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【结 构 式】 
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【药物名称】 【化学名称】4-[4-(4-Fluorophenyl)piperazin-1-ylcarbonyl]-3-methyl-1-oxaspiro[4.5]dec-3-en-2-one 【CA登记号】 【 分 子 式 】C21H25FN2O3 【 分 子 量 】372.4434 |
【开发单位】Université d'Auvergne-Clermont-Ferrand (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs |
合成路线1
The condensation between cyclohexanone (I) and dimethyl itaconate (II) in the presence of NaOMe in cold Et2O afforded the spirobutenolide (III) together with some hydrolyzed product (IV). A further hydrolytic treatment with aqueous NaOH provided acid (IV), which was then converted to acid chloride (V) by treatment with PCl5 in refluxing cyclohexane. Reaction of this acid chloride with N-(4-fluorophenyl)piperazine in CH2Cl2 at 0 C produced the title amide.
| 【1】 Bois, F.; et al.; Spirobutenolides substituted by arylpiperazinyl-carbonyl moieties. Synthesis and antinociceptive properties. Arzneim-Forsch Drug Res 1998, 48, 12, 1156. |
| 【2】 Bador, P.; et al.; Synthesis of acetylenic spirobutenolide derivatives and evaluation of their growth inhibitory effect on cells in culture. Arzneim-Forsch Drug Res 1990, 40(II), 10, 1135-1139. |
| 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) | 11059 | Cyclohexanone | 108-94-1 | C6H10O | 详情 | 详情 |
| (II) | 21416 | dimethyl 2-methylenesuccinate | 617-52-7 | C7H10O4 | 详情 | 详情 |
| (III) | 21417 | methyl 3-methyl-2-oxo-1-oxaspiro[4.5]dec-3-ene-4-carboxylate | C12H16O4 | 详情 | 详情 | |
| (IV) | 21418 | 3-methyl-2-oxo-1-oxaspiro[4.5]dec-3-ene-4-carboxylic acid | C11H14O4 | 详情 | 详情 | |
| (V) | 21419 | 3-methyl-2-oxo-1-oxaspiro[4.5]dec-3-ene-4-carbonyl chloride | C11H13ClO3 | 详情 | 详情 | |
| (VI) | 12143 | 1-(4-Fluorophenyl)piperazine | 2252-63-3 | C10H13FN2 | 详情 | 详情 |
Extended Information