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【结 构 式】

【分子编号】25959

【品名】3-ethoxy-2-cyclopenten-1-one

【CA登记号】

【 分 子 式 】C7H10O2

【 分 子 量 】126.1552

【元素组成】C 66.65% H 7.99% O 25.36%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The bromination of 3-ethoxy-2-cyclopenten-1-one (I) with Br2 and triethylamine in chloroform gives the 2-bromo derivative (II), which is condensed with 4-bromothioanisole (III) by means of BuLi in THF yielding 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one (IV). The oxidation of (IV) with Na2WO4 and H2O2 affords the corresponding sulfone (V), which is finally condensed with lithium diisopropyl 3-pyridylboronate (VII) or the corresponding dimethyl ester (VIII) by means of tris(dibenzylideneacetone)dipalladium (III) (Pd2(dba)3) and triphenylphosphine in toluene/propanol/water. The lithium boronates (VII) and (VIII) have been obtained by reaction of 3-bromopyridine (VI) with triisopropyl borate or trimethyl borate and BuLi in ethyl ether.

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.; Hughes, G.; Wang, Z. (Merck Frosst Canada Inc.); Pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors. EP 0900201; JP 2000509032; US 5922742; WO 9740012 .
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) 25959 3-ethoxy-2-cyclopenten-1-one C7H10O2 详情 详情
(II) 25960 2-bromo-3-ethoxy-2-cyclopenten-1-one C7H9BrO2 详情 详情
(III) 19266 4-bromophenyl methyl sulfide; 1-bromo-4-(methylsulfanyl)benzene 104-95-0 C7H7BrS 详情 详情
(IV) 25957 2-bromo-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one C12H11BrOS 详情 详情
(V) 25958 2-bromo-3-[4-(methylsulfonyl)phenyl]-2-cyclopenten-1-one C12H11BrO3S 详情 详情
(VI) 13265 3-Bromopyridine 626-55-1 C5H4BrN 详情 详情
(VII) 30005 Triisopropoxy(3-pyridyl)boranuide lithium salt C14H25BLiNO3 详情 详情
(VIII) 30006 Trimethoxy(3-pyridyl)boranuide lithium salt C8H13BLiNO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XI)

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