(+/-)-(2S,3S)-2,3-epoxy-3-phenyl-2-trimethylsilylpropanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (+/-)-(2S,3S)-2,3-epoxy-3-phenyl-2-trimethylsilylpropanoic acid
• 英文别名: (2S,3S)-3-phenyl-2-trimethylsilyloxirane-2-carboxylic acid
• 化学式: C₁₂H₁₆O₃Si
• 分子量: 236.343
• InChiKey: AUARECVBIVOAFY-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.83
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(2S,3S)-2,3-epoxy-3-phenyl-2-trimethylsilylpropanoic acid 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 喹啉 为溶剂， 反应 2.0h， 生成 反式-3-苯基环氧丙酸乙酯
  参考文献：
  名称：

  The First Example of an Amide-Carbonyl Stabilized Oxiranyl Anion: Generation from Epoxysilane, Its Properties, and Trapping with Electrophiles

  摘要：

  An epoxysilane having an amide group at the alpha-carbon was synthesized from phenylacetylene. An amide-carbonyl stabilized oxiranyl-ammonium was generated from the epoxysilane in THF with tetrabutylammonium fluoride (TBAF). The generated oxiranyl anion was found to have enough nucleophilicity with aldehydes to give moderate to good yields of the adducts. In some reactions, the oxiranylammonium was found to be configurationally unstable to give the epimers.

  DOI：

  10.3987/com-02-s6
• 作为产物：
  描述：

  [(2R,3S)-3-phenyl-2-trimethylsilyloxiran-2-yl]methanol 在 chromium(VI) oxide 、 高碘酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到(+/-)-(2S,3S)-2,3-epoxy-3-phenyl-2-trimethylsilylpropanoic acid
  参考文献：
  名称：

  The First Example of an Amide-Carbonyl Stabilized Oxiranyl Anion: Generation from Epoxysilane, Its Properties, and Trapping with Electrophiles

  摘要：

  An epoxysilane having an amide group at the alpha-carbon was synthesized from phenylacetylene. An amide-carbonyl stabilized oxiranyl-ammonium was generated from the epoxysilane in THF with tetrabutylammonium fluoride (TBAF). The generated oxiranyl anion was found to have enough nucleophilicity with aldehydes to give moderate to good yields of the adducts. In some reactions, the oxiranylammonium was found to be configurationally unstable to give the epimers.

  DOI：

  10.3987/com-02-s6

文献信息

• The First Example of an Amide-Carbonyl Stabilized Oxiranyl Anion: Generation from Epoxysilane, Its Properties, and Trapping with Electrophiles
  作者：Tsuyoshi Satoh、Takayuki Shimura、Ken Sakai

  DOI：10.3987/com-02-s6

  日期：——

  An epoxysilane having an amide group at the alpha-carbon was synthesized from phenylacetylene. An amide-carbonyl stabilized oxiranyl-ammonium was generated from the epoxysilane in THF with tetrabutylammonium fluoride (TBAF). The generated oxiranyl anion was found to have enough nucleophilicity with aldehydes to give moderate to good yields of the adducts. In some reactions, the oxiranylammonium was found to be configurationally unstable to give the epimers.