| 孙明娜,周 毅,张培全,孙明姣,陶移文.化学通报,2019,82(6):559-562. |
| BF3.Et2O催化的Pechmann反应一锅合成3-氨基-5,7-二羟基-4-甲基香豆素 |
| Synthesis of 3-Amino-5,7-dihydroxy-4-methyl Coumarin via Pechmann Reaction Catalyzed by BF3.Et2O in One Pot |
| 投稿时间：2018-12-27 修订日期：2019-02-13 |
| DOI： |
| 中文关键词: 3-氨基-5,7-二羟基-4-甲基香豆素 BF3.Et2O Pechmann反应 合成 |
| 英文关键词:3-Amino-5,7-dihydroxy-4-methyl coumarin, BF3.Et2O, Pechmann reaction, Synthesis |
| 基金项目:国家自然科学基金资助项目（21702036）、广东省教育厅项目（2015KQNCX128）、广东省自然科学基金-博士启动项目（L18045）、广州省中医药局项目（20171180）资助 |
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| 中文摘要: |
| 3-氨基-5,7-二羟基-4-甲基香豆素（4）是一种新的重要有机合成中间体，可用于多种潜在生物活性物质的合成。本文将间苯三酚与2-乙酰氨基乙酰乙酸乙酯（2）在BF3.Et2O的催化作用下，经串联的Pechmann缩合反应和脱乙酰基反应一锅合成4。化合物2由乙酰乙酸乙酯经成肟、还原、酰化反应制得。中间体和目标物的结构均经1H NMR、13C NMR、MS表征。该方法具有原料廉价易得、步骤短、操作简便易控、反应条件温和、收率高的优点。 |
| 英文摘要: |
| 3-Amino-5,7-dihydroxy-4-methyl coumarin (4) is a new important organic intermediate, which can be used to synthesize various bioactive agents. In this work, compound 4 was synthesized in one pot from phloroglucinol and ethyl 2-acetylamino acetoacetate (2) by Pechmann condensation and deacetylation in series under the catalysis of BF3.Et2O. 2 was prepared from ethyl acetoacetate by oxime formation, reduction and acylation successively. All intermediates and the final product were confirmed by 1H NMR、13C NMR and MS. This method has considerable advantages in terms of the use of easily available raw material, less steps, simple operation, mild reaction conditions and high yield. |
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