trimethyl 4-oxo-5-acetonyl-5-hydroxy-4,5-dihydro-1-methylpyrrolo<2,3-f>quinoline-2,7,9-tricarboxylate | 142422-25-1

• 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: trimethyl 4-oxo-5-acetonyl-5-hydroxy-4,5-dihydro-1-methylpyrrolo<2,3-f>quinoline-2,7,9-tricarboxylate
• 英文别名: Trimethyl 5-hydroxy-1-methyl-4-oxo-5-(2-oxopropyl)pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate
• CAS: 142422-25-1
• 化学式: C₂₁H₂₀N₂O₉
• 分子量: 444.398
• InChiKey: JJGWOYXWQSWQPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-Methyl-4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester 、 丙酮 在 三乙胺 作用下， 反应 1.0h， 以93%的产率得到trimethyl 4-oxo-5-acetonyl-5-hydroxy-4,5-dihydro-1-methylpyrrolo<2,3-f>quinoline-2,7,9-tricarboxylate
  参考文献：
  名称：

  Synthesis and characterization of dimethyl 9,10-dihydro-9,10-dioxobenzo[f]quinoline-2,4-dicarboxylate. Effect of the pyrrole nucleus on the reactivity of coenzyme PQQ

  摘要：

  Dimethyl 9,10-dihydro-9,10-dioxobenzo[f]quinoline-2,4-dicarboxylate (4) was synthesized, and its physical and chemical properties were compared to those of the trimethyl ester of PQQ (PQQTME, 2) and the 1-methyl derivative (3). The synthesis of 4 was accomplished by a Doebner-von Miller-type annulation between 3-amino-2-naphthol and dimethyl 2-oxoglutaconate and a subsequent oxidation with Fremy's salt. The electronic effect of the pyrrole nucleus of coenzyme PQQ (1) was examined by comparing the reactivity of 4 to that of 2 and 3 in the acetone adduct formation reaction, the redox reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant role of the pyrrole nucleus in conducting the intramolecular general base catalysis in the amine oxidation is discussed.

  DOI：

  10.1021/jo00042a028

文献信息

• Synthesis and characterization of dimethyl 9,10-dihydro-9,10-dioxobenzo[f]quinoline-2,4-dicarboxylate. Effect of the pyrrole nucleus on the reactivity of coenzyme PQQ
  作者：Shinobu Itoh、Yoshifumi Fukui、Shigenobu Haranou、Masaki Ogino、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1021/jo00042a028

  日期：1992.7

  Dimethyl 9,10-dihydro-9,10-dioxobenzo[f]quinoline-2,4-dicarboxylate (4) was synthesized, and its physical and chemical properties were compared to those of the trimethyl ester of PQQ (PQQTME, 2) and the 1-methyl derivative (3). The synthesis of 4 was accomplished by a Doebner-von Miller-type annulation between 3-amino-2-naphthol and dimethyl 2-oxoglutaconate and a subsequent oxidation with Fremy's salt. The electronic effect of the pyrrole nucleus of coenzyme PQQ (1) was examined by comparing the reactivity of 4 to that of 2 and 3 in the acetone adduct formation reaction, the redox reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant role of the pyrrole nucleus in conducting the intramolecular general base catalysis in the amine oxidation is discussed.