Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate | 40599-19-7

• 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: Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate
• 英文别名: 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-undecanoic acid ethyl ester
• CAS: 40599-19-7
• 化学式: C₁₃H₉F₁₇O₂
• 分子量: 520.186
• InChiKey: IZMROCTWIWLSIR-UHFFFAOYSA-N

物化性质

• 沸点：
  227.0±35.0 °C(predicted)
• 密度：
  1.531±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate 在 t-butylate de potassium 、 二乙胺 作用下， 反应 98.0h， 生成 2-(perfluorooctyl)methylpropenoic acid ethyl ester
  参考文献：
  名称：

  Synthèseetpolymérisationdemonomèresfluorésacryliques取代了α位。第一部分：乙炔-全氟辛基甲基丙烯酸酯的合成和聚合

  摘要：

  乙基，α-perfluorooctylmethylacrylate的合成[H 2 CC（CH 2 ç 8 ˚F 17）CO 2 CH 2 CH 3 ]（1），已经在从perfluorooctylpropionic酸开始的三个步骤被执行，为82的总产率％。用乙醇将酸酯化，然后在α位进行乙氧基化（92％收率）。最后一步涉及将甲醛添加到酮酯上以产生α-酮-γ-内酯，其可以在水性碱性介质中水解以90％的收率得到单体1。1的均聚是困难的，但要与苯乙烯和N共聚-乙烯基吡咯烷酮可以容易地进行。元素分析和1 H NMR光谱数据提供了有关共聚物组成的信息。

  DOI：

  10.1016/s0022-1139(00)81176-8
• 作为产物：
  描述：

  2-氨基甲苯-5-磺酸 在 吡啶 、 chlorure de thionyle 作用下， 以 四氢呋喃 为溶剂， 反应 74.5h， 生成 Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate
  参考文献：
  名称：

  Synthèseetpolymérisationdemonomèresfluorésacryliques取代了α位。第一部分：乙炔-全氟辛基甲基丙烯酸酯的合成和聚合

  摘要：

  乙基，α-perfluorooctylmethylacrylate的合成[H 2 CC（CH 2 ç 8 ˚F 17）CO 2 CH 2 CH 3 ]（1），已经在从perfluorooctylpropionic酸开始的三个步骤被执行，为82的总产率％。用乙醇将酸酯化，然后在α位进行乙氧基化（92％收率）。最后一步涉及将甲醛添加到酮酯上以产生α-酮-γ-内酯，其可以在水性碱性介质中水解以90％的收率得到单体1。1的均聚是困难的，但要与苯乙烯和N共聚-乙烯基吡咯烷酮可以容易地进行。元素分析和1 H NMR光谱数据提供了有关共聚物组成的信息。

  DOI：

  10.1016/s0022-1139(00)81176-8

文献信息

• Carbonylation of 1-perfluoroalkyl-substituted 2-iodoalkanes catalyzed by transition-metal complexes
  作者：Urata Hisao、Osamu Kosukegawa、Yoshimitsu Ishii、Hideki Yugari、Takamasa Fuchikami

  DOI：10.1016/s0040-4039(00)99372-9

  日期：1989.1

  substituent at β position were synthesized in good yields from 1-perfluoroalkyl-substituted 2-iodoalkanes and carbon monoxide with water or alcohols in the presence of base by using group VIII transition-metal complexes as catalysts.

  使用族过渡金属配合物作为催化剂，在碱存在下，由1-全氟烷基取代的2-碘代烷烃和一氧化碳与水或醇以高收率合成了β位具有全氟烷基取代基的羧酸和酯。
• Co/Zn bimetal redox system promoted hydroperfluoroalkylation of acrylates with perfluoroalkyl iodides
  作者：Chang-Ming Hu、Yao-Ling Qiu

  DOI：10.1016/0040-4039(91)80611-9

  日期：1991.8

  Introduction of perfluoroalkyl unit into acrylates is performed successfully by the catalytic action of cobaloxime/Zn redox couple under mild conditions.

  通过在温和条件下钴肟/锌氧化还原对的催化作用，成功地将全氟烷基单元引入丙烯酸酯。
• Process for preparing fluorine-containing carboxylic acid ester
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0252736B1

  公开（公告）日：1991-07-24
• Reaction of Perfluoroalkyl Iodides with Electron-Deficient Olefins under UV Irradiation
  作者：Zai-Ming Qiu、Donald J. Burton

  DOI：10.1021/jo00116a038

  日期：1995.6

  The reaction of perfluoroalkyl iodides 1 with acrylates, acrylic acid, acrylamide, and acrylonitrile has been investigated. In the presence of a catalytic amount of palladium(0), the reaction of R(f)I with ethyl acrylate produces: mostly polymer. Under irradiation with 254 nm UV light, perfluoroalkyl iodides react with. ethyl acrylate to give high yields of the 1:1 addition products (74-88% isolated yield, CnF(2n+1)CH(2)CHICO(2)Et) and small amounts of 1:2 adducts (<10% NMR yield) at ambient temperature. The functionalized iodide 5-iodo-3-oxaoctafluoropentanesulfonyl fluoride also reacts with ethyl acrylate to give the 1:1 adduct in 88% yield. However, it has been found that the reaction selectivity is related to the length of the perfluoroalkyl group in 1 when methyl acrylate is employed in the reaction under similar conditions. Both 1:1 (56-76%) and 1:2 adducts [CnF(2n+1)- CH2CH(CO(2)Me)CH(2)CHICO(2)Me, 24-34%] are formed when methyl acrylate reacts with short-chain perfluoroalkyl iodides [CnF(2n+1)I, n less than or equal to 4], whereas the reaction of perfluorohexyl or longer chain perfluoroalkyl iodides [CnF(2n+1)I, n greater than or equal to 6] gives predominantly the 1:1 addition products (>85%). The formation of the 1:2 adduct can be efficiently suppressed by using excess R(f)I in the reaction. The reaction of N,N-dimethylacrylamide with perfluoropropyl iodide (1a) produces exclusively the 1:1 adduct. Products from the further elimination, reduction, and decarboxylation of the 1:1 and 1:2 adducts are observed when 1a reacts with methyl methacrylate under similar conditions. The reaction of 1a with acrylonitrile produces the 1:1 and 1:2 adducts in 53% and 47% yields, respectively. An addition-reduction product, n-C3F7CH2CH2CO2H (68%), is obtained in the reaction of acrylic acid with 1a.
• Cobaloxime-catalyzed hydroperfluoroalkylation of electron-deficient alkenes with perfluoroalkyl halides: reaction and mechanism
  作者：Changming Hu、Yaoling Qiu

  DOI：10.1021/jo00038a022

  日期：1992.6

  Direct hydroperfluoroalkylation of electron-deficient alkenes-ethyl acrylates 4, 7, and 8, acrylonitrile (5), and methyl vinyl ketone (6)-with perfluoroalkyl halides R(f)X (1, X = I;2, X = Br) in the presence of cobaloxime(III) (3) and zinc gives 1:1 hydroperfluoroalkylation adducts in good yields. This reaction provides a convenient synthesis of beta-(perfluoroalkyl)carboxylic esters 9, 12, and 13, nitriles 10, and ketones 11. Details of the reaction including effect of solvent, temperature, and ratio of reagents were examined. The reaction is proposed to proceed via a radical mechanism initiated by low-valent cobalt.