Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoate | 165281-74-3

• 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 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoate
• 英文别名: ethyl 2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate；ethyl 2-iodo-3-(n-perfluorohexyl)propanoate；ethyl 2-iodo-3-perfluorohexylpropanoate
• CAS: 165281-74-3
• 化学式: C₁₁H₈F₁₃IO₂
• 分子量: 546.067
• InChiKey: JGUVWYUPMQRWNA-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 1 Torr)
• 密度：
  1.796±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoate 在 lithium aluminium tetrahydride 、 氢碘酸 、 pyridinium chlorochromate 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononal
  参考文献：
  名称：

  R F-油酸-F 13的合成及NMR研究

  摘要：

  Z -13,13,14,14,15,15,16,16,17,17,18,18,18-三溴全氟十八烷基-9-烯酸（油酸-F 13）的七步合成法是报告。关键步骤是Wittig反应，以形成Z：E异构体比率大于20：1的C9-C10双键。在核磁共振（NMR）光谱被包括和明确的指配已与借助于-相关NMR谱（COZY光谱）。

  DOI：

  10.1016/s0022-1139(03)00162-3
• 作为产物：
  描述：

  全氟己基碘烷 、 丙烯酸乙酯 在 sodium thiosulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以97%的产率得到Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoate
  参考文献：
  名称：

  全氟烷基碘与缺电子烯烃的光诱导加成和消除反应

  摘要：

  在Na 2 S 2 O 3水溶液的存在下，实现了各种简单的缺电子烯烃的光诱导自由基全氟烷基化。反应进行顺利，得到加成或加成消除产物。还证明了该产品用作自由基前体或迈克尔受体的能力。

  DOI：

  10.1016/j.tet.2012.06.028

文献信息

• Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides
  作者：Tomoko Yajima、Kanako Yamaguchi、Rie Hirokane、Emiko Nogami

  DOI：10.1016/j.jfluchem.2013.02.019

  日期：2013.6

  The photoinduced radical hydroperfluoroalkylation of unsaturated carboxylic acids using TTMSS as a H-donor was successfully developed. The stereoselective reaction using Oppolzer's camphorsultum was also achieved to give high stereoselectivity. The reaction was also effective for N-phthalimide-dehydroamino acid and the product was easily converted to the corresponding amino acid and a peptide derivative. (C) 2013 Elsevier B.V. All rights reserved.
• 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.