ethyl 1-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate | 100276-63-9

• 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-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
• 英文别名: ethyl 1-amino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate；Ethyl 1-amino-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate
• CAS: 100276-63-9
• 化学式: C₁₂H₉F₃N₂O₃
• 分子量: 286.21
• InChiKey: NNMVZQHNJXGMFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 1-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate 在 lead(IV) acetate 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 Ethyl 6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1-(2-pyridin-2-ylaziridin-1-yl)quinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of N-(1-Aziridinyl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids

  摘要：

  A series of N-(1-aziridinyl)quinoline-3-carboxylic acid derivatives (e.g. 11a-f, 20a-g, 21a-d) have been synthesized by insertion reaction of nitrenes (e.g. ethyl 7-chloro-6-fluoro-1-nitreno-1,4-dihydro-4-oxoquinoline-3-carboxylate (9)) into double bond of different olefins (e.g. styrene (10a), see Schemes 2 and 4). The nitrenes were formed in situ by oxidation of N-aminoquinolin-4(1H)-one derivatives (8, 18a,b) using Pb(OAc)(4) as oxidizing agent.

  DOI：

  10.3987/com-97-7770
• 作为产物：
  描述：

  6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯 在 O-tosylhydroxylamine 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以82%的产率得到ethyl 1-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
  参考文献：
  名称：

  Synthesis of N-(1-Aziridinyl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids

  摘要：

  A series of N-(1-aziridinyl)quinoline-3-carboxylic acid derivatives (e.g. 11a-f, 20a-g, 21a-d) have been synthesized by insertion reaction of nitrenes (e.g. ethyl 7-chloro-6-fluoro-1-nitreno-1,4-dihydro-4-oxoquinoline-3-carboxylate (9)) into double bond of different olefins (e.g. styrene (10a), see Schemes 2 and 4). The nitrenes were formed in situ by oxidation of N-aminoquinolin-4(1H)-one derivatives (8, 18a,b) using Pb(OAc)(4) as oxidizing agent.

  DOI：

  10.3987/com-97-7770

文献信息

• Grohe, Klaus; Heitzer, Helmut, Liebigs Annalen der Chemie, 1987, p. 871 - 880
  作者：Grohe, Klaus、Heitzer, Helmut

  DOI：——

  日期：——
• Synthesis and biological evaluation of N-(1-aziridino)-6-fluoro-quinolone-3-carboxylic acids
  作者：Sándor Bátori、Géza Tímári、István Koczka、István Hermecz

  DOI：10.1016/s0960-894x(96)00259-4

  日期：1996.7

  New racemic N-(1-aziridino)-6-fluoro-7-(4-methylpiperazin-1-yl)-4(1H)-quinolone-3-carboxylic acids (9a-i) were synthesized and their antibacterial activities were tested against Gram-positive and Gramnegative micro-organisms. According to the MIC, all compounds studied are less active than Ciprofloxacin; two of them (9a,b) have similar activity as Nalidixic acid (1). Copyright (C) 1996 Elsevier Science Ltd
• GROHE, KLAUS;HEITZER, HELMUT, LIEBIGS ANN. CHEM.,(1987) N 10, 871-879
  作者：GROHE, KLAUS、HEITZER, HELMUT

  DOI：——

  日期：——
• US4753925A
  申请人：——

  公开号：US4753925A

  公开（公告）日：1988-06-28
• Synthesis of N-(1-Aziridinyl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids
  作者：Sándor Bátori、Géza Tímári、András Messmer、Benjámin Podányi、Lelle Vasvárii-Debreczy、István Hermecz

  DOI：10.3987/com-97-7770

  日期：——

  A series of N-(1-aziridinyl)quinoline-3-carboxylic acid derivatives (e.g. 11a-f, 20a-g, 21a-d) have been synthesized by insertion reaction of nitrenes (e.g. ethyl 7-chloro-6-fluoro-1-nitreno-1,4-dihydro-4-oxoquinoline-3-carboxylate (9)) into double bond of different olefins (e.g. styrene (10a), see Schemes 2 and 4). The nitrenes were formed in situ by oxidation of N-aminoquinolin-4(1H)-one derivatives (8, 18a,b) using Pb(OAc)(4) as oxidizing agent.