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【结 构 式】

【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%

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:(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
Extended Information