ethyl (2E)-3-[(4S,5S)-4-benzyl-N-(tert-butoxycarbonyl)-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-enoate | 1160175-60-9

• 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 (2E)-3-[(4S,5S)-4-benzyl-N-(tert-butoxycarbonyl)-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-enoate
• 英文别名: tert-butyl (4S,5S)-4-benzyl-5-[(E)-3-ethoxy-3-oxoprop-1-enyl]-2-oxo-5-(trifluoromethyl)-1,3-oxazolidine-3-carboxylate
• CAS: 1160175-60-9
• 化学式: C₂₁H₂₄F₃NO₆
• 分子量: 443.42
• InChiKey: QBIRINSBQIIIQW-JCFHGJPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-4-(trifluoromethyl)hex-2-enoate 、 N,N'-羰基二咪唑 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 ethyl (2E)-3-[(4S,5S)-4-benzyl-N-(tert-butoxycarbonyl)-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-enoate 、 ethyl (2E)-3-[(4R,5R)-4-benzyl-N-(tert-butoxycarbonyl)-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-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.