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化学学报
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化学学报 ›› 1988, Vol. 46 ›› Issue (8): 784-890. 上一篇    下一篇

研究论文

胶团噻唑衍生物对安息香不对称合成反应的催化作用

赵晨;陈少林;吴佩强;文重   

  1. 北京大学化学系
  • 发布日期:1988-08-15

Asymmetric benzoin condensation catalyzed by optical active micellar thiazolium salts

ZHAO CHEN;CHEN SHAOLIN;WU PEIQIANG;WEN ZHONG   

  • Published:1988-08-15

PDF

643

被引次数

26

通过α-(1-萘基)-N-硫代甲酰乙胺与卤代酮反应制得六个光学活性的4-烷基-3-α-(1-萘基)乙基噻唑溴化物烷基碳链长=1,2,7.11,15,21). 将其用于催化水溶液中的安息香缩合反应, 所得产物收率约20-30%具有较高的光学纯度(47-57%). 在各种缓冲溶液中测定了S(+)-4-甲基-3-α-(1-萘基)乙基噻唑氯化物(Ta)的胶团性质和由它催化的不对称安息香缩合反应. 临界胶团浓度(cmc)证明(Ta)在反应中确以胶团形式催化. 在硼砂溶液中, 安息香的收率高达61%, 光学纯度23.6%.

关键词: 噻唑 P, 缩合反应, 催化, 胶束, 萘 P, 表面化学, 烷烃 P, 临界质量, 安息香, 不对称反应

Six optically active 4-alkyl-3-a-(1-naphthyl)ethylthiazolium salts I (n = 1, 2, 7, 11, 15, 21) were prepared by the reaction of a-(1-naphthyl)-N-(thioformyl)ethylamine with haloketones. When these optically active thiazolium salts were used as catalysts in the benzoin condensation, reasonable yield (20-30%) and moderate optical purity (47-57%) of benzoin was obtained in aqueous solution The micellar properties of (+)-I (n = 1, X = Cl) (II) in various buffer solution and asym. benzoin condensation using II as catalyst were studied. The observation of crit. micelle concentration (cmc) in various buffer solns. shows that II exists as a micelle to catalyze the benzoin condensation. The yield of benzoin up to 61% with optical purity of 23.6% was obtained in the presence of borax.

Key words: THIAZOLE P, CONDENSATION REACTION, CATALYSIS, MICELLE, NAPHTHALENE P, SURFACE CHEMISTRY, ALKANE P, CRITICAL MASS, GUM BENZOIN

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