ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-4-(trifluoromethyl)hex-2-enoate | 1160175-53-0

• 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: ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-4-(trifluoromethyl)hex-2-enoate
• 英文别名: ethyl (E,4S,5S)-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenyl-4-(trifluoromethyl)hex-2-enoate
• CAS: 1160175-53-0
• 化学式: C₂₀H₂₆F₃NO₅
• 分子量: 417.425
• InChiKey: MPMVCEBWPFKQDY-BSODZPPDSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  547.5±50.0 °C(predicted)
• 密度：
  1.213±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-4-(trifluoromethyl)hex-2-enoate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以100%的产率得到ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-(methylsulfonyloxy)-6-phenyl-4-(trifluoromethyl)hex-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
• 作为产物：
  描述：

  (三氟甲基)三甲基硅烷 、 ethyl (E)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate 在 S-1,1'-联-2-萘酚 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 ethyl (4R,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-4-(trifluoromethyl)hex-2-enoate 、 ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-4-(trifluoromethyl)hex-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.