9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester | 42835-47-2

• 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: 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester
• 英文别名: 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester；ethyl 9-fluoro-5-(R,S)-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate；Ethyl 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo-[ij]quinolizine-2-carboxylate；Ethyl-9-fluor-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzochinolizin-2-carboxylat；ethyl 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate；ethyl 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate
• CAS: 42835-47-2
• 化学式: C₁₆H₁₆FNO₃
• mdl: MFCD04055014
• 分子量: 289.306
• InChiKey: XEGSXHWRENGBSZ-UHFFFAOYSA-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

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester 在 水 作用下， 反应 3.0h， 以70.8%的产率得到氟甲喹
  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：

  Diethyl (2-methyl-6-fluorotetrahydro-quinolin-1-yl)methylenemalonate 在 PPA 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以69.1%的产率得到9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl 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

文献信息

• N-methylene malonate of tetrahydroquinoline and derivatives thereof
  申请人：Riker Laboratories, Inc.

  公开号：US03969463A1

  公开（公告）日：1976-07-13

  Certain substituted 6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acids and hydrazides, esters, amides and salts thereof, intermediates therefor, and a process for their preparation are described; the compounds are active as anti-microbial agents.

  描述了某些取代的6,7-二氢-1-氧代-1H,5H-苯并[ij]-喹啉-2-羧酸和其酰肼、酯、酰胺和盐，以及其中间体，以及它们的制备方法；这些化合物作为抗微生物药剂具有活性。
• Substituted benzo(ij)quinolizine-2-carboxylic acids and derivatives
  申请人：Riker Laboratories, Inc.

  公开号：US04001243A1

  公开（公告）日：1977-01-04

  Certain substituted 6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acids and hydrazides, esters, amides and salts thereof, intermediates therefor, and a process for their preparation are described; the compounds are active as anti-microbial agents.

  本文描述了某些取代的6,7-二氢-1-氧代-1H,5H-苯并[ij]-喹啉-2-羧酸及其肼、酯、酰胺和盐，其中间体以及其制备方法；这些化合物作为抗微生物剂具有活性。
• Substituted benzo[ij]quinolizine-2-carboxylic acids and derivatives
  申请人：Riker Laboratories, Inc.

  公开号：US04014877A1

  公开（公告）日：1977-03-29

  Certain substituted 6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acids and hydrazides, esters, amides and salts thereof, intermediates therefor, and a process for their preparation are described; the compounds are active as anti-microbial agents.

  本文介绍了某些取代的6,7-二氢-1-氧代-1H,5H-苯并[ij]-喹啉-2-羧酸和它们的肼、酯、酰胺和盐，其中间体和制备它们的过程; 这些化合物作为抗微生物剂具有活性。
• MACROLONE COMPOUNDS
  申请人：Forrest Andrew Keith

  公开号：US20090062218A1

  公开（公告）日：2009-03-05

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

  一种化合物的公式(I)，包括该化合物的组合物，其制备过程以及该化合物的用途，特别是用于治疗微生物感染。
• WO2006/50940
  申请人：——

  公开号：——

  公开（公告）日：——