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【结 构 式】 
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【分子编号】62319 【品名】diethyl 2-[2-(4-methoxy-3-nitrophenyl)-2-oxoethyl]malonate 【CA登记号】 |
【 分 子 式 】C16H19NO8 【 分 子 量 】353.3288 【元素组成】C 54.39% H 5.42% N 3.96% O 36.23% |
合成路线1
该中间体在本合成路线中的序号：(II)Condensation of 2-bromo-3'-methoxy-4-nitroacetophenone (I) with diethyl malonate affords the phenacylmalonate derivative (II). This is converted into the corresponding magnesium enolate and then acylated by 3,4,5-trimethoxyphenylacetyl chloride (III) to furnish the disubstituted malonate (IV). Intramolecular aldol condensation of diketone (IV) in the presence of Et3N leads to cyclopentenone (V). Subsequent hydrolysis and decarboxylation of the keto diester (V) under acidic conditions produces (VI). Finally, the nitro group of (VI) is reduced by means of zinc dust in AcOH to yield the title compound.
| 【1】 Nam, N.-H.; Kim, Y.; You, Y.-J.; Hong, D.-H.; Kim, H.-M.; Ahn, B.-Z.; Synthesis, cytotoxicity and antitumor activity of 2,3-diarylcyclopent-2-ene-1-ones. Arch Pharmacal Res 2002, 25, 5, 600. |
| 【2】 Nam, N.-H.; Kim, Y.; You, Y.-J.; Hong, D.-H.; Kim, H.-M.; Ahn, B.-Z.; Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues. Bioorg Med Chem Lett 2002, 12, 15, 1955. |
| 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) | 62318 | C9H8BrNO4 | 详情 | 详情 | ||
| (II) | 62319 | diethyl 2-[2-(4-methoxy-3-nitrophenyl)-2-oxoethyl]malonate | C16H19NO8 | 详情 | 详情 | |
| (III) | 35239 | N-[2-(2-amino-1,3-thiazol-4-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide | C16H21N3O4S | 详情 | 详情 | |
| (IV) | 62320 | C27H31NO12 | 详情 | 详情 | ||
| (V) | 62321 | diethyl 4-(4-methoxy-3-nitrophenyl)-2-oxo-3-(3,4,5-trimethoxyphenyl)-3-cyclopentene-1,1-dicarboxylate | C27H29NO11 | 详情 | 详情 | |
| (VI) | 62322 | C21H21NO7 | 详情 | 详情 |