(Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene | 756-63-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene
• 英文别名: trans-1,2-Difluor-1-triethylsilyl-pentadien-(1,4)；[(1Z)-1,2-difluoropenta-1,4-dienyl]-triethylsilane
• CAS: 756-63-8
• 化学式: C₁₁H₂₀F₂Si
• 分子量: 218.362
• InChiKey: XLWJAPRAUCEMGY-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene 在 potassium fluoride 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (E)-1,2-difluoro-1-(meta-nitrophenyl)-1,4-pentadiene
  参考文献：
  名称：

  Synthesis and functionalization of (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene

  摘要：

  The Zn reagent prepared from (E)-1,2-difluoro-1-iodo-2-triethylsilylethene followed by reaction with allyl bromide gave (Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene. Further reaction of (Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene with KF, n-Bu3SnCI, in DMF at 70 degrees C gave (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene. Coupling of (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene with substituted aryl iodides under Stille-Libeskind (Pd(PPh3)(4)/Cu(I)I) conditions gave the arylated product. Similar coupling of perfluorovinyl iodides stereospecifically gave the corresponding trienes. Hydroboration/oxidation with 9-BBN and H2O2 of (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene gave (Z)-4,5-difluoro-5-tri-n-butylstannyl-4-penten-1-ol. Additional couplings of (Z)-4,5-difluoro-5-tri-n-butylstannyl-4-penten-1-ol with substituted aryl iodides under Stille-Libeskind conditions gave the corresponding difunctionalized molecule. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.12.006
• 作为产物：
  描述：

  硅烷,[(1Z)-1,2-二氟乙烯基]三乙基- 、 3-溴丙烯 在 正丁基锂 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 环己烷 为溶剂， 反应 1.5h， 以75%的产率得到(Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene
  参考文献：
  名称：

  Synthesis and functionalization of (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene

  摘要：

  The Zn reagent prepared from (E)-1,2-difluoro-1-iodo-2-triethylsilylethene followed by reaction with allyl bromide gave (Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene. Further reaction of (Z)-1,2-difluoro-1-triethylsilyl-1,4-pentadiene with KF, n-Bu3SnCI, in DMF at 70 degrees C gave (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene. Coupling of (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene with substituted aryl iodides under Stille-Libeskind (Pd(PPh3)(4)/Cu(I)I) conditions gave the arylated product. Similar coupling of perfluorovinyl iodides stereospecifically gave the corresponding trienes. Hydroboration/oxidation with 9-BBN and H2O2 of (Z)-1,2-difluoro-1-tri-n-butylstannyl-1,4-pentadiene gave (Z)-4,5-difluoro-5-tri-n-butylstannyl-4-penten-1-ol. Additional couplings of (Z)-4,5-difluoro-5-tri-n-butylstannyl-4-penten-1-ol with substituted aryl iodides under Stille-Libeskind conditions gave the corresponding difunctionalized molecule. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.12.006