【作者】 陈小林；

【导师】 张明杰；

【作者基本信息】 天津大学 ， 有机化学， 2004， 硕士

【摘要】 α-芳基丙酸（α-arylpropanic acid）是一类广泛使用的非甾体抗炎药，其独特的解热、消炎和镇痛作用，越来越为人们所接受。特别是萘普生，由于它的疗效高，副作用小等优点，已成为药物市场的主流产品。但由于（R）-萘普生对肝脏的副作用大，现在人们普遍趋向于使用单一手性（S）-(+)-萘普生产品。本论文优化了傅氏烷基化反应合成α-芳基丙酸的方法，用硝基甲烷和三乙胺分别代替毒性大的硝基苯和吡啶，得到了满意的试验结果；并对三种烷基化试剂：对甲苯磺酸乳酸乙酯、丙烯醇及环氧丙烷所进行的反应进行了研究对比。本论文的另一创新之处是采用面包酵母对中间体：α-亚甲基苯乙酸乙酯、α-亚甲基苯乙氰和α-亚甲基苯乙酸分别进行还原，并对还原产物的种类及结构通过气质联用进行了分析，提出了合理的解释，而且针对三种前体的特点分别采用了Wittig-Horner反应、mannich反应和氰水解反应及卡宾法等合成方法，比较了各种合成途径，提出了一条简易合成α-亚甲基苯乙酸的方法，中间体主要通过红外光谱和核磁共振氢谱进行了表征。更多还原

【Abstract】 α-arylpropanic acids have been proved to be of great use on some diseases－rheumatism and rheumatoid arthritis for its highly effect on inflammation,ache and fever as non-steroidal anti-inflammatory agent .they are widely used as antipyrotic, anodyne and acetanilide.Because it was investigated that most of (R)-α-arylpropanic acids have much negative effect on stomach， (S)- α-arylpropanic acids ,which chem- -ists are effort to synthesize pure optically active isomer ，are popular with patients.The dissertation optimizes the condition of Friedel-Crafts reaction,using nitro- -methane and triethylamine instead of nitrobenzene and pyridine, respectively .The innovation of the paper is that Baker’s Yeast has been used to reduce a series of intermediate products of α-arylpropanic acids such as ethyl α-methylenebenzeneacetate , α-methylenebenzeneacetonitrile and α-methylenebenzeneacetic acid.The reduced products are analysed by GC-MS and given a rational explaination.Furthermore,serval ways to synthesizing intermediate products have been investigated , and a simple route to synthesizing α-methylenebenzeneacetic acid come through carbenes was been found.Most of the intermediate products have been characterized by IR and 1H-NMR.更多还原