7-Methoxy-3-(4-methoxy-benzoyl)-2-methoxymethyl-benzofuran-5-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Methoxy-3-(4-methoxy-benzoyl)-2-methoxymethyl-benzofuran-5-carboxylic acid methyl ester
• 英文别名: Methyl 7-methoxy-3-(4-methoxybenzoyl)-2-(methoxymethyl)-1-benzofuran-5-carboxylate
• 化学式: C₂₁H₂₀O₇
• 分子量: 384.386
• InChiKey: JJQIEHAVMKUEKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  一氧化碳 、 4-碘苯甲醚 、 Methyl 4-hydroxy-3-methoxy-5-(3-methoxyprop-1-ynyl)benzoate 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以90%的产率得到7-Methoxy-3-(4-methoxy-benzoyl)-2-methoxymethyl-benzofuran-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylative Annulation of o-Alkynylphenols:  Syntheses of 2-Substituted-3-aroyl-benzo[b]furans

  摘要：

  We report here a general synthetic methodology for palladium-catalyzed carbonylative annulation of o-alkynylphenol to construct 2-substituted-3-aroyl-benzo[b]furan. On the basis of the results, this methodology could be applied to a wider selection of iodide substrates to generate desired products. In accordance with mechanistic studies, this process involves coordination of cationic and less hindered acyl palladium complexes with o-alkynylphenols to create a desired cascade triad (coordination, nucleophilic addition, and reductive elimination). Consistent with this mechanism, addition of 1 equiv of AgBF4 to palladium catalyst Pd(Ph3P)(4) generates an ideal candidate for this unique transformation.

  DOI：

  10.1021/jo010839c

文献信息

• Palladium-Catalyzed Carbonylative Annulation of <i>o-</i>Alkynylphenols:  Syntheses of 2-Substituted-3-aroyl-benzo[<i>b</i>]furans
  作者：Youhong Hu、Yan Zhang、Zhen Yang、Reza Fathi

  DOI：10.1021/jo010839c

  日期：2002.4.1

  We report here a general synthetic methodology for palladium-catalyzed carbonylative annulation of o-alkynylphenol to construct 2-substituted-3-aroyl-benzo[b]furan. On the basis of the results, this methodology could be applied to a wider selection of iodide substrates to generate desired products. In accordance with mechanistic studies, this process involves coordination of cationic and less hindered acyl palladium complexes with o-alkynylphenols to create a desired cascade triad (coordination, nucleophilic addition, and reductive elimination). Consistent with this mechanism, addition of 1 equiv of AgBF4 to palladium catalyst Pd(Ph3P)(4) generates an ideal candidate for this unique transformation.