(E)-methyl 2-methyl-4,4,5,5,6,6,6-heptafluorohex-2-enoate | 88021-94-7

• 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: (E)-methyl 2-methyl-4,4,5,5,6,6,6-heptafluorohex-2-enoate
• 英文别名: Methyl 4,4,5,5,6,6,6-heptafluoro-2-methyl-2-hexenoate；Methyl 4,4,5,5,6,6,6-heptafluoro-2-methylhex-2-enoate；methyl 4,4,5,5,6,6,6-heptafluoro-2-methylhex-2-enoate
• CAS: 88021-94-7
• 化学式: C₈H₇F₇O₂
• 分子量: 268.131
• InChiKey: LRMSPWCOOHABFD-UHFFFAOYSA-N

物化性质

• 沸点：
  151.8±40.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  七氟丁酸 、 甲基丙烯酸甲酯 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 Methyl 4,4,5,5,6,6,6-heptafluoro-2-methylhexanoate 、 (E)-methyl 2-methyl-4,4,5,5,6,6,6-heptafluorohex-2-enoate
  参考文献：
  名称：

  Coe, Paul L.; Owen, David M.; Pedler, Alan E., Journal of the Chemical Society. Perkin transactions I, 1983, p. 1995 - 1998

  摘要：

  DOI：

文献信息

• 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.
• Coe, Paul L.; Owen, David M.; Pedler, Alan E., Journal of the Chemical Society. Perkin transactions I, 1983, p. 1995 - 1998
  作者：Coe, Paul L.、Owen, David M.、Pedler, Alan E.

  DOI：——

  日期：——