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Synthesis of (E)-cinnamyl ester derivatives via a greener Steglich esterification
Bioorganic & Medicinal Chemistry ( IF 3.5 ) Pub Date : 2018-04-20 , DOI: 10.1016/j.bmc.2018.04.007
Andrew B. Lutjen , Mackenzie A. Quirk , Allycia M. Barbera , Erin M. Kolonko

Cinnamic acid derivatives are known antifungal, antimicrobial, antioxidant, and anticancer compounds. We have developed a facile and mild methodology for the synthesis of (E)-cinnamate derivatives using a modified Steglich esterification of (E)-cinnamic acid. Using acetonitrile as the solvent, rather than the typical chlorinated solvent, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) as the coupling agent enables ester conversion in 45 min with mild heating (40–45 °C) and an average yield of 70% without need for further purification. These conditions were used to couple (E)-cinnamic acid with 1° and 2° aliphatic alcohols, benzylic and allylic alcohols, and phenols. This work demonstrates a facile and greener methodology for Steglich esterification reactions.



中文翻译:

通过更绿色的Steglich酯化反应合成(E)-肉桂酸酯衍生物

肉桂酸衍生物是已知的抗真菌,抗微生物,抗氧化剂和抗癌化合物。我们已经开发了用于(合成的容易且温和的方法Ë使用(的变形steglich酯化反应) -肉桂酸酯衍生物ë) -肉桂酸。使用乙腈作为溶剂,而不是典型的氯化溶剂,并使用1-乙基-3-(3-二甲基氨基丙基)碳二亚胺(EDC)作为偶联剂,可以在温和加热(40–45°C)的条件下在45分钟内完成酯转化。平均收率为70%,无需进一步纯化。这些条件用于耦合(E肉桂酸与1°和2°脂肪族醇,苄基和烯丙基醇以及酚。这项工作证明了Steglich酯化反应的简便而绿色的方法。

更新日期:2018-04-20
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