6,7,8-trihydroxy-3-phenyl-3,4-dihydroisocoumarin | 1225049-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,7,8-trihydroxy-3-phenyl-3,4-dihydroisocoumarin
• 英文别名: (+/-)-7-demethylannulatomarin
• CAS: 1225049-44-4
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: BCIDMVAHIHFRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6,7,8-trimethoxy-3-phenyl-3,4-dihydroisocoumarin 在 aluminum (III) chloride 、 乙硫醇 、 水 作用下， 以65%的产率得到6,7,8-trihydroxy-3-phenyl-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Synthesis of (±)-6-O-methyl and 7-demethylannulatomarin

  摘要：

  Synthesis of 6-O-methyl and 7-demethyl derivatives of annulatomarin (1) (6,8-dihydroxy-7-methoxy-3-phenyl-3,4-dihydroisocoumarin) isolated from the aerial parts of Hypericum annulatum is described. The key step involves an efficient, microwave-accelerated solvent and catalyst-free condensation of methyl benzoate with 3,4,5-trimethoxyhomophthalic acid (2) to afford 6,7,8-trimethoxy-3-phenylisocoumarin (3). Saponification of the latter to keto acid (4) followed reduction to furnish 6,7,8-trimethoxy-3-phenyl-3,4-dihydroisocoumarin (5), which was either regioselectively demethylated to (+/-)-6-O-methylannulatomarin (6) or completely demethylated to (+/-)-7-demethylannulatomarin (7).

  DOI：

  10.1080/10286020903451740

文献信息

• Synthesis of (±)-6-<i>O</i>-methyl and 7-demethylannulatomarin
  作者：Aamer Saeed

  DOI：10.1080/10286020903451740

  日期：2010.1.1

  Synthesis of 6-O-methyl and 7-demethyl derivatives of annulatomarin (1) (6,8-dihydroxy-7-methoxy-3-phenyl-3,4-dihydroisocoumarin) isolated from the aerial parts of Hypericum annulatum is described. The key step involves an efficient, microwave-accelerated solvent and catalyst-free condensation of methyl benzoate with 3,4,5-trimethoxyhomophthalic acid (2) to afford 6,7,8-trimethoxy-3-phenylisocoumarin (3). Saponification of the latter to keto acid (4) followed reduction to furnish 6,7,8-trimethoxy-3-phenyl-3,4-dihydroisocoumarin (5), which was either regioselectively demethylated to (+/-)-6-O-methylannulatomarin (6) or completely demethylated to (+/-)-7-demethylannulatomarin (7).