2-Iodoperfluoroheptane | 24394-25-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 2-Iodoperfluoroheptane
• 英文别名: 2-Iodopentadecafluoroheptane；1,1,1,2,2,3,3,4,4,5,5,6,7,7,7-pentadecafluoro-6-iodoheptane
• CAS: 24394-25-0
• 化学式: C₇F₁₅I
• 分子量: 495.958
• InChiKey: OPYCVFHSYCUOGR-UHFFFAOYSA-N

物化性质

• 沸点：
  137.5 °C
• 密度：
  2.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-Iodoperfluoroheptane 在 copper(l) chloride 三正丁基氢锡 、 C.I.酸性橙108 作用下， 以 various solvent(s) 为溶剂， 反应 16.5h， 生成 1,1,1,2,2,3,3,4,4,5,5,6-Dodecafluoro-6-trifluoromethyl-octane
  参考文献：
  名称：

  Controlled step-wise telomerization of vinylidene fluoride, hexafluoropropene and trifluoroethylene with iodofluorinated transfer agents

  摘要：

  Highly fluorinated cotelomers having the structure F(TFE)(w)(VDF)(x)(HFP)(y)(TrFE)(z)I containing one or several tetrafluoroethylene (TFE), vinylidene fluoride (or 1,1-difluoroethylene, VDF), hexafluoropropene (HFP) or trifluoroethylene (TrFE) base units were synthesized by thermal step-wise cotelomerization of these fluoroolefins with perfluoroalkyl iodides. H-1 and F-19 NMR allowed one to characterize these cotelomers and to assess the defects of chaining arid the molecular weights. While the monoadduct produced from VDF exclusively exhibits RFCH2CF2I structure, that prepared from TrFE was composed of RFCFHCF2I and RFCF2CFHI isomers, the ratio of which is directed from the electrophilicity of R-F* radical. The reactivity of the C-I bond in R-F-Q-CXY-I depends on the nature of the Q spacer and on the reactivity of the fluorinated monomer (e.g., thermal initiations of VDF, TrFE and HFP were efficient from 180, 195 and 210 degrees C, respectively). The mechanism of the addition of the radical generated from the iodinated transfer agent to the fluoroalkene is explained by means of its electrophilic attack to the more nucleophilic (i.e., the less electrophilic) side of the olefin. Ethylenation of these fluorocotelomers was successfully achieved from various initiations (thermal, redox or from peroxides) with best results from redox catalysis. Thermal properties of several fluorotelomers (glass transition temperatures, T-g and melting temperatures, T-m) were assessed. They were linked to the number of consecutive CF2 groups (for the crystalline zones) and bulky side groups which induced amorphous regions. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00287-0
• 作为产物：
  描述：

  六氟丙烯 、 全氟碘代丁烷 反应 75.0h， 以42%的产率得到2-Iodoperfluoroheptane
  参考文献：
  名称：

  荧光合成胶。第三方 六氟丙烯全氟烷基化技术

  摘要：

  描述了通过六氟丙烯与支链[（CF 3）2 CFI]或直链（nC 4 F 9 I或nC 6 F 13 I）全氟烷基碘化物的热端聚反应合成高度氟化的端粒。两种线性调聚物都导致前三个加合物具有较高的C n F 2 n + 1I转化率。有趣的是，一加合物由主要的正态C n F 2 n + 1，CF 2 CFICF 3异构体和次要的反向C n F 2 n + 1 CF（CF 3）组成。CF 2 I端粒，其比例取决于温度。该过程的活化能确定为27 kJ mol -1。但是，在类似的反应中，当（CF 3）2 CFI作为调聚原时，选择性地生成了正常的单加合物，但只有8％的调聚原转化率。所有这些端粒均被还原为R F C 3 F 6 H，其1 H和19 F NMR光谱证实了每种衍生物的结构。

  DOI：

  10.1016/0022-1139(95)03241-5

文献信息

• Synthèse de télomères fluorés. Partie IL Télomérisation du trifluoroéthylène avec des iodures de perfluoroalkyle
  作者：J. Balagué、B. Améduri、B. Boutevin、G. Caporiccio

  DOI：10.1016/0022-1139(95)03280-q

  日期：1995.8

  The synthesis of highly fluorinated telomers by thermal telomerization of trifluoroethylene with branched (i-C3F7I, C5F11CFICF3) or linear (C4F9I, C4F9CH2CF2I) fluoroalkyl iodides is presented. All these telomerizations led to the first three telomeric adducts with high R(F)I conversion. Interestingly, the monoadduct was composed of two isomers R(F)CF(2)CFHI (1) and R(F)CFHCF(2)I (2), the ratio of which depends upon the electrophilicity of the radical R(F.). The more electrophilic this radical, the higher the amount of isomer 2, according to a mechanism that responds to both the polar and the mesomeric effects for growing radicals.