(E)-3-amino-3-cyano-2-fluoro-N-[(S)-1-phenylethyl]acrylamide | 1130887-94-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3-amino-3-cyano-2-fluoro-N-[(S)-1-phenylethyl]acrylamide
• CAS: 1130887-94-3
• 化学式: C₁₂H₁₂FN₃O
• 分子量: 233.245
• InChiKey: PSUABCYMHMAPMI-PNLVODKCSA-N

反应信息

• 作为产物：
  描述：

  potassium cyanide 、 (RS)-N-[(S)-1-phenylethyl]-2-fluoro-2-iodoethanamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以89%的产率得到(E)-3-amino-3-cyano-2-fluoro-N-[(S)-1-phenylethyl]acrylamide
  参考文献：
  名称：

  Synthesis and reactions of α-fluoro-α-amino amides

  摘要：

  N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected alpha-fluoro-alpha-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers; of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The alpha-fluoro-alpha-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding alpha-fluorobetaine amide, and subsequent acidic hydrolysis led to alpha-fluorobetaine as the first example of an 'unprotected' alpha-fluoroamino acid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.061