(+/-)-ethyl 9,10-difluoro-2,3-dihydro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate | 100986-91-2

• 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: (+/-)-ethyl 9,10-difluoro-2,3-dihydro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate
• 英文别名: (+/-)-9,10-difluoro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ethyl ester；ethyl 2-[(3,5-dinitrobenzoyl)oxymethyl]-6,7-difluoro-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate
• CAS: 100986-91-2
• 化学式: C₂₂H₁₅F₂N₃O₁₀
• 分子量: 519.372
• InChiKey: VLQXRCMGPSUUIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  174
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl 9,10-difluoro-2,3-dihydro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate 生成 (+/-)-9,10-difluoro-3-hydroxymethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  ATARASHI, SHOHGO;YOKOHAMA, SHUICHI;YAMAZAKI, KEN-ICHI;SAKANO, KATSU-ICHI;+, CHEM. AND PHARM. BULL., 35,(1987) N 5, 1896-1902

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 12-[(3,5-dinitrobenzoyl)oxymethyl]-6,7-difluoro-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate 生成 (+/-)-ethyl 9,10-difluoro-2,3-dihydro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate
  参考文献：
  名称：

  ATARASHI, SHOHGO;YOKOHAMA, SHUICHI;YAMAZAKI, KEN-ICHI;SAKANO, KATSU-ICHI;+, CHEM. AND PHARM. BULL., 35,(1987) N 5, 1896-1902

  摘要：

  DOI：

文献信息

• synthesis and antibacterial activities of optically active ofloxacin and its fluoromethyl derivative.
  作者：SHOHGO ATARASHI、SHUICHI YOKOHAMA、KEN-ICHI YAMAZAKI、KATSU-ICHI SAKANO、MASAZUMI IMAMURA、ISAO HAYAKAWA

  DOI：10.1248/cpb.35.1896

  日期：——

  Two optically active (100% enantiomeric excess) isomers (13a and 13b) of ofloxacin (1) [(±) -ofloxacin; DL-8280; (±) -9-fluoro-2, 3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-7H-pyrido [1, 2, 3-de] [1, 4] benzoxazine-6-carboxylic acid] and their fluoromethyl derivatives (14a and 14b) were prepared via their optically active intermediates resolved by use of high-performance liquid chromatography (HPLC). The isomers (13a and 13b) were also obtained efficiently by an alternative route via separation of the diastereoisomers (18, 19) prepared in the reaction of benzoxazine (17) with L-prolinyl chloride. The (-) -isomers of 1 and its fluoromethyl derivative (2) were approximately twice as active as the corresponding racemates, while the (+) -isomers were considerably less active than the racemates. The absolute configuration at the C3 position in the oxazine ring in a series of (-) -compounds (b) was confirmed by X-ray analysis of the hydrochloride of the (-) -benzoxazine derivative (15b) to be S.

  氧氟沙星（1）[(±) -ofloxacin; DL-8280；(±)-9-氟-2, 3-二氢-3-甲基-10- (4-甲基-1-哌嗪基) -7-氧代-7H-吡啶并[1, 2, 3-de] [1, 4] 苯并恶嗪-6-羧酸]及其氟甲基衍生物 (14a 和 14b)是通过使用高效液相色谱法 (HPLC) 解析其光学活性中间体而制备的。通过苯并恶嗪（17）与 L-脯氨酰氯反应制备的非对映异构体（18、19）的分离，也可以通过另一种途径有效地获得异构体（13a 和 13b）。1 的 (-) - 异构体及其氟甲基衍生物 (2) 的活性大约是相应外消旋体的两倍，而 (+) - 异构体的活性则大大低于外消旋体。通过对 (-) - 苯并恶嗪衍生物 (15b) 的盐酸盐进行 X 射线分析，证实了一系列 (-) - 化合物 (b) 中恶嗪环 C3 位置的绝对构型为 S。
• Optically active pyridobenzoxazine derivatives and intermediates thereof
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04985557A1

  公开（公告）日：1991-01-15

  An optically action pyridobenzoxazine derivative, a process for preparing the same and a novel intermediate useful for preparing the optically active pyridobenzoxazine derivative are disclosed. The optically active pyridobenzoxazine derivative possesses increased antimicrobial activity and reduced toxicity. The intermediate is useful for preparing such optically active pyridobenzoxazine derivatives such as Ofloxacin and anolog compounds.

  本发明公开了一种光学活性的吡啶并苯并噁嗪衍生物，其制备方法以及用于制备光学活性吡啶并苯并噁嗪衍生物的新型中间体。该光学活性吡啶并苯并噁嗪衍生物具有增强的抗微生物活性和降低的毒性。该中间体可用于制备诸如氧氟沙星和类似化合物等光学活性吡啶并苯并噁嗪衍生物。
• Optically active pyridobenzoxazine derivatives and anti-microbial use
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US05053407A1

  公开（公告）日：1991-10-01

  An optically action pyridobenzoxazine derivative, a process for preparing the same and a novel intermediate useful for preparing the optically active pyridobenzoxazine derivative are disclosed. The optically active pyridobenzoxazine derivative possesses increased antimicrobial activity and reduced toxicity. The intermediate is useful for preparing such optically active pyridobenzoxazine derivatives such as Ofloxacin and anolog compounds.

  本发明公开了一种光学活性的吡啶并苯并噁嗪衍生物，其制备方法以及用于制备光学活性吡啶并苯并噁嗪衍生物的新型中间体。该光学活性吡啶并苯并噁嗪衍生物具有增强的抗微生物活性和降低的毒性。该中间体可用于制备Ofloxacin和类似化合物等光学活性吡啶并苯并噁嗪衍生物。
• HAYAKAWA, ISAO;ATARASHI, SHOHGO;YOKOHAMA, SHUICHI;IMAMURA, MASAZUMI;SAKAN+, ANTIMICROB. AGENTS AND CHEMOTHER., 29,(1986) N 1, 163-164
  作者：HAYAKAWA, ISAO、ATARASHI, SHOHGO、YOKOHAMA, SHUICHI、IMAMURA, MASAZUMI、SAKAN+

  DOI：——

  日期：——
• ATARASHI, SHOHGO;YOKOHAMA, SHUICHI;YAMAZAKI, KEN-ICHI;SAKANO, KATSU-ICHI;+, CHEM. AND PHARM. BULL., 35,(1987) N 5, 1896-1902
  作者：ATARASHI, SHOHGO、YOKOHAMA, SHUICHI、YAMAZAKI, KEN-ICHI、SAKANO, KATSU-ICHI、+

  DOI：——

  日期：——