2-((E)-propylidene)-1,1-bis(methoxycarbonyl)cyclopentane | 1172602-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((E)-propylidene)-1,1-bis(methoxycarbonyl)cyclopentane
• 英文别名: dimethyl (2E)-2-propylidenecyclopentane-1,1-dicarboxylate
• CAS: 1172602-17-3
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: BAACAYPDCNLBQS-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethylzinc 、 (E)-dimethyl 2-iodomethylenecyclopentane-1,1-dicarboxylate 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以73%的产率得到2-((E)-propylidene)-1,1-bis(methoxycarbonyl)cyclopentane
  参考文献：
  名称：

  An X⁻ (X = I, Br)-Triggered Ring-Opening Cyclization of Cyclopropenyl-Substituted Alkyl Halides or Mesylates: An Efficient and Highly Regio- and Stereoselective Approach to (E)-Haloalkylidene 4−7-Membered Cyclic Compounds

  摘要：

  Polyfunctionalized (E)-haloalkylidene cyclic products were efficiently synthesized in moderate to excellent yields via a regio- and stereoselective X- (X = I or Br)-triggered ring-opening intramolecular trapping of cyclopropenes 1. The reaction can be used for construction of 4-7-membered products. The E-stereoselectivity of the exo-C=C bond is very high. The carbon-halogen bond in the exo-C=C bond may further be elaborated to prepare differently substituted cyclic products with a stereodefined C=C bond.

  DOI：

  10.1021/jo900389m

文献信息

• An X⁻ (X = I, Br)-Triggered Ring-Opening Cyclization of Cyclopropenyl-Substituted Alkyl Halides or Mesylates: An Efficient and Highly Regio- and Stereoselective Approach to (<i>E)</i>-Haloalkylidene 4−7-Membered Cyclic Compounds
  作者：Jie Chen、Shengming Ma

  DOI：10.1021/jo900389m

  日期：2009.8.7

  Polyfunctionalized (E)-haloalkylidene cyclic products were efficiently synthesized in moderate to excellent yields via a regio- and stereoselective X- (X = I or Br)-triggered ring-opening intramolecular trapping of cyclopropenes 1. The reaction can be used for construction of 4-7-membered products. The E-stereoselectivity of the exo-C=C bond is very high. The carbon-halogen bond in the exo-C=C bond may further be elaborated to prepare differently substituted cyclic products with a stereodefined C=C bond.