5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester | 27181-85-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester
• 英文别名: 5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester；5,7-Dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromen-2-carbonsaeure-aethylester；2-Ethoxycarbonyl-4',5,7-trihydroxy-8-methoxyisoflavon
• CAS: 27181-85-7
• 化学式: C₁₉H₁₆O₈
• 分子量: 372.331
• InChiKey: JIQLAOJUTQFQLB-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  620.3±55.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  126.43
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 在 sodium carbonate 、 丙酮 作用下， 生成 5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  The Synthesis of 4′,5,7-Trihydroxy-8-methoxyisoflavone

  摘要：

  DOI：

  10.1246/bcsj.30.689
• 作为产物：
  描述：

  1,3,5-三羟基2-甲氧基苯 在 吡啶 、 盐酸 、 乙醚 、 zinc(II) chloride 作用下， 生成 5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  The Synthesis of 4′,5,7-Trihydroxy-8-methoxyisoflavone

  摘要：

  DOI：

  10.1246/bcsj.30.689

文献信息

• Efficient Method for the Synthesis of Tectorigenin
  作者：Zhu‐Ping Xiao、Huan‐Qiu Li、Jia‐Yu Xue、Lei Shi、Hai‐Liang Zhu

  DOI：10.1080/00397910701796725

  日期：2008.1.1

  Tectorigenin, isolated from the rhizomes of Belamcanda chinensis, shows a wide variety of biological activities. The interest in its biological activities has been matched by a corresponding interest in its synthesis. We herein reported a convenient synthesis of tectorigenin in good yield. The starting material, 2,4,6-trihydroxyanisole, gave the intermediate 2,4,4',6-tetrahydroxy-3-methoxydeoxybenzoin by a Hoesch reaction with 4-hydroxyphenylacetonitrile. The intermediate was then reacted with methanesulfonyl chloride to produce a mixture of tectorigenin and psi-tectorigenin. Purification of tectorigenin was unnecessary at this stage as psi-tectorigenin in the mixture was isomerized to tectorigenin by refluxing in n-BuOH in the presence of K2CO3.