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【结 构 式】 
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【药物名称】 【化学名称】(5aS,7S)-7-Isopropenyl-3-(3-pyridinyl)-1,5a,6,7,8,9-tetrahydropyrano[4,3-b]chromen-1-one 【CA登记号】194937-76-3 【 分 子 式 】C20H19NO3 【 分 子 量 】321.37933 |
【开发单位】Kansas State University (Originator) 【药理作用】ONCOLYTIC DRUGS, Antimitotic Drugs, Microtubule-Stabilizing Agents |
合成路线1
Claisen condensation of ethyl acetoacetate (I) with ethyl nicotinate (II) using 2.5 equivalents of LDA produced the corresponding diketoester, which was isolated as the enol form (III). Subsequent cyclization of (III) at 150 C with removal of EtOH under reduced pressure afforded pyrone (IV). This was finally coupled with (S)-perillaldehyde (V) in the presence of L-proline to give the target pyranochromene.
| 【1】 Hua, D.H.; et al.; A one-pot condensation of pyrones and enals. Synth. J Org Chem 1997, 62, 20, 6888. |
| 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) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
| (II) | 23226 | ethyl nicotinate | 614-18-6 | C8H9NO2 | 详情 | 详情 |
| (III) | 23227 | ethyl (Z)-5-hydroxy-3-oxo-5-(3-pyridinyl)-4-pentenoate | C12H13NO4 | 详情 | 详情 | |
| (IV) | 23228 | 4-hydroxy-6-(3-pyridinyl)-2H-pyran-2-one | C10H7NO3 | 详情 | 详情 | |
| (V) | 23230 | (4S)-4-isopropenyl-1-cyclohexene-1-carbaldehyde | 18031-40-8 | C10H14O | 详情 | 详情 |
Extended Information