2-nitro-1-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl)-1H-imidazole | 1443039-67-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-nitro-1-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl)-1H-imidazole
• 英文别名: 2-Nitro-1-[2-(2-prop-2-ynoxyethoxy)ethyl]imidazole
• CAS: 1443039-67-5
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: HZGDZDBJDBHGMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-nitro-1-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl)-1H-imidazole 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.33h， 生成 1-(3-(fluorodi(naphthalen-1-yl)silyl)propyl)-4-((2-(2-(2-nitro-1H-imidazol-1-yl)ethoxy)ethoxy)methyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds

  摘要：

  The syntheses of new nitroimidazole compounds using silicon-[F-18]fluorine chemistry for the potential detection of tumor hypoxia are described. [F-18]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/mu mol, however these compounds ([F-18]7 and [F-18]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/mu mol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/mu mol. The labeled compound [F-18]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [F-18]18 is suitable for further in vivo assessments. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.029
• 作为产物：
  描述：

  2-硝基咪唑 、 3-(2-(2-chloroethoxy)ethoxy)prop-1-yne 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到2-nitro-1-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds

  摘要：

  The syntheses of new nitroimidazole compounds using silicon-[F-18]fluorine chemistry for the potential detection of tumor hypoxia are described. [F-18]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/mu mol, however these compounds ([F-18]7 and [F-18]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/mu mol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/mu mol. The labeled compound [F-18]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [F-18]18 is suitable for further in vivo assessments. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.029