3-(2,4-dihydroxyphenyl)-3-(4-isopropylphenyl)phthalide | 1373311-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(2,4-dihydroxyphenyl)-3-(4-isopropylphenyl)phthalide
• 英文别名: 3-(2,4-dihydroxyphenyl)-3-(4-propan-2-ylphenyl)-2-benzofuran-1-one
• CAS: 1373311-65-9
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: SCYKTBMIISJTDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,4-dihydroxyphenyl)-3-(4-isopropylphenyl)phthalide 在 硫酸 、 水 、 potassium hydroxide 作用下， 反应 2.5h， 生成 3-(2,4,6-trihydroxyphenyl)-3-(4-isopropylphenyl)phthalide
  参考文献：
  名称：

  A facile synthesis of new 3,3-disubstituted phthalides of pharmacological interest

  摘要：

  A series of new phthalides of pharmacological interest were synthesized by a protocol involving condensation of two gamma-keto acids, 2-(4-isopropylbenzoyl)benzoic acid (1a) and 2-(4-isopropyl-3-nitrobenzoyl)benzoic acid (1b) with phenolic compounds in the presence of catalytic quantity of concentrated sulphuric acid. The method is simple, efficient, economical and environmentally benign as the reaction is carried out under solvent free condition attempting a green approach. Structural characterization of these newly synthesized compounds was accomplished by IR, UV, H-1 NMR, C-13 NMR, Mass spectral data, elemental analysis and chemical reactions. Some of the synthesized phthalides were found to exhibit antifungal and antibacterial activity against various human pathogenic bacterial and fungal strains.

  DOI：

  10.1007/s00044-012-0049-3
• 作为产物：
  描述：

  苯酐 在 硫酸 作用下， 以 二硫化碳 为溶剂， 反应 1.5h， 生成 3-(2,4-dihydroxyphenyl)-3-(4-isopropylphenyl)phthalide
  参考文献：
  名称：

  A facile synthesis of new 3,3-disubstituted phthalides of pharmacological interest

  摘要：

  A series of new phthalides of pharmacological interest were synthesized by a protocol involving condensation of two gamma-keto acids, 2-(4-isopropylbenzoyl)benzoic acid (1a) and 2-(4-isopropyl-3-nitrobenzoyl)benzoic acid (1b) with phenolic compounds in the presence of catalytic quantity of concentrated sulphuric acid. The method is simple, efficient, economical and environmentally benign as the reaction is carried out under solvent free condition attempting a green approach. Structural characterization of these newly synthesized compounds was accomplished by IR, UV, H-1 NMR, C-13 NMR, Mass spectral data, elemental analysis and chemical reactions. Some of the synthesized phthalides were found to exhibit antifungal and antibacterial activity against various human pathogenic bacterial and fungal strains.

  DOI：

  10.1007/s00044-012-0049-3