dimethyl 9,10-dihydro-9,10-dioxobenzoquinoline-2,4-dicarboxylate | 142422-22-8

• 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: dimethyl 9,10-dihydro-9,10-dioxobenzoquinoline-2,4-dicarboxylate
• 英文别名: dimethyl 9,10-dioxo-9,10-dihydroquinoline-2,4-dicarboxylate；Dimethyl 5,6-dioxobenzo[f]quinoline-1,3-dicarboxylate
• CAS: 142422-22-8
• 化学式: C₁₇H₁₁NO₆
• 分子量: 325.277
• InChiKey: LNIMNSLDRAQUOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 9,10-dihydro-9,10-dioxobenzoquinoline-2,4-dicarboxylate 在 苯肼 作用下， 以 乙腈 为溶剂， 反应 1.33h， 以100%的产率得到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
• 作为产物：
  描述：

  dimethyl 2-oxoglutaconate 在 对甲苯磺酸 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 dimethyl 9,10-dihydro-9,10-dioxobenzoquinoline-2,4-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

文献信息

• C-4 and C-5 adducts of cofactor PQQ (pyrroloquinolinequinone). Model studies directed toward the action of quinoprotein methanol dehydrogenase
  作者：Shinobu Itoh、Masaki Ogino、Yoshifumi Fukui、Hiroshi Murao、Mitsuo Komatsu、Yoshiki Ohshiro、Tsuyoshi Inoue、Yasushi Kai、Nobutami Kasai

  DOI：10.1021/ja00075a012

  日期：1993.11

  Methanol addition to the trimethyl ester of cofactor PQQ (PQQTME) was investigated in detail to obtain information on the action of quinoprotein methanol dehydrogenase. The hemiacetal-type adduct was easily isolated from a methanol solution of PQQTME. The crystal structure of the adduct was determined by X-ray diffraction for the first time, showing that methanol addition occurred at the S-position

  对辅因子 PQQ (PQQTME) 的三甲酯中添加甲醇进行了详细研究，以获得有关喹蛋白甲醇脱氢酶作用的信息。半缩醛型加合物很容易从 PQQTME 的甲醇溶液中分离出来。加合物的晶体结构首次通过 X 射线衍射确定，表明与丙酮加合物形成的情况一样，甲醇加成发生在醌的 S 位 (CS)。另一方面，在酸性条件下在甲醇中处理 PQQTME 得到二甲基缩醛衍生物作为主要产物，通过 X 射线晶体学分析确定甲醇的加成位置为 C-4
• 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.