ethyl (2S,5S,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-4-(trifluoromethyl)hex-3-enoate | 1160175-72-3

• 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: ethyl (2S,5S,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-4-(trifluoromethyl)hex-3-enoate
• 英文别名: ethyl (Z,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-yl-4-(trifluoromethyl)hex-3-enoate
• CAS: 1160175-72-3
• 化学式: C₁₇H₂₈F₃NO₄
• 分子量: 367.409
• InChiKey: GECRHGJJTKDRMT-KONFJKIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (i-Pr)2ZnBr 、 ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-(methylsulfonyloxy)-4-(trifluoromethyl)-hex-2-enoate 在 copper(ll) bromide 、 ammonium hydroxide 、 氯化铵 作用下， 以 N-甲基吡咯烷酮 、 正己烷 、 甲苯 为溶剂， 反应 0.5h， 以20%的产率得到ethyl (2R,5S,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-4-(trifluoromethyl)hex-3-enoate
  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

文献信息

• Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation
  作者：Kazuya Kobayashi、Tetsuo Narumi、Shinya Oishi、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1021/jo9005602

  日期：2009.6.19

  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.