(1S,2S,3R,6S)-2-chloro-6-(dimethylthexylsilyloxy)-2,3-epoxycyclohexyl acetate | 852108-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,2S,3R,6S)-2-chloro-6-(dimethylthexylsilyloxy)-2,3-epoxycyclohexyl acetate
• CAS: 852108-62-4
• 化学式: C₁₆H₂₉ClO₄Si
• 分子量: 348.942
• InChiKey: MYYHJNMMWYNDPN-KNCOVGOOSA-N

物化性质

• 熔点：
  63-65 °C
• 沸点：
  360.5±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  48.06
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,6S)-2-chloro-6-(dimethylthexylsilyloxy)-2,3-epoxycyclohexyl acetate 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 以65%的产率得到(2S,3S,6S)-2-acetoxy-6-azido-3-(dimethylthexylsilyloxy)cyclohexan-1-one
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds

  摘要：

  A series of chiral alpha-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclo-hexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of alpha-chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.012
• 作为产物：
  描述：

  (1S,2S)-3-chlorocyclohex-3-ene-1,2-diol 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 (1S,2S,3R,6S)-2-chloro-6-(dimethylthexylsilyloxy)-2,3-epoxycyclohexyl acetate
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds

  摘要：

  A series of chiral alpha-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclo-hexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of alpha-chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.012