3-chloro-4-oxo-TEMPO | 81635-37-2

• 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: 3-chloro-4-oxo-TEMPO
• 英文别名: 2,2,6,6-tetramethyl-3-chloro-4-oxopiperidine-1-oxide；2,2,6,6,-tetramethyl-3-chloro-4-oxopiperidin 1-oxyl；2,2,6,6-tetramethyl-3-chloro-4-oxopiperidine-1-oxyl
• CAS: 81635-37-2
• 化学式: C₉H₁₅ClNO₂
• 分子量: 204.677
• InChiKey: RXDGUZBNTZZLHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  40.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-chloro-4-oxo-TEMPO 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以60%的产率得到3-chloro-4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl
  参考文献：
  名称：

  Intramolecular rearrangement with ring contraction of 1,4-dihydroxy-3-bromo-2,2,6,6-tetramethylpiperidine

  摘要：

  DOI：

  10.1007/bf01557524
• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶酮盐酸盐 在 磺酰氯 、 溴 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-chloro-4-oxo-TEMPO
  参考文献：
  名称：

  3-Monohalo derivatives of triacetoneamine, 1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine, and 2,2,6,6-tetramethyl-4-oxopiperidin-1-oxyl

  摘要：

  DOI：

  10.1007/bf00948269

文献信息

• Dikanov, S. A.; Grigor'ev, I. A.; Volodarskii, L. B., Russian Journal of Physical Chemistry, 1982, vol. 56, # 11, p. 1696 - 1699
  作者：Dikanov, S. A.、Grigor'ev, I. A.、Volodarskii, L. B.、Tsvetkov, Yu. D.

  DOI：——

  日期：——
• Oxidation of di-tert-alkylhydroxylamines to nitroxide radicals by nitrous acid
  作者：L. A. Krinitskaya、L. B. Volodarskii

  DOI：10.1007/bf00957948

  日期：1983.2
• Predicting Electrocatalytic Properties: Modeling Structure–Activity Relationships of Nitroxyl Radicals
  作者：David P. Hickey、David A. Schiedler、Ivana Matanovic、Phuong Vy Doan、Plamen Atanassov、Shelley D. Minteer、Matthew S. Sigman

  DOI：10.1021/jacs.5b11252

  日期：2015.12.30

  Stable nitroxyl radical-containing compounds, such as 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) and its derivatives, are capable of electrocatalytically oxidizing a wide range of alcohols under mild and environmentally friendly conditions. Herein, we examine the structure function relationships that determine the catalytic activity of a diverse range of water-soluble nitroxyl radical compounds. A strong correlation is described between the difference in the electrochemical oxidation potentials of a compound and its electrocatalytic activity. Additionally, we construct a simple computational model that is able to accurately predict the electrochemical potential and catalytic activity of a wide range of nitroxyl radical derivatives.