3-(N-piperidinecarbamoyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline | 13810-23-6

• 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-(N-piperidinecarbamoyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline
• 英文别名: 3-Piperidinoformyl-2,2,5,5-tetramethyl-pyrrolin-1-oxyl
• CAS: 13810-23-6
• 化学式: C₁₄H₂₃N₂O₂
• 分子量: 251.349
• InChiKey: RBOSRAWYECTMOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.45
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(N-piperidinecarbamoyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 生成 3-(N-piperidinemethyl)-2 2,5,5-tetramethyl-1-oxy-3-pyrroline p-toluenesulfonic acid salt
  参考文献：
  名称：

  An efficient synthesis of 3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline, a promising radioprotector for cancer radiotherapy

  摘要：

  Nitroxides can ameliorate the toxic effects of radiation during cancer therapy. Nitroxides are paramagnetic and can be used in magnetic resonance imaging (MRI) and electron paramagnetic resonance imaging (EPRI) to monitor in vivo oxidative stress status. Compound 5 (3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline) was found to be the most effective nitroxide radioprotector. An efficient synthesis for this promising radioprotector was developed. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.08.028
• 作为产物：
  描述：

  四甲基哌啶酮 在 sodium tungstate dihydrate 、 双氧水 、 溴 、 dipotassium ethylene diamine tetracetate 、 溶剂黄146 、 三乙胺 作用下， 以 水 为溶剂， 反应 6.0h， 生成 3-(N-piperidinecarbamoyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline
  参考文献：
  名称：

  An efficient synthesis of 3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline, a promising radioprotector for cancer radiotherapy

  摘要：

  Nitroxides can ameliorate the toxic effects of radiation during cancer therapy. Nitroxides are paramagnetic and can be used in magnetic resonance imaging (MRI) and electron paramagnetic resonance imaging (EPRI) to monitor in vivo oxidative stress status. Compound 5 (3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline) was found to be the most effective nitroxide radioprotector. An efficient synthesis for this promising radioprotector was developed. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.08.028

文献信息

• 3-[(1-Oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carbonyloxy)-imino]-2-phenyl-3<i>H</i>-indole; A New Convenient Spin Label
  作者：Elena Chiorboli、Lucedio Greci

  DOI：10.1055/s-1986-31622

  日期：——

  The reaction of 3-chlorocarbonyl-2,2,5,5-tetramethyl-2, 5-dihydropyrrole-1-oxyl with 3-oximino-2-phenyl-3H-indole in aqueous sodium hydroxide affords 3-[(1-oxyl-2,2,5,5-tetramethyl-2, 5-dihydropyrrole-3-carbonyloxy)-imino]-3H-indole. This nitroxyl does not undergo noticeable decomposition at room temperature and can be considered as a new convenient spin-labeled activated carboxylic acid derivative. It reacts with primary and secondary amines under mild conditions to form the spin-labeled 2,2,5,5-tetramethyl-1-oxyl-2, 5-dihydropyrrole-3-carboxamides.

  3-Clorocarbonyl-2,2,5,5-tetramethyl-2, 5-dihydropyrrole-1-oxyl 与 3-oximino-2-phenyl-3H-indole 在氢氧化钠水溶液中反应生成 3-[(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carbonyloxy)-imino]-3H-indole。这种硝基在室温下不会发生明显的分解，可视为一种新的方便的自旋标记活化羧酸衍生物。它能在温和的条件下与伯胺和仲胺反应，生成自旋标记的 2,2,5,5-四甲基-1-氧代-2,5-二氢吡咯-3-羧酰胺。