3-<2-(Trimethylsilyl)ethinyl>benzothiophen-2-carbaldehyd | 152874-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-<2-(Trimethylsilyl)ethinyl>benzothiophen-2-carbaldehyd
• 英文别名: 3-<2-(Trimethylsilyl)ethinyl>-2-benzothiophencarbaldehyd；3-(2-trimethylsilylethynyl)-1-benzothiophene-2-carbaldehyde
• CAS: 152874-28-7
• 化学式: C₁₄H₁₄OSSi
• 分子量: 258.416
• InChiKey: PIRUIEWUKQRIPF-UHFFFAOYSA-N

物化性质

• 沸点：
  360.3±42.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-<2-(Trimethylsilyl)ethinyl>benzothiophen-2-carbaldehyd 在 silver nitrate 、 叔丁胺 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure

  摘要：

  An operationally simple silver-catalyzed tandem strategy for the synthesis of benzothienopyridines 7a-t and benzofuropyridines 8a-p by the reaction of o-alkynyl aldehyde 4a-t and 5a-p with tert-butylamine 6 under mild reaction conditions is described. The present methodology provides a facile conversion of easily accessible o-alkynyl aldehydes into medicinally useful heterocycles in good to excellent yields under mild and environmentally friendly reaction conditions with excellent regioselectivity. The developed chemistry has been successfully extended for the selective synthesis of C-4 deuterated benzothienopyridines 7u-v and benzofurop-yridines 8q-r. The role of the ethanolic proton in the reaction was validated by deuterium-labeling experiments.

  DOI：

  10.1021/acs.joc.5b01647
• 作为产物：
  描述：

  3-溴苯并噻吩-2-甲醛 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 3-<2-(Trimethylsilyl)ethinyl>benzothiophen-2-carbaldehyd
  参考文献：
  名称：

  Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure

  摘要：

  An operationally simple silver-catalyzed tandem strategy for the synthesis of benzothienopyridines 7a-t and benzofuropyridines 8a-p by the reaction of o-alkynyl aldehyde 4a-t and 5a-p with tert-butylamine 6 under mild reaction conditions is described. The present methodology provides a facile conversion of easily accessible o-alkynyl aldehydes into medicinally useful heterocycles in good to excellent yields under mild and environmentally friendly reaction conditions with excellent regioselectivity. The developed chemistry has been successfully extended for the selective synthesis of C-4 deuterated benzothienopyridines 7u-v and benzofurop-yridines 8q-r. The role of the ethanolic proton in the reaction was validated by deuterium-labeling experiments.

  DOI：

  10.1021/acs.joc.5b01647

文献信息

• Eberbach, Wolfgang; Laber, Norbert; Bussenius, Joerg, Chemische Berichte, 1993, vol. 126, # 4, p. 975 - 996
  作者：Eberbach, Wolfgang、Laber, Norbert、Bussenius, Joerg、Fritz, Hans、Rihs, Grety

  DOI：——

  日期：——
• Bussenius, Joerg; Laber, Norbert; Mueller, Thomas, Chemische Berichte, 1994, vol. 127, # 1, p. 247 - 260
  作者：Bussenius, Joerg、Laber, Norbert、Mueller, Thomas、Eberbach, Wolfgang

  DOI：——

  日期：——