(R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropanol | 1156508-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropanol
• 英文别名: 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropan-1-ol
• CAS: 1156508-40-5
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: HJRCMSQZQRCZJP-ZCFIWIBFSA-N

物化性质

• 沸点：
  231.9±25.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(R)-1-(2,2-dimethyl-1,3-dioxolan-4-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
• 作为产物：
  描述：

  乙基溴化镁 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯 在 titanium(IV) isopropylate 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 苯 、 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到(R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropanol
  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