(R)-1-(1-hydroxybut-3-enyl)cyclopropanol | 1156508-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-(1-hydroxybut-3-enyl)cyclopropanol
• 英文别名: 1-[(1R)-1-hydroxybut-3-enyl]cyclopropan-1-ol
• CAS: 1156508-57-4
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: NTOVLIAJPHQMCS-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(1-hydroxybut-3-enyl)cyclopropanol 、 甲基磺酰氯 、 乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以73%的产率得到(R)-1-(1-(methylsulfonyloxy)cyclopropyl)but-3-enyl acetate
  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)-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