Methyl 4-hydroxy-3-methoxy-5-(3-methoxyprop-1-ynyl)benzoate | 259739-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 4-hydroxy-3-methoxy-5-(3-methoxyprop-1-ynyl)benzoate
• CAS: 259739-72-5
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: VAWGVHJFDNCSGU-UHFFFAOYSA-N

物化性质

• 沸点：
  396.2±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-碘代苯乙酮 、 Methyl 4-hydroxy-3-methoxy-5-(3-methoxyprop-1-ynyl)benzoate 在 tris(dibenzylideneacetone)dipalladium (0) 2,2'-联吡啶 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以64%的产率得到Methyl 3-(4-acetylphenyl)-7-methoxy-2-(methoxymethyl)-1-benzofuran-5-carboxylate
  参考文献：
  名称：

  Synthesis of Conformationally Restricted 2,3-Diarylbenzo[b]furan by the Pd-Catalyzed Annulation of o-Alkynylphenols:  Exploring a Combinatorial Approach

  摘要：

  The palladium/bpy-catalyzed annulation of o-alkynylphenol with various aryl halides to generate diversified 2,3-diarylbenzo[b]furan is herein described. This method provides an efficient synthetic pathway for the combinatorial synthesis of conformationally restricted 2,3-diarylbenzo[b]furan for drug discovery.

  DOI：

  10.1021/jo0303160
• 作为产物：
  描述：

  4-Acetoxy-3-iodo-5-methoxy-benzoic acid methyl ester 在 bis-triphenylphosphine-palladium(II) chloride ammonium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 Methyl 4-hydroxy-3-methoxy-5-(3-methoxyprop-1-ynyl)benzoate
  参考文献：
  名称：

  A New Complex of Palladium−Thiourea and Carbon Tetrabromide Catalyzed Carbonylative Annulation of o-Hydroxylarylacetylenes:  Efficient New Synthetic Technology for the Synthesis of 2,3-Disubstituted Benzo[b]furans

  摘要：

  [GRAPHICS]A highly effective cocatalysis system (Pdl(2)-thiourea and CBr4) was developed for carbonylative cyclization of bath electron-rich and electron-deficient o-hydroxylarylacetylenes to the corresponding methyl benzo[b]furan-3-carboxylates.

  DOI：

  10.1021/ol991327b

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.
• Synthesis of Conformationally Restricted 2,3-Diarylbenzo[<i>b</i>]furan by the Pd-Catalyzed Annulation of <i>o</i>-Alkynylphenols:  Exploring a Combinatorial Approach
  作者：Youhong Hu、Kenneth J. Nawoschik、Yun Liao、Jian Ma、Reza Fathi、Zhen Yang

  DOI：10.1021/jo0303160

  日期：2004.4.1

  The palladium/bpy-catalyzed annulation of o-alkynylphenol with various aryl halides to generate diversified 2,3-diarylbenzo[b]furan is herein described. This method provides an efficient synthetic pathway for the combinatorial synthesis of conformationally restricted 2,3-diarylbenzo[b]furan for drug discovery.
• A New Complex of Palladium−Thiourea and Carbon Tetrabromide Catalyzed Carbonylative Annulation of <i>o</i>-Hydroxylarylacetylenes:  Efficient New Synthetic Technology for the Synthesis of 2,3-Disubstituted Benzo[<i>b</i>]furans
  作者：Yang Nan、Hua Miao、Zhen Yang

  DOI：10.1021/ol991327b

  日期：2000.2.1

  [GRAPHICS]A highly effective cocatalysis system (Pdl(2)-thiourea and CBr4) was developed for carbonylative cyclization of bath electron-rich and electron-deficient o-hydroxylarylacetylenes to the corresponding methyl benzo[b]furan-3-carboxylates.