4-Allyl-4-methyl-2-azetidinone | 148058-93-9

• 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: 4-Allyl-4-methyl-2-azetidinone
• 英文别名: 4-Methyl-4-prop-2-enylazetidin-2-one
• CAS: 148058-93-9
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: JDNULUVLZHGUPO-UHFFFAOYSA-N

物化性质

• 沸点：
  239.7±9.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘苯 、 4-Allyl-4-methyl-2-azetidinone 在 palladium diacetate sodium formate 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (Z)-3-Methyl-6-phenyl-hex-3-enoic acid amide 、 (E)-3-Methyl-6-phenyl-hex-3-enoic acid amide
  参考文献：
  名称：

  Synthesis of aryl-substituted 3-alkenamides via palladium-catalyzed cross-coupling of aryl iodides and 4-alkenyl-2-azetidinones

  摘要：

  Palladium catalyzes the cross-coupling of aryl iodides and 4-alkenyl-2-azetidinones to give good yields of aryl-substituted 3-alkenamides.

  DOI：

  10.1016/s0040-4039(00)77470-3
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 2-甲基-1,4-戊二烯 在 氢氧化钾 、 sodium sulfite 作用下， 生成 4-Allyl-4-methyl-2-azetidinone
  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

• Synthesis of aryl-substituted 3-alkenamides via palladium-catalyzed cross-coupling of aryl iodides and 4-alkenyl-2-azetidinones
  作者：Richard C. Larock、Shuji Ding

  DOI：10.1016/s0040-4039(00)77470-3

  日期：1993.2

  Palladium catalyzes the cross-coupling of aryl iodides and 4-alkenyl-2-azetidinones to give good yields of aryl-substituted 3-alkenamides.
• 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.