(Z)-α-(1'-Bromoethylidene)-β-vinyl-γ-butyrolactone | 134078-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (Z)-α-(1'-Bromoethylidene)-β-vinyl-γ-butyrolactone
• 英文别名: (3Z)-3-(1-bromoethylidene)-4-ethenyloxolan-2-one
• CAS: 134078-84-5
• 化学式: C₈H₉BrO₂
• 分子量: 217.062
• InChiKey: HLTNKRNLIAPRPE-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4'-Bromo-2'(E)-butenyl 2-butynoate 在 palladium diacetate 、 lithium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 生成 (E)-α-(1'-Bromoethylidene)-β-vinyl-γ-butyrolactone 、 (Z)-α-(1'-Bromoethylidene)-β-vinyl-γ-butyrolactone
  参考文献：
  名称：

  Divalent palladium catalyzed stereoselective synthesis of .alpha.-(Z)-(halomethylene)-.gamma.-butyrolactone derivatives and its mechanism

  摘要：

  Alpha-Methylene-gamma-butyrolactone rings have been constructed by bis(benzonitrile)palladium dihalide or Pd-(OAc)2-LiX catalyzed cyclization reaction of haloallylic 2-alkynoates. A mechanism involving a trans halopalladation, followed by intramolecular insertion of a carbon-carbon double bond to a carbon-palladium bond and subsequent dehalopalladation, is briefly discussed.

  DOI：

  10.1021/jo00017a025

文献信息

• Divalent palladium catalyzed stereoselective synthesis of .alpha.-(Z)-(halomethylene)-.gamma.-butyrolactone derivatives and its mechanism
  作者：Shengming Ma、Xiyan Lu

  DOI：10.1021/jo00017a025

  日期：1991.8

  Alpha-Methylene-gamma-butyrolactone rings have been constructed by bis(benzonitrile)palladium dihalide or Pd-(OAc)2-LiX catalyzed cyclization reaction of haloallylic 2-alkynoates. A mechanism involving a trans halopalladation, followed by intramolecular insertion of a carbon-carbon double bond to a carbon-palladium bond and subsequent dehalopalladation, is briefly discussed.