1,4-diphenyl-3-vinyl-2-azetidinone | 33812-87-2

• 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: 1,4-diphenyl-3-vinyl-2-azetidinone
• 英文别名: 1,4-diphenyl-3-vinyl-azetidin-2-one；3-Ethenyl-1,4-diphenylazetidin-2-one
• CAS: 33812-87-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: QWTZRYZXDPDJOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1,4-diphenyl-3-vinyl-2-azetidinone 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 异丙醇 为溶剂， 反应 2.0h， 生成 3-(2-methyloxiranyl)-1,4-diphenyl-3-vinylazatidin-2-one
  参考文献：
  名称：

  Stereoselective Functionalization of Alkenyl-β-lactams

  摘要：

  Alkenyi-beta-lactams, obtained by palladium-catalyzed [2+2] cycloaddition of imines with allyl halides, were functionalized in a stereoselective way by a simple deprotonation with LDA, and subsequent capture of the formed carbanion by various electrophiles. Alkyl, hydroxy and epoxy functionalities were inserted exclusively at the C-3 carbon atom of the beta-lactamic system, without performing new cyclizations. High stereoselectivity was noticed with the quenching taking place preferentially at the C, with respect to the C. carbon atom of the allylic moiety of the azetidinyl anion generated by deprotonation.

  DOI：

  10.3987/com-05-10508

文献信息

• Stereoselective Functionalization of Alkenyl-β-lactams
  作者：Luigino Troisi、Emanuela Pindinelli、Luisella De Vitis、Catia Granito、Ludovico Ronzini

  DOI：10.3987/com-05-10508

  日期：——

  Alkenyi-beta-lactams, obtained by palladium-catalyzed [2+2] cycloaddition of imines with allyl halides, were functionalized in a stereoselective way by a simple deprotonation with LDA, and subsequent capture of the formed carbanion by various electrophiles. Alkyl, hydroxy and epoxy functionalities were inserted exclusively at the C-3 carbon atom of the beta-lactamic system, without performing new cyclizations. High stereoselectivity was noticed with the quenching taking place preferentially at the C, with respect to the C. carbon atom of the allylic moiety of the azetidinyl anion generated by deprotonation.