Dimethyl 5,6-dihydroxybenzo[f]quinoline-1,3-dicarboxylate | 142422-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: Dimethyl 5,6-dihydroxybenzo[f]quinoline-1,3-dicarboxylate
• CAS: 142422-23-9
• 化学式: C₁₇H₁₃NO₆
• 分子量: 327.293
• InChiKey: DCWVMGCBERSNET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  dimethyl 2-oxoglutaconate 在 对甲苯磺酸 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 苯肼 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 26.33h， 生成 Dimethyl 5,6-dihydroxybenzo[f]quinoline-1,3-dicarboxylate
  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