ethyl (12R)-7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate | 233765-85-0

• 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 (12R)-7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate
• CAS: 233765-85-0
• 化学式: C₁₆H₁₆FNO₃
• mdl: MFCD04055014
• 分子量: 289.306
• InChiKey: XEGSXHWRENGBSZ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (12R)-7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate 在 水 作用下， 反应 3.0h， 以75.4%的产率得到(R)-氟甲喹
  参考文献：
  名称：

  Synthesis, absolute configuration and intermediates of 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (flumequine)

  摘要：

  The antibacterial agent 9-fluoro-6,7-dihydro-5-methyl- 1-oxo- 1H,5H-benzo[iJ]quinolizine-2-carboxylic acid (flumequine) was synthesized in optically active form from 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ). Racemic FTHQ was resolved with the enantiomers of 3-bromocamphor-8-sulfonic acid. The configurations were established by X-ray structures of the two diastereoisomeric salts. Enantiomeric excesses were determined by H-1 NMR analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00071-3
• 作为产物：
  描述：

  (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 在 PPA 作用下， 以 甲苯 为溶剂， 反应 8.5h， 生成 ethyl (12R)-7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate
  参考文献：
  名称：

  Synthesis, absolute configuration and intermediates of 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (flumequine)

  摘要：

  The antibacterial agent 9-fluoro-6,7-dihydro-5-methyl- 1-oxo- 1H,5H-benzo[iJ]quinolizine-2-carboxylic acid (flumequine) was synthesized in optically active form from 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ). Racemic FTHQ was resolved with the enantiomers of 3-bromocamphor-8-sulfonic acid. The configurations were established by X-ray structures of the two diastereoisomeric salts. Enantiomeric excesses were determined by H-1 NMR analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00071-3

文献信息

• MACROLONE COMPOUNDS
  申请人：Frydrych Catherine Simone Victoire

  公开号：US20090111760A1

  公开（公告）日：2009-04-30

  A compound of formula (I) compositions comprising same, processes for their preparation and use of said compounds, particularly in the treatment of microbial infections.

  一种化学式为(I)的化合物、包含该化合物的组合物、制备该化合物的方法以及该化合物的用途，特别是在治疗微生物感染方面的用途。
• Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation
  作者：Magnus Rueping、Mirjam Stoeckel、Erli Sugiono、Thomas Theissmann

  DOI：10.1016/j.tet.2010.04.091

  日期：2010.8

  A highly enantioselective organocatalytic transfer hydrogenation enabling the synthesis of both 6-fluoro-2-methyltetrahydroquinoline and 7,8-difluoro-3-methyl-benzoxazine has been developed. These key building blocks can for the first time be synthesized using the same methodology allowing fast and efficient, metal-free access to the antibiotic fluoroquinolones flumequine and levofloxacine. (C) 2010 Elsevier Ltd. All rights reserved.