具有光学活性的环丙烷-1,2-二羧酸衍生物的合成  

Synthesis of optical derivatives of cyclopropane dicarboxylic acid

作　　者：边庆花[1] 钟江春[1] 刘丹[1] 王敏[1] 

机构地区：[1]中国农业大学理学院,北京100094

出　　处：《化学试剂》2006年第12期714-716,共3页Chemical Reagents

基　　金：国家自然科学基金资助项目(20472111)

摘　　要：以光学纯的(1R,3R)-trans-蒈醛酸乙酯为起始原料,经氧化银氧化为环丙烷二羧酸单乙酯后与乙醇进行酯化反应,可得到(1R,2R)-trans-3,3-二甲基-1,2-环丙烷二羧酸二乙酯,并很好地保持了其光学纯度。将环丙烷二羧酸单乙酯在碱性条件下水解为具有光学活性的环丙烷二羧酸后,与SOCl2反应得到了具有光学活性的(1R,2R)-trans-3,3-二甲基-1,2-环丙烷二酰氯。研究了氢氧化钠用量、反应温度对产物产率和光学纯度的影响。The optical purity diethyl trans-3, 3-dimethyleyclopropane dicarboxylate was prepared via oxidation of （1 R, 3 R ）- ethyl trans-3-formyl-2, 2-dimethylcyclopropanecarboxylate with silver oxide and esterification with ethanol. Meanwhile, （1 R, 2R）-trans-3, 3-dimethyl-cyclopropane dicarbonyl chloride was synthesized through halogenation between SOC12 and the optical trans-3,3-dimethylcyclopropane dicarboxylic acid which could be achieved from hydrolysis of （ 1 R, 3 R ） -trans -3- （ethoxycarbonyl） - 2,2-dimethylcyclopropanecarboxylic acid with sodium hydroxide. Furethemlore, effects of the dosage of sodium hydroxide and reaction temperature on the optical purity of the products were also investigated.

关 键 词：环丙烷羧酸乙酯 环丙烷羧酸酰氯 合成 

分 类 号：O624.5[理学—有机化学]