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【结 构 式】 
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【分子编号】23227 【品名】ethyl (Z)-5-hydroxy-3-oxo-5-(3-pyridinyl)-4-pentenoate 【CA登记号】 |
【 分 子 式 】C12H13NO4 【 分 子 量 】235.23956 【元素组成】C 61.27% H 5.57% N 5.95% O 27.21% |
合成路线1
该中间体在本合成路线中的序号：(III)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 1-cyclohexene-carboxaldehyde (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. |
| 【2】 Perchellet, J.-P.; Hua, D.H. (Kansas State University); Tricyclic and tetracyclic pyrones. US 5958970 . |
| 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) | 23229 | 1-cyclohexene-1-carbaldehyde | 1192-88-7 | C7H10O | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)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 |