7-chloro-6-fluoro-1,4-dihydro-1-[(2-methanesulfonylethoxy)methyl]-4-oxoquinoline-3-carboxylic acid | 681856-62-2

• 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: 7-chloro-6-fluoro-1,4-dihydro-1-[(2-methanesulfonylethoxy)methyl]-4-oxoquinoline-3-carboxylic acid
• 英文别名: 7-chloro-6-fluoro-1-(2-methylsulfonyloxyethoxymethyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 681856-62-2
• 化学式: C₁₄H₁₃ClFNO₇S
• 分子量: 393.777
• InChiKey: JXESGXOTOZMRTB-UHFFFAOYSA-N

物化性质

• 沸点：
  625.6±55.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  sodium thiophenolate 、 7-chloro-6-fluoro-1,4-dihydro-1-[(2-methanesulfonylethoxy)methyl]-4-oxoquinoline-3-carboxylic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以56%的产率得到7-chloro-6-fluoro-1,4-dihydro-1-[(2-phenylthioethoxy)methyl]-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Reactions of Some New 6,7-Dihaloquinolones Bearing Mercapto Groups

  摘要：

  Reaction of the 6-chloro-7-fluoroquinoline 7 with methyl 2-mercapto-acetate, methyl 3-mercaptopropionate, or sodium thiophenolate furnished the quinolone derivatives of 3-carbonylsulfanyl-acetic acid methyl ester 8, the propionoate analogue 10, and 3-carbothioic acid S-phenyl ester 11 respectively. Ester 8 was converted into the 3-carbothioic acid S-carbampyl derivative 9. Analogously, treatment of the 6,7-diflouroquinolone 12 with amino or mercapto precursors led to the formation of 13 and 14 respectively. Reaction of 14 with aqueous NH3 or H2O2/AcOH afforded the acetamide 15 and the sulfoxide 16 analogues, respectively. The 5'-thioalkyl-acyclic quinolone nucleosides 19 and 20 were obtained from reaction of the mesylate derivative 18, prepared from the free nucleoside 17, with the methanthiolate and thiophenolate anions.

  DOI：

  10.1080/714040953
• 作为产物：
  描述：

  甲基磺酰氯 、 7-chloro-6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid 在 吡啶 作用下， 反应 6.0h， 以68%的产率得到7-chloro-6-fluoro-1,4-dihydro-1-[(2-methanesulfonylethoxy)methyl]-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Reactions of Some New 6,7-Dihaloquinolones Bearing Mercapto Groups

  摘要：

  Reaction of the 6-chloro-7-fluoroquinoline 7 with methyl 2-mercapto-acetate, methyl 3-mercaptopropionate, or sodium thiophenolate furnished the quinolone derivatives of 3-carbonylsulfanyl-acetic acid methyl ester 8, the propionoate analogue 10, and 3-carbothioic acid S-phenyl ester 11 respectively. Ester 8 was converted into the 3-carbothioic acid S-carbampyl derivative 9. Analogously, treatment of the 6,7-diflouroquinolone 12 with amino or mercapto precursors led to the formation of 13 and 14 respectively. Reaction of 14 with aqueous NH3 or H2O2/AcOH afforded the acetamide 15 and the sulfoxide 16 analogues, respectively. The 5'-thioalkyl-acyclic quinolone nucleosides 19 and 20 were obtained from reaction of the mesylate derivative 18, prepared from the free nucleoside 17, with the methanthiolate and thiophenolate anions.

  DOI：

  10.1080/714040953