N-(1-oxido-2,2,6,6-tetramethylpiperidin-4-yl)-N-(1-oxido-2,2,5,5-tetramethylpyrolidin-3-yl)amine | 1443050-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(1-oxido-2,2,6,6-tetramethylpiperidin-4-yl)-N-(1-oxido-2,2,5,5-tetramethylpyrolidin-3-yl)amine
• CAS: 1443050-22-3
• 化学式: C₁₇H₃₃N₃O₂
• 分子量: 311.468
• InChiKey: CVSGRXVXFULMSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氧-2,2,6,6-四甲基哌啶-1-氧自由基 、 3-氨基-2,2,5,5-四甲基-1-吡咯烷酮 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.33h， 以46%的产率得到N-(1-oxido-2,2,6,6-tetramethylpiperidin-4-yl)-N-(1-oxido-2,2,5,5-tetramethylpyrolidin-3-yl)amine
  参考文献：
  名称：

  Preparation and Spectroscopic, Magnetic, and Electrochemical Studies of Mono-/Biradical TEMPO Derivatives

  摘要：

  A comparison set of mono-/biradical TEMPO derivatives was prepared, novel compounds were fully characterized, and their physicochemical properties were determined. Cyclic voltammetry revealed reversible redox behavior for all studied nitroxides. Moreover, the electron-withdrawing substituents increased the oxidation potential of the respective nitroxides in comparison to electron-donating groups. While EPR spectra of monoradicals in dichloromethane at 295 K reveal the expected three-line signal, spectra of biradicals show more complex features. DFT and MP2 calculations indicate that the EPR splitting pattern of dinitroxide 7 could be explained by its interactions with solvent molecules. In the solid state, mononitroxides 4 and 5 behave as a Heisenberg antiferromagnetic chain, whereas dinitroxides 6-8 are almost isolated paramagnetic diradicals coupled in an antiferromagnetic manner.

  DOI：

  10.1021/jo400845m

文献信息

• Preparation and Spectroscopic, Magnetic, and Electrochemical Studies of Mono-/Biradical TEMPO Derivatives
  作者：Miroslav Kavala、Roman Boča、Lubomír Dlháň、Vlasta Brezová、Martin Breza、Jozef Kožíšek、Marek Fronc、Peter Herich、Lubomír Švorc、Peter Szolcsányi

  DOI：10.1021/jo400845m

  日期：2013.7.5

  A comparison set of mono-/biradical TEMPO derivatives was prepared, novel compounds were fully characterized, and their physicochemical properties were determined. Cyclic voltammetry revealed reversible redox behavior for all studied nitroxides. Moreover, the electron-withdrawing substituents increased the oxidation potential of the respective nitroxides in comparison to electron-donating groups. While EPR spectra of monoradicals in dichloromethane at 295 K reveal the expected three-line signal, spectra of biradicals show more complex features. DFT and MP2 calculations indicate that the EPR splitting pattern of dinitroxide 7 could be explained by its interactions with solvent molecules. In the solid state, mononitroxides 4 and 5 behave as a Heisenberg antiferromagnetic chain, whereas dinitroxides 6-8 are almost isolated paramagnetic diradicals coupled in an antiferromagnetic manner.