2,2,7,7,9,9-hexamethyl-3-prop-2-ynyl-1,3,8-triazaspiro[4,5]decan-4-one-1,8-di-N-oxyl | 1013400-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 2,2,7,7,9,9-hexamethyl-3-prop-2-ynyl-1,3,8-triazaspiro[4,5]decan-4-one-1,8-di-N-oxyl
• 英文别名: 2,2,7,7,9,9-Hexamethyl-8-oxido-1-oxo-3-prop-2-ynyl-3,8-diaza-1-azoniaspiro[4.5]decan-4-one；2,2,7,7,9,9-hexamethyl-8-oxido-1-oxo-3-prop-2-ynyl-3,8-diaza-1-azoniaspiro[4.5]decan-4-one
• CAS: 1013400-82-2
• 化学式: C₁₆H₂₅N₃O₃
• 分子量: 307.393
• InChiKey: SKTJYUIQHWWVCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四甲基哌啶酮 在 过氧乙酸 、 硫酸 、 氨 、 水 、 sodium hydride 、 碳酸氢钠 、 溶剂黄146 、 2,2-二甲氧基丙烷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 92.08h， 生成 2,2,7,7,9,9-hexamethyl-3-prop-2-ynyl-1,3,8-triazaspiro[4,5]decan-4-one-1,8-di-N-oxyl
  参考文献：
  名称：

  Synthesis of A Novel Spirobisnitroxide Polymer and its Evaluation in an Organic Radical Battery

  摘要：

  A straightforward synthesis of a novel spirobisnitroxide 6 has been developed. Cyclovoltammetry of 6 revealed two distinct reversible oxidation/reduction steps separated by ca. 740 mV indicating the formation of the corresponding oxoammonium cations. Rhodium-catalyzed polymerization of 6 afforded the polyacetylene polymer 7 bearing the pending spirobisnitroxide groups. Additionally, cross-linked 7 was prepared in the presence of 3 mol % of N,N'-diprop-2-ynyl-oxalamide. If oxidation of both nitroxide groups is considered, 7 possesses an unprecedented high theoretical charge capacity of 174 mA h g(-1) Evaluation of the cross-linked polymer 7 as a cathode material for an organic radical battery showed very good cycling stability when the potential was kept below the oxidation potential of the five-membered nitroxide subunit of 6. A presumable irreversible degradation of the polymeric backbone of 7 occurred at higher potentials, limiting the experimentally obtained charge capacity to 73 mA h g(-1).

  DOI：

  10.1021/cm901374u

文献信息

• Synthesis of A Novel Spirobisnitroxide Polymer and its Evaluation in an Organic Radical Battery
  作者：Peter Nesvadba、Lucienne Bugnon、Pascal Maire、Petr Novák

  DOI：10.1021/cm901374u

  日期：2010.2.9

  A straightforward synthesis of a novel spirobisnitroxide 6 has been developed. Cyclovoltammetry of 6 revealed two distinct reversible oxidation/reduction steps separated by ca. 740 mV indicating the formation of the corresponding oxoammonium cations. Rhodium-catalyzed polymerization of 6 afforded the polyacetylene polymer 7 bearing the pending spirobisnitroxide groups. Additionally, cross-linked 7 was prepared in the presence of 3 mol % of N,N'-diprop-2-ynyl-oxalamide. If oxidation of both nitroxide groups is considered, 7 possesses an unprecedented high theoretical charge capacity of 174 mA h g(-1) Evaluation of the cross-linked polymer 7 as a cathode material for an organic radical battery showed very good cycling stability when the potential was kept below the oxidation potential of the five-membered nitroxide subunit of 6. A presumable irreversible degradation of the polymeric backbone of 7 occurred at higher potentials, limiting the experimentally obtained charge capacity to 73 mA h g(-1).