to 0° C. Triethylamine (23 μl, 0.17 mmol) and methanesulfonylchloride (16 μl, 0.21 mmol) were added thereto... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.5 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCO)cc2)cc1.CS(=O)(=O)Cl>C(Cl)Cl>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCOS(C)(=O)=O)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32aedadbaf564aa7aef1ae73987f1ae9 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCSCCCC(F)(F)C(F)(F)F)cc2)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1 | COCOC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCOC1=CC=C(C=C1)OCCSCCCC(C(F)(F)F)(F)F.C(O)([O-])=O.[Na+]>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCOC1=CC=C(C=C1)OCCSCCCC(C(F)(F)F)(F)F | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][S:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][O:23][c:24]2[cH:25][cH:26][c:27]([O:28][CH2:29][CH2:30][S:31][CH2:32][CH2:33][CH2:34][C:35]([F:36])([F:37])[C:38]([F:39])([F:40])[F:41])[cH:42][cH:43]2)[cH:9][cH:8]1>>[CH3:1]... | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCSCCCC(F)(F)C(F)(F)F)cc2)cc1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1 | null | null | O1CCCC1.Cl.CO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(OCCCC2c3ccccc3SCC2c2ccccc2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 87 | [{"value": 87.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCOC1=CC=C(C=C1)OCCSCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCOC1=CC=C(C=C1)OCCSCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | (3RS,4RS)-7-Methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (9) prepared in Step 7 (144 mg, 0.2 mmol) was dissolved in hydrochloric acid/methanol (1 ml) and tetrahydrofuran (0.1 ml), which was then stirred at room temperature for 4 days.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | HO- | O1CCCC1.Cl.CO | null | null | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCOc2ccc(OCCSCCCC(F)(F)C(F)(F)F)cc2)cc1>O1CCCC1.Cl.CO>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb42990211dc49cab520e299d0342920 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 | O.OOS(=O)[O-].[K+].OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCOC1=CC=C(C=C1)OCCSCCCC(C(F)(F)F)(F)F.O>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCOC1=CC=C(C=C1)OCCS(=O)CCCC(C(F)(F)F)(F)F | [CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]2)[CH2:10][S:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]2[CH:19]1[CH2:20][CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([O:28][CH2:29][CH2:30][S:31][CH2:33][CH2:34][CH2:35][C:36]([F:37])([F:38])[C:39]([F:40])([F:41])[F:42])[cH:43][cH:44]1>>[CH3:1][C:2... | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 | null | O | O1CCCC1 | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(OCCCC2c3ccccc3SCC2c2ccccc2)cc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;D1;H0:6])-[C:4]-[C:5] | 57 | [{"value": 57.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCOC1=CC=C(C=C1)OCCS(=O)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | (3RS,4RS)-7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (11) prepared in Step 8 (110 mg, 0.17 mmol) was dissolved in tetrahydrofuran (5 ml), which was then cooled down to 0° C. Oxone® (monopersulfate compound; DuPont product) (63 mg, 0.1 mmol) and w... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | null | O.O1CCCC1 | 0 | 1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1>O.O1CCCC1>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1484ee4f8f4c4d37bc42d1884b092656 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1>>CC(C)(C)OC(=O)NCCCC(F)(F)C(F)(F)F | FC(C(CCCOS(=O)(=O)C1=CC=C(C=C1)C)(F)F)(F)F.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.[N-]=[N+]=[N-].[Na+]>>C(C)(C)(C)OC(NCCCC(C(F)(F)F)(F)F)=O | CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].Cc1ccc(S(=O)(=O)O[CH2:9][CH2:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1 | CC(C)(C)OC(=O)NCCCC(F)(F)C(F)(F)F | null | [Pd] | O.CO | Functional Group Interconversion | OtherReaction | 1c3bf8d7b0e1b97d09ae0ec4903a5bde770eab987ad8bff626cc3965d37593f8 | 4345b651f3c814c79acad4095f91563857dae304c2ad8b59d1b6cc27dc92db0f | null | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:8]-[C:9]-[C:10]):c:c:1>>[C:10]-[C:9]-[CH2;D2;+0:8]-[#7:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 50 | [{"value": 50.0, "product": "C(C)(C)(C)OC(NCCCC(C(F)(F)F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.7, "product": "C(C)(C)(C)OC(NCCCC(C(F)(F)F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | 1,1,1,2,2-Pentafluoro-5-p-toluenesulfonyloxypentane (4.00 mg, 12.0 mmol) was dissolved in methanol (40 ml), NaN3 (936 mg, 14.4 mmol) dissolved in water (10 ml) was added thereto, and the mixture was stirred overnight at 60° C. After the reaction was completed, the reaction mixture was extracted with chloroform and wash... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Anhydride.Carbonic Ester.Carbonic Ester.Boc.Boc | Carbamic ester.Ether.Boc | c1ccccc1 | null | null | TsOH.HO- | [Pd].O.CO | 60 | 8 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)OCCCC(F)(F)C(F)(F)F)cc1>[Pd].O.CO>CC(C)(C)OC(=O)NCCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8472d63b12aa40a89529f8d4a92d389b | CC(C)(C)OC(=O)NCCCC(F)(F)C(F)(F)F.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)Cl)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 | C(C)N(CC)CC.ClS(=O)(=O)CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.Cl.ClN1C(CCC1=O)=O.C(=O)(C(F)(F)F)O.ClS(=O)(=O)CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.[OH-].[Na+].C(C)(C)(C)OC(NCCCC(C(F)(F)F)(F)F)=O.C(C)(=O)SCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.CO>>COCOC1=CC=C2C(C(COC2=C1)... | CC(C)(C)OC(=O)[NH:36][CH2:37][CH2:38][CH2:39][C:40]([F:41])([F:42])[C:43]([F:44])([F:45])[F:46].Cl[S:33]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:48][cH:47]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18... | CC(C)(C)OC(=O)NCCCC(F)(F)C(F)(F)F.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)Cl)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 | null | null | CCCCCC.O.C(Cl)Cl.C(C)(=O)OCC | Acylation | OtherReaction | e5e0353ed7860f5f3e39514139f051e4d6492a60eb2b5be38d0840e87639dc1b | cf59b7e4d6547a1ecb903c2113fc2917df8195614c8f97dab060eab217c2f6c5 | c1ccc(C2COc3ccccc3C2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].Cl-[S;H0;D4;+0:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[C:7]-[C:8]>>[C:8]-[C:7]-[S;H0;D4;+0:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[NH;D2;+0:1]-[C:2]-[C:3] | 16 | [{"value": 16.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCS(=O)(=O)NCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-(9-Acetylthiononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (40.0 mg, 0.0735 mmol) was dissolved in methanol (1 ml) under nitrogen, 2N—NaOH (0.5 ml) was added dropwise thereto, and the mixture was stirred at room temperature for 30 minutes. After the reaction was completed, the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Sulfonamide | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HCl | CCCCCC.O.C(Cl)Cl.C(C)(=O)OCC | null | 0.5 | CC(C)(C)OC(=O)NCCCC(F)(F)C(F)(F)F.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)Cl)cc1>CCCCCC.O.C(Cl)Cl.C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fae7bc854963435c88c7067942589ab2 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F | C(C)(=O)OCC.C(=O)(O)[O-].[Na+].COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCS(=O)(=O)NCCCC(C(F)(F)F)(F)F.CCCCCC>>OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCS(=O)(=O)NCCCC(C(F)(F)F)(F)F | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29](=[O:30])(=[O:31])[NH:32][CH2:33][CH2:34][CH2:35][C:36]([F:37])([F:38])[C:39]([F:40])([F:41])[F:42])[cH:9][cH:8]1>>[CH3:1... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F | null | null | Cl.C(C)(C)O.C1CCOC1 | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 11.1 | [{"value": 11.0, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCS(=O)(=O)NCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.1, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCS(=O)(=O)NCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | 3 | DAY | 7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylaminosulfonyl)nonyl]chroman (8.0 mg, 0.0113 mmol) was dissolved in a solvent mixture of THF (0.2 ml) and isopropanol (0.2 ml), 5N-HCl aqueous solution (0.6 ml) was added dropwise thereto, and the mixture was stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HO- | Cl.C(C)(C)O.C1CCOC1 | null | 72 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F)cc1>Cl.C(C)(C)O.C1CCOC1>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCCS(=O)(=O)NCCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95c10823b4d04134a79b08336feba41f | CC(C)(C)[Si](C)(C)Cl.OCCCCCCBr>>CC(C)(C)[Si](C)(C)OCCCCCCBr | BrCCCCCCO.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>BrCCCCCCO[Si](C)(C)C(C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15] | CC(C)(C)[Si](C)(C)Cl.OCCCCCCBr | CC(C)(C)[Si](C)(C)OCCCCCCBr | null | null | O1CCCC1 | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 92.4 | [{"value": 92.4, "product": "BrCCCCCCO[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "BrCCCCCCO[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | 6-Bromo-1-hexanol (20 g, 110.42 mmol) was dissolved in dry tetrahydrofuran (700 ml) and cooled to 0° C. under argon atmosphere, to which were added imidazole (15 g, 220.84 mmol) and t-butyldimethylsilyl chloride (33 g, 220.84 mmol) and the resulting solution was stirred overnight. After the reaction was completed, the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | O1CCCC1 | 0 | 8 | CC(C)(C)[Si](C)(C)Cl.OCCCCCCBr>O1CCCC1>CC(C)(C)[Si](C)(C)OCCCCCCBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7eed1790609489187af49b9eb17f211 | CC(C)(C)[Si](C)(C)OCCCCCCBr>>C#CCCCCCCO[Si](C)(C)C(C)(C)C | BrCCCCCCO[Si](C)(C)C(C)(C)C.O1CCCC1>>[Si](C)(C)(C(C)(C)C)OCCCCCCC#C | Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16] | CC(C)(C)[Si](C)(C)OCCCCCCBr | C#CCCCCCCO[Si](C)(C)C(C)(C)C | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | 76a22f266c3828d8d385e531510e9259aeb708216648f09c5463e55eddf2cf62 | a5c588ad48058b13dfd7a1f812f73bb74579b9cc3db585f8324eb6fef416f165 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C:4]#[C;D1;H1:5] | 73.8 | [{"value": 73.8, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCC#C", "details": "PERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 1 | DAY | 6-Bromo-1-(t-butyldimethylsilyloxy)hexane (20 g, 110.42 mmol) was dissolved in dry dimethyl sulfoxide (500 ml) and tetrahydrofuran (50 ml) and cooled to 0° C. under argon atmosphere, to which was added lithium acetylide ethylene diamine complex (28.0 g, 304.74 mmol) and the resulting solution was stirred for 1 day at 4... