1-cyclopropyl-7-ethylamino-5,6,8-trifluoro-4(1H)-oxoquinoline-3-carboxylylic acid | 132113-20-3

• 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: 1-cyclopropyl-7-ethylamino-5,6,8-trifluoro-4(1H)-oxoquinoline-3-carboxylylic acid
• 英文别名: 1-cyclopropyl-7-(ethylamino)-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 132113-20-3
• 化学式: C₁₅H₁₃F₃N₂O₃
• 分子量: 326.275
• InChiKey: RWWAQFRCTYHRAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.33
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  奥比沙星杂质F(EP) 、 乙胺 生成 1-cyclopropyl-7-ethylamino-5,6,8-trifluoro-4(1H)-oxoquinoline-3-carboxylylic acid
  参考文献：
  名称：

  SHIBAMORI, KOH-ICHIRO;EGAWA, HIROSHI;MIYAMOTO, TERUYUKI;NISHIMURA, YOSHIR+, CHEM. AND PHARM. BELL., 38,(1990) N, C. 2390-2396

  摘要：

  DOI：

文献信息

• Pyridonecarboxylic acids as antibacterial agents. Part XIII. Regioselective displacement reactions of 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylic acid with amine nucleophiles.
  作者：Koh-ichiro SHIBAMORI、Hiroshi EGAWA、Teruyuki MIYAMOTO、Yoshiro NISHIMURA、Akira ITOKAWA、Junji NAKANO、Jun-ichi MATSUMOTO

  DOI：10.1248/cpb.38.2390

  日期：——

  The displacement reactions of ethyl 1-cyclopropyl-5, 6, 7, 8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate (7) and its carboxylic acid 8 with amine nucleophiles were examined. The nucleophilic displacement occurred regioselectively at the C-5 or C-7 position depending on the substrate (7 or 8) and solvent selected; this finding permitted the introduction of an optional nucleophile preferentially into the required position at either C-5 or C-7, or into both positions with a desired combination of nucleophiles. Taking advantage of this regioselectivity, we prepared various 5-substituted 6, 7, 8-trifluoro- and 7-substituted 5, 6, 8-trifluoro-1-cyclopropyl-4(1H)-oxoquinoline-3-carboxylic acids. Furthermore, the use of the boron-chelated derivative of the carboxylic acid 8 was favorable for the regioselective synthesis of 7-substituted 5, 6, 8-trifluoroquinolones.

  研究了1-环丙基-5,6,7,8-四氟-4(1H)-氧代喹啉-3-甲酸乙酯(7)及其羧酸8与胺亲核试剂的置换反应。根据所选择的底物（7 或 8）和溶剂，亲核置换区域选择性地发生在 C-5 或 C-7 位置；这一发现允许将任选的亲核试剂优先引入到所需的C-5或C-7位置，或者引入具有所需亲核试剂组合的两个位置。利用这种区域选择性，我们制备了各种5-取代的6,7,8-三氟-和7-取代的5,6,8-三氟-1-环丙基-4(1H)-氧代喹啉-3-羧酸。此外，使用羧酸8的硼螯合衍生物有利于7-取代的5,6,8-三氟喹诺酮的区域选择性合成。