2-Butenoic acid, 4-(3,4-dimethoxyphenyl)-2-hydroxy-4-oxo-, (2Z)- | 406946-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Butenoic acid, 4-(3,4-dimethoxyphenyl)-2-hydroxy-4-oxo-, (2Z)-
• 英文别名: (Z)-2-hydroxy-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoic acid
• CAS: 406946-64-3
• 化学式: C₁₂H₁₂O₆
• 分子量: 252.224
• InChiKey: HEXMWWXOZRWBTF-TWGQIWQCSA-N

物化性质

• 沸点：
  454.9±45.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3-二氨基吡啶 、 2-Butenoic acid, 4-(3,4-dimethoxyphenyl)-2-hydroxy-4-oxo-, (2Z)- 以 乙醇 为溶剂， 以53%的产率得到2-[2-(3,4-Dimethoxy-phenyl)-2-oxo-eth-(Z)-ylidene]-1,4-dihydro-2H-pyrido[2,3-b]pyrazin-3-one
  参考文献：
  名称：

  摘要：

  Acylpyruvic acids readily react with 2,3-diaminopyridine to form (Z)-3-acylmethylene-1H-3,4-dihydropyrido[2,3-b]pyrazin-2-ones. 5-Aryl-2,3-dihydrofuran-2,3-diones which can be regarded as lactones derived from gamma -enolized aroylpyruvic acids react with 2,3-diaminopyridine under mild conditions, yielding regioisomeric (Z)-2-aroylmethylene-4H+1,2-dihydropyrido[2,3-b]pyrazin-3-ones. The structure of the products and reaction chemoselectivity are discussed.

  DOI：

  10.1023/a:1012438902959
• 作为产物：
  描述：

  methyl 2-hydroxy-4-oxo-4-(3,4-dimethoxyphenyl)butenoate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以45%的产率得到2-Butenoic acid, 4-(3,4-dimethoxyphenyl)-2-hydroxy-4-oxo-, (2Z)-
  参考文献：
  名称：

  Design, synthesis, and anti-integrase activity of catechol–DKA hybrids

  摘要：

  Following the discovery of diketoacid-containing compounds as HIV-1 integrase (IN) inhibitors, a plethora of new molecules have been published leading to four drugs under clinical trial. In an attempt to rationally design new dimeric diketoacids (DKAs) targeting two divalent metal ions on the active site of IN, potent inhibitors against purified IN were found with varied selectivity for strand transfer. In this context, we designed and synthesized a new series of catechol-DKA hybrids. These compounds presented micromolar anti-integrase activities with moderate antiviral properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.039

文献信息

• Improved preparation and structural investigation of 4-aryl-4-oxo-2-hydroxy-2-butenoic acids and methyl esters
  作者：Cédric Maurin、Fabrice Bailly、Philippe Cotelle

  DOI：10.1016/j.tet.2004.06.030

  日期：2004.7

  A simple and efficient oxalylation of aryl methyl ketones was accomplished with dimethyl oxalate in the presence of sodium methoxide. The unpreviously reported sodium ketoenolate esters were isolated and gently hydrolyzed into the ketoenol esters in good yields. Alternatively the sodium ketoenolate esters hydrolysis could also be conducted to directly afford the ketoenol acids, which represent one of the most promising class of HIV-1 integrase inhibitors. Advantages over previously reported procedures were better yields and simplicity of the purification protocol. (C) 2004 Elsevier Ltd. All rights reserved.