2,2,6,6-tetramethyl-3-methylene-4-oxopiperidine-1-oxyl | 109270-49-7

• 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: 2,2,6,6-tetramethyl-3-methylene-4-oxopiperidine-1-oxyl
• 英文别名: 3-methylene-2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl；3-methylene-2,2,6,6-tetramethyl-4-oxopiperidin-1-oxyl；2,2,6,6-tetramethyl-3-methylidene-4-oxopiperidine 1-oxyl
• CAS: 109270-49-7
• 化学式: C₁₀H₁₆NO₂
• 分子量: 182.243
• InChiKey: UFCWKTLXIHLPMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  21.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,6,6-tetramethyl-3-methylene-4-oxopiperidine-1-oxyl 以 氯仿 为溶剂， 以84%的产率得到2',2',5,5,6',6',7,7-octamethyl-6-oxido-1'-oxospiro[4,8-dihydro-3H-pyrano[3,2-c]pyridine-2,3'-piperidin-1-ium]-4'-one
  参考文献：
  名称：

  Formaldehyde in the synthesis of nitroxyl biradicals

  摘要：

  DOI：

  10.1007/bf00954626
• 作为产物：
  描述：

  2,2,6,6-tetramethyl-3-(N-methylpiperidiniomethyl)-4-oxopiperidine 1-oxyl iodide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2,2,6,6-tetramethyl-3-methylene-4-oxopiperidine-1-oxyl
  参考文献：
  名称：

  Reactions of the paramagnetic quaternary Mannich base in an alkaline medium

  摘要：

  20 °C时，水合氢氧化钠对2,2,6,6-四甲基-3-(N-甲基-哌啶基甲基)-4-氧代哌啶1-氧基碘的催化作用迅速导致形成（k = 57 L mol-1 s-1）具有活化双键的顺磁酮：2,2,6,6-四甲基-3-亚甲基-4-氧代哌啶1-氧基。后者缓慢转化为含活化双键和连接3和3′位置的亚甲基桥的硝基自由基双自由基。

  DOI：

  10.1007/s11172-008-0068-x

文献信息

• Quantitative study of nucleophilic addition of secondary amines to 3,5-dimethylene-2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl
  作者：A. D. Malievskii、A. B. Shapiro、I. V. Yakovleva、S. V. Koroteev

  DOI：10.1007/bf00965375

  日期：1988.3
• Kinetics, mechanism, and reactivity of an activated carbon-carbon double bond in nitroxyl radicals and their diamagnetic analog in interaction with some secondary amines and polyethyleneimine
  作者：A. D. Malievskii、S. V. Koroteev

  DOI：10.1007/bf01431300

  日期：1996.4

  Routes for the reaction of a conjugated methylene group of nitroxyl radicals (NR) with secondary amines were suggested and analyzed. Kinetic parameters of the limiting step of this reaction for the NR-amine and diamagnetic analog of NR-amine systems were estimated. The effect of the medium on these reactions was examined. The specific behavior of polyethyleneimine in the reaction with activated methylene groups of 2,2,6,6-tetramethyl-3,5-dimethylene-4-oxopiperidine-1-oxyl was demonstrated.
• Formaldehyde in the synthesis of nitroxyl biradicals
  作者：A. B. Shapiro、V. I. Suskina

  DOI：10.1007/bf00954626

  日期：1986.8
• Reactions of the paramagnetic quaternary Mannich base in an alkaline medium
  作者：A. D. Malievskii、A. B. Shapiro

  DOI：10.1007/s11172-008-0068-x

  日期：2008.2

  The catalytic action of aqueous NaOH at 20 °C on 2,2,6,6-tetramethyl-3-(N-methyl-piperidiniomethyl)-4-oxopiperidine 1-oxyl iodide rapidly resulted in the formation (k = 57 L mol−1 s−1) of a paramagnetic ketone with an activated double bond: 2,2,6,6-tetramethyl-3-methylidene-4-oxopiperidine 1-oxyl. The latter underwent slow transformation into a nitroxyl biradical containing an activated double bond and a methylene bridge linking positions 3 and 3′.

  20 °C时，水合氢氧化钠对2,2,6,6-四甲基-3-(N-甲基-哌啶基甲基)-4-氧代哌啶1-氧基碘的催化作用迅速导致形成（k = 57 L mol-1 s-1）具有活化双键的顺磁酮：2,2,6,6-四甲基-3-亚甲基-4-氧代哌啶1-氧基。后者缓慢转化为含活化双键和连接3和3′位置的亚甲基桥的硝基自由基双自由基。