Ethyl 1-acetyl-2-(3-methylsulfonyloxypropyl)cycloprop-2-ene-1-carboxylate | 1172601-91-0

• 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: Ethyl 1-acetyl-2-(3-methylsulfonyloxypropyl)cycloprop-2-ene-1-carboxylate
• CAS: 1172601-91-0
• 化学式: C₁₂H₁₈O₆S
• 分子量: 290.337
• InChiKey: GEKGJSUICTWVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 1-acetyl-2-(3-methylsulfonyloxypropyl)cycloprop-2-ene-1-carboxylate 在 lithium bromide monohydrate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以87%的产率得到2-((E)-bromomethylene)-1-acetyl-1-(ethoxycarbonyl)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