1-乙酰氧基-3-甲氧羰基-2,2,5,5-四甲基吡咯烷 | 439858-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-乙酰氧基-3-甲氧羰基-2,2,5,5-四甲基吡咯烷
• 中文别名: 1-乙酰氧基-3-甲氧基羰基-2,2,5,5-四甲基吡咯烷
• 英文名称: 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine
• 英文别名: AMCPy；methyl 1-acetyloxy-2,2,5,5-tetramethylpyrrolidine-3-carboxylate
• CAS: 439858-38-5
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: KSWKLBFXRCFELO-UHFFFAOYSA-N

物化性质

• 沸点：
  276.9±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羧基-PROXYL 在 盐酸 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.5h， 生成 1-乙酰氧基-3-甲氧羰基-2,2,5,5-四甲基吡咯烷
  参考文献：
  名称：

  Acyl-Protected Hydroxylamines as Spin Label Generators for EPR Brain Imaging

  摘要：

  In a search for novel electron paramagnetic resonance (EPR) brain imaging agents, we have designed and synthesized the acyl-protected hydroxylamines 1-acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine (AMCPe), 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (AMCPy), and 1-acetoxy-3-(acetoxymethoxy)carbonyl-2,2,5,5-tetramethylpyrrolidine (DACPy), in which both the ring size and the number of ester functions were varied. In all of them, the nitroxide was first reduced and the resultant hydroxylamine was then protected with an acetyl group. These compounds are lipophilic, which is a major prerequisite for blood-brain barrier penetration. Once in the brain, esterases and oxidants quickly convert these derivatives into ionic, water-soluble radicals and thus EPR detectable species that then reside in the central nervous system for periods of time sufficient for detection and imaging. The biological relevancy of these new compounds in mice has been assessed, and their biodistribution patterns have been compared. The five-membered ring derivative AMCPy emerged as a potent EPR brain imaging agent while the other two derivatives, AMCPe and DACPy, were quite ineffective.

  DOI：

  10.1021/jm0105169

文献信息

• Acyl-Protected Hydroxylamines as Spin Label Generators for EPR Brain Imaging
  作者：Alexander T. Yordanov、Ken-ichi Yamada、Murali C. Krishna、Angelo Russo、John Yoo、Sean English、James B. Mitchell、Martin W. Brechbiel

  DOI：10.1021/jm0105169

  日期：2002.5.1

  In a search for novel electron paramagnetic resonance (EPR) brain imaging agents, we have designed and synthesized the acyl-protected hydroxylamines 1-acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine (AMCPe), 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (AMCPy), and 1-acetoxy-3-(acetoxymethoxy)carbonyl-2,2,5,5-tetramethylpyrrolidine (DACPy), in which both the ring size and the number of ester functions were varied. In all of them, the nitroxide was first reduced and the resultant hydroxylamine was then protected with an acetyl group. These compounds are lipophilic, which is a major prerequisite for blood-brain barrier penetration. Once in the brain, esterases and oxidants quickly convert these derivatives into ionic, water-soluble radicals and thus EPR detectable species that then reside in the central nervous system for periods of time sufficient for detection and imaging. The biological relevancy of these new compounds in mice has been assessed, and their biodistribution patterns have been compared. The five-membered ring derivative AMCPy emerged as a potent EPR brain imaging agent while the other two derivatives, AMCPe and DACPy, were quite ineffective.