5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid | 101446-12-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid
• 英文别名: 5,7-dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromene-2-carboxylic acid；5,7-Dihydroxy-3-(4-hydroxy-phenyl)-8-methoxy-4-oxo-4H-chromen-2-carbonsaeure；4',5,7-Trihydroxy-8-methoxy-isoflavon-2-carbonsaeure
• CAS: 101446-12-2
• 化学式: C₁₇H₁₂O₈
• 分子量: 344.277
• InChiKey: PVFDVSDNOSYKTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  137.43
• 氢给体数：
  4.0
• 氢受体数：
  7.0

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 在 吡啶 、 喹啉 、 铜 作用下， 生成 5,7-diacetoxy-3-(4-acetoxy-phenyl)-8-methoxy-chromen-4-one
  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：

  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

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.