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1-乙酰氧基-4-甲氧羰基-2,2,6,6-四甲基哌啶 | 439858-37-4

中文名称
1-乙酰氧基-4-甲氧羰基-2,2,6,6-四甲基哌啶
中文别名
1-乙酰氧基-4-甲氧基羰基-2,2,6,6-四甲基哌啶
英文名称
1-acetoxy-4-methoxycarbonyl-2,2,6,6,-tetramethylpiperidine
英文别名
AMCPe;1-Acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine;methyl 1-acetyloxy-2,2,6,6-tetramethylpiperidine-4-carboxylate
1-乙酰氧基-4-甲氧羰基-2,2,6,6-四甲基哌啶化学式
CAS
439858-37-4
化学式
C13H23NO4
mdl
——
分子量
257.33
InChiKey
CEOYQDAGXCYAQM-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    296.3±50.0 °C(Predicted)
  • 密度:
    1.07±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.9
  • 重原子数:
    18
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.85
  • 拓扑面积:
    55.8
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    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
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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.
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