Z,3-Perfluorononyl,3-fluoro-propenoate d'ethyle | 172287-10-4

• 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: Z,3-Perfluorononyl,3-fluoro-propenoate d'ethyle
• 英文别名: ethyl (Z)-3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-icosafluorododec-2-enoate
• CAS: 172287-10-4
• 化学式: C₁₄H₆F₂₀O₂
• 分子量: 586.168
• InChiKey: SGZFOLYTCMHYKK-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  Z,3-Perfluorononyl,3-fluoro-propenoate d'ethyle 在 镍 sodium azide 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 formamide 、 乙酸乙酯 为溶剂， 20.0~80.0 ℃ 、8.0 MPa 条件下， 反应 62.0h， 生成 3-Benzyloxycarbonylamino-4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-nonadecafluoro-dodecanoic acid ethyl ester
  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：

  乙醇 、 (Z)-3-Perfluorononyl-3-fluoropropenoic acid 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到Z,3-Perfluorononyl,3-fluoro-propenoate d'ethyle
  参考文献：
  名称：

  反应产物2-全氟烷基-链烷酸酯d'烷基

  摘要：

  已经研究了醇化物与全氟烷基乙酸（I）和3-全氟烷基-3-氟-丙酸（II）的酯的反应。烯醇酯III或缩醛IV的醚的形成取决于所用的化学计量条件。产物的形成是通过迈克尔型加成和从作为中间体的烯醇化物中消除氟离子进行的。

  DOI：

  10.1016/0022-1139(94)03219-p

文献信息

• Réaction d'alcoolates sur les 2-perfluoroalkyl-éthanoate d'alkyle
  作者：Sylvie Thiebaut、Christine Gerardin、Jack Amos、Claude Selve

  DOI：10.1016/0022-1139(94)03219-p

  日期：1995.8

  The reaction of alcoholates with esters of perfluoroalkylethanoic acid (I) and 3-perfluoroalkyl-3-fluoro-propenoic acid (II) has been studied. Formation of ethers of the enol ester III or the acetal IV depends on the stoichiometric conditions used. The formation of the products proceeds via a Michael-type addition and elimination of fluoride ions from the enolate formed as an intermediate.

  已经研究了醇化物与全氟烷基乙酸（I）和3-全氟烷基-3-氟-丙酸（II）的酯的反应。烯醇酯III或缩醛IV的醚的形成取决于所用的化学计量条件。产物的形成是通过迈克尔型加成和从作为中间体的烯醇化物中消除氟离子进行的。
• Amphiphilic analogues of peptidoamines with perfluorinated side chains
  作者：Sedat Cosgun、Mehmet Özer、Faouzia Hamdoune、Christine Gerardin、Sylvie Thiebaut、Bernard Henry、Jacques Amos、Ludwig Rodehüser、Claude Selve

  DOI：10.1016/s0022-1139(00)00381-x

  日期：2001.2

  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.