2,2,5,5-四甲基-1-吡咯烷基氧基 | 3229-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2,2,5,5-四甲基-1-吡咯烷基氧基
• 中文别名: 1H-吡唑-4-甲酰胺,5-氨基-1-(2,6-二甲基苯基)-
• 英文名称: 2,2,5,5-tetramethyl-1-pyrrolidinyloxy
• 英文别名: 2,2,5,5-tetramethylpyrrolidinyloxy radical；2,2,6,6-tetramethyl-1-dihydropyrrolinoxyl；proxyl；2,2,5,5-tetramethylpyrrolidinyloxy；2,2,5,5-tetramethyl-3-pyrrolidin-1-yloxy；Proxyl nitroxide
• CAS: 3229-53-6
• 化学式: C₈H₁₆NO
• 分子量: 142.221
• InChiKey: RPDUDBYMNGAHEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,5,5-四甲基-1-吡咯烷基氧基 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以78%的产率得到2,2,5,5-Tetramethyl-pyrrolidin-1-ol; hydrochloride
  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
• 作为产物：
  描述：

  四甲基哌啶酮 在 氢氧化钾 、 sodium tungstate 、 sodium hypobromide 、 ammonium acetate 、 双氧水 、 溴 、 一水合肼 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 38.0h， 生成 2,2,5,5-四甲基-1-吡咯烷基氧基
  参考文献：
  名称：

  Influerce of chemical structure of nitroxyl spin labels on their reduction by ascorbic acid

  摘要：

  DOI：

  10.1016/s0040-4020(01)96516-0

文献信息

• Copper(II)-Promoted C-C Bond Formation by Oxidative Coupling of Two C(sp³)-H Bonds Adjacent to Carbonyl Group to Construct 1,4-Diketones and Tetrasubstituted Furans
  作者：Shuai Mao、Ya-Ru Gao、Shao-Liang Zhang、Dong-Dong Guo、Yong-Qiang Wang

  DOI：10.1002/ejoc.201403274

  日期：2015.2

  The copper(II)-promoted C–C bond formation from the coupling of two C(sp3)–H bonds that are adjacent to a carbonyl group was achieved. This protocol offers a simple and efficient approach to 2,3-disubstituted 1,4-diketones and tetrasubstituted furans. This method features a wide substrate scope and high functional group tolerance.

  通过与羰基相邻的两个 C(sp3)-H 键的偶联，实现了铜 (II) 促进的 C-C 键形成。该协议为 2,3-二取代 1,4-二酮和四取代呋喃提供了一种简单有效的方法。该方法具有广泛的底物范围和高官能团耐受性。
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  作者：Porter, Leigh C.、Dickman, Michael H.、Doedens, Robert J.

  DOI：——

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• Homosolvolysis
  作者：Alan C. Scott、John M. Tedder、John C. Walton、Sushila Mhatre

  DOI：10.1039/p29800000260

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• Nitroxydes 105: cinetique de reduction d'un radical nitroxyde par l'acide ascorbique en presence de β-cyclodextrine
  作者：C. Ebel、K.U. Ingold、J. Michon、A. Rassat

  DOI：10.1016/s0040-4039(00)89125-x

  日期：1985.1
• Mathieu, Corinne; Tuccio, Beatrice; Lauricella, Robert, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 12, p. 2501 - 2505
  作者：Mathieu, Corinne、Tuccio, Beatrice、Lauricella, Robert、Mercier, Anne、Tordo, Paul

  DOI：——

  日期：——