N-(4-nitrophenyl)-2-aminotropone | 1265478-25-8

• 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-(4-nitrophenyl)-2-aminotropone
• 英文别名: 2-(4-nitroanilino)cyclohepta-2,4,6-trien-1-one
• CAS: 1265478-25-8；908109-61-5
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: NGTPUDDLYPIVJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-2,4,6-环庚三烯-1-酮 、 4-硝基苯胺 在 三乙胺 作用下， 以 苯 为溶剂， 反应 166.0h， 以16%的产率得到N-(4-nitrophenyl)-2-aminotropone
  参考文献：
  名称：

  Prototropic tautomerism and solid-state photochromism of N-phenyl-2-aminotropones

  摘要：

  N-(4-X-phenyl)-2-aminotropones (X = methoxy, chloro, or nitro substituent) and their clathrate crystals with deoxycholic acid (DCA) were prepared and their prototropic phenomena were determined. Each 2-aminotropone derivative existed as a keto amine form in the crystal state irrespective of its substituent, which influenced the stability of keto amine or enol imine structure in solution. X-Ray crystal structure analysis of N-(4-methoxyphenyl)-2-aminotropone revealed the existence of bimolecular hydrogen bonds and close molecular packing, which would inhibit structural change necessary to photo-induced prototropic tautomerization. Thus, N-phenyl-2-aminotropones did not show photocoloration in the crystal state, while their clathrate crystals with DCA were found to exhibit photochromism. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.06.001

文献信息

• Prototropic tautomerism and solid-state photochromism of N-phenyl-2-aminotropones
  作者：Yasuhiro Ito、Kiichi Amimoto、Toshio Kawato

  DOI：10.1016/j.dyepig.2010.06.001

  日期：2011.6

  N-(4-X-phenyl)-2-aminotropones (X = methoxy, chloro, or nitro substituent) and their clathrate crystals with deoxycholic acid (DCA) were prepared and their prototropic phenomena were determined. Each 2-aminotropone derivative existed as a keto amine form in the crystal state irrespective of its substituent, which influenced the stability of keto amine or enol imine structure in solution. X-Ray crystal structure analysis of N-(4-methoxyphenyl)-2-aminotropone revealed the existence of bimolecular hydrogen bonds and close molecular packing, which would inhibit structural change necessary to photo-induced prototropic tautomerization. Thus, N-phenyl-2-aminotropones did not show photocoloration in the crystal state, while their clathrate crystals with DCA were found to exhibit photochromism. (C) 2010 Elsevier Ltd. All rights reserved.