(2S)-2,5,5-trimethyl-2-(4-hydroxyphenyl)pyrrolidine-1-oxyl | 620627-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S)-2,5,5-trimethyl-2-(4-hydroxyphenyl)pyrrolidine-1-oxyl
• 英文别名: (S)-2-(4-hydroxyphenyl)-2,5,5-trimethylpyrrolidin-1-oxyl
• CAS: 620627-61-4
• 化学式: C₁₃H₁₈NO₂
• 分子量: 220.291
• InChiKey: QTOFVVFDAFHHBJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2,5,5-trimethyl-2-(4-hydroxyphenyl)pyrrolidine-1-oxyl 在 六氯环三磷腈 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以30%的产率得到(5S)-2,2,5-trimethyl-5-[4-[[2,4,6-tris[4-[(2S)-2,5,5-trimethyl-1-oxidopyrrolidin-2-yl]phenoxy]-4,6-bis[4-[(2S)-2,5,5-trimethyl-1-oxopyrrolidin-1-ium-2-yl]phenoxy]-1-aza-3,5-diazanida-2lambda5-phospha-4,6-diphosphoniacyclohexen-2-yl]oxy]phenyl]pyrrolidin-1-ium 1-oxide
  参考文献：
  名称：

  Use of Cyclotriphosphazene as a Molecular Scaffold for Building Chiral Multispin Systems

  摘要：

  Chiral mononitroxide-, dinitroxide-, tetranitroxide- and hexanitroxide-cyclotriphosphazene hybrid compounds, along with a chiral 2,2'-bridged trinitroxide-bis (cyclotriphosphazene) hybrid compound, have been prepared to examine the potential use of the cyclotriphosphazene framework as a molecular scaffold for elaborating chiral multispin systems. EPR spectroscopic studies in solution and in frozen solvent matrixes indicate that strong intramolecular through-space electron-exchange interactions are observed for the tetranitroxide and hexanitroxide hybrid compounds, while magnetic susceptibility measurements show that weak antiferromagnetic interactions are uniformly recognized in the solid states for all of them. The X-ray crystallographic analysis of the dinitroxide hybrid compound ascribes the latter antiferromagnetic behavior to an intermolecular origin.

  DOI：

  10.1080/15421400590957657
• 作为产物：
  描述：

  (4-溴苯氧基)叔丁基二甲基硅烷 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2,5,5-trimethyl-2-(4-hydroxyphenyl)pyrrolidine-1-oxyl
  参考文献：
  名称：

  Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides

  摘要：

  Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.

  DOI：

  10.1021/ol050401p