1-phenyl-3-methyl-3-(β-cyanoethyl)triazine 1-oxide | 131164-16-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-phenyl-3-methyl-3-(β-cyanoethyl)triazine 1-oxide
• 英文别名: 3-Methyl-3-cyanoethyl-1-phenyltriazene 1-Oxide；3-methyl-1-phenyl-3-cyanoethyltriazene 1-oxide；[2-cyanoethyl(methyl)hydrazinylidene]-oxido-phenylazanium
• CAS: 131164-16-4
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: DZHLTPDMERPWFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-methyl-1-(β-cyanoethyl)hydrazine 、 亚硝基苯 在 甲酸 、 溴 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以72%的产率得到1-phenyl-3-methyl-3-(β-cyanoethyl)triazine 1-oxide
  参考文献：
  名称：

  Reaction of 1,1-disubstituted hydrazines with bromine in the presence of aryl- and heteroarylnitroso compounds in acid media: A general method for the synthesis of 1-aryl(heteroaryl)-3,3-disubstituted triazene 1-oxides

  摘要：

  We have worked out a method for the synthesis of 1,3,3-trisubstituted triazene 1-oxides based upon reaction of 1,1-disubstituted hydrazines with bromine in the presence of aryl- and heteroarylnitroso compounds in acid media. Obtained are a broad range of triazene 1-oxides, among which hitherto unknown compounds of the series of pyrazole and 3,3-dialkyltriazene 1-oxides that contain functional groups at the alkyl part of the molecule. We propose a reaction scheme which includes in situ formation of diazenium cations and reaction of them with nitroso compounds that are present in the system. By means of PMR, C-13, and N-14 NMR spectroscopy, and mass spectroscopy, it has been shown that in all the prepared compounds the oxidated nitrogen atom is at the N1 position of the triazene N-oxide group.

  DOI：

  10.1007/bf00864338

文献信息

• Reaction of nitrosobenzene with 1,1-dialkyldiazenium salts as a new method for the synthesis of 3,3-dialkyltriazene 1-oxides
  作者：S. G. Zlotin、O. V. Prokshits、O. A. Luk'yanov

  DOI：10.1007/bf00958880

  日期：1990.11
• Reaction of 1,1-disubstituted hydrazines with dibromoisocyanurate in the presence of nitrosobenzene
  作者：S. G. Zlotin、O. V. Prokshits、N. F. Karpenko、O. A. Luk'yanov

  DOI：10.1007/bf00957882

  日期：1990.7

  A study was carried out on the reaction of 1,1-disubstituted hydrazines with dibromoisocyanurate in the presence of nitrosobenzene. Depending on the structure of the hydrazine component, the reaction may proceed either to 3,3-disubstituted 2-phenyltriazene 1-oxides or the products of the oxidative dimerization of hydrazine derivatives, namely, 1,1,4,4-tetrasubstituted tetrazenes.
• Reaction of 1,1-disubstituted hydrazines with bromine in the presence of aryl- and heteroarylnitroso compounds in acid media: A general method for the synthesis of 1-aryl(heteroaryl)-3,3-disubstituted triazene 1-oxides
  作者：S. G. Zlotin、O. V. Prokshits、N. F. Karpenko、Yu. A. Strelenko、O. A. Luk'yanov

  DOI：10.1007/bf00864338

  日期：1992.8

  We have worked out a method for the synthesis of 1,3,3-trisubstituted triazene 1-oxides based upon reaction of 1,1-disubstituted hydrazines with bromine in the presence of aryl- and heteroarylnitroso compounds in acid media. Obtained are a broad range of triazene 1-oxides, among which hitherto unknown compounds of the series of pyrazole and 3,3-dialkyltriazene 1-oxides that contain functional groups at the alkyl part of the molecule. We propose a reaction scheme which includes in situ formation of diazenium cations and reaction of them with nitroso compounds that are present in the system. By means of PMR, C-13, and N-14 NMR spectroscopy, and mass spectroscopy, it has been shown that in all the prepared compounds the oxidated nitrogen atom is at the N1 position of the triazene N-oxide group.