(1R)-2,2-dimethyl-3-oxocyclohexyl acetate | 1092452-05-5

• 分子结构分类: 有机化合物
• 英文名称: (1R)-2,2-dimethyl-3-oxocyclohexyl acetate
• 英文别名: [(1R)-2,2-dimethyl-3-oxocyclohexyl] acetate
• CAS: 1092452-05-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: GGDLESZXMDYJJS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-2,2-dimethyl-3-oxocyclohexyl acetate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以92%的产率得到(1R)-3-hydroxy-2,2-dimethylcyclohexanone
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Both Enantiomers of 3-Hydroxy-2,2-dimethylcyclohexanone

  摘要：

  The stereoselective acetylation of meso-2,2-dimethyl-1,3-cyclohexanediol by vinyl acetate in the presence of three lipases gave the (1R,3S)-monoester in high enantiomeric excess (ee >= 98%). The hydrolysis of the corresponding meso-diacetate in the presence of Candida antarctica lipase in phosphate buffer provided the opposite enantiomer. Optically active monciacetates were converted to both enantiomers of 3-hydroxy-2.2-dimethylcyclohexanone, a versatile chiral building block.

  DOI：

  10.1021/jo801954v
• 作为产物：
  描述：

  (1R,3S)-3-hydroxy-2,2-dimethylcyclohexyl acetate 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(1R)-2,2-dimethyl-3-oxocyclohexyl acetate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Both Enantiomers of 3-Hydroxy-2,2-dimethylcyclohexanone

  摘要：

  The stereoselective acetylation of meso-2,2-dimethyl-1,3-cyclohexanediol by vinyl acetate in the presence of three lipases gave the (1R,3S)-monoester in high enantiomeric excess (ee >= 98%). The hydrolysis of the corresponding meso-diacetate in the presence of Candida antarctica lipase in phosphate buffer provided the opposite enantiomer. Optically active monciacetates were converted to both enantiomers of 3-hydroxy-2.2-dimethylcyclohexanone, a versatile chiral building block.

  DOI：

  10.1021/jo801954v