2-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octyl)-malonic acid dimethyl ester | 220075-01-4

• 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: 2-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octyl)-malonic acid dimethyl ester
• 英文别名: Propanedioic acid, 2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-, 1,3-dimethyl ester；dimethyl 2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)propanedioate
• CAS: 220075-01-4
• 化学式: C₁₃H₁₁F₁₃O₄
• 分子量: 478.207
• InChiKey: LVYNMXGZSWLMOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octyl)-malonic acid dimethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-<2-(Perfluorhexyl)ethyl>-malonsaeure
  参考文献：
  名称：

  Nouveaux procédés de préparation des isocyanates F-alkylés linéaires ou ramifiés à partir des iodures de 2-F-alkyléthyle

  摘要：

  Isocyanates are extremely versatile compounds in organic synthesis, but their synthesis is not easy. One of the most convenient methods uses acids as intermediates. In the F-alkyl series, it is sometimes difficult to obtain them by a general way. We have managed an efficient synthetic route to F-alkyl acids through malonates from 2-F-alkylethyl iodides.

  DOI：

  10.1016/s0022-1139(98)00235-8
• 作为产物：
  描述：

  1-碘-1H,1H,2H,2H-全氟辛烷 、 丙二酸二甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octyl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Superhydrophobic and oleophobic surfaces containing wrinkles and nanoparticles of PEDOT with two short fluorinated chains

  摘要：

  通过电沉积含有两条短氟化链的原始 PEDOT 衍生物，可获得超疏水性和疏油性表面。这种憎液特性是由于两条氟化链的存在使聚合物具有较高的固有疏水性和疏油性，以及电沉积过程中形成的皱纹和球形颗粒。褶皱和球形颗粒的存在以及由此产生的表面疏水性和疏油性与氟化链长度和电化学参数（恒定电位沉积时的沉积电荷以及循环伏安法沉积时的扫描速率和扫描次数）相关。在这里，皱纹和球形颗粒数量的增加会导致表面粗糙度的增加，尤其是表面疏水性的增加，而表面疏油性并不总是受到影响。不过，通过仔细选择电化学参数，也有可能增加表面疏油性。这项研究还可以制备氟含量低的超级憎液表面（生物累积潜力低的材料）。

  DOI：

  10.1039/c3ra47479h

文献信息

• Nucleophilic displacements of 2-perfluoroalkyl-1-iodoethanes: improved synthesis of fluorine-containing malonic esters
  作者：H Trabelsi、F Szönyi、S Geribaldi

  DOI：10.1016/s0022-1139(00)00388-2

  日期：2001.1

  The replacement of iodide in 2-perfluoroalkyl-1-iodoethanes by anions derived from dialkyl malonate affords α-(2-perfluoroalkyl)ethyl malonic esters in high yields with negligible elimination and dialkylation, using bases such as K2CO3 or NaH in THF. The physical properties of the products are described.

  通过从丙二酸二烷基酯，得到α-衍生的阴离子中的2-全氟烷基-1- iodoethanes更换碘化物（2-全氟烷基）乙基高收率具有可忽略的消除和二烷基化，使用碱如K丙二酸酯2 CO 3或NaH的THF 。描述了产品的物理性质。
• One <i>F</i>-Octyl versus Two <i>F</i>-Butyl Chains in Surfactant Aggregation Behavior
  作者：Abdoulaye Dramé、Elisabeth Taffin de Givenchy、Samba Yandé Dieng、Sonia Amigoni、Mamadou Oumar、Alioune Diouf、Thierry Darmanin、Frédéric Guittard

