biphenyl-4-yl-(4-nitro-benzyliden)-amine | 71478-76-7

• 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: biphenyl-4-yl-(4-nitro-benzyliden)-amine
• 英文别名: Biphenyl-4-yl-(4-nitro-benzyliden)-amin；4-Nitro-benzaldehyd-biphenyl-4-ylimin；1-(4-nitrophenyl)-N-(4-phenylphenyl)methanimine
• CAS: 71478-76-7
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: CWRQMOVDWNTEGE-UHFFFAOYSA-N

物化性质

• 熔点：
  181-183 °C(Solv: ethanol (64-17-5))
• 沸点：
  497.6±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  biphenyl-4-yl-(4-nitro-benzyliden)-amine 、 N-苯基-N-甲基甘氨酸盐酸盐 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 苯 为溶剂， 以83%的产率得到cis-1-(4-biphenylyl)-3-(methylphenylamino)-4-(p-nitrophenyl)-2-azetidinone
  参考文献：
  名称：

  Cycloaddition of (N-alkyl-N-phenylamino)ketene with imines

  摘要：

  (N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a [2 + 2] cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones. The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition. The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines. In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine. These results are discussed in terms of a two-step zwitterionic intermediate.

  DOI：

  10.1021/jo00021a029
• 作为产物：
  描述：

  4-氨基联苯 、 对硝基苯甲醛 以 苯 为溶剂， 生成 biphenyl-4-yl-(4-nitro-benzyliden)-amine
  参考文献：
  名称：

  Cycloaddition of (N-alkyl-N-phenylamino)ketene with imines

  摘要：

  (N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a [2 + 2] cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones. The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition. The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines. In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine. These results are discussed in terms of a two-step zwitterionic intermediate.

  DOI：

  10.1021/jo00021a029

文献信息

• One‐Pot Synthesis of Fused Tetrahydroquinoline‐Iminosugar Derivatives
  作者：Jilai Wu、Song Xie、Xin Xu、Ziyi Zhou、Likai Zhou、Chao Wei、Xiaoliu Li、Chen Wu、Hua Chen

  DOI：10.1002/ejoc.202300915

  日期：2023.11.21

  Under the catalysis of Yb(OTf)3, the cyclization of iminium-ion intermediates and imines was promoted through the aza-Diels-Alder mechanism, providing a simple reaction for the synthesis of tetrahydroquinoline-iminosugars derivatives with good stereoselectivity. The absolute structures of compounds 1 a and 5 a were confirmed by single crystal X-ray diffraction and 2D NMR.

  在Yb(OTf) 3催化下，通过aza-Diels-Alder机理促进亚胺离子中间体与亚胺的环化，为合成具有良好立体选择性的四氢喹啉亚氨基糖衍生物提供了简单的反应。通过单晶X射线衍射和2D NMR确认了化合物1a和5a的绝对结构。