(3-furan-2-yl-1-trifluoromethyl-allyloxy)-trimethylsilane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (3-furan-2-yl-1-trifluoromethyl-allyloxy)-trimethylsilane
• 英文别名: trimethyl-[(E)-1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-yl]oxysilane
• 化学式: C₁₁H₁₅F₃O₂Si
• 分子量: 264.32
• InChiKey: KQXQYEANFBSZBE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 、 (三氟甲基)三甲基硅烷 在 tetra-n-butylammonium dimethyl phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以91%的产率得到(3-furan-2-yl-1-trifluoromethyl-allyloxy)-trimethylsilane
  参考文献：
  名称：

  Facile Synthesis of TMS-Protected Trifluoromethylated Alcohols Using Trifluoromethyltrimethylsilane (TMSCF₃) and Various Nucleophilic Catalysts in DMF

  摘要：

  Organofluorine compounds are becoming increasingly important in different fields, such as material science, agro chemistry, and the pharmaceutical industry. Nucleophilic trifluoromethylation is one of the widely used methods to incorporate a trifluoromethyl moiety into organic molecules. We have carried out extensive studies to develop varieties of easily accessible nucleophilic catalysts to promote such reactions. TMS-protected trifluoromethylated alcohols were prepared from both aldehydes and ketones in excellent yields using catalytic amount of amine N-oxide. Carbonate and phosphate salts also showed efficient catalytic activity toward this reaction. These reactions were highly solvent dependent, and DMF was found to be the most suitable one among the various solvents studied. All these reactions proceeded under very mild conditions, giving clean products and avoiding the use of any fluoride initiators or expensive catalysts, and extremely water-free conditions. The mechanism for the reaction is discussed in detail. DFT calculations were performed on the possible reaction intermediates using the Gaussian 03 program at B3LYP/6-311+G* level to support the proposed mechanism.

  DOI：

  10.1021/jo060835d