4-Hydroxy-quinoline-2,6-dicarboxylic acid dimethyl ester | 942227-31-8

• 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: 4-Hydroxy-quinoline-2,6-dicarboxylic acid dimethyl ester
• 英文别名: 1,4-Dihydro-4-oxoquinoline-2,6-dicarboxylic acid dimethyl ester；dimethyl 4-oxo-1H-quinoline-2,6-dicarboxylate
• CAS: 942227-31-8
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: WVWSWXCMCVZJQF-UHFFFAOYSA-N

物化性质

• 沸点：
  424.8±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-quinoline-2,6-dicarboxylic acid dimethyl ester 在 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 4-[Cyano-(3,4-dimethoxy-phenyl)-methyl]-quinoline-2,6-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Quinoline-Carboxylic acids are potent inhibitors that inhibit the binding of insulin-Like growth factor (IGF) to IGF-Binding proteins

  摘要：

  4-Benzylquinolines 5, based on a series of isoquinolines 1, were prepared and tested as inhibitors of the IGF/IGFBP-3 complex based on their ability to displace IGF-I from its binding to IGF-binding protein-3. SAR studies on the 6,7-dihydroxy moiety of the quinoline 5a showed that the catecol moiety could be replaced with other functional groups. Computational modeling of the 5a/mini-IGFBP-5 complex revealed the possible binding site of 5a on IGFBP-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00322-6
• 作为产物：
  描述：

  dimethyl 2-(4-(methoxycarbonyl)phenylamino)maleate 在 四磷十氧化物 作用下， 以90%的产率得到4-Hydroxy-quinoline-2,6-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A Mild and Efficient Synthesis of 4-Quinolones and Quinolone Heterocycles

  摘要：

  The cycloacylation of aniline derivatives to 4-quinolones in the presence of Eaton's reagent is described. This high-yielding methodology is applicable to a wide variety of functionalized anilines and requires milder conditions than those traditionally employed. This cyclization protocol is used to prepare a host of heterocycles and bis-quinolones and is characterized by relatively low reaction temperature and ease of product isolation.

  DOI：

  10.1021/jo070181o