有机化学教学综合实验设计:制备药物菲尼布特外消旋前体

Design Comprehensive Organic Chemistry Teaching Experiment:Synthesis of Racemic Precursor of Drug Phenibut

菲尼布特药物能治疗焦虑和失眠等病症,介绍采用一个有机化学教学综合设计实验合成药物菲尼布特(Phenibut)外消旋前体。以便宜易得的硝基甲烷、苯甲醛为原料,通过“一锅法”两步反应(Henry反应和β-消除反应)高效获得β-硝基苯乙烯,碱性条件下,丙二酸二甲酯对其进行Michael加成反应得到药物菲尼布特外消旋前体,通过^(1)H NMR、^(13)C NMR和红外光谱等方法对反应产物结构进行表征。

Phenibut drug can treat anxiety and insomnia.An organic chemistry teaching comprehensive design experiment was described here,which applied the easily available nitromethane and benzaldehyde as starting materials.They underwent sequential Henry reaction/β-elimination reaction in“one pot”to giveβ-nitrostyrene.Dimethyl malonate reacted with nitrostyrene to obtain the racemic precursor of phenibut.They were characterized by 1H NMR,13C NMR and IR spectra analysis.