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Alkyne | null | null | null | Br- | CS(=O)C | 4 | 24 | CC(C)(C)[Si](C)(C)OCCCCCCBr>CS(=O)C>C#CCCCCCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0687bd6360714687a6b4063ebd39624c | C#CCCCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCC#C.C(CCC)[Li].COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)=O>>[Si](C)(C)(C(C)(C)C)OCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O | [CH:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[C:19]2=[O:20])[cH:37][cH:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([... | C#CCCCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | af22e63626241b7ef7b156ca9e8464011387cb2140508f9d238feb5631c67f1a | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc(C2CSc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#16:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | 870.1 | [{"value": 99.3, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 870.1, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | 8-(t-Butyldimethylsilyloxy)-1-octyne (12 g, 49.9 mmol) was dissolved in dry tetrahydrofuran (150 ml) under argon atmosphere and then cooled to −78C. 2.5M n-Butyllithium (18 ml, 44.9 mmol) was added dropwise thereto, and the mixture was warmed to −10° C. and stirred for 1 hour and then cooled to −78° C. 7-Methoxy-3-(4-m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | null | O1CCCC1 | -10 | 1 | C#CCCCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>O1CCCC1>COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8f3a55a43a74e6ba428e2e64d7b4e5d | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O.C(#N)[BH3-].[Na+]>>[Si](C)(C)(C(C)(C)C)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | O[C:19]1([C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][Si:29]([CH3:30])([CH3:31])[C:32]([CH3:33])([CH3:34])[CH3:35])[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]2)([CH3:8])[CH2:9][S:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | ClCCCl | Reduction | OtherReaction | d2aa8219231ca3214ee68c1d0f06bffad88339f62bb1d6f328c0cd70f09e2bc5 | 60a7236e2fc7f14079d4445ee3fd2aaed5c023fa0e86b6d5702a23963f159e6a | c1ccc(C2CSc3ccccc3C2)cc1 | O-[C;H0;D4;+0:1]1(-[C;H0;D2;+0:2]#[C;H0;D2;+0:3]-[C:4]-[C:5])-[c:6](:[c:7]):[c:8]-[#16:9]-[C:10]-[C:11]-1(-[C;D1;H3:12])-[c:13]>>[C:5]-[C:4]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[CH;D3;+0:1]1-[c:6](:[c:7]):[c:8]-[#16:9]-[C:10]-[C:11]-1(-[C;D1;H3:12])-[c:13] | 80.4 | [{"value": 79.5, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 4-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (14 g, 25.2 mmol) was dissolved in 1,2-dichloroethane (300 mL) and cooled to 0° C. Zinc iodide(II) (24.2 g, 75.69 mmol) and sodium cyanoborohydride (9.51 g, 151.38 mmol) was sequentially added and slowly warmed to room... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Alkyne | null | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | ClCCCl | 0 | 2 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCCCO[Si](C)(C)C(C)(C)C)cc1>ClCCCl>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de0b0b87a18c4a4586ef595a0c495b2b | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO)cc1 | [Si](C)(C)(C(C)(C)C)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | CC(C)(C)[Si](C)(C)[O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)([CH3:8])[CH2:9][S:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO)cc1 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(C2CSc3ccccc3C2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 93 | [{"value": 93.0, "product": "OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (3RS,4RS)-4-[8-(t-Butyldimethylsilyloxy)-1-octyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (4.5 g, 8.29 mmol) was dissolved in tetrahydrofuran (100 ml), and cooled to 0°. To this solution was added tetrabutylammonium fluoride (16.6 ml, 16.58 mmol), and the reaction mixture was stirred at room temperature for 2... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | O1CCCC1 | null | 2 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>O1CCCC1>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70c2aa26b085423b84879bbc27fc4af0 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO)cc1.CS(=O)(=O)Cl>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCOS(C)(=O)=O)cc1 | O.C(C)N(CC)CC.CS(=O)(=O)Cl.OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC>>CS(=O)(=O)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[cH:33][cH:34]1.Cl[S:29]([CH3:30])(=[O:31])=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO)cc1.CS(=O)(=O)Cl | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCOS(C)(=O)=O)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2CSc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 97.7 | [{"value": 97.7, "product": "CS(=O)(=O)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "CS(=O)(=O)OCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | (3RS,4RS)-4-(8-hydroxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (3.25 g, 7.58 mmol) was dissolved in dichloromethane (100 ml), to which were added triethylamine (1.59 ml, 11.37 mmol) and methanesulfonyl chloride (0.88 ml, 11 37 mmol). The reaction mixture was stirred at room temperature for 1 hour. After... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | HCl | ClCCl | null | 1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCO)cc1.CS(=O)(=O)Cl>ClCCl>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCOS(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68567e9f77644b129cad0d4e13d30b5f | CCOC(=O)CC(=O)OCC.FC(F)(F)C(F)(F)CCCI>>CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC | FC(C(CCCI)(F)F)(F)F.[H-].[Na+].C(CC(=O)OCC)(=O)OCC>>FC(CCCC(C(=O)OCC)C(=O)OCC)(C(F)(F)F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:17](=[O:18])[O:19][CH2:20][CH3:21].I[CH2:7][CH2:8][CH2:9][C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][CH2:9][C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[F:16])[C:17](=[O:18])[O:19][CH2:20][CH3:21] | CCOC(=O)CC(=O)OCC.FC(F)(F)C(F)(F)CCCI | CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | null | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12] | 78.4 | [{"value": 78.4, "product": "FC(CCCC(C(=O)OCC)C(=O)OCC)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "FC(CCCC(C(=O)OCC)C(=O)OCC)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of sodium hydride (60%) (3.90 g, 96.07 mol) in tetrahydrofuran (160 ml) was added dropwise a solution of diethyl malonate (16.6 ml, 110.85 mol) under ice-cooling, which was then stirred for 30 minutes. Then, 1,1,1,2,2-Pentafluoro-5-iodopentane (21 g, 73.9 mol) was added dropwise thereto, and reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | null | HI | O1CCCC1 | null | 0.5 | CCOC(=O)CC(=O)OCC.FC(F)(F)C(F)(F)CCCI>O1CCCC1>CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4810b82c804b41a28eba417fe9173a71 | CSC(=NC#N)SC.NCCCC(F)(F)C(F)(F)F>>CSC(=NCCCC(F)(F)C(F)(F)F)NC#N | FC(CCCN)(C(F)(F)F)F.CSC(=NC#N)SC>>C(#N)NC(SC)=NCCCC(C(F)(F)F)(F)F | CS[C:3]([S:2][CH3:1])=[N:15][C:16]#[N:17].[NH2:4][CH2:5][CH2:6][CH2:7][C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14]>>[CH3:1][S:2][C:3](=[N:4][CH2:5][CH2:6][CH2:7][C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14])[NH:15][C:16]#[N:17] | CSC(=NC#N)SC.NCCCC(F)(F)C(F)(F)F | CSC(=NCCCC(F)(F)C(F)(F)F)NC#N | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 300f7d9a618f3758fc5076640daf673cbf021e3850b2dd0e49a3703f9f7b1cb8 | f38037f62f5604d71d7c04376a0df3e46e3a3102ce115e0c5238525c162dbd0f | null | C-S-[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])=[N;H0;D2;+0:4]-[C:5]#[N;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]#[N;D1;H0:6] | 69.3 | [{"value": 69.0, "product": "C(#N)NC(SC)=NCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "C(#N)NC(SC)=NCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4,4,5,5,5-pentafluoropentylamine (0.118M, 30 ml, 3.55 mmole) and of dimethyl N-cyanodithioiminocarbonate (700 mg, 4.26 mmole) in ethanol (30 ml) was heated under reflux for 18 hours. Concentration under reduced pressure, followed by crystallization from ethyl acetate and petroleum ether afforded 1-cyano-3... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Cyanamide.Monosulfide | null | null | null | Other | C(C)O | null | null | CSC(=NC#N)SC.NCCCC(F)(F)C(F)(F)F>C(C)O>CSC(=NCCCC(F)(F)C(F)(F)F)NC#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2473e86ed154425c94d139013e8f9c60 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCN=[N+]=[N-]>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCN | N(=[N+]=[N-])CCCCCCCCCC1C(CSC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O>>NCCCCCCCCCC1C(CSC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O | [N-]=[N+]=[N:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:2]([CH3:1])([c:3]2[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]2)[CH2:10][S:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]21>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]2)[CH2:10][S:11][c:12]2[cH:13][c:14]([OH... | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCN=[N+]=[N-] | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCN | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(C2CSc3ccccc3C2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 98.8 | [{"value": 98.0, "product": "NCCCCCCCCCC1C(CSC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "NCCCCCCCCCC1C(CSC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methanol (70 ml) and 10% Pd/C (137 mg) were added to (3RS,4RS)-4-(azidononyl)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman (410 mg, 0.93 mmol) and the mixture was stirred for 2 h under hydrogen (normal pressure). When the reaction was completed, the mixture was filtered through celite pad, the filtrate was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | Other | [Pd].CO | null | 2 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCN=[N+]=[N-]>[Pd].CO>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCN |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-05194e24a7d94b56b66c94a62f3f92e7 | Cc1cccc(OCCCC(F)(F)C(F)(F)F)c1S(=O)(=O)[O-].NCc1ccccc1>>FC(F)(F)C(F)(F)CCCNCc1ccccc1 | O.C(C1=CC=CC=C1)N.C([O-])([O-])=O.[K+].[K+].FC(CCCOC1=C(C(=CC=C1)C)S(=O)(=O)[O-])(C(F)(F)F)F>>FC(CCCNCC1=CC=CC=C1)(C(F)(F)F)F | Cc1cccc(O[CH2:10][CH2:9][CH2:8][C:5]([C:2]([F:1])([F:3])[F:4])([F:6])[F:7])c1S(=O)(=O)[O-].[NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[F:1][C:2]([F:3])([F:4])[C:5]([F:6])([F:7])[CH2:8][CH2:9][CH2:10][NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Cc1cccc(OCCCC(F)(F)C(F)(F)F)c1S(=O)(=O)[O-].NCc1ccccc1 | FC(F)(F)C(F)(F)CCCNCc1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | eaa99a4826d4066954f88735de65650244572fbfaf73649e3d0ecb90318af21d | 22738ca5f1db2e143117de509f1682943e6cd68ddfaf369d0e5d8e83ec9762cf | c1ccccc1 | C-c1:c:c:c:c(-O-[CH2;D2;+0:1]-[C:2]-[C:3]):c:1-S(=O)(=O)-[O-].