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【结 构 式】 
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【分子编号】25961 【品名】2-bromo-3-ethoxy-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol 【CA登记号】 |
【 分 子 式 】C14H17BrO2S 【 分 子 量 】329.25778 【元素组成】C 51.07% H 5.2% Br 24.27% O 9.72% S 9.74% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XIII)The bromination of 3-ethoxy-2-cyclopentenone (XI) gives the 2-bromo derivative (XII), which is condensed with the aryl lithium (V) as before yielding the tertiary alcohol (XIII). Then (XIII) was submitted to an acid rearrangement to provide 2-bromo-3-[4-(sulfanylmethyl)phenyl]-2-cyclopentenone (IX), already obtained in the preceding approaches. The synthetic approaches can also be performed with the arylmagnesium analogue of lithium derivative (V).
| 【1】 Chan, C.-C.; Brideau, C.; Black, W.C.; et al.; 2,3-Diarylcyclopentenones as orally active, highly selective cyclooxygenase-2 inhibitors. J Med Chem 1999, 42, 7, 1274. |
| 【2】 Black, C. (Merck Frosst Canada Inc.); 2-(3,5-Difluorophenyl)-3-(4-(methyl-sulfonyl)phenyl)-2-cyclopenten-1-one useful as an inhibitor of cyclooxygenase-2. EP 0863134; JP 1998251220 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 18808 | [4-(methylsulfanyl)phenyl]lithium | C7H7LiS | 详情 | 详情 | |
| (IX) | 25957 | 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one | C12H11BrOS | 详情 | 详情 | |
| (XI) | 25959 | 3-ethoxy-2-cyclopenten-1-one | C7H10O2 | 详情 | 详情 | |
| (XII) | 25960 | 2-bromo-3-ethoxy-2-cyclopenten-1-one | C7H9BrO2 | 详情 | 详情 | |
| (XIII) | 25961 | 2-bromo-3-ethoxy-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol | C14H17BrO2S | 详情 | 详情 |
Extended Information