有机化学 ›› 1990, Vol. 10 ›› Issue (5): 464-470. 上一篇    下一篇

研究论文

光学活性芳族氰醇的合成及其稳定性的研究

童跃进;丁孟贤   

  1. 中国科学院长春应用化学研究所
  • 发布日期:1990-10-25

Synthesis of optically active cyanohydrins and study on their stabilities

TONG YUEJIN;DING MENGXIAN   

  • Published:1990-10-25

光学活性芳族氰醇以及由它转变而成的α-羟基酸, α-羟基酯, α-羟基酮和β一羟基胺等光活性异构体都是主要的农药和医药中间体, 从实用观点看, 利用催化不对称合成来制取光活性氰醇, 更具有重要意义, 因此, 寻找原料易得, 合成方法简便的新型光学活性催化剂很有必要, 另一方面, 有关光学活性催化剂的可能催化机理, 立体选择能力的评价以及氰醇的旋光稳定性和化学稳定性等与氰醇不对称合成紧密相关的问题至今尚较少涉及, 值得深入研究, 本文对光学活性芳族氰醇的合成及其稳定性作了研究。

关键词: 稳定性, 醇, 氰化合物, 反应机理, 红外分光光度法, 核磁共振谱法, 元素分析, 芳香族化合物, 不对称反应, 消旋

Twenty chiral catalysts, among which twelve were prepared or purified in this work, have been used in the asym. synthesis of cyanohydrins from benzaldehyde. The activity and enantioselectivity of these catalysts in the reaction have been observed The optical yields of these asym. reaction varied from zero to about 60%. The investigation on the stability of the cyanohydrins showed that the purified cyanohydrins could be optically stable within a week without apparent decrease of their optical rotation and chem. stable over 5 mo. The mechanism of the reaction and the evaluation of enantioselectivity of the catalysts have also been discussed.

Key words: REACTION MECHANISM, STABILITY, INFRARED SPECTROPHOTOMETRY, ALCOHOL, CYANOGEN COMPOUNDS, NMR SPECTROMETRY, ELEMENTAL ANALYSIS, AROMATIC COMPOUNDS, RACEMIZATION

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