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 74 | [{"value": 74.0, "product": "FC(CCCNCC1=CC=CC=C1)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "FC(CCCNCC1=CC=CC=C1)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4,4,5,5,5-Pentafluoropentyloxytoluenesulfonate (1 g, 3 mmol) was dissolved in acetonitrile (10 ml). Benzylamine (646 mg, 6 mmol) and potassium carbonate (829 mg, 6 mmol) were added. The mixture was refluxed for 10 h under nitrogen atmosphere. When the reaction was completed, the mixture was cooled to room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Sulfonic acid | Secondary amine | c1ccccc1 | null | c1ccccc1 | HO- | C(C)#N | null | null | Cc1cccc(OCCCC(F)(F)C(F)(F)F)c1S(=O)(=O)[O-].NCc1ccccc1>C(C)#N>FC(F)(F)C(F)(F)CCCNCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8bf610a196742608cac70a9ef2c53bd | C1CCNCC1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1 | COCOC1=CC=C2CC(COC2=C1)(C)C1=CC=C(C=C1)OCOC.N1CCCCC1.C(Cl)Cl>>COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCCCC1CCNCC1 | [CH2:24]1[CH2:25][CH2:35][NH:36][CH2:27][CH2:39]1.[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH2:23]2)[cH:41][cH:42]1>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c... | C1CCNCC1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 18501e625c390f3b597809244e7545159ce2eee53bf63686675d0ee0bf2262f3 | 9a8a7ebbad55357ca2df0e551524ed83e7b8ca12e75218e3fa557eb3a29fd025 | c1ccc(C2COc3ccccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#8:5]-[c:6]:[c:7](:[c:8])-[CH2;D2;+0:9]-1.[CH2;D2;+0:10]1-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[NH;D2;+0:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-1>>[C:16]-[#8:17]-[c;H0;D3;+0:14]1:[c:18]:[cH;D2;+0:11]:[c;H0;D3;+0:10](-[CH;D3;+0:9]2-[c:7](:[c:8]):[c:6]-[#8:5]-[C:4]-[C:2]-2(-[C;D1;H3:1])-[c:3]):[c:19... | 150.5 | [{"value": 75.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCCCC1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 150.5, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCCCC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To (3RS,4RS)-4-[4-(4-chlorobutyloxy)phenyl]-(7-(methoxymethoxy)-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (393 mg, 0.75 mmol) was added piperidine (738 mg, 7.5 mmol) and the mixture was refluxed for 12 h. After cooling, the mixture was extracted with ethyl acetate, dried over MgSO4, and filtered. The filtrate was ev... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Ether.Secondary amine | C1CCNCC1.c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1ccccc1.C1CCNCC1 | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1.C1CCNCC1 | Other | CO | null | null | C1CCNCC1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2)cc1>CO>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-46de277a28f5426fa2317691a87066e3 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC2CCNCC2)cc1 | COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCCCCC1CCNCC1.C(Cl)Cl>>OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(C=C1)OCCCCC1CCNCC1 | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[c:20]2[cH:21][cH:22][c:23]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]3)[cH:35][cH:36]2)[cH:9][cH:8]1>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([OH:7])[cH:8][c... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC2CCNCC2)cc1 | null | null | CO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | A mixture of (3RS,4RS)-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methyl-4-[4-(4-piperidylbutyloxy)phenyl]chroman (325 mg, 0.56 mmol) p-toluenesulfonic acid (1.42 g, 5.6 mmol) and methanol was stirred at reflux for 12 h. After cooling, the mixture was extracted with ethyl acetate, dried over MgSO4, and filtered. T... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1.C1CCNCC1 | HO- | CO | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OCCCCC3CCNCC3)cc2)cc1>CO>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bc2e03d9f3304b1c8aa18d08880755d0 | ClC[C@@H]1CO1.OCCSCCCC(F)(F)C(F)(F)F>>FC(F)(F)C(F)(F)CCCSCCOCC1CO1 | [OH-].[Na+].C1[C@H](O1)CCl.FC(CCCSCCO)(C(F)(F)F)F>>O1C(C1)COCCSCCCC(C(F)(F)F)(F)F | Cl[CH2:15][C@@H:16]1[CH2:17][O:18]1.[F:1][C:2]([F:3])([F:4])[C:5]([F:6])([F:7])[CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][OH:14]>>[F:1][C:2]([F:3])([F:4])[C:5]([F:6])([F:7])[CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]1[CH2:17][O:18]1 | ClC[C@@H]1CO1.OCCSCCCC(F)(F)C(F)(F)F | FC(F)(F)C(F)(F)CCCSCCOCC1CO1 | null | S(=O)(=O)(O)[O-].C(C)(C)(C)[NH3+] | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1CO1 | Cl-[CH2;D2;+0:1]-[C@H;D3;+0:2]1-[#8:3]-[C:4]-1.[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[#8:3]-[C:4]-1 | 63 | [{"value": 63.0, "product": "O1C(C1)COCCSCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "O1C(C1)COCCSCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of 50% acqueous NaOH (1.85 ml), S-epichlorohydrin (1.142 g, 12.34 mmole) and t-butylammonium hydrogen sulfate (24 mg) was vigorously stirred at 0° C., for half an hour and allowed to reach room temperature. To this mixture was added 2-(4,4,5,5,5-pentafluoropentylthio)ethan-1-ol (735 mg, 3.08 mmole) at room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CO1 | HCl | S(=O)(=O)(O)[O-].C(C)(C)(C)[NH3+] | 0 | null | ClC[C@@H]1CO1.OCCSCCCC(F)(F)C(F)(F)F>S(=O)(=O)(O)[O-].C(C)(C)(C)[NH3+]>FC(F)(F)C(F)(F)CCCSCCOCC1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc4b6fb557c949cdacf059adb68c10e0 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1.FC(F)(F)C(F)(F)CCCSCCOCC1CO1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc2)cc1 | COCOC1=CC=C2C(C(COC2=C1)(C1=CC=C(C=C1)OCOC)C)C1=CC=C(C=C1)O.O1C(C1)COCCSCCCC(C(F)(F)F)(F)F.C(C)#N>>COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[c:24]2[cH:25][cH:26][c:27]([OH:28])[cH:47][cH:48]2)[cH:49][cH:50]1.[CH2:29]1[CH:30]([CH2:32][O:33][CH2:34][CH2:35][S:36][CH2:37][CH2:38][CH2:39][C:40]([F:41])([F:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1.FC(F)(F)C(F)(F)CCCSCCOCC1CO1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc2)cc1 | null | N1=CC=CC=C1 | O | Heteroatom Alkylation and Arylation | OtherReaction | c8f37de1487a64e5d0f374942194fdf1fb5ee79a4a7c0eead7f4385797f6a345 | d65f28c52f0777a08a008cfdcfc030aaa24bdbbd95c8114c9f5ad2abd4641bd1 | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | [#8:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 86.3 | [{"value": 86.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O", "details": "CALCULATEDPE... | null | null | null | null | A mixture of (3RS,4RS)-7-methoxymethoxy-3-methyl-3-(4-methoxymethoxyphenyl)-4-(4-hydroxyphenyl)chroman (31 1 mg, 0.71 mmole), 1-((2-oxiranyl)methoxy)-2-(4,4,5,5,5-pentafluoropentylthio)ethane (568 mg, 1.93 mmole), acetonitrile (9 ml), water (3 ml) and pyridine (5 drops) was refluxed for 10 hours. After cooling, the rea... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Secondary alcohol | C1CO1 | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | null | N1=CC=CC=C1.O | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1.FC(F)(F)C(F)(F)CCCSCCOCC1CO1>N1=CC=CC=C1.O>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f9b9695d7a74cc08901aa116f018223 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc2)cc1>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc1 | O.COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O.Cl>>OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[c:20]2[cH:21][cH:22][c:23]([O:24][CH2:25][C@H:26]([OH:27])[CH2:28][O:29][CH2:30][CH2:31][S:32][CH2:33][CH2:34][CH2:35][C:36]([F:37])([F:38])[C:39]([F:40])([F:41])[F:42])[cH:43][cH:44]2)[cH:9][cH:8]1... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc2)cc1 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc1 | null | null | CO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 68.3 | [{"value": 68.0, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(C=C1)OC[C@@H](COCCSCCCC(C(F)(F)F)(F)F)O", "details": "CALCULATEDPERCENTYIELD",... | 70 | CELSIUS | 40 | MINUTE | To a solution of 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(4-(3-(2-(4,4,5,5,5-pentafluoropentylthio)ethoxy)-(R)-2-hydroxypropyloxy)phenyl)chroman (440 mg, 0.613 mmol) in methanol (9 ml) was added 6N HCl (3 ml) at room temperature, which was stirred for 40 minutes at 70° C. Water was added thereto, and the... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HO- | CO | 70 | 0.666667 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc2)cc1>CO>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OC[C@H](O)COCCSCCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc2517359cb34385bb9b5302035fc2bd | C#CCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCC#C.C(CCC)[Li].COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)=O>>[Si](C)(C)(C(C)(C)C)OCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O | [CH:25]#[C:26][CH2:27][CH2:28][O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36].[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[C:23]2=[O:24])[cH:37][cH:38]1>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7... | C#CCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 32c43bb8c46f4cb5536ede6cee58ac07810f00f75e5d5068c9f1bf838a1ce5f8 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc(C2COc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#8:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#8:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | 93 | [{"value": 93.0, "product": "[Si](C)(C)(C(C)(C)C)OCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "[Si](C)(C)(C(C)(C)C)OCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | 4-(t-Butyldimethylsilyloxy)-1-butyne (1.17 g, 6.4 mmol) was dissolved in dry tetrahydrofuran (20 ml) under argon atmosphere, which was then cooled down to −78° C. n-Butyllithium (2.29 ml, 5.72 mmol, 2.5M solution in tetrahydrofuran) was slowly added dropwise thereto, and the mixture was stirred at −78° C. for 30 minute... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | null | O1CCCC1 | -78 | 0.5 | C#CCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1>O1CCCC1>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7b88fd5bae64d6f9748f798e29b7a11 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCO[Si](C)(C)C(C)(C)C)cc1 | [Si](C)(C)(C(C)(C)C)OCCC#CC1(C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O>>[Si](C)(C)(C(C)(C)C)OCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | O[C:23]1([C:24]#[C:25][CH2:26][CH2:27][O:28][Si:29]([CH3:30])([CH3:31])[C:32]([CH3:33])([CH3:34])[CH3:35])[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:37][cH:36]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCO[Si](C)(C)C(C)(C)C)cc1 | null | [Pd] | C(C)(=O)OCC | Reduction | OtherReaction | dd0f7926f8b783b529320846249c3df6a6f2662939c7a847635c271fc30085c5 | 60a7236e2fc7f14079d4445ee3fd2aaed5c023fa0e86b6d5702a23963f159e6a | c1ccc(C2COc3ccccc3C2)cc1 | O-[C;H0;D4;+0:1]1(-[C;H0;D2;+0:2]#[C;H0;D2;+0:3]-[C:4]-[C:5])-[c:6](:[c:7]):[c:8]-[#8:9]-[C:10]-[C:11]-1(-[C;D1;H3:12])-[c:13]>>[C:5]-[C:4]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[CH;D3;+0:1]1-[c:6](:[c:7]):[c:8]-[#8:9]-[C:10]-[C:11]-1(-[C;D1;H3:12])-[c:13] | 44 | [{"value": 44.