methyl (E)-3-[4-hydroxy-3-methoxy-5-(2-phenylethynyl)phenyl]prop-2-enoate | 419543-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-[4-hydroxy-3-methoxy-5-(2-phenylethynyl)phenyl]prop-2-enoate
• CAS: 419543-30-9
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: FMYGQTIEZZRNRA-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-碘代苯乙酮 、 一氧化碳 、 methyl (E)-3-[4-hydroxy-3-methoxy-5-(2-phenylethynyl)phenyl]prop-2-enoate 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以61%的产率得到methyl (E)-3-[3-(4-acetylbenzoyl)-7-methoxy-2-phenyl-1-benzofuran-5-yl]prop-2-enoate
  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
• 作为产物：
  描述：

  苯乙炔 、 methyl (E)-3-(4-acetyloxy-3-iodo-5-methoxyphenyl)prop-2-enoate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 氨 作用下， 以 丙酮 、 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 以98%的产率得到methyl (E)-3-[4-hydroxy-3-methoxy-5-(2-phenylethynyl)phenyl]prop-2-enoate
  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.