(1S,3R)-3-(2,2,2-trideuterioacetoxy)-1-cyclohexanol | 888025-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R)-3-(2,2,2-trideuterioacetoxy)-1-cyclohexanol
• CAS: 888025-01-2
• 化学式: C₈H₁₄O₃
• 分子量: 161.174
• InChiKey: KKGVEAWZDIBQMT-VYYPIGHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3R)-3-(2,2,2-trideuterioacetoxy)-1-cyclohexanol 在 Candida antarctica lipase B 作用下， 以 phosphate buffer 、 甲苯 为溶剂， 反应 49.0h， 生成 (1R,3S)-3-acetoxy-1-cyclohexanol
  参考文献：
  名称：

  Enzymatic Resolution, Desymmetrization, and Dynamic Kinetic Asymmetric Transformation of 1,3-Cycloalkanediols

  摘要：

  An efficient desymmetrization of cis-1,3-cyclohexanediol to (1S, 3R)-3-(acetoxy)-1-cyclohexanol ((R, S)-2a) was performed via Candida antarctica lipase B (CALB)-catalyzed transesterification, in high yield (up to 93%) and excellent enantioselectivity (ee's up to > 99.5%). (R, R)-Diacetate ((R, R)-3a) was obtained in a DYKAT process at room temperature from (1S, 3R)-3-acetoxy-1-cyclohexanol ((R, S)-2a), in a high trans/cis ratio (91: 9) and in excellent enantioselectivity of > 99%. Metal- and enzyme-catalyzed dynamic transformation of cis/trans-1,3-cyclohexanediol using PS-C gave a high diastereoselectivity for cis-diacetate (cis/trans) 97: 3). The (1R, 3S)-3-acetoxy-1-cyclohexanol (ent-(R, S)-2a) was obtained from cis-diacetate by CALB-catalyzed hydrolysis in an excellent yield (97%) and selectivity (> 99% ee). By deuterium labeling it was shown that intramolecular acyl migration does not occur in the transformation of cis-monoacetate to the cis-diacetate.

  DOI：

  10.1021/jo060002n
• 作为产物：
  描述：

  cis-1,3-cyclohexanediol 、 在 Candida antarctica lipase B 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以43%的产率得到(1S,3R)-3-(2,2,2-trideuterioacetoxy)-1-cyclohexanol
  参考文献：
  名称：

  Enzymatic Resolution, Desymmetrization, and Dynamic Kinetic Asymmetric Transformation of 1,3-Cycloalkanediols

  摘要：

  An efficient desymmetrization of cis-1,3-cyclohexanediol to (1S, 3R)-3-(acetoxy)-1-cyclohexanol ((R, S)-2a) was performed via Candida antarctica lipase B (CALB)-catalyzed transesterification, in high yield (up to 93%) and excellent enantioselectivity (ee's up to > 99.5%). (R, R)-Diacetate ((R, R)-3a) was obtained in a DYKAT process at room temperature from (1S, 3R)-3-acetoxy-1-cyclohexanol ((R, S)-2a), in a high trans/cis ratio (91: 9) and in excellent enantioselectivity of > 99%. Metal- and enzyme-catalyzed dynamic transformation of cis/trans-1,3-cyclohexanediol using PS-C gave a high diastereoselectivity for cis-diacetate (cis/trans) 97: 3). The (1R, 3S)-3-acetoxy-1-cyclohexanol (ent-(R, S)-2a) was obtained from cis-diacetate by CALB-catalyzed hydrolysis in an excellent yield (97%) and selectivity (> 99% ee). By deuterium labeling it was shown that intramolecular acyl migration does not occur in the transformation of cis-monoacetate to the cis-diacetate.

  DOI：

  10.1021/jo060002n