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.4, "product": "[Si](C)(C)(C(C)(C)C)OCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-[4-(t-butyl dimethylsilyloxy)-1-butynyl]4-hydroxy-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (1.6 g, 2.95 mmol) was dissolved in ethyl acetate (30 ml), and then 10% Pd/C (0.6 g) was added thereto. The reaction suspension was stirred under hydrogen for 1 hour, filtered, and concentrated. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Alkyne | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | [Pd].C(C)(=O)OCC | null | 1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCCO[Si](C)(C)C(C)(C)C)cc1>[Pd].C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2933858986d942dca62ba01a4267a183 | C1CCOC1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCO)cc1 | COCOC1=CC=C2CC(COC2=C1)(C)C1=CC=C(C=C1)OCOC.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [CH2:24]1[CH2:25][CH2:26][CH2:27][O:28]1.[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH2:23]2)[cH:29][cH:30]1>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:1... | C1CCOC1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCO)cc1 | null | null | null | C-C Coupling | OtherReaction | 0d402243fa6071b1bf19428df3868376cde9e65cfaacb8bf3820065b708786dc | 00ba751883474d7cfe7b882354bfe6f6e69aab672fa94c344071bebe5eb67707 | c1ccc(C2COc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#8:5]-[c:6]:[c:7](:[c:8])-[CH2;D2;+0:9]-1.[C:10]1-[C:11]-[C:12]-[O;H0;D2;+0:13]-[CH2;D2;+0:14]-1>>[C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#8:5]-[c:6]:[c:7](:[c:8])-[CH;D3;+0:9]-1-[CH2;D2;+0:14]-[C:10]-[C:11]-[C:12]-[OH;D1;+0:13] | 92.4 | [{"value": 92.4, "product": "OCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 6 | HOUR | (3RS,4RS)-4-[4-(t-butyl dimethylsilyloxy)-1-butyl 3-(7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (680 mg, 1.28 mmol) was dissolved in tetrahydrofuran (10 ml), and cooled to 0° C. To this solution was added tetrabutylammonium fluoride (2.6 ml, 2.56 mmol), and the reaction mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | C1CCOC1.c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | null | null | 0 | 6 | C1CCOC1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d36a91cb6554254afe25a8ebb482884 | BrCc1ccccc1.C1CCOC1.CCOC(C)=O>>OCCCCOCc1ccccc1 | C(C)(=O)OCC.[H-].[Na+].C1CCOC1.CCCCCC.C(C1=CC=CC=C1)Br>>C1(=CC=CC=C1)COCCCCO | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.C1[CH2:3][CH2:4][CH2:5][O:6]1.CCO[C:2](C)=[O:1]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | BrCc1ccccc1.C1CCOC1.CCOC(C)=O | OCCCCOCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 12f13b161fdabb90681f91ba8e55dc940ad62bf7164961553f155eb95da38f05 | e52e531861792ab00573b3db263bd7ead92d5b476ea2f8bf5af25debf9c25139 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C-O-[C;H0;D3;+0:5](-C)=[O;H0;D1;+0:6].C1-[CH2;D2;+0:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-1>>[OH;D1;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 16 | [{"value": 16.0, "product": "C1(=CC=CC=C1)COCCCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of diol compound (4.51 g, 50 mmol) in dry THF (50 ml) was added 60% NaH (1.6 g, 43 mmol) at 0° C. After stirring for 2 hours, benzyl bromide (5.7 g, 33 mmol) was added dropwise and stirred for 15 hours. After the reaction was completed, ice-water was added, and the mixture was extracted with ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether | Ether.Primary alcohol | C1CCOC1 | null | c1ccccc1 | HBr | null | null | 2 | BrCc1ccccc1.C1CCOC1.CCOC(C)=O>>OCCCCOCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d9719f91449449e8cea4f01ba43a8ea | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCI)cc1.N#C[NH-]>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCNC#N)cc1 | O.ICCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.C([O-])([O-])=O.[K+].[K+].C(#N)[NH-]>>C(#N)NCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | I[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]2)([CH3:8])[CH2:9][S:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21.[NH-:29][C:30]#[N:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:1... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCI)cc1.N#C[NH-] | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCNC#N)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 159bd3409a09fe25ca40db93670537318d41197d3dac50a4099202ef52b8c2b3 | ef1178d6b7abc737a24d1e1e0820bf322b7dbbc60e93f20cdb207c398af783a9 | c1ccc(C2CSc3ccccc3C2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[N;D1;H0:4]#[C:5]-[NH-;D1:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]#[N;D1;H0:4] | 74 | [{"value": 74.0, "product": "C(#N)NCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.9, "product": "C(#N)NCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 4 | HOUR | To a solution of (3RS,4RS)-4-[9-iodononyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (381 mg, 0.69 mmol) in anhydrous dimethylformamide (2 ml) were added potassium carbonate (238 mg, 1.72 mmol) and cyanoamide (116 mg, 2.76 mmol), which was then stirred for 4 h at 50° C. Water was added thereto, and the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Cyanamide | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | I- | CN(C=O)C | 50 | 4 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCI)cc1.N#C[NH-]>CN(C=O)C>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCNC#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b5f43cf482f48e3aeb92b00209f2216 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCBr)cc1.[N-]=[N+]=[N-]>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN=[N+]=[N-])cc1 | CCCCCC.BrCCCCOCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.CS(=O)C.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CCCCOCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | Br[CH2:32][CH2:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:37][cH:36]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21.[N-:33]=[N+:34]=[N-:35]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCBr)cc1.[N-]=[N+]=[N-] | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN=[N+]=[N-])cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | c1ccc(C2COc3ccccc3C2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[N-;H0;D1:4]=[#7;+:5]=[N;-;D1;H0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D2;+0:4]=[#7;+:5]=[N;-;D1;H0:6] | null | [] | 80 | CELSIUS | 3 | HOUR | To (3RS,4RS)-4-(9-bromo-5-oxanonyl)-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (276 mg, 0.5 mmol) in. DMSO was added sodium azide (65.1 mg, 1 mmol). The mixture was stirred at 80° C. for 3 h. After cooling, the mixture was extracted with ethyl acetate, dried over MgSO4, and filtered. The filtrate was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Br- | C(C)(=O)OCC | 80 | 3 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCBr)cc1.[N-]=[N+]=[N-]>C(C)(=O)OCC>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN=[N+]=[N-])cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16076b831d744e4eacc73f1a90ab5db8 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN=[N+]=[N-])cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN)cc1 | N(=[N+]=[N-])CCCCOCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC>>NCCCCOCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | [N-]=[N+]=[N:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:35][cH:34]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([C... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN=[N+]=[N-])cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN)cc1 | null | [Pd] | null | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(C2COc3ccccc3C2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 183.5 | [{"value": 183.5, "product": "NCCCCOCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The (3RS,4RS)-4-(9-azido-5-oxanonyl)-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (250 mg, 0.19 mmol) was dissolved in methanoltetrahydofura (1.8/0.2 mL). Palladium charchol (75 mg, 0.05 mmol) was added, and resulting mixture was stirred at rt under hydrogen for 2 h. The mixture solution was concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | [Pd] | null | 2 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN=[N+]=[N-])cc1>[Pd]>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCOCCCCN)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7af65a5ad4c44dc39c3e66abdfe7ff09 | CC(Br)Br.CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC>>CCOC(=O)C(CCBr)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | O.[H-].[Na+].FC(CCCC(C(=O)OCC)C(=O)OCC)(C(F)(F)F)F.BrC(C)Br>>BrCCC(C(=O)OCC)(C(=O)OCC)CCCC(C(F)(F)F)(F)F | Br[CH:8]([CH3:7])[Br:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:10][CH2:11][CH2:12][C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19])[C:20](=[O:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][Br:9])([CH2:10][CH2:11][CH2:12][C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19])[C:20](=... | CC(Br)Br.CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC | CCOC(=O)C(CCBr)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | null | null | C(OC)COC | C-C Coupling | OtherReaction | 08dbade1ac53fa117a4c435d97671d8cce48898bc2eb7f1e5ba3aab7aaaf9bb2 | 12d4ebf75d32a547bc6f1ee62ac338f5a296e49bfc939ff5177370adfa8e61d6 | null | Br-[CH;D3;+0:1](-[Br;D1;H0:2])-[CH3;D1;+0:3].[C:4]-[C:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[Br;D1;H0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[C;H0;D4;+0:6](-[C:5]-[C:4])(-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 71.9 | [{"value": 71.9, "product": "BrCCC(C(=O)OCC)(C(=O)OCC)CCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Diethyl 2-(4,4,5,5,5-pentafluoropentyl)propane-1,3-dioate (51 0 mg, 1.592 mmol) was dissolved in anhydrous dimethoxyethane (5 ml). Sodium hydride (60%. 88 mg, 2.2 mmol) was added to the solution and then stirred at room temperature for 1 h under nitrogen atmosphere. Dibromoethane (0.82 ml, 9.55 mmol) was added to the m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ester.Ester | Primary halide.Ester.Ester | null | null | null | HBr | C(OC)COC | null | 1 | CC(Br)Br.CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC>C(OC)COC>CCOC(=O)C(CCBr)(CCCC(F)(F)C(F)(F)F)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b71317802264f7b9f5ec3409093907e | COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2O)cc1 | COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)=O.[BH4-].[Na+].[NH4+].