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.
• Photoinduced addition and addition–elimination reactions of perfluoroalkyl iodides to electron-deficient olefins
  作者：Tomoko Yajima、Ishrat Jahan、Takayuki Tonoi、Manami Shinmen、Aya Nishikawa、Kanako Yamaguchi、Izumi Sekine、Hajime Nagano

  DOI：10.1016/j.tet.2012.06.028

  日期：2012.8

  Photoinduced radical perfluoroalkylation of various simple electron-deficient olefins was achieved in the presence of an aqueous Na2S2O3 solution. The reactions proceeded smoothly to give addition or addition–elimination products. The ability of the products to be used as radical precursors or Michael acceptors was also demonstrated.

  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。
• Synthesis and NMR study of RF-oleic acid-F13
  作者：Gerald W. Buchanan、Rufus Smits、Elena Munteanu

  DOI：10.1016/s0022-1139(03)00162-3

  日期：2003.10

  A seven-step synthesis of Z-13,13,14,14,15,15,16,16,17,17,18,18,18-tridecafluoro-octadec-9-enoic acid (oleic acid-F13) is reported. The key step is a Wittig reaction to form the C9–C10 double bond with a Z:E isomeric ratio greater than 20:1. The nuclear magnetic resonance (NMR) spectrum is included and unambiguous assignments have been made with the aid of – correlation NMR spectroscopy (COSY spectra)

  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）。