1-oxyl-4-(N,N-n-dibutylamino)-2,2,6,6-tetamethylpiperidine

• 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: 1-oxyl-4-(N,N-n-dibutylamino)-2,2,6,6-tetamethylpiperidine
• 化学式: C₁₇H₃₅N₂O
• 分子量: 283.478
• InChiKey: LLOVLUUASLIWIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  7.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxyl-4-(N,N-n-dibutylamino)-2,2,6,6-tetamethylpiperidine 在 六氟磷酸钾 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  离子液体中的离子TEMPO：酒精有氧氧化的特定促进

  摘要：

  这项研究的主要目的是设计一种可循环利用的TEMPO（2,2,6,6-四甲基哌啶基-N-氧基）衍生物，该衍生物可通过使用NaNO 2在离子液体溶剂中用作需氧氧化醇的催化剂和HCl作为助催化剂。为此，需要一个带有季铵基团的TEMPO衍生物[4-Bu 2 MeN-TEMPO] [PF 6 ]（1），已做好准备。随后显示该离子TEMPO衍生物是用于各种伯醇和仲醇的需氧氧化的有效催化剂。它具有与离子液体溶剂的协同作用，并且在化学性质上优于二氯甲烷中的类似氧化反应。此外，离子型TEMPO可以循环使用五次而不会损失活性。

  DOI：

  10.1002/cctc.201600491
• 作为产物：
  描述：

  4-氧-2,2,6,6-四甲基哌啶-1-氧自由基 、 二正丁胺盐酸盐 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以35%的产率得到1-oxyl-4-(N,N-n-dibutylamino)-2,2,6,6-tetamethylpiperidine
  参考文献：
  名称：

  Studies of Structure−Activity Relationship of Nitroxide Free Radicals and Their Precursors as Modifiers Against Oxidative Damage

  摘要：

  The protective effects of stable nitroxides, as well as their hydroxylamine and amine precursors, have been tested in Chinese hamster V79 cells subjected to H2O2 exposure at fixed concentration or exposure to ionizing radiation. Cytotoxicity was evaluated by monitoring the viability of the cells assessed by the clonogenic assay. The compounds tested at fixed concentration varied in terms of ring size, oxidation state, and ring substituents. Electrochemical studies were carried out to measure the redox midpoint potentials. The studies show that in the case of protection against H2O2 exposure, the protection was determined by the ring size, oxidation state, and redox midpoint potentials. In general the protection factors followed the order nitroxides > hydroxylamines > amines. Both the six-membered ring nitroxides and substituted five-membered ring nitroxides were efficient protectors. For six-membered ring nitroxides, the compounds exhibiting the lowest midpoint potentials exhibited maximal protection. In the case of X-radiation, nitroxides were the most protective though some hydroxylamines were also efficient. The amines were in some cases found to sensitize the toxicity of aerobic radiation exposure. The protection observed by the nitroxides was not dependent on the ring size. However, the ring substituents had significant influence on the protection. Compounds containing a basic side chain were found to provide enhanced protection. The results in this study suggest that these compounds are novel antioxidants which can provide cytoprotection in mammalian cells against diverse types of oxidative insult and identify structural determinants optimal for protection against individual types of damage.

  DOI：

  10.1021/jm9802160

文献信息

• Studies of Structure−Activity Relationship of Nitroxide Free Radicals and Their Precursors as Modifiers Against Oxidative Damage
  作者：Murali C. Krishna、William DeGraff、Olga H. Hankovszky、Cecília P. Sár、Tamás Kálai、József Jekő、Angelo Russo、James B. Mitchell、Kálmán Hideg

  DOI：10.1021/jm9802160

  日期：1998.8.1

  The protective effects of stable nitroxides, as well as their hydroxylamine and amine precursors, have been tested in Chinese hamster V79 cells subjected to H2O2 exposure at fixed concentration or exposure to ionizing radiation. Cytotoxicity was evaluated by monitoring the viability of the cells assessed by the clonogenic assay. The compounds tested at fixed concentration varied in terms of ring size, oxidation state, and ring substituents. Electrochemical studies were carried out to measure the redox midpoint potentials. The studies show that in the case of protection against H2O2 exposure, the protection was determined by the ring size, oxidation state, and redox midpoint potentials. In general the protection factors followed the order nitroxides > hydroxylamines > amines. Both the six-membered ring nitroxides and substituted five-membered ring nitroxides were efficient protectors. For six-membered ring nitroxides, the compounds exhibiting the lowest midpoint potentials exhibited maximal protection. In the case of X-radiation, nitroxides were the most protective though some hydroxylamines were also efficient. The amines were in some cases found to sensitize the toxicity of aerobic radiation exposure. The protection observed by the nitroxides was not dependent on the ring size. However, the ring substituents had significant influence on the protection. Compounds containing a basic side chain were found to provide enhanced protection. The results in this study suggest that these compounds are novel antioxidants which can provide cytoprotection in mammalian cells against diverse types of oxidative insult and identify structural determinants optimal for protection against individual types of damage.
• Ionic TEMPO in Ionic Liquids: Specific Promotion of the Aerobic Oxidation of Alcohols
  作者：Tsunehisa Hirashita、Makoto Nakanishi、Tomoya Uchida、Masakazu Yamamoto、Shuki Araki、Isabel W. C. E. Arends、Roger A. Sheldon

  DOI：10.1002/cctc.201600491

  日期：2016.8.22

  a catalyst in an ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO2 and HCl as co‐catalysts. To this end, a TEMPO derivative bearing a quaternary ammonium group, [4‐Bu2MeN‐TEMPO][PF6] (1), was prepared. It was subsequently shown that this ionic TEMPO derivative is an efficient catalyst for the aerobic oxidation of a variety of primary and secondary alcohols. It exhibits a synergistic

  这项研究的主要目的是设计一种可循环利用的TEMPO（2,2,6,6-四甲基哌啶基-N-氧基）衍生物，该衍生物可通过使用NaNO 2在离子液体溶剂中用作需氧氧化醇的催化剂和HCl作为助催化剂。为此，需要一个带有季铵基团的TEMPO衍生物[4-Bu 2 MeN-TEMPO] [PF 6 ]（1），已做好准备。随后显示该离子TEMPO衍生物是用于各种伯醇和仲醇的需氧氧化的有效催化剂。它具有与离子液体溶剂的协同作用，并且在化学性质上优于二氯甲烷中的类似氧化反应。此外，离子型TEMPO可以循环使用五次而不会损失活性。