[Cl-]>>OC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[C:19]2=[O:20])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[CH:19]2[OH:20])[cH:21][cH:22]1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2O)cc1 | null | null | CCO.C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 2ad5f2e76a20f8959d746d09a75554b6c0a56cc59770a70bc7e29fd6d566db2e | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C2CSc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[CH;D3;+0:9]-1-[OH;D1;+0:10] | 84.2 | [{"value": 84.0, "product": "OC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "OC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (6.29 g, 20 mmol) in THF (20 ml) and EtOH (10 ml) was added NaBH4 (1.51 g, 40 mmol), which was stirred overnight at room temperature. The reaction solution was added saturated aqueous NH4Cl solution, extracted with CHCl3, and washed with brine. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | null | CCO.C1CCOC1 | null | 8 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>CCO.C1CCOC1>COc1ccc(C2(C)CSc3cc(OC)ccc3C2O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6665b512621e40c1aae7183b5bfa7284 | C=CC[Si](C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2O)cc1>>C=CCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | OC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.C(C=C)[Si](C)(C)C>>C(C=C)C1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | C[Si](C)(C)[CH2:3][CH:2]=[CH2:1].O[CH:4]1[c:5]2[cH:6][cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]2[S:13][CH2:14][C:15]1([CH3:16])[c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]1>>[CH2:1]=[CH:2][CH2:3][CH:4]1[c:5]2[cH:6][cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]2[S:13][CH2:14][C:15]1([CH3:16])[c:17]1[cH:18][cH:19][c:2... | C=CC[Si](C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2O)cc1 | C=CCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | null | [I-].[Zn+2].[I-] | ClCCCl | C-C Coupling | Nucleophilic substitution OH - alkyl silane | 87f3f89061a4e94ebf46af955596d077932420b8159eb9be9fea68220523dc6e | 9f49af4eb471ea40ac6539f257a36dd6a007733cab86db0b0c2ff45e49694fd6 | c1ccc(C2CSc3ccccc3C2)cc1 | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].O-[CH;D3;+0:4]1-[c:5](:[c:6]):[c:7]-[#16:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[c:5](:[c:6]):[c:7]-[#16:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12] | 74.4 | [{"value": 74.0, "product": "C(C=C)C1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.4, "product": "C(C=C)C1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | To a solution of 4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (11.4 g, 36.3 mmol) in 1,2-dichloroethane (360 ml) was added zinc iodide (13.9 g, 43.5 mmol) and allyltrimethylsilane (11.5 ml, 72.5 mmol) which was stirred for 1 day at room temperature. The reaction solution was added saturated aqueous NHCl ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Allyl.Silyl protective group | Allyl | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2.c1ccccc1 | HO- | [I-].[Zn+2].[I-].ClCCCl | null | 24 | C=CC[Si](C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2O)cc1>[I-].[Zn+2].[I-].ClCCCl>C=CCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9626e03549574634b9d29376fd4f936e | CC(C)(C)OC(=O)CBr.OCC(F)(F)F>>CC(C)(C)OC(=O)COCC(F)(F)F | FC(CO)(F)F.[H-].[Na+].BrCC(=O)OC(C)(C)C>>FC(COCC(=O)OC(C)(C)C)(F)F | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:9][CH2:10][C:11]([F:12])([F:13])[F:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][CH2:10][C:11]([F:12])([F:13])[F:14] | CC(C)(C)OC(=O)CBr.OCC(F)(F)F | CC(C)(C)OC(=O)COCC(F)(F)F | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4541d644834c1bca555c4310180b1edadd2271c26488a32c314314a2e4f9c76f | 1858e49e1dc71f5ec31a1f9e719a3d52cdbfbbd98e3e0f8a48e0f56789173453 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[C:13]-[OH;D1;+0:14]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:14]-[C:13]-[C:10](-[F;D1;H0:9])(-[F;D1;H0:11])-[F;D1;H0:12] | 100.8 | [{"value": 100.8, "product": "FC(COCC(=O)OC(C)(C)C)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a suspension of NaH (240 mg, 60–72%) in tetrahydrofuran (5 ml) was added 2,2,2-trifluoroethanol (500 mg, 5 mmol) at 0° C. After the mixture was stirred for 45 minutes at room temperature, t-butyl bromoacetate (0.9 ml, 6 mmol) was added and stirred at room temperature for 15 hours. The mixture was poured into ice-wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Ester.Ether | null | null | null | HBr | O1CCCC1 | null | 0.75 | CC(C)(C)OC(=O)CBr.OCC(F)(F)F>O1CCCC1>CC(C)(C)OC(=O)COCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81e0c8117db443f88defe8568bf332c7 | CC(C)(C)OC(=O)COCC(F)(F)F>>OCCOCC(F)(F)F | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(C)(C)OC(COCC(F)(F)F)=O>>FC(COCCO)(F)F | CC(C)(C)O[C:2](=[O:1])[CH2:3][O:4][CH2:5][C:6]([F:7])([F:8])[F:9]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([F:7])([F:8])[F:9] | CC(C)(C)OC(=O)COCC(F)(F)F | OCCOCC(F)(F)F | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 005ed55ca3498ead0a405ca36187c0e85620a6bf11f425e5d3f35c18fb5c1feb | b685880638f3f6d2edbccd81c5d4aa218aa09f2b7a06a7fe669dee5c38c3c0e3 | null | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 81.3 | [{"value": 81.0, "product": "FC(COCCO)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "FC(COCCO)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | To a suspension of LAH (750 mg, 19.7 mmol) in ether (40 ml) was added crude t-butyl-2,2,2-trifluoroethoxyacetate (2.0 g, 9.3 mmol) in ether (10 ml) at 0° C. The mixture was stirred for 45 minutes at 0° C. Then, the mixture was poured into ice-water and extracted with ether. The organic layer was dried over anhydrous ma... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Primary alcohol | null | null | null | HO- | CCOCC | 0 | 0.75 | CC(C)(C)OC(=O)COCC(F)(F)F>CCOCC>OCCOCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4ad9f16d5af4185bdfa0c2a0ae05eb7 | Cc1ccc(S(=O)(=O)Cl)cc1.OCCOCC(F)(F)F>>Cc1ccc(S(=O)(=O)OCCOCC(F)(F)F)cc1 | O.FC(COCCO)(F)F.C(C)N(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)OCCOCC(F)(F)F)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH2:11][O:12][CH2:13][C:14]([F:15])([F:16])[F:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1 | Cc1ccc(S(=O)(=O)Cl)cc1.OCCOCC(F)(F)F | Cc1ccc(S(=O)(=O)OCCOCC(F)(F)F)cc1 | null | null | ClCCl | 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] | 63 | [{"value": 63.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)OCCOCC(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "C1(=CC=C(C=C1)S(=O)(=O)OCCOCC(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a suspension of LAH (750 mg, 19.7 mmol) in ether (40 ml) was added crude t-butyl-2,2,2-trifluoroethoxyacetate (2.0 g, 9.3 mmol) in ether (10 ml) at 0° C. The mixture was stirred for 45 minutes at 0° C. Then, the mixture was poured into ice-water and extracted with ether. The organic layer was dried over anhydrous ma... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | ClCCl | null | 48 | Cc1ccc(S(=O)(=O)Cl)cc1.OCCOCC(F)(F)F>ClCCl>Cc1ccc(S(=O)(=O)OCCOCC(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9e49ffc9799b405ba0b3b5399a789cc0 | CC([O-])=S.Cc1ccc(S(=O)(=O)OCCOCC(F)(F)F)cc1>>CC(=S)OCCOCC(F)(F)F | C1(=CC=C(C=C1)S(=O)(=O)OCCOCC(F)(F)F)C.C(C)(=S)[O-].[K+].O>>C(C)(=S)OCCOCC(F)(F)F | [CH3:1][C:2](=[S:3])[O-:4].Cc1ccc(S(=O)(=O)O[CH2:5][CH2:6][O:7][CH2:8][C:9]([F:10])([F:11])[F:12])cc1>>[CH3:1][C:2](=[S:3])[O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([F:10])([F:11])[F:12] | CC([O-])=S.Cc1ccc(S(=O)(=O)OCCOCC(F)(F)F)cc1 | CC(=S)OCCOCC(F)(F)F | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 09f00ef41d592c2a2e82cae5f794c4155e4db8f72d5ba18e5ecb35e69d61c0b3 | 3e9ec1d45a0c4b1376941cacc989fb4a4b53e4fab84f83b353ec22cbdeb4599b | null | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#8:3]):c:c:1.[C;D1;H3:4]-[C:5](-[O-;H0;D1:6])=[S;D1;H0:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5](-[C;D1;H3:4])=[S;D1;H0:7] | 87.3 | [{"value": 87.0, "product": "C(C)(=S)OCCOCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "C(C)(=S)OCCOCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | 2-(2,2,2-trifluoroethoxy)ethyl p-toluenesulfonate (14.0 g, 47 mmol) and potassium thioacetate (10.0 g, 88 mmol) were dissolved in acetone (100 ml) and the mixture was stirred at room temperature for 2 days. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous ma... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Thiocarbonyl | Ether | c1ccccc1 | null | null | TsOH.HO- | CC(=O)C | null | 48 | CC([O-])=S.Cc1ccc(S(=O)(=O)OCCOCC(F)(F)F)cc1>CC(=O)C>CC(=S)OCCOCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8c7a6864281443d9dd32c687151bd2f | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCCCCCCCSCCOCC(F)(F)F)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCOCC(F)(F)F | COCOC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCSCCOCC(F)(F)F>>OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCOCC(F)(F)F | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][S:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29][CH2:30][CH2:31][O:32][CH2:33][C:34]([F:35])([F:36])[F:37])[cH:9][cH:8]1>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([OH:7])[c... | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCCCCCCCSCCOCC(F)(F)F)cc1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCOCC(F)(F)F | null | null | Cl.CO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2CSc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 85.1 | [{"value": 85.0, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCOCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCOCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | (3RS,4RS)-7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{9-[2-(2,2,2-trifluoroethoxy)ethylthio]nonyl}thiochroman (136 mg, 0.211 mmol) was dissolved in 10% HCl/MeOH (20 ml) and the mixture was stirred at room temperature for 1 day. After the reaction was completed, the mixture was concentrated, and silica gel c... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | HO- | Cl.CO | null | 24 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2CCCCCCCCCSCCOCC(F)(F)F)cc1>Cl.CO>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCOCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c135dc6d7ce4007b8a2dc6b882435cc | C#CCCCCO.CC(C)(C)[Si](C)(C)Cl>>C#CCCCCO[Si](C)(C)C(C)(C)C | O.C(CCCC#C)O.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>[Si](C)(C)(C(C)(C)C)OCCCCC#C | [CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].Cl[Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14] | C#CCCCCO.CC(C)(C)[Si](C)(C)Cl | C#CCCCCO[Si](C)(C)C(C)(C)C | null | null | CN(C=O)C | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 99 | [{"value": 99.