摘要
异香豆素是一些天然产物的基本骨架结构,这些化合物具有多种良好的生物活性,如抗癌、杀菌、消炎等。然而由于有效合成方法的缺失,寻找一条方便快捷的合成路线对异香豆素类化合物的合成,具有重要意义。以取代的邻羧基苯乙酸为原料,与三氯氧磷发生关环反应得到3-氯代的异香豆素衍生物。或者在质子酸的催化作用下使邻羧基苯乙酸与不同的醇进行酯化,可以选择性的得到相应的苯乙酸酯后,在五氯化磷的作用下进行关环,合成一系列3-烷氧基-4-氯异香豆素类化合物,并对合成路线条件进行了探索,获得了令人满意的收率。这些化合物的结构均利用IR和-1H NMR等多种手段进行鉴定,并研究了UV、IR光谱性质。
Isocoumarin is of the key structure which is the pharmacophore motif in some natural products and often exhibits perfect biological activities,such as antitumor,antifungal and anti-inflammation. However,the price of these compounds is usually quite high due to the lack of efficient synthetic methods. It is significant to develop a short and convenient synthetic route for isocoumarin production. In this work,some substituted homophthalic acids were used as the starting materials and 3-chloroisocoumarins was synthesized by the reaction of substituted homophthalic acids with phosphorus oxychloride. Homophthalic acids were also reacted with alcohols to generate selectively phenylacetic acid ester in the presence of Bronsted acid,which was further reacted with phosphorus pentachloride to afford the 3-alkyoxy-4-chloro-isocoumarins. The yields of these isocoumarins were satisfactory under the optimal conditions of the esterification and ring closure reactions. The structures of isocoumarin derivatives were determined by IR and -1 HNMR spectra and their UV and IR spectroscopic properties were studied.
出处
《广西大学学报（自然科学版）》
CAS
北大核心
2016年第6期2023-2030,共8页
Journal of Guangxi University（Natural Science Edition）
基金
国家自然科学基金资助项目(21462003)
广西自然科学基金资助项目(2014GXNSFCA118005)
广西科技攻关项目(1348006-4)
广西教育厅重点项目(2013ZD003)
广西大学科研基金资助项目(XGZ111491)
