5-ethyl-6-methyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid ethyl ester | 66176-23-6

• 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: 5-ethyl-6-methyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid ethyl ester
• 英文别名: ethyl 5-ethyl-6-methyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate
• CAS: 66176-23-6
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: KUUMXKUOCYZKQG-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C
• 沸点：
  459.9±45.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-ethyl-6-methyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 反应 1.0h， 生成 5-ethyl-6-methyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
  参考文献：
  名称：

  Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

  摘要：

  A flexible reaction sequence has been developed which starts with readily available anthranilic acids or isatoic anhydrides and leads regiospecifically to 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids after reaction with 1,3-dicarbonyl compounds. The sequence is superior to earlier published methods by allowing electron-releasing and -withdrawing groups in any position on the aro;atic ring, by allowing convenient substitution at C2, and better overall yield. A number of new and known antimicrobial agents were prepared and tested in vitro, demonstrating, inter alia, that substitution of the H at C2 abolished antibacterial activity.

  DOI：

  10.1021/jm00203a018
• 作为产物：
  描述：

  2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione 、 乙酰乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-ethyl-6-methyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

  摘要：

  A flexible reaction sequence has been developed which starts with readily available anthranilic acids or isatoic anhydrides and leads regiospecifically to 1-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids after reaction with 1,3-dicarbonyl compounds. The sequence is superior to earlier published methods by allowing electron-releasing and -withdrawing groups in any position on the aro;atic ring, by allowing convenient substitution at C2, and better overall yield. A number of new and known antimicrobial agents were prepared and tested in vitro, demonstrating, inter alia, that substitution of the H at C2 abolished antibacterial activity.

  DOI：

  10.1021/jm00203a018

文献信息

• MITSCHER L. A.; GRACEY H. E.; CLARK G. W.; SUZUKI T., J. MED. CHEM., 1978, 21, NO 5, 485-489
  作者：MITSCHER L. A.、 GRACEY H. E.、 CLARK G. W.、 SUZUKI T.

  DOI：——

  日期：——