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCC#C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "[Si](C)(C)(C(C)(C)C)OCCCCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 5-hexyne-1-ol (4.81 g, 49.0 mmol) in N,N-dimethylformamide (100 ml) were added imidazole (4.0 g, 59.0 mmol) and t-butyldimethylsilylchloride (8.12 g, 54.0 mmol) at 0° C., which was then stirred at the same temperature for 3 hour After the reaction was completed, water was added to the reaction solution... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | CN(C=O)C | null | 3 | C#CCCCCO.CC(C)(C)[Si](C)(C)Cl>CN(C=O)C>C#CCCCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae864e8e07614a33b661deb59b3726e9 | C#CCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCO[Si](C)(C)C(C)(C)C)cc1 | [Cl-].[NH4+].COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)=O.[Si](C)(C)(C(C)(C)C)OCCCCC#C.C(CCC)[Li]>>[Si](C)(C)(C(C)(C)C)OCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O | [CH:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][Si:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[CH3:34].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[C:19]2=[O:20])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[C... | C#CCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | af22e63626241b7ef7b156ca9e8464011387cb2140508f9d238feb5631c67f1a | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc(C2CSc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#16:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | 93.1 | [{"value": 93.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "[Si](C)(C)(C(C)(C)C)OCCCCC#CC1(C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 1 | HOUR | To a solution of 6-(t-butyldimethylsilyloxy)-1-hexyne (10.8 g, 50.9 mmol) in dry tetrahydrofiuran (100 ml) was added dropwise n-butyl lithium (30.1 ml, 48.9 mmol, 1.63M in tetrahydrofuran) at −78° C., which was then stirred at −20° C. for 1 hour. To the reaction mixture , was then added 7-methoxy-3-(4-methoxyphenyl)-3-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | null | O1CCCC1 | -20 | 1 | C#CCCCCO[Si](C)(C)C(C)(C)C.COc1ccc(C2(C)CSc3cc(OC)ccc3C2=O)cc1>O1CCCC1>COc1ccc(C2(C)CSc3cc(OC)ccc3C2(O)C#CCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb0f4149bade4b4d8ec79d5f0cbb71ff | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCO)cc1>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCC=O)cc1 | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C.OCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC>>COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCC=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][S:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:1... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCO)cc1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCC=O)cc1 | null | null | ClCCl.O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(C2CSc3ccccc3C2)cc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 94 | [{"value": 94.0, "product": "COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCC=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of oxalyl chloride (238 mg, 1.88 mmol) in dichloromethane (5 ml) was added dimethylsulfoxide (316 mg, 3.75 mmol) in dichloromethane (1 ml) at −70° C., which was then stirred at the same temperature for 10 minutes. Next, to the solution was added 4-(6-hydroxyhexyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | null | ClCCl.O | null | 0.166667 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCO)cc1>ClCCl.O>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCC=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4a3eea3c883b434baacd67f68df6e803 | COC(=O)C=CCCCCCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1>>COC(=O)CCCCCCCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | CCCCCC.COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCC=CC(=O)OC.[BH4-].[Na+].O>>COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCCCC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]2[S:21][CH2:22][C:23]1([CH3:24])[c:25]1[cH:26][cH:27][c:28]([O:29][CH3:30])[cH:31][cH:32]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[c:13... | COC(=O)C=CCCCCCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | COC(=O)CCCCCCCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | null | [Ni] | O1CCCC1.CO.C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc(C2CSc3ccccc3C2)cc1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8] | 76 | [{"value": 73.0, "product": "COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCCCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.0, "product": "COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)CCCCCCCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of methyl 8-[7-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]-2-octenate (160 mg, 0.34 mmol) in methanol (3 ml) and tetrahydrofuran (1 ml) were added sodium borohydride (129 mg, 3.40 mmol) and nickel (1 ml) chloride hexahydrate (16 mg, 0.068 mmol) at 0° C., which was then stirred at the same temper... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccc2c(c1)CCCS2.c1ccccc1 | null | [Ni].O1CCCC1.CO.C(C)(=O)OCC | null | 2 | COC(=O)C=CCCCCCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1>[Ni].O1CCCC1.CO.C(C)(=O)OCC>COC(=O)CCCCCCCC1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-486aeabdab91462684b384f10f955acb | CC(C)(C)[Si](C)(C)OCCOCCO.CCCCCC>>C#CCOCCOCCO[Si](C)(C)C(C)(C)C | O.[Si](C)(C)(C(C)(C)C)OCCOCCO.[H-].[Na+].CCCCCC>>[Si](C)(C)(C(C)(C)C)OCCOCCOCC#C | [OH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17].CCC[CH2:1][CH2:2][CH3:3]>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17] | CC(C)(C)[Si](C)(C)OCCOCCO.CCCCCC | C#CCOCCOCCO[Si](C)(C)C(C)(C)C | null | null | O1CCCC1.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 31df8da2da2f64a391c7b39cd4750357cec37e3ef4a267b58feeb6fc7193be62 | e296dea26626f297ec84ee3a5e339e8c1a0f57ab4772edb1a14b70d305134301 | null | C-C-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH3;D1;+0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:3]-[C;H0;D2;+0:2]#[CH;D1;+0:1] | 38 | [{"value": 38.0, "product": "[Si](C)(C)(C(C)(C)C)OCCOCCOCC#C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-(t-butyldimethylsilyloxy)-3-oxa-1-pentanol (2.16 g, 9.8 mmol) in dry tetrahydrofuran (20 ml) was added sodium hydride (432 mg, 60% in oil, 10.8 mmol) at room temperature. The mixture was stirred for 30 minutes, and propalgyl bromide (2.9 g, 19.6 mmol) was added thereto. The mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether.Alkyne | null | null | null | Other | O1CCCC1.C(C)(=O)OCC | null | 0.5 | CC(C)(C)[Si](C)(C)OCCOCCO.CCCCCC>O1CCCC1.C(C)(=O)OCC>C#CCOCCOCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-985ad99cf9e547d79a98f2f0c6090a19 | C#CCOCCOCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2=O)cc1>>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2(O)C#CCOCCOCCO[Si](C)(C)C(C)(C)C)cc1 | [Cl-].[NH4+].COCOC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OCOC)=O.[Si](C)(C)(C(C)(C)C)OCCOCCOCC#C.C(CCC)[Li]>>[Si](C)(C)(C(C)(C)C)OCCOCCOCC#CC1(C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O | [CH:25]#[C:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][Si:35]([CH3:36])([CH3:37])[C:38]([CH3:39])([CH3:40])[CH3:41].[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][S:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[C:23]2=[O:24])[cH:42][cH:43]1>>[CH3:... | C#CCOCCOCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2=O)cc1 | COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2(O)C#CCOCCOCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | af22e63626241b7ef7b156ca9e8464011387cb2140508f9d238feb5631c67f1a | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc(C2CSc3ccccc3C2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#16:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | 68.1 | [{"value": 68.0, "product": "[Si](C)(C)(C(C)(C)C)OCCOCCOCC#CC1(C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "[Si](C)(C)(C(C)(C)C)OCCOCCOCC#CC1(C(CSC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | -20 | CELSIUS | 1 | HOUR | To a solution of 9-(t-butyldimethylsilyloxy)-4,7-dioxa-1-nonyne (1.03 g, 4.01 mmol) in dry tetrahydrofuran (10 ml) was added dropwise -n-butyl lithium (2.3 ml, 3.74 mmol, 1.63 mole/l in tetrahydrofuran) at −78° C., which was then stirred at −20° C. for 1 hour. Then, to this reaction mixture was added 7-methoxymethoxy-3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2 | null | O1CCCC1 | -20 | 1 | C#CCOCCOCCO[Si](C)(C)C(C)(C)C.COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2=O)cc1>O1CCCC1>COCOc1ccc(C2(C)CSc3cc(OCOC)ccc3C2(O)C#CCOCCOCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4473e85e2974a549bde94f5d4c89367 | C#CCCCO.CC(C)(C)[Si](C)(C)OCCCBr>>C#CCCCOCCCO[Si](C)(C)C(C)(C)C | O.BrCCCO[Si](C)(C)C(C)(C)C.C(CCC#C)O.[H-].[Na+]>>[Si](C)(C)(C(C)(C)C)OCCCOCCCC#C | [CH:1]#[C:2][CH2:3][CH2:4][CH2:5][OH:6].Br[CH2:7][CH2:8][CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17] | C#CCCCO.CC(C)(C)[Si](C)(C)OCCCBr | C#CCCCOCCCO[Si](C)(C)C(C)(C)C | null | null | CCCCCC.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 21 | [{"value": 21.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCOCCCC#C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.6, "product": "[Si](C)(C)(C(C)(C)C)OCCCOCCCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | To a solution of 4-pentyn-1-ol (2.1 g, 26.1 mmol) in dry N,N-dimetylformamide (100 ml) was added sodium hydride (1.04 g, 60% in oil, 26.1 mmol) at room temperature. The mixture was stirred for 40 minutes, and 1-bromo-3-(t-butyldimethylsilyloxy) propane (4.4 g, 17.4 mmol) was added thereto. The mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | null | HBr | CCCCCC.CN(C=O)C.C(C)(=O)OCC | null | 0.666667 | C#CCCCO.CC(C)(C)[Si](C)(C)OCCCBr>CCCCCC.CN(C=O)C.C(C)(=O)OCC>C#CCCCOCCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53026435b997496fbc94e942803c281e | C#CCCCCO.CCOC(=O)CBr>>C#CCCCCOCC(=O)OCC | O.BrCC(=O)OCC.C(CCCC#C)O.[H-].[Na+]>>C(COCCCCC#C)(=O)OCC | [CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].Br[CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13] | C#CCCCCO.CCOC(=O)CBr | C#CCCCCOCC(=O)OCC | null | null | CCCCCC.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4541d644834c1bca555c4310180b1edadd2271c26488a32c314314a2e4f9c76f | 1858e49e1dc71f5ec31a1f9e719a3d52cdbfbbd98e3e0f8a48e0f56789173453 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C:7]-[C:6] | 37 | [{"value": 37.0, "product": "C(COCCCCC#C)(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "C(COCCCCC#C)(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-hexyn-1-ol (2.0 g, 20.4 mmol) in N,N-dimethylformamide (40 ml) was added sodium hydride (815 g, 60% in oil, 20.41 mmol) at 0° C. The mixture was stirred for 1 hour, and ethyl bromoacetate (3.4 ml, 30.5 mmol) was added thereto. The mixture was stirred at the same temperature for 1 hour. After the reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Ester.Ether | null | null | null | HBr | CCCCCC.CN(C=O)C.C(C)(=O)OCC | null | 1 | C#CCCCCO.CCOC(=O)CBr>CCCCCC.CN(C=O)C.C(C)(=O)OCC>C#CCCCCOCC(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2235ddf34e06478eb42a7b73609e4d6d | CC(C)(C)[Si](C)(C)OCCCCO.