1-acetyl-4-methyl-4-vinyl-2-azetidinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-acetyl-4-methyl-4-vinyl-2-azetidinone
• 英文别名: 1-Acetyl-4-ethenyl-4-methylazetidin-2-one
• 化学式: C₈H₁₁NO₂
• mdl: MFCD18812909
• 分子量: 153.181
• InChiKey: ADDUTEMMEFNWMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-4-methyl-4-vinyl-2-azetidinone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三丁基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (Z)-N-acetyl-3-methyl-2,4-pentadienamide 、 (E)-N-acetyl-3-methyl-2,4-pentadienamide
  参考文献：
  名称：

  Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion

  摘要：

  Ring opening reactions of 1-acetyl-4-vinyl-2-azetidinones in the presence of palladium(0)-n-Bu(3)P catalyst gave 2,4-pentadienamides in good yields, whereas 2-substituted-1,3-dienes were produced by the reaction of 1-sulfonyl-2-vinyl-2-methylazetidines. Ring opening dimerization took place to give 1,7-ditrifluoromethanesulfonyl-1,7-diazacyclododecane in the reaction of 1-trifluoromethanesulfonyl-2-vinylazetidine.

  DOI：

  10.1016/0040-4020(95)00217-v
• 作为产物：
  描述：

  4-methyl-4-vinylazetidin-2-one 、 乙酰氯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到1-acetyl-4-methyl-4-vinyl-2-azetidinone
  参考文献：
  名称：

  Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion

  摘要：

  Ring opening reactions of 1-acetyl-4-vinyl-2-azetidinones in the presence of palladium(0)-n-Bu(3)P catalyst gave 2,4-pentadienamides in good yields, whereas 2-substituted-1,3-dienes were produced by the reaction of 1-sulfonyl-2-vinyl-2-methylazetidines. Ring opening dimerization took place to give 1,7-ditrifluoromethanesulfonyl-1,7-diazacyclododecane in the reaction of 1-trifluoromethanesulfonyl-2-vinylazetidine.

  DOI：

  10.1016/0040-4020(95)00217-v

文献信息

• Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion
  作者：Akiharu Satake、Hideo Ishii、Isao Shimizu、Yoichi Inoue、Hajime Hasegawa、Akio Yamamoto

  DOI：10.1016/0040-4020(95)00217-v

  日期：1995.5

  Ring opening reactions of 1-acetyl-4-vinyl-2-azetidinones in the presence of palladium(0)-n-Bu(3)P catalyst gave 2,4-pentadienamides in good yields, whereas 2-substituted-1,3-dienes were produced by the reaction of 1-sulfonyl-2-vinyl-2-methylazetidines. Ring opening dimerization took place to give 1,7-ditrifluoromethanesulfonyl-1,7-diazacyclododecane in the reaction of 1-trifluoromethanesulfonyl-2-vinylazetidine.