(R)-6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid | 107298-27-1

• 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: (R)-6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid
• 英文别名: (12R)-7-fluoro-8,12-dimethyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid
• CAS: 107298-27-1
• 化学式: C₁₅H₁₄FNO₃
• 分子量: 275.279
• InChiKey: DXKRGNXUIRKXNR-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氟-2,5-二甲基-1,2,3,4-四氢喹啉 在 PPA 、 sodium ethanolate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R)-6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis, absolute configuration, and antibacterial activity of 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

  摘要：

  The tricyclic quinolone antibacterial agent 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine -2-carboxylic acid has an asymmetric center at position 5 of the molecule. The R and S isomers of the compound have been prepared from the corresponding (R)- and (S)-2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydroquinolines, which were separated via their diastereomeric amides of N-tosyl-(S)-proline. The absolute configuration was established by X-ray analysis of one of the diastereomeric amides. The 5-desmethyl analogue was prepared for antibacterial comparison with the isomers and the racemic mixture. It has now been established that the S isomer is much more active than the R isomer. The 5-desmethyl analogue was found to be more active than the R isomer but not as active as the S isomer or the racemic mixture. The importance of stereochemistry at position 5 in this system has been established.

  DOI：

  10.1021/jm00388a016

文献信息

• GERSTER J. F.; ROHLFING S. R.; PECORE S. E.; WINANDY R. M.; STERN R. M.; +, J. MED. CHEM., 30,(1987) N 5, 839-843
  作者：GERSTER J. F.、 ROHLFING S. R.、 PECORE S. E.、 WINANDY R. M.、 STERN R. M.、 +

  DOI：——

  日期：——
• Synthesis, absolute configuration, and antibacterial activity of 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
  作者：John F. Gerster、Steve R. Rohlfing、Sharon E. Pecore、Richard M. Winandy、Richard M. Stern、June E. Landmesser、Roger A. Olsen、William B. Gleason

  DOI：10.1021/jm00388a016

  日期：1987.5

  The tricyclic quinolone antibacterial agent 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine -2-carboxylic acid has an asymmetric center at position 5 of the molecule. The R and S isomers of the compound have been prepared from the corresponding (R)- and (S)-2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydroquinolines, which were separated via their diastereomeric amides of N-tosyl-(S)-proline. The absolute configuration was established by X-ray analysis of one of the diastereomeric amides. The 5-desmethyl analogue was prepared for antibacterial comparison with the isomers and the racemic mixture. It has now been established that the S isomer is much more active than the R isomer. The 5-desmethyl analogue was found to be more active than the R isomer but not as active as the S isomer or the racemic mixture. The importance of stereochemistry at position 5 in this system has been established.