1-acetoxy-2-nitro-1-pentafluorophenylpropane | 905954-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-acetoxy-2-nitro-1-pentafluorophenylpropane
• CAS: 905954-41-8
• 化学式: C₁₁H₈F₅NO₄
• 分子量: 313.181
• InChiKey: DVCGIBHEFIXMBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-acetoxy-2-nitro-1-pentafluorophenylpropane 在 N-甲基吗啉 、 sodium tetrahydroborate 、 1,1,2,3-四甲基胍 、 硫酸 、 双氧水 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 128.17h， 生成 sodium 1-pentafluorophenyl-2,7,9-trimethyl-3H,5H-dipyrrolo[1,2-c:2',1'-f]pyrimidine-3,5-dione-8-sulfonate
  参考文献：
  名称：

  Synthesis, properties, and hepatic metabolism of strongly fluorescent fluorodipyrrinones

  摘要：

  From non-fluorescent 8-H fluorophenyldipyrrinones, highly fluorescent (phi(F) 0.4-0.6) analogs have been synthesized by reaction with 1,1'-carbonyidiimidazole to bridge the dipyrrinone nitrogens and form an NiN'-carbonyldipyrrinone (3H,5H-dipyrrolo[1,2-c:2',1'-f]-pyrimidine-3,5-dione). Amphiphilic, water-soluble 8-sulfonic acid derivatives are then obtained by reaction with coned H2SO4. The resulting fluorinated and sulfonated N,N'-carbonyl-bridged dipyrrinones, isolated as their sodium salts, are potential cholephilic fluorescence and F-19 MRI imaging agents for use in probing liver and biliary metabolism. After intravenous injection in the rat they were excreted rapidly and largely unchanged in bile. F-19 NMR spectroscopy of a pentafluorophenyl-tosylpyrrolinone synthetic precursor exhibited rarely seen diastereotopicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.046
• 作为产物：
  描述：

  五氟苯甲醛 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 46.0h， 生成 1-acetoxy-2-nitro-1-pentafluorophenylpropane
  参考文献：
  名称：

  Synthesis, properties, and hepatic metabolism of strongly fluorescent fluorodipyrrinones

  摘要：

  From non-fluorescent 8-H fluorophenyldipyrrinones, highly fluorescent (phi(F) 0.4-0.6) analogs have been synthesized by reaction with 1,1'-carbonyidiimidazole to bridge the dipyrrinone nitrogens and form an NiN'-carbonyldipyrrinone (3H,5H-dipyrrolo[1,2-c:2',1'-f]-pyrimidine-3,5-dione). Amphiphilic, water-soluble 8-sulfonic acid derivatives are then obtained by reaction with coned H2SO4. The resulting fluorinated and sulfonated N,N'-carbonyl-bridged dipyrrinones, isolated as their sodium salts, are potential cholephilic fluorescence and F-19 MRI imaging agents for use in probing liver and biliary metabolism. After intravenous injection in the rat they were excreted rapidly and largely unchanged in bile. F-19 NMR spectroscopy of a pentafluorophenyl-tosylpyrrolinone synthetic precursor exhibited rarely seen diastereotopicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.046