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【结 构 式】 
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【分子编号】25954 【品名】2-(3,5-difluorophenyl)-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol 【CA登记号】 |
【 分 子 式 】C18H16F2OS 【 分 子 量 】318.3872464 【元素组成】C 67.9% H 5.07% F 11.93% O 5.03% S 10.07% |
合成路线1
该中间体在本合成路线中的序号：(VI)The bromination of 2-cyclopentenone (I) gives 2-bromocyclopentenone (II), which is condensed with 3,5-difluorophenylboronic acid (III) by means of a Pd catalyst yielding 2-(3,5-difluorophenyl)-2-cyclopentenone (IV). The reaction of (IV) with the aryl lithium (V) affords the cyclopentenol derivative (VI), which is submitted to an oxidation with PDC with simultaneous allylic transposition to give 2-(3,5-difluorophenyl)-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one (VII). Finally, this compound is oxidized with H 2O2 (Na2WO4) to the target sulfone. The preceding synthetic approach can also be performed with 2-iodo-2-cyclopentenone (obtained by iodination of (I) instead of its bromo analogue (II). The synthetic approaches can also be performed with the arylmagnesium analogue of lithium derivative (V).
| 【1】 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 |
|---|---|---|---|---|---|---|
| (I) | 25950 | 2-cyclopenten-1-one | 930-30-3 | C5H6O | 详情 | 详情 |
| (II) | 25951 | 2-bromo-2-cyclopenten-1-one | C5H5BrO | 详情 | 详情 | |
| (III) | 25952 | 3,5-difluorophenylboronic acid | 156545-07-2 | C6H5BF2O2 | 详情 | 详情 |
| (IV) | 25953 | 2-(3,5-difluorophenyl)-2-cyclopenten-1-one | C11H8F2O | 详情 | 详情 | |
| (V) | 18808 | [4-(methylsulfanyl)phenyl]lithium | C7H7LiS | 详情 | 详情 | |
| (VI) | 25954 | 2-(3,5-difluorophenyl)-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol | C18H16F2OS | 详情 | 详情 | |
| (VII) | 25955 | 2-(3,5-difluorophenyl)-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one | C18H14F2OS | 详情 | 详情 |