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【结 构 式】 
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【分子编号】58039 【品名】2-nitro-1-vinylcyclohexanol 【CA登记号】 |
【 分 子 式 】C8H13NO3 【 分 子 量 】171.19616 【元素组成】C 56.13% H 7.65% N 8.18% O 28.04% |
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：(XV)Addition of vinylmagnesium bromide to 2-nitrocyclohexanone (XIV) afforded the nitro alcohol (XV). Ring cleavage of (XVI) in the presence of anhydrous CuSO4 absorbed on silica gel gave the nitro ketone (XVI). Nitro group hydrolysis in (XVI) by successive treatment with NaOMe and H2SO4 in MeOH furnished oxo ester (XVII) as the main product. This was enantiospecifically reduced with baker's yeast to yield the (S)-alcohol (XVIII). Selective methyl ether cleavage with tetrabutylammonium iodide and BF3 provided the dihydroxy ester precursor (XIII).
| 【1】 Bezbarua, M.S.; et al.; A short enantioselective formal synthesis of methyl (S)-(-)-6,8-dihydroxyoctanoate: A key intermediate for the synthesis of R-(+)-alpha-lipoic acid. Synthesis (Stuttgart) 1996, 11, 1289. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 57977 | methyl (6S)-6,8-dihydroxyoctanoate | C9H18O4 | 详情 | 详情 | |
| (XIV) | 58038 | 2-Nitrocyclohexanone | C6H9NO3 | 详情 | 详情 | |
| (XV) | 58039 | 2-nitro-1-vinylcyclohexanol | C8H13NO3 | 详情 | 详情 | |
| (XVI) | 58040 | 8-nitro-1-octen-3-one | C8H13NO3 | 详情 | 详情 | |
| (XVII) | 58041 | methyl 8-methoxy-6-oxooctanoate | C10H18O4 | 详情 | 详情 | |
| (XVIII) | 58042 | methyl (6S)-6-hydroxy-8-methoxyoctanoate | C10H20O4 | 详情 | 详情 |
Extended Information