(3-乙酰基苯基)三乙基硅烷 | 1048371-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3-乙酰基苯基)三乙基硅烷
• 英文名称: (3-acetylphenyl)triethylsilane
• 英文别名: 1-(3-Triethylsilylphenyl)ethanone
• CAS: 1048371-91-0
• 化学式: C₁₄H₂₂OSi
• 分子量: 234.414
• InChiKey: GLISJHOEDBRWLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 3-碘苯乙酮 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate potassium phosphate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 96.0h， 以83%的产率得到(3-乙酰基苯基)三乙基硅烷
  参考文献：
  名称：

  Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst

  摘要：

  We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-alpha, is also described.

  DOI：

  10.1021/jo8008148