| 139871-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• CAS: 139871-48-0
• 化学式: C₆H₁₀ClN₂O
• 分子量: 163.595
• InChiKey: GBVMBJZRKZIRRP-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  5,5-dimethyl<2,3,3-²H3>-1-pyrroline 1-oxide 在 KH₂PO₄-H₃PO₄-buffer 、 次氯酸 、 氯化铵 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Reaction of 5,5-dimethyl-1-pyrroline 1-oxide with hypochlorite-treated ammonia: the structure of a novel N-chloroimine nitroxyl radical

  摘要：

  A novel nitroxyl radical was observed by electron paramagnetic resonance spectroscopy (EPR) of reaction mixtures containing ammonium ion, hypochlorous acid (HOCl), and 5,5-dimethyl-1-pyrroline 1-oxide (DMPO). The structure of this radical was established as 2-(N-chloroimino)-5,5-dimethylpyrrolidine-1-oxyl on the basis of EPR studies of isotopically-labeled compounds, thin-layer chromatography (TLC), and chemical synthesis by an independent route. Incorporation of deuterium into DMPO and solvent stabilized the radical without affecting the multiplicity of the EPR signal. The use of [N-15]ammonium ion gave 2-(N-15-chloroimino)-5,5-dimethylpyrrolidine-1-oxyl radical. Detection of the radical upon TLC was based on its reaction with potassium iodide-starch to give a purple color, consistent with an N-chloroimine functionality. Synthesis of the new nitroxyl radical was accomplished by the Michael reaction of acrylonitrile and 2-nitropropane, catalytic hydrogenation of the Michael product, and reaction of the reduced compound with HOCl. The formation and EPR detection of 2-(N-chloroimino)-5,5-dimethylpyrrolidine-1-oxyl radical may be useful as a sensitive method for detecting hypochlorous acid and ammonium ion in biological systems.

  DOI：

  10.1021/jo00035a021