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【结 构 式】

【分子编号】34448

【品名】(4-bromophenyl)[4-(2-[3-[(trimethylsilyl)oxy]-1-azabicyclo[2.2.2]oct-3-yl]ethynyl)phenyl]methanone

【CA登记号】

【 分 子 式 】C25H28BrNO2Si

【 分 子 量 】482.49236

【元素组成】C 62.23% H 5.85% Br 16.56% N 2.9% O 6.63% Si 5.82%

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:(V)

Addition of lithium trimethylsilylacetylide (II) to quinuclidin-3-one (I) in THF at -70 C afforded the O-silylated ethynyl quinuclidinol (III). Subsequent palladium-catalyzed coupling of (III) with 4,4'-dibromobenzophenone (IV) gave adduct (V). Finally, the Meyer-Schuster rearrangement of (V) in concentrated H2SO4 furnished the title unsaturated ketone.

1 Brown, G.R.; Stokes, E.S.E.; Hollinshead, D.M.; et al.; Quinuclidine inhibitors of 2,3-oxidosqualene cyclase-lanosterol synthase: Optimization from lipid profiles. J Med Chem 1999, 42, 7, 1306.
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) 16925 3-quinuclidinone; 1-azabicyclo[2.2.2]octan-3-one 1193-65-3 C7H11NO 详情 详情
(II) 16299 Lithium (trimethylsilyl)acetylide; [2-(Trimethylsilyl)ethynyl]lithium 54655-07-1 C5H9LiSi 详情 详情
(III) 34446 3-ethynyl-3-[(trimethylsilyl)oxy]quinuclidine; 3-ethynyl-1-azabicyclo[2.2.2]oct-3-yl trimethylsilyl ether C12H21NOSi 详情 详情
(IV) 34447 bis(4-bromophenyl)methanone 3988-03-2 C13H8Br2O 详情 详情
(V) 34448 (4-bromophenyl)[4-(2-[3-[(trimethylsilyl)oxy]-1-azabicyclo[2.2.2]oct-3-yl]ethynyl)phenyl]methanone C25H28BrNO2Si 详情 详情
Extended Information