ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate | 1427278-03-2

• 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: ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate
• 英文别名: 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic Acid Ethyl Ester；ethyl 3-bromo-2,4-dioxo-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-3-carboxylate
• CAS: 1427278-03-2
• 化学式: C₁₅H₁₄BrNO₄
• 分子量: 352.184
• InChiKey: DAFKGNFSHYJJLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate 在 溴 、 溶剂黄146 、 丙酮 作用下， 反应 2.0h， 生成 9-bromo-7-hydroxy-N-(4-methylphenyl)-5-oxo-2,3-dihydro-1H,5H-pyrido[3.2.1-ij]quinoline-6-carboxamide
  参考文献：
  名称：

  4-Hydroxy-2-Quinolones. 233*. Synthesis and Diuretic Activity of 9-Bromo-7-Hydroxy-5-Oxo-2,3-Dihydro-1H,5H-Pyrido[3,2,1-ij]Quinoline-6-Carboxylic Acid Anilides

  摘要：

  The ethyl ester of 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylic acid reaction with bromine in anhydrous acetic acid producing a mixture of the 9-bromo-substituted product and 6-ethoxycarbonyl-5,7-dihydroxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide in a 1:1 ratio. It has been established experimentally that the diuretic activity of 9-bromo-7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxanilides increases substantially in comparison with their non-brominated analogs.

  DOI：

  10.1007/s10593-013-1381-3
• 作为产物：
  描述：

  ethyl 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以90%的产率得到ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate
  参考文献：
  名称：

  4-Hydroxy-2-Quinolones. 233*. Synthesis and Diuretic Activity of 9-Bromo-7-Hydroxy-5-Oxo-2,3-Dihydro-1H,5H-Pyrido[3,2,1-ij]Quinoline-6-Carboxylic Acid Anilides

  摘要：

  The ethyl ester of 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylic acid reaction with bromine in anhydrous acetic acid producing a mixture of the 9-bromo-substituted product and 6-ethoxycarbonyl-5,7-dihydroxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide in a 1:1 ratio. It has been established experimentally that the diuretic activity of 9-bromo-7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxanilides increases substantially in comparison with their non-brominated analogs.

  DOI：

  10.1007/s10593-013-1381-3

文献信息

• 4-Hydroxy-2-quinolones. 220*. Bromination of ethyl 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate
  作者：I. V. Ukrainets、N. Yu. Golik、I. N. Chernenok、S. V. Shishkina、V. A. Parshikov

  DOI：10.1007/s10593-013-1190-8

  日期：2013.2

  7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate with bromine in aqueous acetic acid solution gave not only the expected ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate, but also an admixture of its 9-bromo-substituted isomer. The structural features of the major and minor reaction products are discussed.

  在乙酸水溶液中用溴处理7-羟基-5-氧代-2,3-二氢-1 H，5 H-吡啶并[3,2,1- ij ]喹啉-6-羧酸乙酯2-溴-1,3-二氧杂-2-乙基，3,6,7-四氢-1 H，5 H-吡啶基[3,2,1- ij ]喹啉-2-羧酸乙酯，也可以是其9的混合物-溴取代的异构体。讨论了主要和次要反应产物的结构特征。