Methanesulfonic acid (3aS,5R,7aS)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxol-5-yl ester | 852108-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (3aS,5R,7aS)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxol-5-yl ester
• CAS: 852108-53-3
• 化学式: C₁₀H₁₆O₆S
• 分子量: 264.299
• InChiKey: CGGZSCMLZUGIJV-FJXKBIBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (3aS,5R,7aS)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxol-5-yl ester 在 sodium azide 、 Dowex 50W₈-200 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2S,3S,6S)-6-azido-2,3-dihydroxycyclohexan-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：

  (2S,3S,6S)-6-chloro-2,3-isopropylidenedioxycyclohexan-1-one 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.58h， 生成 Methanesulfonic acid (3aS,5R,7aS)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxol-5-yl ester
  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