Dimethyl 8-hydroxy-5-methylquinoline-2,4-dicarboxylate | 144283-92-1

• 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: Dimethyl 8-hydroxy-5-methylquinoline-2,4-dicarboxylate
• 英文别名: dimethyl 8-hydroxy-5-methylquinoline-2,4-dicarboxylate
• CAS: 144283-92-1
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: JGCGBFPNWXJBNS-UHFFFAOYSA-N

物化性质

• 沸点：
  449.6±40.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-hydroxy-5-methylquinoline-2,4-dicarboxylate 在 polymer supported 2-iodoxybenzoic acid (IBX) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以99%的产率得到Dimethyl 5-methyl-7,8-dioxoquinoline-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
• 作为产物：
  描述：

  dimethyl 2-oxoglutaconate 、 邻氨基对甲苯酚 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 Dimethyl 8-hydroxy-5-methylquinoline-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

文献信息

• Substituted Quinoline Quinones as Surrogates for the PQQ Cofactor: An Electrochemical and Computational Study
  作者：Walter L. Dorfner、Patrick J. Carroll、Eric J. Schelter

  DOI：10.1021/acs.orglett.5b00486

  日期：2015.4.17

  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.
• Synthetic modeling of the structure and function of the rare-earth dependent methanol dehydrogenase cofactor
  作者：Alison L. Knasin、Eric J. Schelter

  DOI：10.1016/bs.mie.2021.01.037

  日期：——