2-[1,1,2-trifluoro-2-(heptafluoropropoxy)ethyl]tetrahydrofuran | 185697-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 2-[1,1,2-trifluoro-2-(heptafluoropropoxy)ethyl]tetrahydrofuran
• 英文别名: (C4H7O)CF2CHF-O-CF2CF2CF3；2-[1,1,2-Trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethyl]oxolane；2-[1,1,2-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethyl]oxolane
• CAS: 185697-75-0
• 化学式: C₉H₈F₁₀O₂
• 分子量: 338.145
• InChiKey: REUAAGSKXMOGMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  全氟正丙基乙烯基醚 、 2-[1,1,2-trifluoro-2-(heptafluoropropoxy)ethyl]tetrahydrofuran 在 丙酮 作用下， 反应 9.0h， 以16%的产率得到2,5-Bis[1,1,2-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethyl]oxolane
  参考文献：
  名称：

  Radical additions to fluoro-olefins. photochemical mono-fluoroalkylation and sequential bis-fluoroalkylation of oxolane

  摘要：

  Oxolane was fluoroalkylated by its photoadditions under atmospheric pressure. Monofluoro-alkylations were carried out with hexafluoropropene (1) and perfluorovinyl ethers C3F7O-[CF(CF3)CF2O](n)-CF=CF2 (2-4, n = 0-2) by direct photoexcitation of the olefins to give high yields of addition products 9-12 (81-94%). The reactions were completely regioselective at the oxolane molecule and almost completely regioselective (93-99%) at the double bond of fluoro-olefins; no bis-fluoroalkylated oxolanes were detected. The completely selective introduction of a second fluoroalkyl into position 5 of the oxolane molecule was accomplished by acetone-sensitised photoaddition of 2-fluoroalkylated oxolanes 9, 10 to fluoro-olefins 1 and 2. By products from reactions of the dimethylketyl radical which is formed in the initiation step were isolated and have given some evidence about the reaction mechanism that is discussed.

  DOI：

  10.1016/s0022-1139(96)03511-7
• 作为产物：
  描述：

  全氟(2-甲基-3-氧杂己基)氟化物 在 sodium hydroxide 、 sodium fluoride 作用下， 反应 2.0h， 生成 2-[1,1,2-trifluoro-2-(heptafluoropropoxy)ethyl]tetrahydrofuran
  参考文献：
  名称：

  Radical additions to fluoro-olefins. photochemical mono-fluoroalkylation and sequential bis-fluoroalkylation of oxolane

  摘要：

  Oxolane was fluoroalkylated by its photoadditions under atmospheric pressure. Monofluoro-alkylations were carried out with hexafluoropropene (1) and perfluorovinyl ethers C3F7O-[CF(CF3)CF2O](n)-CF=CF2 (2-4, n = 0-2) by direct photoexcitation of the olefins to give high yields of addition products 9-12 (81-94%). The reactions were completely regioselective at the oxolane molecule and almost completely regioselective (93-99%) at the double bond of fluoro-olefins; no bis-fluoroalkylated oxolanes were detected. The completely selective introduction of a second fluoroalkyl into position 5 of the oxolane molecule was accomplished by acetone-sensitised photoaddition of 2-fluoroalkylated oxolanes 9, 10 to fluoro-olefins 1 and 2. By products from reactions of the dimethylketyl radical which is formed in the initiation step were isolated and have given some evidence about the reaction mechanism that is discussed.

  DOI：

  10.1016/s0022-1139(96)03511-7

文献信息

• Radical Additions of Heptafluoropropyl Trifluorovinyl Ether
  作者：Akihiro Hosoya、Tadashi Narita、Hiroshi Hamana

  DOI：10.1135/cccc20081663

  日期：——

  The radical addition reactions of heptafluoropropyl trifluorovinyl ether (CF₂=CF-O-C₃F₇) with cyclic ethers such as tetrahydrofuran, tetrahydropyran, 1,4-dioxane and 1,3-dioxolane were investigated to afford the corresponding one to one addition products in fairly high yields in the presence of dibenzoyl peroxide at 60 °C. The method provides a facile way to prepare cyclic ethers possessing fluoroalkyl substituents.

  heptafluoropropyl trifluorovinyl ether（CF2=CF-O-C3F7）与环氧化合物（如四氢呋喃、四氢吡喃、1,4-二氧六环和1,3-二氧杂环）的自由基加成反应在60°C下在过氧化二苯甲酰的存在下进行研究，得到了相应的一对一加成产物，收率相当高。该方法提供了一种简便的制备具有氟烷基取代基的环氧化合物的方法。
• Radical additions to fluoroolefins. Photochemical fluoroalkylation of alkanols and alkane diols with perfluoro vinyl ethers; photo-supported O-alkylation of butane-1,4-diol with hexafluoropropene
  作者：Vladimír Cîrkva、Radek Polák、Oldřich Paleta

  DOI：10.1016/s0022-1139(96)03514-2

  日期：1996.10

  photoaddition reactions with hexafluoropropene and perfluoro (propyl vinyl) ether under atmospheric pressure, by which monofluoroalkylated and bis-fluoroalkylated products were obtained. 1,3-Diols were completely unreactive under the conditions. 2,2,2-Trifluoroethanol, tert.butyl alcohol and methyl tert.butyl ether appeared to be inert solvents for the additions while acetonitrile quenched the reactions. The

  在大气压下，通过与六氟丙烯和全氟（丙基乙烯基）醚的光加成反应，将丁烷-1,4-二醇进行氟烷基化，从而获得单氟烷基化和双氟烷基化的产物。1,3-二醇在这种条件下是完全不反应的。2,2,2-三氟乙醇，叔丁醇和甲基叔丁基醚似乎是添加的惰性溶剂，而乙腈则使反应猝灭。在全氟乙烯基醚与与六氟丙烯相比具有较低区域选择性（相对于区域异构体为7％相对）的烷醇的光加成反应中，对全氟乙烯基醚的反应性进行了研究（测试）。出人意料的是，在乙腈中观察到了光支撑的碱诱导的丁烷1，，4-二醇的亲核性单双加双加成反应。