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【结 构 式】 
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【药物名称】 【化学名称】(Z)-2-(1-Azabicyclo[2.2.2]oct-3-ylidene)-1-[4-(4-bromobenzoyl)phenyl]ethanone 【CA登记号】223726-07-6 【 分 子 式 】C22H20BrNO2 【 分 子 量 】410.3142 |
【开发单位】AstraZeneca (Originator) 【药理作用】Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Lanosterol Synthase Inhibitors |
合成路线1
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