2-bromo-2-cyclopenten-1-one -Drug Synthesis Database

【结构式】

【分子编号】25951

【品名】2-bromo-2-cyclopenten-1-one

【CA登记号】

【分子式】C₅H₅BrO

【分子量】160.9981

【元素组成】C 37.3% H 3.13% Br 49.63% O 9.94%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

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).

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(II)

The condensation of 2-bromo-2-cyclopentenone (II) with the aryl lithium compound (V) gives the tertiary alcohol (VIII), which is submitted to an oxidation with PDC with simultaneous allylic transposition to provide 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one (IX). The oxidation of (IX) with H2O2 (Na2WO4) or MCPBA yields the corresponding sulfone (X), which is finally condensed with boronic acid (III) by means of a Pd catalyst as before. The synthetic approaches can also be performed with the arylmagnesium analogue of lithium derivative (V).

参考文献中间体

合成目标

【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
(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
(V)	18808	[4-(methylsulfanyl)phenyl]lithium		C₇H₇LiS	详情	详情
(VIII)	25956	2-bromo-1-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-ol		C₁₂H₁₃BrOS	详情	详情
(IX)	25957	2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one		C₁₂H₁₁BrOS	详情	详情
(X)	25958	2-bromo-3-[4-(methylsulfonyl)phenyl]-2-cyclopenten-1-one		C₁₂H₁₁BrO₃S	详情	详情

Extended Information