1-<(2-acetoxyethoxy)methyl>-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid | 143231-27-0

• 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: 1-<(2-acetoxyethoxy)methyl>-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 1-[(2-acetoxyethoxy)methyl]-6-chloro-7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-(2-Acetyloxyethoxymethyl)-7-chloro-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 143231-27-0
• 化学式: C₁₅H₁₃ClFNO₆
• 分子量: 357.723
• InChiKey: FJRFVPPLXLAGFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-<(2-acetoxyethoxy)methyl>-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以90%的产率得到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
• 作为产物：
  描述：

  7-氯-6-氟-4-氧代-1H-喹啉-3-羧酸 在 amino sulphate 、 四丁基碘化铵 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 1-<(2-acetoxyethoxy)methyl>-7-chloro-6-fluoro-1,4-dihydro-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：——