(E)-4-Methyl-4-(3-phenyl-2-propenyl)-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: (E)-4-Methyl-4-(3-phenyl-2-propenyl)-2-azetidinone
• 英文别名: 4-methyl-4-[(E)-3-phenylprop-2-enyl]azetidin-2-one
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: GXTQMEIJGNWJNY-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-Allyl-4-methyl-2-azetidinone 、 氯化苯汞 在 氯化铵 、 lithium chloride 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-Methyl-4-(3-phenyl-2-propenyl)-2-azetidinone 、 (Z)-3-Methyl-3-hexenamide 、 (E)-3-Methyl-3-hexenamide
  参考文献：
  名称：

  Palladium(II)-promoted cross-coupling of 4-alkenyl-2-azetidinones with organomercurials

  摘要：

  The palladium-promoted cross-coupling of 4-alkenyl-2-azetidinones with aryl and vinylic mercurials provides 5-aryl-3-alkenamides and 3,6-alkadienamides, respectively. Modest to excellent stereoselectivity for formation of the new carbon-carbon double bond is observed. The reaction becomes catalytic in palladium when cupric chloride and oxygen are introduced. This process constitutes the first organometallic ring opening of 2-azetidinones to acyclic unsaturated amides.

  DOI：

  10.1021/jo00060a024

文献信息

• Palladium(II)-promoted cross-coupling of 4-alkenyl-2-azetidinones with organomercurials
  作者：Richard C. Larock、Shuji Ding

  DOI：10.1021/jo00060a024

  日期：1993.4

  The palladium-promoted cross-coupling of 4-alkenyl-2-azetidinones with aryl and vinylic mercurials provides 5-aryl-3-alkenamides and 3,6-alkadienamides, respectively. Modest to excellent stereoselectivity for formation of the new carbon-carbon double bond is observed. The reaction becomes catalytic in palladium when cupric chloride and oxygen are introduced. This process constitutes the first organometallic ring opening of 2-azetidinones to acyclic unsaturated amides.