1-hydroxy-5,5-dimethylpyrrolidin-2-imine | 34211-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-hydroxy-5,5-dimethylpyrrolidin-2-imine
• 英文别名: 5,5-dimethyl-1-oxy-4,5-dihydro-3H-pyrrol-2-ylamine；2-amino-5,5-dimethylpyrroline 1-oxide；5,5-dimethyl-1-oxy-4,5-dihydro-3H-pyrrol-2-ylamine；5,5-Dimethyl-1-oxy-4,5-dihydro-3H-pyrrol-2-ylamin；2-Amino-5,5-dimethyl-1-pyrrolin-N-oxid
• CAS: 34211-69-3
• 化学式: C₆H₁₂N₂O
• 分子量: 128.174
• InChiKey: MCCVCYBNVLUVOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  9.0
• 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：
  52.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-5,5-dimethylpyrrolidin-2-imine 在 sodium hypochlorite 作用下， 以 水 为溶剂， 以46%的产率得到2-(N-chloroimino)-5,5-dimethylpyrrolidine-1-oxyl radical
  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
• 作为产物：
  描述：

  4-methyl-4-nitrovaleronitrile 在 aluminum amalgam 作用下， 以 乙醚 为溶剂， 反应 0.75h， 以85%的产率得到1-hydroxy-5,5-dimethylpyrrolidin-2-imine
  参考文献：
  名称：

  通过铝汞齐还原硝基腈和酮而获得的2-取代的硝酮和异构羟胺-一种新的方便的中间体，用于制备亚硝基羰基化合物

  摘要：

  使用铝汞齐作为湿二乙醚或THF的还原剂，可以从叔γ-硝基酮和腈中以高收率获得高收率的五元取代环环状硝基环（吡咯啉N-氧化物）。从α-或β-硝基腈获得环状氨基硝酮的尝试失败了，仅分离了相应的羟胺。硝酮和羟胺都已用于合成叔C-亚硝基腈或酮。

  DOI：

  10.1016/j.tet.2010.03.023

文献信息

• 2-Substituted nitrones and isomeric hydroxylamines – obtained via aluminium amalgam reduction of nitro nitriles and ketones—a new access to convenient intermediates for nitroso carbonyl compounds preparation
  作者：Karol Grela、Leszek Konopski

  DOI：10.1016/j.tet.2010.03.023

  日期：2010.5

  Substituted five-membered cyclic nitrones (pyrroline N-oxides) have been obtained in good to high yields from tertiary γ-nitro ketones and nitriles employing aluminium amalgam as a reducing agent in moist diethyl ether or THF. Attempts to obtain cyclic amino nitrones from α- or β-nitro nitriles failed and only the corresponding hydroxylamines have been isolated. Both nitrones and hydroxylamines have

  使用铝汞齐作为湿二乙醚或THF的还原剂，可以从叔γ-硝基酮和腈中以高收率获得高收率的五元取代环环状硝基环（吡咯啉N-氧化物）。从α-或β-硝基腈获得环状氨基硝酮的尝试失败了，仅分离了相应的羟胺。硝酮和羟胺都已用于合成叔C-亚硝基腈或酮。
• Reaction of 5,5-dimethyl-1-pyrroline 1-oxide with hypochlorite-treated ammonia: the structure of a novel N-chloroimine nitroxyl radical
  作者：B. M. Ratnayake Bandara、Oscar Hinojosa、Carl Bernofsky

  DOI：10.1021/jo00035a021

  日期：1992.4

  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.