9-Hydroxy-7-methoxy-2-methyl-pyrrolo[3,4-b]quinoline-1,3-dione | 220623-44-9

• 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: 9-Hydroxy-7-methoxy-2-methyl-pyrrolo[3,4-b]quinoline-1,3-dione
• 英文别名: 7-methoxy-2-methyl-4H-pyrrolo[3,4-b]quinoline-1,3,9-trione
• CAS: 220623-44-9
• 化学式: C₁₃H₁₀N₂O₄
• 分子量: 258.233
• InChiKey: KOFSKUSLHJINFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Hydroxy-7-methoxy-2-methyl-pyrrolo[3,4-b]quinoline-1,3-dione 在 ammonium hydroxide 、 一水合肼 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 生成 10-Amino-8-methoxy-2,3-dihydro-pyridazino[4,5-b]quinoline-1,4-dione
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones

  摘要：

  Substituted anilines reacted with methyl 1-methyl-4-methyrthio-2,5-dioxo-3-pyrroline-3-carboxylate (1) in refluxing methanol to give the corresponding methyl 1-methyl-2,5-dioxo-4-phenylamino-3-pyrroline-3-carboxylates (3a-e) which were converted in good yields to 2-methylpyrrolo[3,4-b]quinoline derivatives (4a-e) by heating in diphenyl ether. Reaction of 4a-e with hydrazine hydrate gave 10-hydroxypyridazino[4,5-b]quinoline-1,4(2H,3H)-diones (5a-e) in good yields. The desired 10-aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones (8a-e) were obtained by the chlorination of 4a-e with phosphorus oxychloride followed by ammonolysis with 28% ammonium hydroxide in good yields. Compounds (5) and (8) were found to be efficiently chemiluminescent in a similarly to luminol in the presence of H2O2 and horseradish peroxidase in a solution of a phosphate buffer pH 8.0.

  DOI：

  10.3987/com-98-s(h)20
• 作为产物：
  描述：

  methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate 以 甲醇 、 二苯醚 为溶剂， 反应 1.0h， 生成 9-Hydroxy-7-methoxy-2-methyl-pyrrolo[3,4-b]quinoline-1,3-dione
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones

  摘要：

  Substituted anilines reacted with methyl 1-methyl-4-methyrthio-2,5-dioxo-3-pyrroline-3-carboxylate (1) in refluxing methanol to give the corresponding methyl 1-methyl-2,5-dioxo-4-phenylamino-3-pyrroline-3-carboxylates (3a-e) which were converted in good yields to 2-methylpyrrolo[3,4-b]quinoline derivatives (4a-e) by heating in diphenyl ether. Reaction of 4a-e with hydrazine hydrate gave 10-hydroxypyridazino[4,5-b]quinoline-1,4(2H,3H)-diones (5a-e) in good yields. The desired 10-aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones (8a-e) were obtained by the chlorination of 4a-e with phosphorus oxychloride followed by ammonolysis with 28% ammonium hydroxide in good yields. Compounds (5) and (8) were found to be efficiently chemiluminescent in a similarly to luminol in the presence of H2O2 and horseradish peroxidase in a solution of a phosphate buffer pH 8.0.

  DOI：

  10.3987/com-98-s(h)20

文献信息

• Synthesis and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones
  作者：Yoshinori Tominaga、Noriko Yoshioka、Seigo Kataoka、Yasuhiro Shigemitsu、Takashi Hirota、Kenji Sasaki

  DOI：10.3987/com-98-s(h)20

  日期：——

  Substituted anilines reacted with methyl 1-methyl-4-methyrthio-2,5-dioxo-3-pyrroline-3-carboxylate (1) in refluxing methanol to give the corresponding methyl 1-methyl-2,5-dioxo-4-phenylamino-3-pyrroline-3-carboxylates (3a-e) which were converted in good yields to 2-methylpyrrolo[3,4-b]quinoline derivatives (4a-e) by heating in diphenyl ether. Reaction of 4a-e with hydrazine hydrate gave 10-hydroxypyridazino[4,5-b]quinoline-1,4(2H,3H)-diones (5a-e) in good yields. The desired 10-aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones (8a-e) were obtained by the chlorination of 4a-e with phosphorus oxychloride followed by ammonolysis with 28% ammonium hydroxide in good yields. Compounds (5) and (8) were found to be efficiently chemiluminescent in a similarly to luminol in the presence of H2O2 and horseradish peroxidase in a solution of a phosphate buffer pH 8.0.