2-(1-nitro-2,3,3-trichloro-2-propenylidene)-4-ethoxybenzazetine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(1-nitro-2,3,3-trichloro-2-propenylidene)-4-ethoxybenzazetine
• 英文别名: 4-ethoxy-2-(2,3,3-trichloro-1-nitro-2-propenylidene)benzazetine；4-ethoxy-2-(2,3,3-trichloro-1-nitro-2-propenylidene)-1,2-dihydrobenzazete；(8Z)-3-ethoxy-8-(2,3,3-trichloro-1-nitroprop-2-enylidene)-7-azabicyclo[4.2.0]octa-1,3,5-triene；(8Z)-3-ethoxy-8-(2,3,3-trichloro-1-nitroprop-2-enylidene)-7-azabicyclo[4.2.0]octa-1(6),2,4-triene
• 化学式: C₁₂H₉Cl₃N₂O₃
• 分子量: 335.574
• InChiKey: BDWZKZLRIUWYJC-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-nitro-2,3,3-trichloro-2-propenylidene)-4-ethoxybenzazetine 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以95%的产率得到4-ethoxy-3-nitro-2-(1-nitro-2,3,3-trichloro-2-propenylidene)benzazetine
  参考文献：
  名称：

  Synthesis and Spectral Characteristics of Unsymmetrical Porphirazines with Triphrnylmethyl Groups

  摘要：

  Nitration of 4-alkoxy (Alk = Me, Et)-2-(1-nitro-2,3,3-tricbloro-2-propenylidene)benzazetines with anhydrous HNO3 in glacial acetic acid afforded the corresponding 4-alkoxy-3-nitro-2-(1-nitro-2,-3,3-trichloro-2-propenylidene)benzazetines. Reaction of compounds obtained with amines involved an isornerization of the benzazetine system into a benzazete one accompanied with conversion of the nitro compound into an aci-form. As a result formed 2,3,3-trichloro-1-(4-alkoxy-3-nitrobenzazet-2-yl)-2-propene-1-nitronic acids salts. The reaction of 4-methoxy-3-nitro-2-(1-nitro-2,3,3-trichloro-2- propenylidene)benzazetine with benzoyl chloride furnished as final product a mixed anhydride of 2,3,3-trichloro- 1-(4-alkoxy-3-nitrobenzazet-2-yl)-2-propene-1-nitronic acid.

  DOI：

  10.1023/b:rujo.0000043722.09128.17
• 作为产物：
  描述：

  (E)-1-(benzotriazol-1-yl)-3,4,4-trichloro-1-(4-ethoxyphenylamino)-2-nitrobuta-1,3-diene 在 甲醇 作用下， 反应 15.0h， 以91%的产率得到2-(1-nitro-2,3,3-trichloro-2-propenylidene)-4-ethoxybenzazetine
  参考文献：
  名称：

  摘要：

  Heating of 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadienes and 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4-dichloro-4-bromo-1,3-butadienes (R = BuO, EtO, MeO, Me; azolyl = 1-benzotriazolyl, 3,5-dimethyl-1-pyrazolyl, and 1,2,4-triazol-1-yl) in methanol or acetic acid gave the corresponding 2-(1-nitrotrihalopropenylidene)-4-R-benzazetines. The latter reacted with amines, sodium alkoxides, and sodium thiolates, affording salts of the aci-nitro form. The reactions with benzoyl chloride and chloroacetyl chloride in the presence of pyridine led to formation of mixed anhydrides.

  DOI：

  10.1023/a:1012451901837

文献信息

• ——
  作者：V. I. Potkin、V. A. Knizhnikov、A. A. Yanuchok、R. V. Kaberdin

  DOI：10.1023/a:1012431330062

  日期：——

  The reactions of 4-ethoxy-2-(2,3,3-trichloro-1-nitro-2-propenylidene)benzazetine with methyl- and phenyllithium at a ratio of 1:2 result in replacement of one chlorine atom and formation, respectively, of 4-ethoxy-2-(2,3-dichloro-3-methyl-1-nitro-2-propenylidene)benzazetine and 4-ethoxy-2-(2,3-dichloro-1-nitro3-phenyl-2-propenylidene)benzazetine in 45 and 52% yield. With excess phenyllithium (reactant ratio 1:5), a mixture of products is formed due to replacement of one, two, and three chlorine atoms by phenyl groups. An analogous reaction with methyllithium is nonselective.
• ——
  作者：V. I. Potkin、V. A. Zapol'skii、V. A. Knizhnikov、R. V. Kaberdin、A. A. Yanuchok、S. K. Petkevich

  DOI：10.1023/a:1012451901837

  日期：——

  Heating of 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadienes and 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4-dichloro-4-bromo-1,3-butadienes (R = BuO, EtO, MeO, Me; azolyl = 1-benzotriazolyl, 3,5-dimethyl-1-pyrazolyl, and 1,2,4-triazol-1-yl) in methanol or acetic acid gave the corresponding 2-(1-nitrotrihalopropenylidene)-4-R-benzazetines. The latter reacted with amines, sodium alkoxides, and sodium thiolates, affording salts of the aci-nitro form. The reactions with benzoyl chloride and chloroacetyl chloride in the presence of pyridine led to formation of mixed anhydrides.
• Synthesis and Spectral Characteristics of Unsymmetrical Porphirazines with Triphrnylmethyl Groups
  作者：V. I. Potkin、S. K. Petkevich、N. I. Nechai、R. V. Kaberdin

  DOI：10.1023/b:rujo.0000043722.09128.17

  日期：2004.5

  Nitration of 4-alkoxy (Alk = Me, Et)-2-(1-nitro-2,3,3-tricbloro-2-propenylidene)benzazetines with anhydrous HNO3 in glacial acetic acid afforded the corresponding 4-alkoxy-3-nitro-2-(1-nitro-2,-3,3-trichloro-2-propenylidene)benzazetines. Reaction of compounds obtained with amines involved an isornerization of the benzazetine system into a benzazete one accompanied with conversion of the nitro compound into an aci-form. As a result formed 2,3,3-trichloro-1-(4-alkoxy-3-nitrobenzazet-2-yl)-2-propene-1-nitronic acids salts. The reaction of 4-methoxy-3-nitro-2-(1-nitro-2,3,3-trichloro-2- propenylidene)benzazetine with benzoyl chloride furnished as final product a mixed anhydride of 2,3,3-trichloro- 1-(4-alkoxy-3-nitrobenzazet-2-yl)-2-propene-1-nitronic acid.