7-chloro-6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid | 143231-29-2

• 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-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 7-chloro-6-fluoro-1,4-dihydro-1-[(2-hydroxyethoxy)methyl]-4-oxoquinoline-3-carboxylic acid；7-Chloro-6-fluoro-1-(2-hydroxyethoxymethyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 143231-29-2
• 化学式: C₁₃H₁₁ClFNO₅
• 分子量: 315.685
• InChiKey: KYGDKAYAUHFINN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-chloro-6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 7-chloro-6-fluoro-1,4-dihydro-1-[(2-methylthioethoxy)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：

  7-Chloro-6-fluoro-4-oxo-1-trimethylsilylquinoline-3-carboxylic acid 在 ammonium hydroxide 、 四丁基碘化铵 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 10.0h， 生成 7-chloro-6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Synthesis of acyclic 6,7-dihaloquinolone nucleoside analogues as potential antibacterial and antiviral agents

  摘要：

  Reaction of the quinolone carboxylic acids 1 and 2 with (2-acetoxyethoxy)methyl chloride 3 in the presence of n-Bu4NI afforded the N-alkylated products 4 and 6, which could be deblocked to the free nucleoside analogues 5 and 7, respectively. The alkylated quinolone carboxylic acids 9 and 10 were obtained by condensation of 1 and 2 with 1,4-dichlorobut-2-ene 8 in the presence of NaH. Hydrolysis of 9 gave the alcohol 11. Similar treatment of 1 with 8 in the presence of K2CO3 at relatively high temperature furnished 12. Prolonged heating of the ester 13 with 8 in NaH/DMF afforded the conjugated-diene 15. Treatment of 1 and 2 with dimethyl acetylenedicarboxylate 16 Furnished the pyrano[4,3-b]quinolones 17 and 18, respectively. Antibacterial and antiviral evaluations of the new products are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00067-5

文献信息

• Cruz, A. de la; Elguero, J.; Goya, P., Journal of Chemical Research, Miniprint, 1992, # 7, p. 1682 - 1693
  作者：Cruz, A. de la、Elguero, J.、Goya, P.、Martinez, A.、Gotor, V.、et al.

  DOI：——

  日期：——