4-Acetoxy-3-iodo-5-methoxy-benzoic acid methyl ester | 259739-83-8

• 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: 4-Acetoxy-3-iodo-5-methoxy-benzoic acid methyl ester
• 英文别名: Methyl 4-acetyloxy-3-iodo-5-methoxybenzoate
• CAS: 259739-83-8
• 化学式: C₁₁H₁₁IO₅
• 分子量: 350.11
• InChiKey: YGIUFBACKUXZDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-羟基-3-碘-5-甲氧基苯甲酸甲酯 、 乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到4-Acetoxy-3-iodo-5-methoxy-benzoic acid methyl ester
  参考文献：
  名称：

  Regiospecific Carbonylative Annulation of Iodophenol Acetates and Acetylenes To Construct the Flavones by a New Catalyst of Palladium−Thiourea−dppp Complex

  摘要：

  [GRAPHICS]Regiospecific carbonylative annulation of sigma-iodophenol acetates and acetylenes mediated by palladium-thiourea-dppp complex in the presence of base at 40 degrees C under a balloon pressure of CO generates diversified flavones in high yields. This newly developed synthetic technology provides a highly efficient method for potential application to the combinatorial synthesis of those heterocycles on the solid support.

  DOI：

  10.1021/ol000087t

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.