Methyl 3-perfluoropentyl-β-alanyl alaninate | 331262-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Methyl 3-perfluoropentyl-β-alanyl alaninate
• 英文别名: methyl (2S)-2-[(3-amino-4,4,5,5,6,6,7,7,8,8,8-undecafluorooctanoyl)amino]propanoate
• CAS: 331262-40-9
• 化学式: C₁₂H₁₃F₁₁N₂O₃
• 分子量: 442.229
• InChiKey: ZOLVFEPMAYHCDI-ROLXFIACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 3-perfluoropentyl-β-alanyl alaninate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以80%的产率得到(S)-2-(3-Amino-4,4,5,5,6,6,7,7,8,8,8-undecafluoro-octanoylamino)-propionic acid
  参考文献：
  名称：

  Amphiphilic analogues of peptidoamines with perfluorinated side chains

  摘要：

  A new synthetic pathway for preparing perfluorinated p-alanines is described. 2-Perfluoroalkyl-ethanols are oxidized, dehydro-fluorinated, substituted with an azide group and finally hydrogenated with excellent yields. The C-perfluoroalkylated beta -alanines obtained in this way are subsequently used as hydrophobic moieties for the synthesis of amphiphilic lipo-peptides and lipo-peptidoamines. The choice of the peptidoamine structure is justified by the anti-oxidative and complexing properties of natural analogues such as carcinine and cannosine. Measurements of the surface tension of aqueous solutions of the compounds synthesized reveal their surfactant properties. Potentiometric and spectroscopic investigations give evidence for their good ability to complex copper(II) ions in solution. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00381-x
• 作为产物：
  描述：

  3-(N-benzyloxycarbonyl)amino undecafluoro,2H, ethyloctanoic acid 在 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 10.0h， 生成 Methyl 3-perfluoropentyl-β-alanyl alaninate
  参考文献：
  名称：

  Amphiphilic analogues of peptidoamines with perfluorinated side chains

  摘要：

  A new synthetic pathway for preparing perfluorinated p-alanines is described. 2-Perfluoroalkyl-ethanols are oxidized, dehydro-fluorinated, substituted with an azide group and finally hydrogenated with excellent yields. The C-perfluoroalkylated beta -alanines obtained in this way are subsequently used as hydrophobic moieties for the synthesis of amphiphilic lipo-peptides and lipo-peptidoamines. The choice of the peptidoamine structure is justified by the anti-oxidative and complexing properties of natural analogues such as carcinine and cannosine. Measurements of the surface tension of aqueous solutions of the compounds synthesized reveal their surfactant properties. Potentiometric and spectroscopic investigations give evidence for their good ability to complex copper(II) ions in solution. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00381-x