7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-5,6,8-trifluoro-4(1H)-oxoquinoline-3-carboxylic acid | 106890-66-8

• 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: 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-5,6,8-trifluoro-4(1H)-oxoquinoline-3-carboxylic acid
• 英文别名: 7-[3-amino-1-pyrrolidinyl]-1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid；7-[3-amino-1-pyrrolidinyl]-1-cyclopropyl-5,6,8-trifluror-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid；7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 106890-66-8
• 化学式: C₁₇H₁₆F₃N₃O₃
• 分子量: 367.328
• InChiKey: AJRDXJVCIORVSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-氨基吡咯烷 、 奥比沙星杂质F(EP) 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以90%的产率得到7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-5,6,8-trifluoro-4(1H)-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.38.2390

文献信息

• Trifluoro- quinoline -3- carboxylic acids and their use as
  申请人：Warner-Lambert Company

  公开号：US04657913A1

  公开（公告）日：1987-04-14

  Novel difluoro-naphthyridine- and trifluoroquinoline-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  描述了新型二氟基萘啉和三氟基喹啉羧酸作为抗菌剂，以及它们的制备、配方和用于治疗细菌感染的方法，包括用于制备抗菌剂的某些新型中间体的描述。
• 5,6-Difluoronaphthyridines and 5,6,8-trifluoro-quinolines as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0202763A1

  公开（公告）日：1986-11-26

  Novel difluoro-naphthyridine-and trifluoroquinoline-carboxylic acids of formula (I) as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  描述了作为抗菌剂的新型二氟萘啶和三氟喹啉羧酸的式 (I) 描述了作为抗菌剂的新型二氟萘啶和三氟喹啉羧酸及其制造、配制和用于治疗细菌感染的方法，包括描述了用于制造抗菌剂的某些新型中间体。
• SHIBAMORI, KOH-ICHIRO;EGAWA, HIROSHI;MIYAMOTO, TERUYUKI;NISHIMURA, YOSHIR+, CHEM. AND PHARM. BELL., 38,(1990) N, C. 2390-2396
  作者：SHIBAMORI, KOH-ICHIRO、EGAWA, HIROSHI、MIYAMOTO, TERUYUKI、NISHIMURA, YOSHIR+

  DOI：——

  日期：——
• US4657913A
  申请人：——

  公开号：US4657913A

  公开（公告）日：1987-04-14
• 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。