3-(7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbonylsulfanyl)acetic acid methyl ester | 681856-54-2

• 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: 3-(7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbonylsulfanyl)acetic acid methyl ester
• 英文别名: methyl 2-(7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carbonyl)sulfanylacetate
• CAS: 681856-54-2
• 化学式: C₁₅H₁₃ClFNO₄S
• 分子量: 357.79
• InChiKey: KRBFXGHWCHSRBU-UHFFFAOYSA-N

物化性质

• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.37
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbonylsulfanyl)acetic acid methyl ester 在 ammonium hydroxide 作用下， 反应 10.0h， 以60%的产率得到7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbothioic acid S-carbamoylmethyl ester
  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：

  ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 、 巯基乙酸甲酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以69%的产率得到3-(7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbonylsulfanyl)acetic acid methyl ester
  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