1-formylcyclopropyl pivalate | 1156508-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-formylcyclopropyl pivalate
• 英文别名: Propanoic acid, 2,2-dimethyl-, 1-formylcyclopropyl ester；(1-formylcyclopropyl) 2,2-dimethylpropanoate
• CAS: 1156508-34-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: SDFKHKVGNZVJQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-formylcyclopropyl pivalate 、 烯丙基三丁基锡 在 titanium(IV) isopropylate 、 S-1,1'-联-2-萘酚 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 730.5h， 以45%的产率得到1-(1-hydroxycyclopropyl)but-3-enyl pivalate
  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：

  1-vinylcyclopropyl pivalate 在 臭氧 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 以85%的产率得到1-formylcyclopropyl pivalate
  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