(2S,5S,3Z)-5-amino-2-methyl-6-phenyl-4-(trifluoromethyl)hex-3-enoic acid hydrochloride | 1160175-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,5S,3Z)-5-amino-2-methyl-6-phenyl-4-(trifluoromethyl)hex-3-enoic acid hydrochloride
• CAS: 1160175-76-7
• 化学式: C₁₄H₁₆F₃NO₂*ClH
• 分子量: 323.743
• InChiKey: VVEWQLISQOZTPI-XRIWSRQTSA-N

反应信息

• 作为产物：
  描述：

  ethyl (5S,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-methyl-6-phenyl-4-(trifluoromethyl)hex-3-enoate 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 24.0h， 生成 (2S,5S,3Z)-5-amino-2-methyl-6-phenyl-4-(trifluoromethyl)hex-3-enoic acid hydrochloride 、 (2R,5S,3Z)-5-amino-2-methyl-6-phenyl-4-(trifluoromethyl)hex-3-enoic acid hydrochloride
  参考文献：
  名称：

  Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation

  摘要：

  A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.

  DOI：

  10.1021/jo9005602