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【结 构 式】 
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【分子编号】56175 【品名】methyl 1-methyl-1-{(2R)-2-[4-(trifluoromethyl)phenyl]oxiranyl}ethyl sulfone; (2R)-2-[1-methyl-1-(methylsulfonyl)ethyl]-2-[4-(trifluoromethyl)phenyl]oxirane 【CA登记号】 |
【 分 子 式 】C13H15F3O3S 【 分 子 量 】308.3215096 【元素组成】C 50.64% H 4.9% F 18.49% O 15.57% S 10.4% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Condensation of isobutyrophenone (IV) with the lithium derivative of (S)-methyl p-tolyl sulfoxide (IX) produced alcohol (X) as a diastereomeric mixture. After chromatographic separation of the desired diastereoisomer, the methylsulfanyl group was selectively oxidized to sulfone (XI) with m-chloroperbenzoic acid. Reduction of the tolyl sulfoxide moiety of (XI) by means of NaI in the presence of acetyl chloride led to the corresponding sulfide (XII). Cyclization of the hydroxy sulfide (XII) to epoxide (XIII) was accomplished via S-alkylation with triethyloxonium tetrafluoroborate. Finally, opening of the chiral epoxide (XIII) with triazole (XIV) in the presence of K2CO3 furnished the title compound.
| 【1】 Tokizawa, M.; Kanamaru, Y.; Matsumoto, M.; Asaoka, T.; Matsuda, H.; Kuraishi, T.; Maebashi, K.; Taido, N.; Kawahara, R. (SSP Co., Ltd.); Triazole derivs.. EP 0435081; JP 1991223266; US 5147886 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (Xa) | 56171 | (2R)-3-methyl-1-[(4-methylphenyl)sulfinyl]-3-(methylsulfanyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol | C20H23F3O2S2 | 详情 | 详情 | |
| (Xb) | 56172 | (2S)-3-methyl-1-[(4-methylphenyl)sulfinyl]-3-(methylsulfanyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol | C20H23F3O2S2 | 详情 | 详情 | |
| (IV) | 56166 | 2-methyl-2-(methylsulfanyl)-1-[4-(trifluoromethyl)phenyl]-1-propanone | C12H13F3OS | 详情 | 详情 | |
| (IX) | 56170 | methyl 4-methylphenyl sulfoxide; methyl(4-methylphenyl)oxo-lambda~4~-sulfane | C8H10OS | 详情 | 详情 | |
| (XI) | 56173 | (2R)-3-methyl-1-[(4-methylphenyl)sulfinyl]-3-(methylsulfonyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol | C20H23F3O4S2 | 详情 | 详情 | |
| (XII) | 56174 | (2R)-3-methyl-1-[(4-methylphenyl)sulfanyl]-3-(methylsulfonyl)-2-[4-(trifluoromethyl)phenyl]-2-butanol | C20H23F3O3S2 | 详情 | 详情 | |
| (XIII) | 56175 | methyl 1-methyl-1-{(2R)-2-[4-(trifluoromethyl)phenyl]oxiranyl}ethyl sulfone; (2R)-2-[1-methyl-1-(methylsulfonyl)ethyl]-2-[4-(trifluoromethyl)phenyl]oxirane | C13H15F3O3S | 详情 | 详情 | |
| (XIV) | 13135 | 1H-1,2,4-Triazole; 1,2,4-Triazole | 288-88-0 | C2H3N3 | 详情 | 详情 |