[(1S,2R,3R)-2-chloro-3-isopropyl-1-phenethyl-2-((R)-p-tolylsulfinyl)cyclopropyl]methyl phenyl carbonate | 1569076-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S,2R,3R)-2-chloro-3-isopropyl-1-phenethyl-2-((R)-p-tolylsulfinyl)cyclopropyl]methyl phenyl carbonate
• CAS: 1569076-99-8
• 化学式: C₂₉H₃₁ClO₄S
• 分子量: 511.082
• InChiKey: OKIZCZFFOTYOEQ-CNOQBEIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3R)-2-chloro-3-isopropyl-1-phenethyl-2-((R)-p-tolylsulfinyl)cyclopropyl]methyl phenyl carbonate 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以59%的产率得到(1R,5S,6R)-1-chloro-6-isopropyl-5-phenethyl-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Synthesis of cyclopropane-fused α-chlorolactones utilizing the nucleophilicity of cyclopropylmagnesium carbenoids

  摘要：

  A novel method for the synthesis of cyclopropane-fused alpha-chloro-gamma-lactones was developed utilizing the nucleophilicity of cyclopropylmagnesium carbenoids. Cyclopropylmagnesium carbenoids were generated from i-PrMgCl and 1-chlorocyclopropyl p-tolyl sulfoxides with a [(phenoxycarbonyl)oxy]methyl group at the 2-position of the cyclopropane ring. The resulting cyclopropylmagnesium carbenoids reacted with an intramolecular carbonate unit to give 1-chloro-3-oxabicyclo[3.1.0]hexan-2-ones in moderate to good yields. The asymmetric synthesis of 1-chloro-3-oxabicyclo[3.1.0]hexan-2-one was achieved using optically active dichloromethyl p-tolyl sulfoxide as a starting material. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.038
• 作为产物：
  描述：

  [(1S,2R,3R)-2-chloro-3-isopropyl-1-(2-phenylethyl)-2-((R)-p-tolylsulfinyl)cyclopropyl]methanol 、 氯甲酸苯酯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以86%的产率得到[(1S,2R,3R)-2-chloro-3-isopropyl-1-phenethyl-2-((R)-p-tolylsulfinyl)cyclopropyl]methyl phenyl carbonate
  参考文献：
  名称：

  Synthesis of cyclopropane-fused α-chlorolactones utilizing the nucleophilicity of cyclopropylmagnesium carbenoids

  摘要：

  A novel method for the synthesis of cyclopropane-fused alpha-chloro-gamma-lactones was developed utilizing the nucleophilicity of cyclopropylmagnesium carbenoids. Cyclopropylmagnesium carbenoids were generated from i-PrMgCl and 1-chlorocyclopropyl p-tolyl sulfoxides with a [(phenoxycarbonyl)oxy]methyl group at the 2-position of the cyclopropane ring. The resulting cyclopropylmagnesium carbenoids reacted with an intramolecular carbonate unit to give 1-chloro-3-oxabicyclo[3.1.0]hexan-2-ones in moderate to good yields. The asymmetric synthesis of 1-chloro-3-oxabicyclo[3.1.0]hexan-2-one was achieved using optically active dichloromethyl p-tolyl sulfoxide as a starting material. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.038