(1R,2R,4S,6S)-2-chloro-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one | 1459202-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4S,6S)-2-chloro-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one
• CAS: 1459202-31-3
• 化学式: C₁₀H₁₅ClO₂
• 分子量: 202.681
• InChiKey: NRGIUQXTXHOWHZ-DOACCVQLSA-N

物化性质

• 沸点：
  302.2±22.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  cis-3α,4α-caranediol 在 二氧化氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以40%的产率得到(1R,2R,4S,6S)-2-chloro-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one
  参考文献：
  名称：

  Oxidation of terpenoid diols with chlorine dioxide: Preparation of ketols and α-chlorohydroxyketones of carane and pinane structures

  摘要：

  Vicinal terpenoid diols of carane- and pinane-type structures have been oxidized with chlorine dioxide in pyridine to form the corresponding ketols in the preparative yield of 52-72%, the selectivity of alpha-hydroxyketones formation being 80-90%. It has been shown that the diols reactivity towards oxidation with ClO2 depends mainly on the stereochemistry of hydroxy groups. The catalysts, VO(acac)(2), Mo(CO6), and MoCl5 have practically no effect on the oxidation process. When the reaction has been performed in dimethylformamide, the hydroxyketone chlorination occurred at high conversion.

  DOI：

  10.1134/s1070363213080124