trans-7-O-methyldihydroquercetin 3-acetate | 100595-93-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: trans-7-O-methyldihydroquercetin 3-acetate
• 英文别名: padmatin 3-acetate；3-O-acetylpadmatin；[(2R,3R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydrochromen-3-yl] acetate
• CAS: 100595-93-5
• 化学式: C₁₈H₁₆O₈
• 分子量: 360.32
• InChiKey: WWYQJKVSCKMFCP-MSOLQXFVSA-N

物化性质

• 沸点：
  635.7±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 3-O-acetyltaxifolin 以 甲醇 、 乙醚 为溶剂， 反应 27.0h， 以30%的产率得到trans-7-O-methyldihydroquercetin 3-acetate
  参考文献：
  名称：

  Methylation of Dihydroquercetin Acetates:  Synthesis of 5-O-Methyldihydroquercetin

  摘要：

  The major products of methylation of dihydroquercetin (1, dhq) with diazomethane have been identified as 7-O-methyldhq (9), 7,3'-di-0-methyldhq (10), 7,4'-di-O-methyldhq (11), and 7,3',4'-tri-O-methyldhq (2). With dhq 3,7,3',4'-tetraacetate (6), dhq 3,5,3',4'-tetraacetate (5), dhq 3,3',4'-triacetate (7), dhq 7,3',4'triacetate (8), and dhq 3-acetate (4) the same reaction affords mainly 5-O-methyldhq 3,7,3',4'-tetraacetate (15), 7-O-methyldhq 3,5,3',4'-tetraacetate (13), 7-O-methyldhq 3,3',4'-triacetate (14), 5-O-methyldhq 7,3',4'triacetate (25), and 7-O-methyldhq 3-acetate (12), respectively. The methylation of 8 is accompanied by intermolecular acetyl migration from phenolic oxygen to the hydroxy group of the heterocyclic ring. 5-O-Methyldhq (28) is accessible by deacetylation of 25. 5,7-Di-O-methyldhq (29), four known methyl ethers, 13 new and three known methyl ether acetates of dhq, and six new isomers with 2,3-cis stereochemistry were spectroscopically identified.

  DOI：

  10.1021/np034005w