2-((R)-6-Fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester | 233765-83-8

• 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: 2-((R)-6-Fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester
• CAS: 233765-83-8
• 化学式: C₁₈H₂₂FNO₄
• 分子量: 335.375
• InChiKey: XFDLJNAGQPPZFJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((R)-6-Fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester 在 polyphosphoric acid 作用下， 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：

  Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.04.091
• 作为产物：
  描述：

  6-氟-1,2,3,4-四氢-2-甲基喹啉 反应 2.5h， 生成 2-((R)-6-Fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester
  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