cis-N-(p-Anisyl)-3-benzyl-3-fluoro-4-phenyl-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: cis-N-(p-Anisyl)-3-benzyl-3-fluoro-4-phenyl-2-azetidinone
• 英文别名: (3R,4S)-3-benzyl-3-fluoro-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• 化学式: C₂₃H₂₀FNO₂
• 分子量: 361.416
• InChiKey: AWXPZMXIYRHAOC-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-亚苄基-4-甲氧基苯胺 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 cis-N-(p-Anisyl)-3-benzyl-3-fluoro-4-phenyl-2-azetidinone
  参考文献：
  名称：

  Stereocontrol by the carbon-fluorine bond and its application to asymmetric synthesis of 3-fluoro .beta.-lactams

  摘要：

  Optically active 3-fluoro-beta-lactams 4 and 5 were prepared via a ketene-imine cycloaddition reaction using fluoroacetyl chloride and an imine derived from (R)-glyceraldehyde acetonide. The high stereoselectivity observed can be rationalized as a consequence of stereoelectronic effects. Deprotonated beta-lactams 4 and 12 were reacted with alkylating agents to give exclusively cis-3-alkyl-substituted derivatives of 3-fluoro beta-lactams. The directed aldol reaction of beta-lactams 4 and 12 with aldehydes and ketones provides cis-3-hydroxyalkyl derivatives with high stereoselectivity; however, diastereoisomeric control was not maintained at the hydroxylated carbon atom. The desired stereochemistry in the side chain was achieved by reduction of 3-acetyl-3-fluoro beta-lactam 22. The lithium enolates of beta-lactams 4 and 12 have been investigated by low-temperature F-19 NMR studies.

  DOI：

  10.1021/jo00061a019

文献信息

• Stereocontrol by the carbon-fluorine bond and its application to asymmetric synthesis of 3-fluoro .beta.-lactams
  作者：John T. Welch、Koichi Araki、Robert Kawecki、John A. Wichtowski

  DOI：10.1021/jo00061a019

  日期：1993.4

  Optically active 3-fluoro-beta-lactams 4 and 5 were prepared via a ketene-imine cycloaddition reaction using fluoroacetyl chloride and an imine derived from (R)-glyceraldehyde acetonide. The high stereoselectivity observed can be rationalized as a consequence of stereoelectronic effects. Deprotonated beta-lactams 4 and 12 were reacted with alkylating agents to give exclusively cis-3-alkyl-substituted derivatives of 3-fluoro beta-lactams. The directed aldol reaction of beta-lactams 4 and 12 with aldehydes and ketones provides cis-3-hydroxyalkyl derivatives with high stereoselectivity; however, diastereoisomeric control was not maintained at the hydroxylated carbon atom. The desired stereochemistry in the side chain was achieved by reduction of 3-acetyl-3-fluoro beta-lactam 22. The lithium enolates of beta-lactams 4 and 12 have been investigated by low-temperature F-19 NMR studies.