6-hydroxy-3-(naphthalen-2-yl)-3-phenylbenzofuran-2(3H)-one | 1373335-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 6-hydroxy-3-(naphthalen-2-yl)-3-phenylbenzofuran-2(3H)-one
• 英文别名: 6-Hydroxy-3-naphthalen-2-yl-3-phenyl-1-benzofuran-2-one
• CAS: 1373335-27-3
• 化学式: C₂₄H₁₆O₃
• 分子量: 352.389
• InChiKey: QVMKPOCPQDNKQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基-2-(萘-2-基)-2-苯基乙酸甲酯 、 间苯二酚 在 高氯酸 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以96%的产率得到6-hydroxy-3-(naphthalen-2-yl)-3-phenylbenzofuran-2(3H)-one
  参考文献：
  名称：

  Metal-Free Tandem Friedel–Crafts/Lactonization Reaction to Benzofuranones Bearing a Quaternary Center at C3 Position

  摘要：

  A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO4 was reported. A variety of tertiary alpha-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. H-1 NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.

  DOI：

  10.1021/jo300395x

文献信息

• Metal-Free Tandem Friedel–Crafts/Lactonization Reaction to Benzofuranones Bearing a Quaternary Center at C3 Position
  作者：Long Chen、Feng Zhou、Tao-Da Shi、Jian Zhou

  DOI：10.1021/jo300395x

  日期：2012.5.4

  A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO4 was reported. A variety of tertiary alpha-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. H-1 NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.