N-(4-nitrobenzylidene)naphthalene-1-amine | 967-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-nitrobenzylidene)naphthalene-1-amine
• 英文别名: N-(α-naphthyl)-4-nitrobenzylimine；p-Nitrobenzal-α-naphthylamin
• CAS: 967-13-5
• 化学式: C₁₇H₁₂N₂O₂
• mdl: MFCD00194137
• 分子量: 276.294
• InChiKey: QDPIWAUWWLKADK-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.5
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-nitrobenzylidene)naphthalene-1-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79%的产率得到trans-1-α-naphthyl-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：

  1-萘胺 、 对硝基苯甲醛 以 苯 为溶剂， 生成 N-(4-nitrobenzylidene)naphthalene-1-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

• STRODS YA. A.; LIELBRIEDIS I. EH.; NEJLAND O. YA., XIMIYA GETEROTSIKL. SOEDIN., 1977, HO 7, 977-979
  作者：STRODS YA. A.、 LIELBRIEDIS I. EH.、 NEJLAND O. YA.

  DOI：——

  日期：——
• SHARMA S. D.; KAUR S.; MEHRA USHA, INDIAN J. CHEM., 25,(1986) N 2, 141-144
  作者：SHARMA S. D.、 KAUR S.、 MEHRA USHA

  DOI：——

  日期：——
• Cycloaddition of (N-alkyl-N-phenylamino)ketene with imines
  作者：William T. Brady、Mohammad M. Dad

  DOI：10.1021/jo00021a029

  日期：1991.10

  (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.