3-methyl-1-[2-nitro-4-(trifluoromethyl)phenyl]-2-pyrazolin-5-one | 300695-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-1-[2-nitro-4-(trifluoromethyl)phenyl]-2-pyrazolin-5-one
• 英文别名: 5-methyl-2-[2-nitro-4-(trifluoromethyl)phenyl]-4H-pyrazol-3-one
• CAS: 300695-03-8
• 化学式: C₁₁H₈F₃N₃O₃
• mdl: MFCD00589538
• 分子量: 287.198
• InChiKey: HKXHVANNDMHCTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-methyl-1-[2-nitro-4-(trifluoromethyl)phenyl]-2-pyrazolin-5-one 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 以83%的产率得到4-(hydroxyimino)-3-methyl-1-[2-nitro-4-(trifluoromethyl)phenyl]-2-pyrazolin-5-one
  参考文献：
  名称：

  摘要：

  Cyclic voltammetry and electrolysis in combination with ESR were used to study the electrochemical oxidation of 1-R-4-hydroxyimino-3-methyl-2-pyrazolin-5-ones (R = H. C6H5,4-BrC6H4, and 2-NO2-4-CF3C6H3) in acetonitrile on the background of 0.1 M Et4NClO4 on glassy carbon and platinum electrodes in the absence and in the presence of bases (pyridine, piperidine, tetraethylammonium hydroxide). With all the compounds, one-electron transfer gives rise to iminoxyl radicals (g 2.0045, a(N)6 30.78-31.33, a(N)1 1.87-2.12). In alkaline medium the iminoxyl radical derived from 4-hydroxyimino-3-methyl-2-pyrazolin-5-one is unstable and oxidizes to 3-methyl-4-nitroso-1-pyrazolin-5-one. The oxidation potentials are much reduced with decreasing electron-acceptor power of the substituents and increasing basicity of the bases.

  DOI：

  10.1023/a:1013923624905
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 反应 1.0h， 以70%的产率得到3-methyl-1-[2-nitro-4-(trifluoromethyl)phenyl]-2-pyrazolin-5-one
  参考文献：
  名称：

  摘要：

  Cyclic voltammetry and electrolysis in combination with ESR were used to study the electrochemical oxidation of 1-R-4-hydroxyimino-3-methyl-2-pyrazolin-5-ones (R = H. C6H5,4-BrC6H4, and 2-NO2-4-CF3C6H3) in acetonitrile on the background of 0.1 M Et4NClO4 on glassy carbon and platinum electrodes in the absence and in the presence of bases (pyridine, piperidine, tetraethylammonium hydroxide). With all the compounds, one-electron transfer gives rise to iminoxyl radicals (g 2.0045, a(N)6 30.78-31.33, a(N)1 1.87-2.12). In alkaline medium the iminoxyl radical derived from 4-hydroxyimino-3-methyl-2-pyrazolin-5-one is unstable and oxidizes to 3-methyl-4-nitroso-1-pyrazolin-5-one. The oxidation potentials are much reduced with decreasing electron-acceptor power of the substituents and increasing basicity of the bases.

  DOI：

  10.1023/a:1013923624905

文献信息

• ——
  作者：V. V. Yanilkin、A. V. Toropchina、V. I. Morozov、A. I. Movchan、L. P. Sysoeva、B. I. Buzykin、G. A. Chmutova

  DOI：10.1023/a:1013923624905

  日期：——

  Cyclic voltammetry and electrolysis in combination with ESR were used to study the electrochemical oxidation of 1-R-4-hydroxyimino-3-methyl-2-pyrazolin-5-ones (R = H. C6H5,4-BrC6H4, and 2-NO2-4-CF3C6H3) in acetonitrile on the background of 0.1 M Et4NClO4 on glassy carbon and platinum electrodes in the absence and in the presence of bases (pyridine, piperidine, tetraethylammonium hydroxide). With all the compounds, one-electron transfer gives rise to iminoxyl radicals (g 2.0045, a(N)6 30.78-31.33, a(N)1 1.87-2.12). In alkaline medium the iminoxyl radical derived from 4-hydroxyimino-3-methyl-2-pyrazolin-5-one is unstable and oxidizes to 3-methyl-4-nitroso-1-pyrazolin-5-one. The oxidation potentials are much reduced with decreasing electron-acceptor power of the substituents and increasing basicity of the bases.