cis-1-allyl-4-[(2-chloro-1,1-dimethyl)ethyl]-3-methoxyazetidin-2-one

• 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: cis-1-allyl-4-[(2-chloro-1,1-dimethyl)ethyl]-3-methoxyazetidin-2-one
• 英文别名: Oappvcyyyqutsb-iucakerbsa-；(3S,4R)-4-(1-chloro-2-methylpropan-2-yl)-3-methoxy-1-prop-2-enylazetidin-2-one
• 化学式: C₁₁H₁₈ClNO₂
• 分子量: 231.722
• InChiKey: OAPPVCYYYQUTSB-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1-allyl-4-[(2-chloro-1,1-dimethyl)ethyl]-3-methoxyazetidin-2-one 、 甲醇 在 sodium methylate 作用下， 反应 4.0h， 以60%的产率得到Z-methyl 5-allylamino-4,4-dimethyl-2-methoxypent-2-enoate
  参考文献：
  名称：

  Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines

  摘要：

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.

  DOI：

  10.1021/jo040161b
• 作为产物：
  描述：

  3-氯-2,2-二甲基-1-丙醇 在 magnesium sulfate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 cis-1-allyl-4-[(2-chloro-1,1-dimethyl)ethyl]-3-methoxyazetidin-2-one
  参考文献：
  名称：

  Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines

  摘要：

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.

  DOI：

  10.1021/jo040161b

文献信息

• Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines
  作者：Yves Dejaegher、Norbert De Kimpe

  DOI：10.1021/jo040161b

  日期：2004.9.1

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.

表征谱图