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCCCCO[Si](C)(C)C(C)(C)C)cc1 | O.[Si](C)(C)(C(C)(C)C)OCCCCO.C(C)N(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)OCCCCO[Si](C)(C)C(C)(C)C)C | [OH:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH... | CC(C)(C)[Si](C)(C)OCCCCO.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCCCCO[Si](C)(C)C(C)(C)C)cc1 | null | null | ClCCl.CCCCCC.C(C)(=O)OCC | 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] | 81.4 | [{"value": 81.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)OCCCCO[Si](C)(C)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "C1(=CC=C(C=C1)S(=O)(=O)OCCCCO[Si](C)(C)C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4-(t-butyldimethylsilyloxy)-1-butanol (2.8 g, 13.7 mmol) in dichloromethane (30 ml) were added triethyamine (3.83 ml, 27.4 mmol) and p-toluenesulfonyl chloride (2.88 g, 15.1 mmol) at 0° C., which was then stirred at the same temperature for 2 hours. After the reaction was completed, water was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | ClCCl.CCCCCC.C(C)(=O)OCC | null | 2 | CC(C)(C)[Si](C)(C)OCCCCO.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl.CCCCCC.C(C)(=O)OCC>Cc1ccc(S(=O)(=O)OCCCCO[Si](C)(C)C(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a2e73f06549427d8cbb512565fe019d | CCCC(CC=CCC(=O)O)C1c2ccc(O)cc2SCC1(C)c1ccc(OC)cc1>>CCCC(CCCCC(=O)O)C1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)C(CC=CCC(=O)O)CCC.C(C)(=O)OCC>>COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)C(CCCCC(=O)O)CCC | [CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH:6]=[CH:7][CH2:8][C:9](=[O:10])[OH:11])[CH:12]1[c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:19][c:20]2[S:21][CH2:22][C:23]1([CH3:24])[c:25]1[cH:26][cH:27][c:28]([O:29][CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[OH:11])[CH:12]1[c:13]2[... | CCCC(CC=CCC(=O)O)C1c2ccc(O)cc2SCC1(C)c1ccc(OC)cc1 | CCCC(CCCCC(=O)O)C1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 | null | O.[Pt](=O)=O | null | Miscellaneous | OtherReaction | 5b3aadc337038ce4d56616083181fcdb7df90626e7a012c21497c4b51b07950e | b3459c109bd254a21bc857ecee1ac83a8b4bf01bca8b217fb3b07e012c0f1c4b | c1ccc(C2CSc3ccccc3C2)cc1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:13]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | 87 | [{"value": 87.0, "product": "COC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)OC)C(CCCCC(=O)O)CCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 6-[7-hydroxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]-3-nonenoic acid (254 mg, 0.56 mmol) in ethyl acetate (5 ml) was added platinum(IV) oxide hydrate (130 mg, 0.56 mmol) and the mixture was stirred for 16 h at room temperature under hydrogen atmosphere. The catalyst was filtered off and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCS2.c1ccccc1 | Other | O.[Pt](=O)=O | null | 16 | CCCC(CC=CCC(=O)O)C1c2ccc(O)cc2SCC1(C)c1ccc(OC)cc1>O.[Pt](=O)=O>CCCC(CCCCC(=O)O)C1c2ccc(OC)cc2SCC1(C)c1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7f5d06a6ac7405898a9e00a73e7a97e | Brc1cccc(C2OCCO2)c1.COc1ccc(C2CSc3cc(OC)ccc3C2=O)cc1>>COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(C3OCCO3)c2)cc1 | O.COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)=O.BrC=1C=C(C=CC1)C1OCCO1.C(CCC)[Li]>>O1C(OCC1)C=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O | Br[c:20]1[cH:21][cH:22][cH:23][c:24]([CH:25]2[O:26][CH2:27][CH2:28][O:29]2)[cH:30]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]3[C:18]2=[O:19])[cH:31][cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[... | Brc1cccc(C2OCCO2)c1.COc1ccc(C2CSc3cc(OC)ccc3C2=O)cc1 | COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(C3OCCO3)c2)cc1 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | f0567a74177aa806ebb3ffac94faf10ea69f9c819848294f7ad3cc7907e44cb1 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2CSc3ccccc3C2c2cccc(C3OCCO3)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[C:8](-[c:9])-[C:10]-[#16:11]-[c:12]:[c:13]-1:[c:14]>>[OH;D1;+0:6]-[C;H0;D4;+0:7]1(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:8](-[c:9])-[C:10]-[#16:11]-[c:12]:[c:13]-1:[c:14] | 50 | [{"value": 50.0, "product": "O1C(OCC1)C=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "O1C(OCC1)C=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | MINUTE | To a solution of 2-(3-bromophenyl)-1,3-dioxolane (3.04 g, 13.28 mmol) in dry tetrahydrofuran (35 ml) was added n-butyl lithium (8.37 ml, 13.316 mmol, 1.59 mol/l tetrahydrofuran solution) dropwise as −78° C. over 10 minutes and stirred for 50 minutes at the same temperature. Then to the reaction mixture was added 7-meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1.C1COCO1 | Br- | O1CCCC1 | null | 0.833333 | Brc1cccc(C2OCCO2)c1.COc1ccc(C2CSc3cc(OC)ccc3C2=O)cc1>O1CCCC1>COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(C3OCCO3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-183140d4111443ef90741e80372e6977 | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1.COc1ccc(C2CSc3cc(OC)ccc3C2=O)cc1>>COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 | O.COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)=O.BrC=1C=C(CO[Si](C)(C)C(C)(C)C)C=CC1.C(CCC)[Li]>>[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O | Br[c:20]1[cH:21][cH:22][cH:23][c:24]([CH2:25][O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]3[C:18]2=[O:19])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9... | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1.COc1ccc(C2CSc3cc(OC)ccc3C2=O)cc1 | COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | f0567a74177aa806ebb3ffac94faf10ea69f9c819848294f7ad3cc7907e44cb1 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2CSc3ccccc3C2c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[C:8](-[c:9])-[C:10]-[#16:11]-[c:12]:[c:13]-1:[c:14]>>[OH;D1;+0:6]-[C;H0;D4;+0:7]1(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:8](-[c:9])-[C:10]-[#16:11]-[c:12]:[c:13]-1:[c:14] | 28.1 | [{"value": 28.0, "product": "[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.1, "product": "[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | 50 | MINUTE | To a solution of (3-bromobenzyloxy)-t-butyldimethylsilane (2.207 g, 7.326 mmol) in dry tetrahydrofuran (20 ml) was added n-butyl lithium (4.18 ml, 6.66 mmol, 1.59M tetrahydrofuran solution) at −78° C. over 25 minutes and stirred for 50 minutes. Then to the reaction mixture was added 7-methoxy-3-(4-methoxyphenyl)thiochr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | Br- | O1CCCC1 | null | 0.833333 | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1.COc1ccc(C2CSc3cc(OC)ccc3C2=O)cc1>O1CCCC1>COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7cf417c78fd8440aba2a5f7d3af6b5d0 | COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1>>COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 | [Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1(C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC)O.C(#N)[BH3-].[Na+].O>>[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC | O[C:18]1([c:19]2[cH:20][cH:21][cH:22][c:23]([CH2:24][O:25][Si:26]([CH3:27])([CH3:28])[C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33]2)[CH:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][cH:34]2)[CH2:8][S:9][c:10]2[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:1... | COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 | null | [I-].[Zn+2].[I-] | ClCCCl | Reduction | OtherReaction | 32c18b8f01f6265a398b8df4f5d0033739d3c8e378cd915941473fb5993b3ae4 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2CSc3ccccc3C2c2ccccc2)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5](-[c:6])-[C:7]-[#16:8]-[c:9]:[c:10]-1:[c:11]>>[c:11]:[c:10]1:[c:9]-[#16:8]-[C:7]-[C:5](-[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 61 | [{"value": 61.0, "product": "[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 68 | CELSIUS | 2.5 | HOUR | To a solution of 4-[3-(t-butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3 (4-methoxyphenyl)thiochroman-4-ol (619 mg, 1.184 mmol) in 1,2-dichloroethane (70 ml) were added zinc iodide (567 mg, 1.776 mmol) and sodium cyanoborohydride (558 mg, 8.88 mmol) and stirred at 68° C. for 2.5 hours. When the reaction was completed, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | Other | [I-].[Zn+2].[I-].ClCCCl | 68 | 2.5 | COc1ccc(C2CSc3cc(OC)ccc3C2(O)c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1>[I-].[Zn+2].[I-].ClCCCl>COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-306e8fbcafdb4ceabca4323d2ded0b76 | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1>>COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO)c2)cc1 | [Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)C1C(CSC2=CC(=CC=C12)OC)C1=CC=C(C=C1)OC.Cl.O>>COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)C=1C=C(CO)C=CC1 | CC(C)(C)[Si](C)(C)[O:25][CH2:24][c:23]1[cH:22][cH:21][cH:20][c:19]([CH:18]2[CH:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]3)[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]32)[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16... | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1 | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO)c2)cc1 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(C2CSc3ccccc3C2c2ccccc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[c:3]>>[OH;D1;+0:1]-[C:2]-[c:3] | 96.3 | [{"value": 96.0, "product": "COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)C=1C=C(CO)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)C=1C=C(CO)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 4-[3-(t-butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman (480 mg, 0.947 mmol) was dissolved in tetrahydrofuran (40 ml), and added 3N hydrochloric acid solution (2.7 ml) thereto. The reaction mixture was stirred at room temperature for 4 h. When the reaction was completed, water was added to ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | Other | O1CCCC1 | null | 4 | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO[Si](C)(C)C(C)(C)C)c2)cc1>O1CCCC1>COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef62e84dcdca4ffda1fe1b2c01035c6c | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO)c2)cc1>>COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(C=O)c2)cc1 | COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)C=1C=C(CO)C=CC1>>COC1=CC=C2C(C(CSC2=C1)C1=CC=C(C=C1)OC)C=1C=C(C=O)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]3[CH:18]2[c:19]2[cH:20][cH:21][cH:22][c:23]([CH2:24][OH:25])[cH:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][S:9][c:10]3[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]3[CH:18]2[c:... | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO)c2)cc1 | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(C=O)c2)cc1 | null | [O-2].