(1R,2S)-1-dimethylcarbamoyloxy-2-cyclohexanol | 787554-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-1-dimethylcarbamoyloxy-2-cyclohexanol
• 英文别名: cis-1-dimethylcarbamoyloxy-2-cyclohexanol；rel-(1R,2S)-2-Hydroxycyclohexyl N,N-dimethylcarbamate；[(1R,2S)-2-hydroxycyclohexyl] N,N-dimethylcarbamate
• CAS: 787554-08-9
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: SCOPKQSBJIPFQD-JGVFFNPUSA-N

物化性质

• 沸点：
  282.4±29.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丁酸酐 、 (1SR,2RS)-cis-1-dimethylcarbamoyloxy-2-cyclohexanol 在 (S)-N-2,4,6-iPr3PhSO2-N(ϖ)Me-histidinol tBuPh2 ether 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 (1R,2S)-1-dimethylcarbamoyloxy-2-cyclohexanol 、 (1S,2R)-1-dimethylcarbamoyloxy-2-cyclohexyl isobutyrate 、 (1R,2S)-1-dimethylcarbamoyloxy-2-cyclohexyl isobutyrate
  参考文献：
  名称：

  Rational Design of an l-Histidine-Derived Minimal Artificial Acylase for the Kinetic Resolution of Racemic Alcohols

  摘要：

  This communication describes the rational design of an l-histidine-derived minimal artificial acylase. Our new artificial acylase, tert-butyldiphenylsilyl ether of N-(2,4,6-triisopropylbenzenesulfonyl)-pi(Me)-l-histidinol, is a simple and small molecule (molecular weight = 660) that contains only one chiral carbon center that originates from natural l-histidine. The kinetic acylation of racemic secondary alcohols induced by this compound showed an S (kfast/kslow) value of up to 93. A reusable polystyrene-bound artificial acylase was also developed to examine its practical usability.

  DOI：

  10.1021/ja045850j