(2E,4E)-3,7-Bis-(4-chloro-phenyl)-2-(4-nitro-phenyl)-7-oxo-5-phenyl-hepta-2,4-dienenitrile

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2E,4E)-3,7-Bis-(4-chloro-phenyl)-2-(4-nitro-phenyl)-7-oxo-5-phenyl-hepta-2,4-dienenitrile
• 英文别名: 3,7-Bis(4-chlorophenyl)-2-(4-nitrophenyl)-7-oxo-5-phenylhepta-2,4-dienenitrile
• 化学式: C₃₁H₂₀Cl₂N₂O₃
• 分子量: 539.417
• InChiKey: UNLZWHHCRAWVBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-3,7-Bis-(4-chloro-phenyl)-2-(4-nitro-phenyl)-7-oxo-5-phenyl-hepta-2,4-dienenitrile 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以50%的产率得到
  参考文献：
  名称：

  Ringtransformationen heterocyclischer Verbindungen. I. 2-Amino-benzophenone und 7-Oxo-hepta-2,4-diennitrile durch Reaktion von 2,4,6-Triaryl-pyryliumsalzen mit 4-Nitro-benzylcyanid

  摘要：

  2,4,6-Triarylpyrylium salts 1 react with 4-nitrobenzyl cyanide in the presence of sodium acetate, triethylamine or triethylamine/acetic acid to give 7-oxo-hepta-2,4-dienenitriles 2. With stronger bases such as sodium methanolate or ethanolate a ring transformation of the salts 1 occurs giving rise to 2-amino-benzophenones 3 which can also be obtained by cyclization of the nitriles 2. Under the same conditions the 3-methyl-2,4,6-triphenylpyrylium salt 4 forms the 4-methyl-7-oxo-hepta-2,4-dienenitrile 5 by regioselective addition of the 4-nitrobenzyl cyanide at C-2 or it is converted to the 2-amino-5-methyl-benzophenone 6. The ring transformation of the pyrylium salts 1/4 by 4-nitrobenzyl cyanide represents a new and simple method for the preparation of 2-amino-benzophenones. - Spectroscopic data of the novel compounds are discussed; the structure of 5 was confirmed by a single crystal X-ray analysis.

  DOI：

  10.1002/prac.19933350408
• 作为产物：
  描述：

  2,6-bis-(4-chloro-phenyl)-4-phenyl-pyrylium; perchlorate 、 对硝基苯乙腈 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到(2E,4E)-3,7-Bis-(4-chloro-phenyl)-2-(4-nitro-phenyl)-7-oxo-5-phenyl-hepta-2,4-dienenitrile
  参考文献：
  名称：

  Ringtransformationen heterocyclischer Verbindungen. I. 2-Amino-benzophenone und 7-Oxo-hepta-2,4-diennitrile durch Reaktion von 2,4,6-Triaryl-pyryliumsalzen mit 4-Nitro-benzylcyanid

  摘要：

  2,4,6-Triarylpyrylium salts 1 react with 4-nitrobenzyl cyanide in the presence of sodium acetate, triethylamine or triethylamine/acetic acid to give 7-oxo-hepta-2,4-dienenitriles 2. With stronger bases such as sodium methanolate or ethanolate a ring transformation of the salts 1 occurs giving rise to 2-amino-benzophenones 3 which can also be obtained by cyclization of the nitriles 2. Under the same conditions the 3-methyl-2,4,6-triphenylpyrylium salt 4 forms the 4-methyl-7-oxo-hepta-2,4-dienenitrile 5 by regioselective addition of the 4-nitrobenzyl cyanide at C-2 or it is converted to the 2-amino-5-methyl-benzophenone 6. The ring transformation of the pyrylium salts 1/4 by 4-nitrobenzyl cyanide represents a new and simple method for the preparation of 2-amino-benzophenones. - Spectroscopic data of the novel compounds are discussed; the structure of 5 was confirmed by a single crystal X-ray analysis.

  DOI：

  10.1002/prac.19933350408