4-<2-(Ethoxycarbonyl)ethyl>-3,3,5,5-tetramethyl-1-pyrroline N-oxide | 139461-53-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-<2-(Ethoxycarbonyl)ethyl>-3,3,5,5-tetramethyl-1-pyrroline N-oxide
• 英文别名: ethyl 3-(2,2,4,4-tetramethyl-1-oxido-3H-pyrrol-1-ium-3-yl)propanoate
• CAS: 139461-53-3
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: UMAGJLHTPFSFCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<2-(Ethoxycarbonyl)ethyl>-3,3,5,5-tetramethyl-1-pyrroline N-oxide 在 ferrous ammonium sulphate 、 双氧水 作用下， 以 水 为溶剂， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Design of modified pyrroline N-oxide derivatives as spin traps specific for hydroxyl radical

  摘要：

  Nitrones, 4-[2-(ethoxycarbonyl)ethyl]-3,3,5,5-tetramethyl-1-pyrroline N-oxide (7a) and 4-[2-(ethoxycarbonyl)ethyl]-5,5-di([H-2(3)[methyl)-3,3-dimethyl-1-pyrrolidine N-oxide (7b) have been synthesized. The ability of the nitrone (7a) to spin trap hydroxyl and superoxide radicals has been compared with nitrones 11a and 5,5-dimethyl-1-pyrroline N-oxide (DMPO, 8). Nitrone 11a bears a carbethoxy group at C-4, whereas nitrone 7a has a spacer of two methylene units between the carbethoxy and the basic nitrone ring skeleton. Nitrone 11a trapped both hydroxyl and superoxide radicals, while nitrone 7a trapped only hydroxyl radical. The hydroxyl radical adducts of 7a and 11a were more resistant toward superoxide-mediated reduction than the hydroxyl radical adduct of DMPO (8).

  DOI：

  10.1021/jo00034a020
• 作为产物：
  描述：

  N-(Benzyloxycarbonyl)-3-(hydroxymethyl)-2,2,4,4-tetramethylpyrrolidine 在 palladium on activated charcoal sodium tungstate 、 氢气 、 双氧水 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 4-<2-(Ethoxycarbonyl)ethyl>-3,3,5,5-tetramethyl-1-pyrroline N-oxide
  参考文献：
  名称：

  Design of modified pyrroline N-oxide derivatives as spin traps specific for hydroxyl radical

  摘要：

  Nitrones, 4-[2-(ethoxycarbonyl)ethyl]-3,3,5,5-tetramethyl-1-pyrroline N-oxide (7a) and 4-[2-(ethoxycarbonyl)ethyl]-5,5-di([H-2(3)[methyl)-3,3-dimethyl-1-pyrrolidine N-oxide (7b) have been synthesized. The ability of the nitrone (7a) to spin trap hydroxyl and superoxide radicals has been compared with nitrones 11a and 5,5-dimethyl-1-pyrroline N-oxide (DMPO, 8). Nitrone 11a bears a carbethoxy group at C-4, whereas nitrone 7a has a spacer of two methylene units between the carbethoxy and the basic nitrone ring skeleton. Nitrone 11a trapped both hydroxyl and superoxide radicals, while nitrone 7a trapped only hydroxyl radical. The hydroxyl radical adducts of 7a and 11a were more resistant toward superoxide-mediated reduction than the hydroxyl radical adduct of DMPO (8).

  DOI：

  10.1021/jo00034a020