Dimethyl 8-hydroxyquinoline-2,4-dicarboxylate

• 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 8-hydroxyquinoline-2,4-dicarboxylate
• 英文别名: dimethyl 8-hydroxyquinoline-2,4-dicarboxylate
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: VGHCXJUEOZKSNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 8-hydroxyquinoline-2,4-dicarboxylate 在 polymer-supported o-iodoxybenzoic acid 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 Dimethyl 7,8-dioxoquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Synthetic modeling of the structure and function of the rare-earth dependent methanol dehydrogenase cofactor

  摘要：

  DOI：

  10.1016/bs.mie.2021.01.037
• 作为产物：
  描述：

  dimethyl 2-oxoglutaconate 、 2-氨基苯酚 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以24%的产率得到Dimethyl 8-hydroxyquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Substituted Quinoline Quinones as Surrogates for the PQQ Cofactor: An Electrochemical and Computational Study

  摘要：

  Pyrroloquinoline quinones (PQQ) are important cofactors that shuttle redox equivalents in diverse metalloproteins. Quinoline 7,8-quinones have been synthesized and characterized as surrogates for PQQ to elucidate redox energetics within metalloenzyme active sites. The quinoline 7,8-quinones were accessed using polymer-supported iodoxybenzoic acid and the compounds evaluated using solution electrochemistry. Together with a family of quinones, the products were evaluated computationally and used to generate a predictive correlation between a computed ?G and the experimental reduction potentials.

  DOI：

  10.1021/acs.orglett.5b00486

文献信息

• Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system
  作者：Christina N. Carrigan、C. Sean Esslinger、Richard D. Bartlett、Richard J. Bridges、Charles M. Thompson

  DOI：10.1016/s0960-894x(99)00444-8

  日期：1999.9

  Twenty-six quinoline-2,4-dicarboxylic acids (QDC's) were synthesized by a modified Doebner-von Miller pathway and tested as inhibitors against the glutamate vesicular transport (GVT) protein. The QDC's were active as inhibitors with the most potent QDC's found to contain halogens at the 6-/8-position, a hydroxyl at the 8-position, or a tethered aromatic moiety at the 6- or 7-position of the quinoline. (C) 1999 Elsevier Science Ltd. All rights reserved.