ethyl [1-(15)N,2-(13)C]-1-(4-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate | 1206836-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl [1-(15)N,2-(13)C]-1-(4-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
• CAS: 1206836-58-9
• 化学式: C₁₈H₁₂F₃NO₃
• 分子量: 349.276
• InChiKey: ADFROHOWXJREBY-DUZUJXPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl [1-(15)N,2-(13)C]-1-(4-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 3.0h， 以1.232 g的产率得到[1-(15)N,2-(13)C]-1-(4-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of [1-15N,2-13C]-labeled difloxacin

  摘要：

  The synthesis of [1-N-15,2-C-13]-difloxacin, an arylfluoroquinolone antibacterial agent, is reported. As a crucial initial step, the starting materials ethyl 2,4,5-trifluorobenzoylacetate, [formyl-C-13]-triethyl orthoformate, and [N-15]-4-fluoroaniline were reacted to ethyl [N-15,3-C-13]-3-(4-fluoroanilino)-2-(2,4,5-trifluorobenzoyl) acrylate. After cyclization and ester cleavage, the resulting intermediate was reacted with 1-methylpiperazine to [1-N-15,2-C-13]-1-(4-fluorophenyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate, i.e., [1-N-15,2-C-13]-difloxacin. The overall yield was 62% based on the non-labeled and 43% based on the labeled starting materials (both used in 1.4 molar excess). The product was identified by H-1-, C-13-, and N-15-NMR spectroscopy and by cochromatography (TLC, HPLC) with an authentic reference; its purity (HPLC) was above 98%. Prior to synthesis of [1-N-15,2-C-13]-difloxacin, non-labeled difloxacin was synthesized in order to optimize procedures and to identify and characterize all intermediates.

  DOI：

  10.1007/s00706-009-0158-y
• 作为产物：
  描述：

  2,4,5-三氟苯甲酰乙酸乙酯 在 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 7.0h， 生成 ethyl [1-(15)N,2-(13)C]-1-(4-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of [1-15N,2-13C]-labeled difloxacin

  摘要：

  The synthesis of [1-N-15,2-C-13]-difloxacin, an arylfluoroquinolone antibacterial agent, is reported. As a crucial initial step, the starting materials ethyl 2,4,5-trifluorobenzoylacetate, [formyl-C-13]-triethyl orthoformate, and [N-15]-4-fluoroaniline were reacted to ethyl [N-15,3-C-13]-3-(4-fluoroanilino)-2-(2,4,5-trifluorobenzoyl) acrylate. After cyclization and ester cleavage, the resulting intermediate was reacted with 1-methylpiperazine to [1-N-15,2-C-13]-1-(4-fluorophenyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate, i.e., [1-N-15,2-C-13]-difloxacin. The overall yield was 62% based on the non-labeled and 43% based on the labeled starting materials (both used in 1.4 molar excess). The product was identified by H-1-, C-13-, and N-15-NMR spectroscopy and by cochromatography (TLC, HPLC) with an authentic reference; its purity (HPLC) was above 98%. Prior to synthesis of [1-N-15,2-C-13]-difloxacin, non-labeled difloxacin was synthesized in order to optimize procedures and to identify and characterize all intermediates.

  DOI：

  10.1007/s00706-009-0158-y

文献信息

• Synthesis of [1-15N,2-13C]-labeled difloxacin
  作者：Burkhard Schmidt、Ramona Schumacher-Buffel、Brigitte Thiede、Andreas Schäffer

  DOI：10.1007/s00706-009-0158-y

  日期：2009.10

  The synthesis of [1-N-15,2-C-13]-difloxacin, an arylfluoroquinolone antibacterial agent, is reported. As a crucial initial step, the starting materials ethyl 2,4,5-trifluorobenzoylacetate, [formyl-C-13]-triethyl orthoformate, and [N-15]-4-fluoroaniline were reacted to ethyl [N-15,3-C-13]-3-(4-fluoroanilino)-2-(2,4,5-trifluorobenzoyl) acrylate. After cyclization and ester cleavage, the resulting intermediate was reacted with 1-methylpiperazine to [1-N-15,2-C-13]-1-(4-fluorophenyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate, i.e., [1-N-15,2-C-13]-difloxacin. The overall yield was 62% based on the non-labeled and 43% based on the labeled starting materials (both used in 1.4 molar excess). The product was identified by H-1-, C-13-, and N-15-NMR spectroscopy and by cochromatography (TLC, HPLC) with an authentic reference; its purity (HPLC) was above 98%. Prior to synthesis of [1-N-15,2-C-13]-difloxacin, non-labeled difloxacin was synthesized in order to optimize procedures and to identify and characterize all intermediates.