[1H-indol-3-yl(phenyl)methoxy]-trimethylsilane | 1554539-46-6

• 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: [1H-indol-3-yl(phenyl)methoxy]-trimethylsilane
• CAS: 1554539-46-6
• 化学式: C₁₈H₂₁NOSi
• 分子量: 295.456
• InChiKey: QPRNFNUENOHEII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1H-indol-3-yl(phenyl)methoxy]-trimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以163 mg的产率得到(1H-indol-3-yl)(phenyl)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：

  苯甲醛 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 [1H-indol-3-yl(phenyl)methoxy]-trimethylsilane
  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

文献信息

• Friedel–Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyl Trifluoromethanesulfonate
  作者：C. Wade Downey、Christopher D. Poff、Alissa N. Nizinski

  DOI：10.1021/acs.joc.5b01681

  日期：2015.10.16

  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.
• Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel–Crafts Reactions
  作者：Ming-Hua Zhuo、Yi-Jun Jiang、Yan-Sen Fan、Yang Gao、Song Liu、Suoqin Zhang

  DOI：10.1021/ol403680c

  日期：2014.2.21

  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.