N-benzoyl-3-(bromomethyl)-3-chloroazetidine | 222527-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-3-(bromomethyl)-3-chloroazetidine
• 英文别名: [3-(Bromomethyl)-3-chloroazetidin-1-yl]-phenylmethanone
• CAS: 222527-61-9
• 化学式: C₁₁H₁₁BrClNO
• 分子量: 288.571
• InChiKey: JRDRQWTWLZKYED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzoyl-3-(bromomethyl)-3-chloroazetidine 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到三氯(三丙基胺)硼
  参考文献：
  名称：

  Synthesis ofN-Substituted Azetidin-3-ones

  摘要：

  Addition of RC(O)CI (R = Oft, Me, or Ph) across the highly strained N-C(3) sigma-bond in 3-bromomethyl-1-azabicyclo[1.1.0]butane (1) afforded the corresponding N-acyl-3-bromomethyl-3-chloroazetidines (2a-2c, respectively). Subsequent zinc promoted eliminative dehalogenation of 2a-2c produced the corresponding N-acyl-3-methyleneazetidines (3a-3c, respectively). Finally, ozonolysis of 3a-3c afforded the corresopnding N-acylazetidin-3-ones (4a-4c, respectively).

  DOI：

  10.1080/00397919908086047
• 作为产物：
  描述：

  苯甲酰氯 、 1-aza-3-(bromomethyl)bicyclo<1.1.0>butane 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以74%的产率得到N-benzoyl-3-(bromomethyl)-3-chloroazetidine
  参考文献：
  名称：

  Synthesis ofN-Substituted Azetidin-3-ones

  摘要：

  Addition of RC(O)CI (R = Oft, Me, or Ph) across the highly strained N-C(3) sigma-bond in 3-bromomethyl-1-azabicyclo[1.1.0]butane (1) afforded the corresponding N-acyl-3-bromomethyl-3-chloroazetidines (2a-2c, respectively). Subsequent zinc promoted eliminative dehalogenation of 2a-2c produced the corresponding N-acyl-3-methyleneazetidines (3a-3c, respectively). Finally, ozonolysis of 3a-3c afforded the corresopnding N-acylazetidin-3-ones (4a-4c, respectively).

  DOI：

  10.1080/00397919908086047

文献信息

• Synthesis of<i>N</i>-Substituted Azetidin-3-ones
  作者：Alan P. Marchand、Arokiasamy Devasagayaraj

  DOI：10.1080/00397919908086047

  日期：1999.3

  Addition of RC(O)CI (R = Oft, Me, or Ph) across the highly strained N-C(3) sigma-bond in 3-bromomethyl-1-azabicyclo[1.1.0]butane (1) afforded the corresponding N-acyl-3-bromomethyl-3-chloroazetidines (2a-2c, respectively). Subsequent zinc promoted eliminative dehalogenation of 2a-2c produced the corresponding N-acyl-3-methyleneazetidines (3a-3c, respectively). Finally, ozonolysis of 3a-3c afforded the corresopnding N-acylazetidin-3-ones (4a-4c, respectively).