2,5,5-Trimethyl-2-(3-hydroxyphenyl)pyrrolidin-1-yloxyl radical

• 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: 2,5,5-Trimethyl-2-(3-hydroxyphenyl)pyrrolidin-1-yloxyl radical
• 英文别名: (+/-)-2-(3-hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxyl
• 化学式: C₁₃H₁₈NO₂
• 分子量: 220.291
• InChiKey: VDALDVCMOWMPFX-UHFFFAOYSA-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

• 作为产物：
  描述：

  3-(tert-butyldimethylsilyloxy)phenylmagnesium bromide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 2,5,5-Trimethyl-2-(3-hydroxyphenyl)pyrrolidin-1-yloxyl radical
  参考文献：
  名称：

  Characterization of the Crystalline Nature of the Racemates of Novel Chiral Five-Membered Cyclic Nitroxides

  摘要：

  Racemic samples of chiral five-membered cyclic nitroxides, 2,2,5,5-tetrasubstituted pyrrolidine-1-oxyls bearing one or two 4-hydroxyphenyl groups on the stereogenic centers [C(2) or C(2) & C(5)] adjacent to the NO radical moiety, exist as a racemic conglomerate in the crystalline state, whereas those having one or two 3-hydroxyphenyl groups at the same positions belong to a racemic compound. The key intermolecular interactions in controlling whether these racemates crystallize in a homochiral way or a heterochiral manner have been investigated by X-ray crystallographic analysis and magnetic susceptibility measurements.

  DOI：

  10.1080/15421400590957602

文献信息

• Synthesis of 2-Substituted Pyrrolidine Nitroxide Radicals
  作者：Szilvia Gadányi、Tamás Kálai、József Jekö、Zoltán Berente、Kálmán Hideg

  DOI：10.1055/s-2000-8727

  日期：——

  Grignard reaction of nitrone 1 with arylmagnesium bromides afforded different pyrrolidine nitroxide radicals 2a-f, which were converted further to spin labelled ebselen 6, saccharine 11, phenols 5, 12, 13, quinone 16 and heterocycles 20, 21, 24. Paramagnetic sulfonyl chlorides 7a, 7b, 9a and methanethiosulfonate 25d capable of amino and thiol labelling, respectively, were also prepared.

  腈酮 1 与芳基溴化镁发生格氏反应，可得到不同的吡咯烷亚硝基 2a-f，再进一步转化为自旋标记的依布硒 6、糖精 11、酚 5、12、13、醌 16 和杂环 20、21、24。此外，还制备了顺磁磺酰氯 7a、7b、9a 和甲硫磺酸盐 25d，它们分别能对氨基和硫醇进行标记。