【作者】 徐传祥；

【导师】 许家喜；

【作者基本信息】 北京化工大学 ， 化学， 2010， 硕士

【摘要】 牛磺酸是一种人体必需的含硫氨基酸,具有多种生理功能,已被广泛应用于临床和食品添加剂中；一些取代牛磺酸也具有重要的生理活性,因此取代牛磺酸的合成具有重要的意义。目前已有多种取代牛磺酸的合成方法,但是合成1-取代牛磺酸和1,1-二取代牛磺酸的方法并不十分理想,且对脂肪和芳香取代的牛磺酸的合成没有通用性。本文开发了一种新的1-位取代牛磺酸的合成方法。首先从醛酮或烯烃出发,采用几种简单易行的方法制备了一系列硝基烯烃；然后通过硝基烯烃与黄原酸钠的亲核加成反应,以较好的产率合成了一系列硝基黄原酸酯；接着用过氧甲酸对硝基黄原酸酯氧化得到硝基磺酸,随后无需提纯直接经钯碳催化的氢气的还原,以中等的产率合成了一系列1-取代牛磺酸和几种1,1-二取代牛磺酸；并提出了过酸氧化硝基黄原酸酯的机理。本文提出的这种1-位取代牛磺酸的合成方法适用于脂肪和芳香取代基的1-取代和1,1-二取代牛磺酸的制备。该方法具有原料易得,合成路线短,总体产率高,无盐法制备等优点,是一种比较通用的合成1-位取代牛磺酸的方法。更多还原

【Abstract】 Taurine is an essential sulfur-containing amino acid due to its various physiological functions.It has been widely used in clinical and food additives. Some substituted taurines also show importantly physiological activity. Thus, it is desired to develop the efficient and practical synthetic methods for substituted taurines.Although several methods have been documented for the synthesis of 1-mono-and 1,1-disubstituted taurines, all of them are not versatile for aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines.A versatile and practical synthesis of 1-mono-and 1,1-disubstituted taurines has been developed in this dissertation.A series of nitroolefins were prepared from aldehydes,ketones,or olefins by some convenient methods.They underwent the nucleophilic addition reaction with sodium ethylxanthan to give rise to nitroalkyl xanthates in satisfactory to good yields.After the oxidation with performic acid and subsequent reduction with hydrogen in the presence of Pd/C, the nitroalkyl xanthates were converted to 1-mono and 1,1-disubstituted taurines in moderate overall yields.The current method can be used to synthesize both aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines. The method is indeed a versatile and practical route to the synthesis of 1-mono-and 1,1-disubstitued taurines because of readily available starting materials, good overall yields, short synthetic steps, and salt-free process.更多还原