(R)-1-(oxiran-2-yl)cyclopropyl methanesulfonate | 1156508-55-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-1-(oxiran-2-yl)cyclopropyl methanesulfonate
• CAS: 1156508-55-2
• 化学式: C₆H₁₀O₄S
• 分子量: 178.209
• InChiKey: BKRHQFCWRCCRGW-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.9
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-1-(oxiran-2-yl)cyclopropyl methanesulfonate 、 乙烯基溴化镁 在 copper(l) cyanide 、 ammonium hydroxide 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以75%的产率得到(R)-1-(1-hydroxybut-3-enyl)cyclopropyl methanesulfonate
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003
• 作为产物：
  描述：

  (R)-2-hydroxy-2-(1-(methylsulfonyloxy)cyclopropyl)ethyl 4-methylbenzenesulfonate 在 氢氧化钾 、 苄基三乙基氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以94%的产率得到(R)-1-(oxiran-2-yl)cyclopropyl methanesulfonate
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003