(E)-1-chloro-2-(3,3,4,4,5,5,6,6,6-nonafluoro-hexen-1-yl)-benzene | 1415225-26-1

• 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: (E)-1-chloro-2-(3,3,4,4,5,5,6,6,6-nonafluoro-hexen-1-yl)-benzene
• CAS: 1415225-26-1
• 化学式: C₁₂H₆ClF₉
• 分子量: 356.618
• InChiKey: LMQSJZUPFPFLGN-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  1-氯-2-碘苯 、 1,3-bis(1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexan-1-yl)tetramethyldisiloxane 在 potassium fluoride 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以70%的产率得到(E)-1-chloro-2-(3,3,4,4,5,5,6,6,6-nonafluoro-hexen-1-yl)-benzene
  参考文献：
  名称：

  Siloxane based syntheses of fluorous ethenes and their tandem Heck reactions with aryl iodides

  摘要：

  Perfluoroalkyl-ethenes (RfnCH=CH2, 6a-c; a, n = 4; b, n = 6; c, n = 8) were prepared in good isolated yields (67-89%) and high purity (GC assay > 98%) from various fluorinated organosilanes in fluoride-anion assisted protodesilylation reactions. The environmentally more benign 'KF/NEt3/H2O' reagent combination introduced here was found as an effective substitute for the commonly used tetrabutylammonium-fluoride trihydrate (TBAF center dot 3H(2)O) as a fluoride source. Fluorous styrenes ((E)-RfnCH=CH-Ar, 8) were then prepared in good isolated yields (58-93%/iodoarene) and purities (GC assay > 95%) with the Pd(0) catalyzed Heck coupling of iodoarenes (Ar-1, 7) and perfluoroalkyl-ethenes generated in situ by the fluoride assisted cleavage of (beta-perfluoroalkyl-alpha-iodo-ethyl)-siloxane ((RfnCH2CH(I)SiMe2](2)O, 3) precursors in DMF solution at elevated temperatures. They are accessible by the one-pot reaction of dimethylvinylchlorosilane (CH2=CHSiMe2Cl, 2) and perfluoroalkyl iodides (R-I, 1) as we reported earlier. Similarly, the radical chain addition of C8F17I to CH2=CHSi(OMe)(3) (9) gave (beta-perfluorooctyl-alpha-iodo-ethyl)-trimethoxysilane ([C8F17CH2CH(I)]Si(OMe)(3), 10) in good yield, which then was reacted with silica gel in dry toluene to obtain an SiO2-bonded (perfluorooctyl)ethene surrogate [silica(-O-)(3)Si-CH(I)CH2C8F17, 11]. The fluoride assisted cleavage of 11 and tandem Heck reaction with iodobenzene afforded the appropriate cross-coupled product (E)-C8F17CH=CHPh. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.07.010