1H,1H-perfluorohexyl nonaflate | 924894-08-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1H,1H-perfluorohexyl nonaflate
• 英文别名: 2,2,3,3,4,4,5,5,6,6,6-Undecafluorohexyl nonafluorobutane-1-sulfonate；2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 924894-08-6
• 化学式: C₁₀H₂F₂₀O₃S
• 分子量: 582.158
• InChiKey: BQOLVFQIEAAHQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  1H,1H-perfluorohexyl nonaflate 在 potassium fluoride 作用下， 以 三甘醇二甲醚 为溶剂， 反应 3.0h， 以68%的产率得到1H,1H-perfluorohexane
  参考文献：
  名称：

  An efficient stereoselective preparation of cis-perfluoroalkenylzinc reagents [(E)-RFCFCFZnCl] by the metallation of 1H,1H-perfluoroalkanes and their derivatization to cis-1-arylperfluoroalkenes [(Z)-RFCFCFAr]

  摘要：

  Various 1H1H-perfluoroalkanes (RFCF2CH2F, R-F = CF3, C2F5, C4F9, C5F11, C6F13, C10F21) were metallated using LDA in a THF solution of ZnCl2 at RT or -78 degrees C to produce the corresponding perfluoroalkenylzinc reagents (RFCF=CFZnCl) in a cis-selective fashion. An increased yield (75-83%) and cis-selectivity (>89%) of the perfluoroalkenylzinc reagents were observed for metallation reactions performed at -78 degrees C. The cis selectivity was excellent for 1H,1H-perfluoroalkanes with larger RF groups (C4F9, C5F11, C6F13, >96%). The cis-perfluoroalkenylzinc [(E)-RFCF=CFZnCl] reagents were coupled with aryl iodides to obtain cis-1-arylperfluoroalkenes [(Z)-RFCF=CFAr] in 71-95% isolated yields. The cis-perfluoroalkenylzinc reagents upon iodinolysis produced cis-1-iodoperfluoroalkenes [(E)-RFCF=CFI] in 68-70% isolated yield. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.022
• 作为产物：
  描述：

  十一氟正己烷-1-醇 、 全氟丁基磺酰氟 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到1H,1H-perfluorohexyl nonaflate
  参考文献：
  名称：

  An efficient stereoselective preparation of cis-perfluoroalkenylzinc reagents [(E)-RFCFCFZnCl] by the metallation of 1H,1H-perfluoroalkanes and their derivatization to cis-1-arylperfluoroalkenes [(Z)-RFCFCFAr]

  摘要：

  Various 1H1H-perfluoroalkanes (RFCF2CH2F, R-F = CF3, C2F5, C4F9, C5F11, C6F13, C10F21) were metallated using LDA in a THF solution of ZnCl2 at RT or -78 degrees C to produce the corresponding perfluoroalkenylzinc reagents (RFCF=CFZnCl) in a cis-selective fashion. An increased yield (75-83%) and cis-selectivity (>89%) of the perfluoroalkenylzinc reagents were observed for metallation reactions performed at -78 degrees C. The cis selectivity was excellent for 1H,1H-perfluoroalkanes with larger RF groups (C4F9, C5F11, C6F13, >96%). The cis-perfluoroalkenylzinc [(E)-RFCF=CFZnCl] reagents were coupled with aryl iodides to obtain cis-1-arylperfluoroalkenes [(Z)-RFCF=CFAr] in 71-95% isolated yields. The cis-perfluoroalkenylzinc reagents upon iodinolysis produced cis-1-iodoperfluoroalkenes [(E)-RFCF=CFI] in 68-70% isolated yield. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.022