5-(4-acetamidophenyldiazenyl)-8-hydroxyquinoline | 26424-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(4-acetamidophenyldiazenyl)-8-hydroxyquinoline
• 英文别名: 5-(p-Acetamidophenylazo)-8-quinolinol hydrochloride；N-[4-[(8-hydroxyquinolin-5-yl)diazenyl]phenyl]acetamide
• CAS: 26424-51-1；63716-56-3
• 化学式: C₁₇H₁₄N₄O₂
• 分子量: 306.324
• InChiKey: DKRPSSOODLBKPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 、 4′-氨基乙酰苯胺 在 盐酸 、 sodium nitrite 、 potassium hydroxide 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以78%的产率得到5-(4-acetamidophenyldiazenyl)-8-hydroxyquinoline
  参考文献：
  名称：

  Azo-8-hydroxyquinoline dyes: The synthesis, characterizations and determination of tautomeric properties of some new phenyl- and heteroarylazo-8-hydroxyquinolines

  摘要：

  Two series of new heterocyclic and carbocyclic disperse azo dyes based on 8-hydroxyquinoline were prepared and characterized by FT-IR, H-1 NMR, mass spectroscopic techniques and elemental analysis. Their solvatochromic properties in different solvents were investigated and their absorption spectra were strongly solvent dependent The acid and base effects on this equilibrium were also examined. In addition, the colors of dyes were discussed with respect to the nature of the carbocyclic and heterocyclic rings and substituent therein. To determine the tautomeric forms of the prepared dyes in solid state, X-ray data for 5-(5-methylthiazol-2-yldiazenyl)-8-hydroxyquinoline were recorded. The X-ray results showed that the dye exists as an azo tautomer in the solid state. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2014.02.027

文献信息

• Azo-8-hydroxyquinoline dyes: The synthesis, characterizations and determination of tautomeric properties of some new phenyl- and heteroarylazo-8-hydroxyquinolines
  作者：Aytül Saylam、Zeynel Seferoğlu、Nermin Ertan

  DOI：10.1016/j.molliq.2014.02.027

  日期：2014.7

  Two series of new heterocyclic and carbocyclic disperse azo dyes based on 8-hydroxyquinoline were prepared and characterized by FT-IR, H-1 NMR, mass spectroscopic techniques and elemental analysis. Their solvatochromic properties in different solvents were investigated and their absorption spectra were strongly solvent dependent The acid and base effects on this equilibrium were also examined. In addition, the colors of dyes were discussed with respect to the nature of the carbocyclic and heterocyclic rings and substituent therein. To determine the tautomeric forms of the prepared dyes in solid state, X-ray data for 5-(5-methylthiazol-2-yldiazenyl)-8-hydroxyquinoline were recorded. The X-ray results showed that the dye exists as an azo tautomer in the solid state. (C) 2014 Elsevier B.V. All rights reserved.