5,5-dimethyl<2,3,3-²H3>-1-pyrroline 1-oxide | 128217-05-0

• 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: 5,5-dimethyl<2,3,3-²H3>-1-pyrroline 1-oxide
• 英文别名: 4,4,5-trideuterio-2,2-dimethyl-1-oxido-3H-pyrrol-1-ium
• CAS: 128217-05-0
• 化学式: C₆H₁₁NO
• 分子量: 116.136
• InChiKey: VCUVETGKTILCLC-MSYDVTBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 在 氘氧化钠 、 重水 作用下， 反应 12.0h， 以90%的产率得到5,5-dimethyl<2,3,3-²H3>-1-pyrroline 1-oxide
  参考文献：
  名称：

  Synthesis of deuterium- and nitrogen-15-containing pyrroline 1-oxides: a spin-trapping study

  摘要：

  DOI：

  10.1021/jo00301a042

文献信息

• Regioselective Deuteration of a 3,4-Dialkoxypyrroline <i>N</i> -Oxide and Synthesis of 8a-<i>d</i> -Indolizidines
  作者：Anna Ranzenigo、Chiara Mercurio、Maurice Karrenbrock、Franca M. Cordero、Gianni Cardini、Marco Pagliai、Alberto Brandi

  DOI：10.1002/ejoc.202000402

  日期：2020.6.23

  A dialkoxy five‐membered cyclic nitrone smoothly undergoes a base‐catalyzed direct H/D exchange through umpolung reactivity of the carbon atom of the nitrone moiety. Deuterium is incorporated into a useful and versatile building block with total selectivity and a high percentage. Kinetic and in silico data indicate the formation of a transient carbenoid anion.

  二烷氧基五元环硝酮通过硝酮部分碳原子的化学反应性，平稳地进行碱催化的直接H / D交换。氘以总选择性和高百分比被并入有用的多功能构建基块中。动力学和计算机模拟数据表明形成了短暂的类胡萝卜素阴离子。
• POU, SOVITJ;ROSEN, GERALD M., J. ORG. CHEM., 55,(1990) N4, C. 4438-4443
  作者：POU, SOVITJ、ROSEN, GERALD M.

  DOI：——

  日期：——