[Mn+4].[O-2] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(C2CSc3ccccc3C2c2ccccc2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 40 | CELSIUS | 3 | HOUR | The mixture of 3-[7-methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzyl alcohol (358 mg, 0.912 mmol) and manganese(IV) oxide (634 mg, 7.296 mmol) in methylene chloride (80 ml) was stirred at 40° C. for 3 h. When the reaction was completed, methylene chloride was added to the reaction mixture, which was then filtrated ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | null | [O-2].[Mn+4].[O-2].C(Cl)Cl | 40 | 3 | COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(CO)c2)cc1>[O-2].[Mn+4].[O-2].C(Cl)Cl>COc1ccc(C2CSc3cc(OC)ccc3C2c2cccc(C=O)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-618d76bb37f04bedb7d1a9a4b5ec1dd6 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1.N#CCCCCS>>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCCC#N)cc1 | C(#N)CCCCS.CS(=O)(=O)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.C(C)(=S)OCCCCC#N.C[O-].[Na+]>>C(#N)CCCCSCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC | CS(=O)(=O)O[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]2)([CH3:8])[CH2:9][S:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21.[SH:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[N:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]... | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1.N#CCCCCS | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCCC#N)cc1 | null | null | O1CCCC1.O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 5ef6153311053d1fb9aeb0863ac740df1693ec5dc2fd63b54be9bba291d50d91 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(C2CSc3ccccc3C2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[SH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[C:5]-[C:4] | null | [] | null | null | 1 | HOUR | To a solution of 4-cyanobutyl thioacetate (613 mg, 3.90 mmol) in methanol (10 ml) and was added 1M sodium methoxide (3.06 ml) and stirred at room temperature for 1 h. Then (3RS,4RS)-4-(9-methansulfonyloxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (290 mg, 0.557 mmol) dissolved in dry tetrahydrofuran (5 ml... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccc2c(c1)CCCS2 | MsOH.HO- | O1CCCC1.O.CO | null | 1 | COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1.N#CCCCCS>O1CCCC1.O.CO>COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCCC#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed6dc82dc74744d98d88e5069ca0df98 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F.COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCCC#N)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCCC#N | C(#N)CCCCSCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC.OC1=CC=C2C(C(CSC2=C1)(C)C1=CC=C(C=C1)O)CCCCCCCCCSCCCC(C(F)(F)F)(F)F>>C(#N)CCCCSCCCCCCCCCC1C(CSC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O | CC1(c2[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F.COc1cc[c:3]([C:2]2([CH3:1])[CH2:10][S:11][c:12]3[cH:13][c:14]([O:15]C)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[N:35])cc1>>[CH... | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F.COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCCC#N)cc1 | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCCC#N | null | null | null | Miscellaneous | OtherReaction | 397d1e59bbd0507cc28876a7da7045c72cf04d61aaefd1b2f70466f0656c0f85 | 1e83cd6a7a0457dfda9d46bca6c82ee6426bb919ef96568328c1bd53a6e6227d | c1ccc(C2CSc3ccccc3C2)cc1 | C-C1(-c2:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:2)-C-S-c2:c:c(-O):c:c:c:2-C-1-C-C-C-C-C-C-C-C-C-S-C-C-C-C(-F)(-F)-C(-F)(-F)-F.C-O-c1:c:c:[c;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])(-[C:9])-[C:10]-[#16:11]):c:c:1.C-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[#16:11]-[C:10]-[C:7](-[C;D1;H3:8])(-[c;H0;D3;+0:6]1:[cH;D2;+0:1]:[c:... | null | [] | null | null | null | null | The title compound was prepared from 4-[9-(4-cyanobutylthio)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman according to the same method for the synthesis of (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]thiochroman described in International Patent Appln. No. PCT... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Tertiary halide.Tertiary halide.Ether.Ether.Aromatic alcohol.Monosulfide.Monosulfide | Aromatic alcohol | c1ccccc1.c1ccc2c(c1)CCCS2.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCS2 | HF | null | null | null | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCC(F)(F)C(F)(F)F.COc1ccc(C2(C)CSc3cc(OC)ccc3C2CCCCCCCCCSCCCCC#N)cc1>>CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCCCCCCCSCCCCC#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-550930fe43a0448fb9673af3bba9b2db | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1=O.COCCl>>COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2=O | O.COCCl.OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)=O.[H-].[Na+]>>OC1=CC=C(C=C1)C1(COC2=CC(=CC=C2C1=O)OCOC)C | [OH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][C:13]([CH3:14])([c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]1)[C:22]2=[O:23].Cl[CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][C:13]([CH3:14])([c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]1)[C:22]2=... | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1=O.COCCl | COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | O=C1c2ccccc2OCC1c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 66 | [{"value": 66.0, "product": "OC1=CC=C(C=C1)C1(COC2=CC(=CC=C2C1=O)OCOC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "OC1=CC=C(C=C1)C1(COC2=CC(=CC=C2C1=O)OCOC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 7-hydroxyl-3-(4-hydroxyphenyl)-3-methylchroman-4-one (4.65 g, 17.20 mmol) in dry dimethylformamide (120 ml) was added sodium hydride (454 mg, 18.92 mmol) at room tempetarure and stirred for 30 minutes. To the reaction mixture was then added methoxymethyl chloride (1.523 g, 18.92 mmol) at the same tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccc2c(c1)CCCO2.c1ccccc1 | HCl | CN(C=O)C | null | 0.5 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1=O.COCCl>CN(C=O)C>COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47fba20e611b40fda7efa01f69a68d31 | BrCc1ccccc1.COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2=O>>COCOc1ccc2c(c1)OCC(C)(c1ccc(OCc3ccccc3)cc1)C2=O | O.OC1=CC=C(C=C1)C1(COC2=CC(=CC=C2C1=O)OCOC)C.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1(COC2=CC(=CC=C2C1=O)OCOC)C | Br[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][C:13]([CH3:14])([c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:27][cH:28]1)[C:29]2=[O:30]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][C:13]([CH3:14])([c:15]1[cH... | BrCc1ccccc1.COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2=O | COCOc1ccc2c(c1)OCC(C)(c1ccc(OCc3ccccc3)cc1)C2=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1c2ccccc2OCC1c1ccc(OCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 100.5 | [{"value": 100.5, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1(COC2=CC(=CC=C2C1=O)OCOC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 3-(4-hydroxyphenyl)-7-methoxymethyloxy-3-methylchroman-4-one (3.55 g, 11.293 mmol) and potassium carbonate (9.35 g, 67.76 mmol) in acetone (130 ml) was added benzyl bromide (5.795 g, 33.879 mmol) at room temperature and stirred overnight. When the reaction was completed, water was added to the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCO2.c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | 8 | BrCc1ccccc1.COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2=O>CC(=O)C>COCOc1ccc2c(c1)OCC(C)(c1ccc(OCc3ccccc3)cc1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-28aa8e3571ed4446a2010d33b45c1a23 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2CCCCCCCCCO[Si](C)(C)C(C)(C)C | [Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(COC2=CC(=CC=C12)OCOC)C>>[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)O | COC[O:19][c:18]1[cH:17][cH:16][c:15]([C:13]2([CH3:14])[CH2:12][O:11][c:9]3[c:8]([cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:10]3)[CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][Si:33]([CH3:34])([CH3:35])[C:36]([CH3:37])([CH3:38])[CH3:39])[cH:21][cH:20]1>>[CH3:1][O:2][CH2:3][O:4... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1 | COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2CCCCCCCCCO[Si](C)(C)C(C)(C)C | null | null | null | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1ccc(C2COc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from 3-(4-benzyloxy]phenyl)-4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethyloxy-3-methylchroman according to the same method for the synthesis of 4-[9-(t-butyldimethylsilyloxy)-1-nonyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman described in International Pa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCCO2.c1ccccc1 | HO- | null | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCO[Si](C)(C)C(C)(C)C)cc1>>COCOc1ccc2c(c1)OCC(C)(c1ccc(O)cc1)C2CCCCCCCCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4fa541ffae70467b9e3a401e83db8b40 | C#CCOc1ccc(CCCO[Si](C)(C)C(C)(C)C)cc1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)=O.[Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCC#C)C=C1.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC>>[Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCC#CC2(C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)O)C=C1 | [CH:25]#[C:26][CH2:27][O:28][c:29]1[cH:30][cH:31][c:32]([CH2:33][CH2:34][CH2:35][O:36][Si:37]([CH3:38])([CH3:39])[C:40]([CH3:41])([CH3:42])[CH3:43])[cH:44][cH:45]1.[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[C:23]2... | C#CCOc1ccc(CCCO[Si](C)(C)C(C)(C)C)cc1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | null | null | null | C-C Coupling | OtherReaction | 32c43bb8c46f4cb5536ede6cee58ac07810f00f75e5d5068c9f1bf838a1ce5f8 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | C(#CC1c2ccccc2OCC1c1ccccc1)COc1ccccc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[C:4]-[#8:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[C:11]-[C:12]#[CH;D1;+0:13]>>[C:11]-[C:12]#[C;H0;D2;+0:13]-[C;H0;D4;+0:9]1(-[OH;D1;+0:10])-[c:7](:[c:8]):[c:6]-[#8:5]-[C:4]-[C:2]-1(-[C;D1;H3:1])-[c:3] | null | [] | null | null | null | null | The title compound was prepared from 7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-one and 3-[4-(3-t-butyldimethylsilyloxypropyl)phenoxy]-1-propyn according to the same method for the synthesis of 4-[9-(t-butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | null | null | null | null | C#CCOc1ccc(CCCO[Si](C)(C)C(C)(C)C)cc1.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2=O)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 |
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