3-((4-bromophenyl)((trimethylsilyl)oxy)methyl)-1H-indole | 1554539-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-((4-bromophenyl)((trimethylsilyl)oxy)methyl)-1H-indole
• CAS: 1554539-59-1
• 化学式: C₁₈H₂₀BrNOSi
• 分子量: 374.352
• InChiKey: MEAPKPXBPJJZPU-UHFFFAOYSA-N

物化性质

• 沸点：
  467.7±35.0 °C(predicted)
• 密度：
  1.291±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-((4-bromophenyl)((trimethylsilyl)oxy)methyl)-1H-indole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以287 mg的产率得到(4-bromophenyl)(1H-indol-3-yl)methanol
  参考文献：
  名称：

  Friedel–Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyl Trifluoromethanesulfonate

  摘要：

  Indoles and N-alkylindoles undergo Friedel Crafts addition to aldehydes in the presence of trimethylsilyl trifluoromethanesulfonate and a trialkylamine to produce 3-(1-silyloxyalkyl)-indoles. Neutralization of the reaction mixture with pyridine followed by deprotection under basic conditions with tetrabutylammonium fluoride provides the 1:1 adduct as the free alcohol. This method prevents spontaneous conversion of the desired products to the thermodynamically favored bisindolyl(aryl)methanes, a process typically observed when indoles are reacted with aldehydes under acidic conditions.

  DOI：

  10.1021/acs.joc.5b01681
• 作为产物：
  描述：

  吲哚 在 咪唑 、 四甲基胍 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.5h， 生成 3-((4-bromophenyl)((trimethylsilyl)oxy)methyl)-1H-indole
  参考文献：
  名称：

  Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel–Crafts Reactions

  摘要：

  The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)BINOL frameworks with different 3,3'-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.

  DOI：

  10.1021/ol403680c