N-benzenesulphinyl-2,2,6,6-tetramethylpiperidine

• 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-benzenesulphinyl-2,2,6,6-tetramethylpiperidine
• 化学式: C₁₅H₂₃NOS
• 分子量: 265.42
• InChiKey: DPESXOKHYGQZMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 苯硫酚 以 苯 为溶剂， 反应 0.5h， 以14%的产率得到2,2,6,6-tetramethylpiperidinium benzenesulphinate
  参考文献：
  名称：

  Unexpected Deoxygenation of 2,2,6,6-Tetramethylpiperidine-1-Oxyl (TEMPO) by Thiyl Radicals through the Formation of Arylsulphinyl Radicals

  摘要：

  2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO), upon reaction with thiophenols, undergoes deoxygenation leading mainly to the formation of tetramethylpiperidinium arylsulphinates and arylsulphonates. Other identified products of the reaction are aryldisulphides, 2,2,6,6-tetramethylpiperidine, S-aryl-arylthiosulphonates, N-arylsulphinyl- and N-arylsulphonyl-2,2,6,6-tetramethylpiperidine. The formation of the reaction products is discussed on the basis of the interaction of arylsulphinyl and arylsulphonyl radicals with TEMPO as well as on the basis of the evolution of the arylsulphinyl radical itself.

  DOI：

  10.1016/0040-4020(95)00800-n

文献信息

• Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant
  作者：Yuexia Zhang、Zeng Rong Wong、Xingxing Wu、Sherman J. L. Lauw、Xuan Huang、Richard D. Webster、Yonggui Robin Chi

  DOI：10.1039/c6cc08631d

  日期：——

  Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-fluorobenzenesulfonimide (NFSI)...

  亚砜是重要的功能分子。我们通过使硫醇与烯烃或炔烃在温和且不含金属的条件下反应，开发出此类分子的短程（一锅法）合成方法。N-氟苯磺酰亚胺（NFSI）...
• Unexpected Deoxygenation of 2,2,6,6-Tetramethylpiperidine-1-Oxyl (TEMPO) by Thiyl Radicals through the Formation of Arylsulphinyl Radicals
  作者：Patricia Carloni、Elisabetta Damiani、Marco Iacussi、Lucedio Greci、Pierluigi Stipa、Daniele Cauzi、Corrado Rizzoli、Paolo Sgarabotto

  DOI：10.1016/0040-4020(95)00800-n

  日期：1995.11

  2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO), upon reaction with thiophenols, undergoes deoxygenation leading mainly to the formation of tetramethylpiperidinium arylsulphinates and arylsulphonates. Other identified products of the reaction are aryldisulphides, 2,2,6,6-tetramethylpiperidine, S-aryl-arylthiosulphonates, N-arylsulphinyl- and N-arylsulphonyl-2,2,6,6-tetramethylpiperidine. The formation of the reaction products is discussed on the basis of the interaction of arylsulphinyl and arylsulphonyl radicals with TEMPO as well as on the basis of the evolution of the arylsulphinyl radical itself.