2-acetamido-2''-amino-ortho-bisazobenzene | 1202564-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-acetamido-2''-amino-ortho-bisazobenzene
• 英文别名: 2-acetamido-2"-amino-ortho-bisazobenzene
• CAS: 1202564-22-4
• 化学式: C₂₀H₁₈N₆O
• 分子量: 358.403
• InChiKey: XXYPLQWOLPVTLC-OGGGYYITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  104.56
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-2''-amino-ortho-bisazobenzene 、 1-硝基-2-亚硝基苯 以 溶剂黄146 、 甲苯 为溶剂， 反应 144.0h， 以58%的产率得到2-acetamido-2'''-nitro-tris-ortho-azobenzene
  参考文献：
  名称：

  Synthesis and Photochemical Properties of Oligo-ortho-azobenzenes

  摘要：

  Azobenzenes have attracted great interest in recent years because of their ability to change conformation upon irradiation. This property has been featured in several applications not only in organic chemistry but also in biology. Even though monoazobenzenes have been extensively studied and documented in the literature, only a few methods are available for the synthesis of oligo-ortho-azobenzenes. Also, their photochemical properties have not been reported so far. This study shows an efficient strategy for the preparation of oligo-ortho-azobenzenes and the investigation of their photochemical properties. It is demonstrated that the absorption spectra are highly influenced by the substituents. Interestingly, none of the ortho-bis-, tris-, or tetra-azobenzenes showed any E -> Z isomerization. Only the ortho-nitrogen-substituted monoazobenzenes photochromic behavior upon UV irradiation was observed.

  DOI：

  10.1021/jo201996w
• 作为产物：
  描述：

  邻氨基乙酰苯胺 在 oxone 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 61.0h， 生成 2-acetamido-2''-amino-ortho-bisazobenzene
  参考文献：
  名称：

  Synthesis and Photochemical Properties of Oligo-ortho-azobenzenes

  摘要：

  Azobenzenes have attracted great interest in recent years because of their ability to change conformation upon irradiation. This property has been featured in several applications not only in organic chemistry but also in biology. Even though monoazobenzenes have been extensively studied and documented in the literature, only a few methods are available for the synthesis of oligo-ortho-azobenzenes. Also, their photochemical properties have not been reported so far. This study shows an efficient strategy for the preparation of oligo-ortho-azobenzenes and the investigation of their photochemical properties. It is demonstrated that the absorption spectra are highly influenced by the substituents. Interestingly, none of the ortho-bis-, tris-, or tetra-azobenzenes showed any E -> Z isomerization. Only the ortho-nitrogen-substituted monoazobenzenes photochromic behavior upon UV irradiation was observed.

  DOI：

  10.1021/jo201996w