4,4'-bis(tridecafluoro-n-hexyl)phenyl ether | 151707-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-bis(tridecafluoro-n-hexyl)phenyl ether
• 英文别名: 4,4'-bis(perfluoro-n-hexyl)diphenyl ether；1,1'-Oxybis[4-(tridecafluorohexyl)benzene]；1-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-4-[4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenoxy]benzene
• CAS: 151707-03-8
• 化学式: C₂₄H₈F₂₆O
• 分子量: 806.285
• InChiKey: CLBGZIRSQYPYBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  二苯基氯化膦 、 4,4'-bis(tridecafluoro-n-hexyl)phenyl ether 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 bis[(2-diphenylphosphino-4-tridecafluoro-n-hexyl)phenyl]ether
  参考文献：
  名称：

  Towards the synthesis of perfluoroalkylated derivatives of Xantphos

  摘要：

  An analogue of Xantphos incorporating four perfluoroalkyl groups has been prepared and successfully used as a ligand in the rhodium-catalysed hydroformylation of 1-octene in toluene. A number of perfluoroalkylated xanthene backbones have also been synthesised, but their conversion into preferentially perfluorocarbon solvent soluble Xantphos-type ligands, suitable for catalysis in fluorocarbon solvents, has not been successful. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.070
• 作为产物：
  描述：

  全氟己基碘烷 、 4,4'-二溴二苯醚 在 2,2'-联吡啶 、 铜 作用下， 以 氟苯 、 二甲基亚砜 为溶剂， 反应 72.0h， 以77%的产率得到4,4'-bis(tridecafluoro-n-hexyl)phenyl ether
  参考文献：
  名称：

  Towards the synthesis of perfluoroalkylated derivatives of Xantphos

  摘要：

  An analogue of Xantphos incorporating four perfluoroalkyl groups has been prepared and successfully used as a ligand in the rhodium-catalysed hydroformylation of 1-octene in toluene. A number of perfluoroalkylated xanthene backbones have also been synthesised, but their conversion into preferentially perfluorocarbon solvent soluble Xantphos-type ligands, suitable for catalysis in fluorocarbon solvents, has not been successful. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.070

文献信息

• Perfluoroalkylations and perfluorooxaalkylations. Part 1. Bromoaromatics as substrates in copper-mediated cross-coupling
  作者：Grace J. Chen、Loomis S. Chen、Kalathil C. Eapen

  DOI：10.1016/s0022-1139(00)80402-9

  日期：1993.7

  Tribromobenzenes, bromobiphenyl ethers and a bromoterphenyl ether have been used as substrates in copper-mediated cross-coupling reactions with perfluoroalkyl and per fluorooxaalkyl iodides. Excellent yields were obtained from perfluoroalkyl iodides as well as the ether iodides in which the ether oxygen was situated at position 5 or higher. However, ether iodides where the ether oxygen was at the 3-position gave only traces of the cross-coupled product, if any. This difference in reactivity is based on the relative position of the ether linkage to the reaction site and was more pronounced in reactions with aryl bromides than in reactions with aryl iodides.
• US5302760A
  申请人：——

  公开号：US5302760A

  公开（公告）日：1994-04-12
• Towards the synthesis of perfluoroalkylated derivatives of Xantphos
  作者：Dave J. Adams、David J. Cole-Hamilton、Duncan A.J. Harding、Eric G. Hope、Peter Pogorzelec、Alison M. Stuart

  DOI：10.1016/j.tet.2004.02.070

  日期：2004.4

  An analogue of Xantphos incorporating four perfluoroalkyl groups has been prepared and successfully used as a ligand in the rhodium-catalysed hydroformylation of 1-octene in toluene. A number of perfluoroalkylated xanthene backbones have also been synthesised, but their conversion into preferentially perfluorocarbon solvent soluble Xantphos-type ligands, suitable for catalysis in fluorocarbon solvents, has not been successful. (C) 2004 Elsevier Ltd. All rights reserved.