4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-6-[2-(3-methoxy-4-phenylmethoxyphenyl)ethynyl]phenol | 259739-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-6-[2-(3-methoxy-4-phenylmethoxyphenyl)ethynyl]phenol
• CAS: 259739-69-0
• 化学式: C₃₀H₃₆O₅Si
• 分子量: 504.698
• InChiKey: TWMJXICFVDJVAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 一氧化碳 、 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-6-[2-(3-methoxy-4-phenylmethoxyphenyl)ethynyl]phenol 在 四溴化碳 、 PdI₂*thiourea 、 caesium carbonate 作用下， 以85%的产率得到Methyl 5-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-methoxy-2-(3-methoxy-4-phenylmethoxyphenyl)-1-benzofuran-3-carboxylate
  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：

  Acetic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-2-iodo-6-methoxy-phenyl 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 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-6-[2-(3-methoxy-4-phenylmethoxyphenyl)ethynyl]phenol
  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.
• 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.