5-methyl-3-phenyl-3-(p-tolyl)benzofuran-2(3H)-one | 1373335-09-1

• 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: 5-methyl-3-phenyl-3-(p-tolyl)benzofuran-2(3H)-one
• 英文别名: 5-Methyl-3-(4-methylphenyl)-3-phenyl-1-benzofuran-2-one
• CAS: 1373335-09-1
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: PLDNSEKZQZYXRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲酚 、 2-羟基-2-苯基-2-(对甲苯基)乙酸甲酯 在 高氯酸 作用下， 以 硝基甲烷 为溶剂， 反应 25.0h， 以70%的产率得到5-methyl-3-phenyl-3-(p-tolyl)benzofuran-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

• A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3<i>H</i>)-ones
  作者：Bhaskar B. Dhotare、Sahil Kumar、Amey Wadawale、Sandip K. Nayak、Mukesh Kumar、Dibakar Goswami

  DOI：10.1039/d2nj03404b

  日期：——

  A novel metal-free approach to the synthesis of a variety of 3-substituted-3-arylbenzofuran-2(3H)-ones is developed via H2SO4-mediated dehydrative substitution of 3-hydroxy-3-phenylbenzofuran-2(3H)-ones with electron-rich arenes/1,3-diones/alcohols/thiols as nucleophiles in moderate to good yields. Mechanistically, the substitution with the alkoxy group proceeds via a phenolic–hydroxyester intermediate

  通过H 2 SO 4介导的3-羟基-3-苯基苯并呋喃-2( 3 H )-具有富电子芳烃/1,3-二酮/醇/硫醇作为亲核试剂，产率适中。从机理上讲，烷氧基的取代通过酚-羟基酯中间体进行，并通过级联脱水-再内酯化步骤形成所需的产物。
• 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.