(Z)-3-perfluoropentyl-3-decyloxypropenoic acid

• 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-perfluoropentyl-3-decyloxypropenoic acid
• 英文别名: (Z)-3-decoxy-4,4,5,5,6,6,7,7,8,8,8-undecafluorooct-2-enoic acid
• 化学式: C₁₈H₂₃F₁₁O₃
• 分子量: 496.361
• InChiKey: FASPBNCLUOVHRO-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (Z)-3-perfluoropentyl-3-decyloxypropenoic acid 在 氯化亚砜 作用下， 反应 8.0h， 以60%的产率得到(Z)-3-全氟戊基-3-癸氧基丙烯酰氯
  参考文献：
  名称：

  Synthesis of triphilic, Y-shaped molecular surfactants

  摘要：

  Novel multiphilic molecules comprising three chains with antagonistic affinities have been synthesized. These 'triphilic' surfactants (FnHmEOy) contain a perfluorinated arm (Fn=CnF2n+1), a hydrocarbon arm (Hm=CmH2m+1), and a methyl-caped, poly(ethylene glycol) arm (EOy=CH3(OC2H4)(y)O). These moieties have variable lengths (n=5 or 7, m=8, 10, or 14, and y=2-7) and are interconnected in a Y shape; hence, each unit is directly connected to the other two. The key intermediates in the synthetic route are 3-F-alkyl-3-alkyloxypropanoic acids, on which the polar EOy chain is subsequently grafted. Monodisperse methyl-caped diethylene glycol (EO2) and triethylene glycol (EO3) led to the corresponding monodisperse triaffine surfactants. In parallel, a library of five F5H10EOy triaffines (y=3-7) has been obtained simultaneously when starting from the polydisperse methyl-caped poly(ethylene glycol) MPEG 350. Separation of pure individual compounds was achieved through column chromatography on silica gel. The relative concentration of the Z and E isomers has been quantified in the reaction mixtures of the intermediates and final products by H-1 NMR (Z largely predominant). Several products have been obtained in their isomerically pure form. Chemical characterization (H-1, C-13, and F-19 NMR, elemental analysis) was consistent with the expected structures. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.003
• 作为产物：
  描述：

  癸醇 、 2H,2H-全氟辛酸 在 氢氧化钾 作用下， 反应 48.0h， 以28%的产率得到(Z)-3-perfluoropentyl-3-decyloxypropenoic acid
  参考文献：
  名称：

  Synthesis of triphilic, Y-shaped molecular surfactants

  摘要：

  Novel multiphilic molecules comprising three chains with antagonistic affinities have been synthesized. These 'triphilic' surfactants (FnHmEOy) contain a perfluorinated arm (Fn=CnF2n+1), a hydrocarbon arm (Hm=CmH2m+1), and a methyl-caped, poly(ethylene glycol) arm (EOy=CH3(OC2H4)(y)O). These moieties have variable lengths (n=5 or 7, m=8, 10, or 14, and y=2-7) and are interconnected in a Y shape; hence, each unit is directly connected to the other two. The key intermediates in the synthetic route are 3-F-alkyl-3-alkyloxypropanoic acids, on which the polar EOy chain is subsequently grafted. Monodisperse methyl-caped diethylene glycol (EO2) and triethylene glycol (EO3) led to the corresponding monodisperse triaffine surfactants. In parallel, a library of five F5H10EOy triaffines (y=3-7) has been obtained simultaneously when starting from the polydisperse methyl-caped poly(ethylene glycol) MPEG 350. Separation of pure individual compounds was achieved through column chromatography on silica gel. The relative concentration of the Z and E isomers has been quantified in the reaction mixtures of the intermediates and final products by H-1 NMR (Z largely predominant). Several products have been obtained in their isomerically pure form. Chemical characterization (H-1, C-13, and F-19 NMR, elemental analysis) was consistent with the expected structures. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.003

文献信息

• Synthesis of triphilic, Y-shaped molecular surfactants
  作者：Margarita Sanchez-Dominguez、Nicole Benoit、Marie Pierre Krafft

  DOI：10.1016/j.tet.2007.11.003

  日期：2008.1

  Novel multiphilic molecules comprising three chains with antagonistic affinities have been synthesized. These 'triphilic' surfactants (FnHmEOy) contain a perfluorinated arm (Fn=CnF2n+1), a hydrocarbon arm (Hm=CmH2m+1), and a methyl-caped, poly(ethylene glycol) arm (EOy=CH3(OC2H4)(y)O). These moieties have variable lengths (n=5 or 7, m=8, 10, or 14, and y=2-7) and are interconnected in a Y shape; hence, each unit is directly connected to the other two. The key intermediates in the synthetic route are 3-F-alkyl-3-alkyloxypropanoic acids, on which the polar EOy chain is subsequently grafted. Monodisperse methyl-caped diethylene glycol (EO2) and triethylene glycol (EO3) led to the corresponding monodisperse triaffine surfactants. In parallel, a library of five F5H10EOy triaffines (y=3-7) has been obtained simultaneously when starting from the polydisperse methyl-caped poly(ethylene glycol) MPEG 350. Separation of pure individual compounds was achieved through column chromatography on silica gel. The relative concentration of the Z and E isomers has been quantified in the reaction mixtures of the intermediates and final products by H-1 NMR (Z largely predominant). Several products have been obtained in their isomerically pure form. Chemical characterization (H-1, C-13, and F-19 NMR, elemental analysis) was consistent with the expected structures. (c) 2007 Elsevier Ltd. All rights reserved.