3-氰基-7-羟基香豆素的合成  

Synthesis of 3-Cyano-7-Hydroxycoumarin

作　　者：张超 牛亮峰 徐杨 贾乙森 周云豪 姚沣函 

机构地区：[1]许昌学院化工与材料学院,河南 许昌

出　　处：《有机化学研究》2024年第3期459-465,共7页Journal of Organic Chemistry Research

摘　　要：3-氰基-7-羟基香豆素是一种重要的香豆素类有机合成中间体,被广泛用于医药合成和构建荧光染料的骨架等。本文研究了两种3-氰基-7-羟基香豆素的合成方法,起始原料选用2,4-二羟基苯甲醛,另一反应物分别选择了丙二腈、氰基乙酸酯两种化合物,以收率、合成经济性和“三废”处理的难度为评价标准,比较得出了较优方法,随后优化了该方法中的催化剂、溶剂和反应时间等条件,并用红外光谱(IR)、核磁波谱(NMR)和高效液相色谱对目标产物进行了结构确证与纯度分析。实验结果显示产物收率为86%,结构正确,纯度≥95%,该合成方法可以实现3-氰基-7-羟基香豆素的高效制备。3-cyano-7-hydroxy-coumarin is an important intermediate of coumarin, which is widely used in pharmaceutical synthesis, construction of fluorescent dye skeleton and so on. In this paper, two synthesis methods of 3-cyano-7-hydroxy-coumarin were studied. The starting material was 2,4-dihydroxybenzaldehyde, and the other reactant was malonitrile and cyanoacetate, respectively, to construct benzopyranone ring parent nucleus. Based on the evaluation criteria of yield, synthesis economy and difficulty of “three wastes” treatment, a better method was obtained. The catalyst, solvent and reaction time of this method were optimized, and the target products were analyzed by infrared spectroscopy (IR), NMR and HPLC. The experimental results showed that the yield of the product was 86%, the structure of the product is correct, and the purity was ≥95%. This synthesis method could realize the efficient preparation of 3-cyano-7-hydroxycoumarin.

关 键 词：3-氰基-7-羟基香豆素 2 4-二羟基苯甲醛 催化剂 高效制备 

分 类 号：O62[理学—有机化学]