  DOI：10.1021/la403173v

  日期：2013.12.3

  An easy synthetic procedure in two or three steps from perfluoroalkylethyl iodide derivatives led to six novel fluorinated carboxylates monomeric and gemini surfactants with one or two hydrophobic tails, respectively: R-F(C2H4)CH(CO2-)(2),2Na(+) and [RF(C2H4)](2)C(CO2-),Na+, where R-F = C4F9, C6F13, and C8F12. These anionic surfactants exhibited very low surface tension from 15 to 33 mN/m as well as low critical micelle concentration until 1.3 x 10(-4) mol/L. Furthermore, the surface properties of the gemini compound with two short fluoroalkyl chains (R-F = C4F9) were found to be almost equal to those of the monomeric surfactant with one long fluoroalkyl chain (R-F = C8F17), which could provide an interesting alternative to the bioaccumulative long-chain perfluorinated surfactant.
• A General Approach to Biocompatible Branched Fluorous Tags for Increased Solubility in Perfluorocarbon Solvents
  作者：Margeaux A. Miller、Ellen M. Sletten

  DOI：10.1021/acs.orglett.8b02976

  日期：2018.11.2

  A modular, cost-effective route to a library of branched fluorous tags with two short, biocompatible, fluorinated chains (C6F13) is reported. These branched fluorous tags provide high fluorous content without the use of long-chain linear perfluorocarbons, which have rising health concerns due to their bioaccumulation. By attaching these tags to a porphyrin, it is demonstrated that high solubility can be achieved in fluorous solvents that are readily cleared from mammals. This work enhances the biocompatibility of perfluorocarbon nanoemulsions for photodynamic therapy.
• Nouveaux procédés de préparation des isocyanates F-alkylés linéaires ou ramifiés à partir des iodures de 2-F-alkyléthyle
  作者：P. Lucas、M.A. Jouani、H. Trabelsi、A. Cambon

  DOI：10.1016/s0022-1139(98)00235-8

  日期：1998.10

  Isocyanates are extremely versatile compounds in organic synthesis, but their synthesis is not easy. One of the most convenient methods uses acids as intermediates. In the F-alkyl series, it is sometimes difficult to obtain them by a general way. We have managed an efficient synthetic route to F-alkyl acids through malonates from 2-F-alkylethyl iodides.
• Superhydrophobic and oleophobic surfaces containing wrinkles and nanoparticles of PEDOT with two short fluorinated chains
  作者：Abdoulaye Dramé、Thierry Darmanin、Samba Yandé Dieng、Elisabeth Taffin de Givenchy、Frédéric Guittard

  DOI：10.1039/c3ra47479h

  日期：——

  Superhydrophobic and oleophobic surfaces are obtained by electrodeposition of original PEDOT derivatives containing two short fluorinated chains. The liquid-repellent properties are due to the combination of high intrinsic hydrophobicity and oleophobicity of polymers due the presence of two fluorinated chains, and the formation of wrinkles and spherical particles induced by the electrodeposition process. The presence of wrinkles and spherical particles and as a consequence the surface hydrophobicity and oleophobicity is correlated to the fluorinated chain length and electrochemical parameters (the deposition charge for the depositions at constant potential and the scan rate and number of scans for the depositions by cyclic voltammetry). Here, the increase in the number of wrinkles and spherical particles induces an increase in the surface roughness increasing especially the surface hydrophobicity while the surface oleophobicity is not always affected. However, it is also possible to increase the surface oleophobicity by a careful choice in the electrochemical parameters. This work also allows the elaboration of super liquid-repellent surfaces with low fluorine content (materials with low bioaccumulative potential).

  通过电沉积含有两条短氟化链的原始 PEDOT 衍生物，可获得超疏水性和疏油性表面。这种憎液特性是由于两条氟化链的存在使聚合物具有较高的固有疏水性和疏油性，以及电沉积过程中形成的皱纹和球形颗粒。褶皱和球形颗粒的存在以及由此产生的表面疏水性和疏油性与氟化链长度和电化学参数（恒定电位沉积时的沉积电荷以及循环伏安法沉积时的扫描速率和扫描次数）相关。在这里，皱纹和球形颗粒数量的增加会导致表面粗糙度的增加，尤其是表面疏水性的增加，而表面疏油性并不总是受到影响。不过，通过仔细选择电化学参数，也有可能增加表面疏油性。这项研究还可以制备氟含量低的超级憎液表面（生物累积潜力低的材料）。