三亚苯衍生物的合成——将苯环的构筑引入有机化学实验教学

Synthesis of Triphenylene Derivatives:Introducing the Formation of Benzene Rings into the Experimental Teaching of Organic Chemistry

将多环芳烃这一研究热点引入本科实验教学,开发了一种基于羟醛缩合和Diels-Alder反应构筑苯环的合成实验。以9,10-菲醌及二苄基甲酮为原料经羟醛缩合获得环戊二烯酮衍生物1,1进一步与丁炔二酸二乙酯经Diels-Alder反应获得三亚苯衍生物2。本实验试剂易得,反应温和,现象明显,提纯简单且可靠性高。学生在掌握羟醛缩合和Diels-Alder反应原理及操作的同时学习了此构筑苯环的重要策略。

In this study,the research hotspot of polycyclic aromatic hydrocarbons was introduced into undergraduate experimental teaching,and a synthesis experiment based on the aldol and Diels-Alder reactions was developed for benzene ring formation.Using 9,10-phenanthrenequinone and dibenzyl ketone as raw materials,the cyclopentadienone derivative 1 was obtained by the aldol reaction,and 1 was further reacted with diethyl acetylene dicarboxylate to obtain triphenylene derivative 2 by the Diels-Alder reaction.The reagents in this study are easily accessible,the reaction conditions are mild,the phenomenon is clear,the purification is simple,and the reliability is high.Students can master the principle and operation of the aldol and Diels-Alder reactions and gain an understanding of the important strategy for forming benzene rings.