1,3-bis(4-{3-[(tert-butoxycarbonyl)amino]propyloxy}-2,6-diisopropylphenyl)imidazolium iodide | 1620922-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,3-bis(4-{3-[(tert-butoxycarbonyl)amino]propyloxy}-2,6-diisopropylphenyl)imidazolium iodide
• CAS: 1620922-84-0
• 化学式: C₄₃H₆₇N₄O₆*I
• 分子量: 862.933
• InChiKey: SUSDDONFJKALKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  54.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  103.93
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-{3-[(tert-butoxycarbonyl)amino]propyloxy}-2,6-diisopropylphenyl)imidazolium iodide 在 N,N-二异丙基乙胺 、 乙酰氯 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 1,3-bis{4-[3-(norbornene-2-carboxamido)propyloxy]-2,6-diisopropylphenyl}imidazolium hexafluorophosphate
  参考文献：
  名称：

  功能化可烷氧基连接的N-杂环碳原子配体的模块化合成和用于布赫瓦尔德-哈特维格胺胺化的活性催化剂

  摘要：

  AbstractModular syntheses of functionalised, alkoxy‐tethered 1,3‐bis(2,4,6‐trimethylphenyl)imidazolium (IMes⋅H+) and 1,3‐bis(2,6‐diisopropylphenyl)imidazolium (IPr⋅H+) derivatives 1,3‐bis(4‐alkyloxy‐2,4,6‐trimethylphenyl)imidazolium (IXyOR⋅H+) and 1,3‐bis(4‐alkyloxy‐2,6‐diisopropylphenyl)imidazolium (IPrOR⋅H+) are reported. A reliable synthesis of the key starting material 4‐amino‐3,5‐diisopropylphenol is also described. Etherification of hydroxy‐decorated ligand intermediates before formation of the imidazolium core and subsequent modification, or direct etherification of the versatile synthon IPrOH⋅HCl, allowed access to various linker types including triethoxysilyl, primary amino and norbornenyl, which are not accessible by other methods. An IPrOR–palladium(II) complex was prepared, and its catalytic activity was evaluated in challenging Buchwald–Hartwig aminations of aryl chlorides. This precatalyst displayed excellent activity and selectivity under mild reaction conditions, achieving in some cases a 10‐fold improvement in TOF relative to the IPr‐based version. An unexpected activity profile was observed wherein sterically demanding anilines were coupled more easily than those lacking ortho‐substitution.magnified image

  DOI：

  10.1002/adsc.201300903
• 作为产物：
  描述：

  2,6-diisopropylnitrobenzene 在 甲酸 、 硫酸 、 potassium carbonate 、 氯化铵 作用下， 以 乙醚 、 乙醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 75.67h， 生成 1,3-bis(4-{3-[(tert-butoxycarbonyl)amino]propyloxy}-2,6-diisopropylphenyl)imidazolium iodide
  参考文献：
  名称：

  功能化可烷氧基连接的N-杂环碳原子配体的模块化合成和用于布赫瓦尔德-哈特维格胺胺化的活性催化剂

  摘要：

  AbstractModular syntheses of functionalised, alkoxy‐tethered 1,3‐bis(2,4,6‐trimethylphenyl)imidazolium (IMes⋅H+) and 1,3‐bis(2,6‐diisopropylphenyl)imidazolium (IPr⋅H+) derivatives 1,3‐bis(4‐alkyloxy‐2,4,6‐trimethylphenyl)imidazolium (IXyOR⋅H+) and 1,3‐bis(4‐alkyloxy‐2,6‐diisopropylphenyl)imidazolium (IPrOR⋅H+) are reported. A reliable synthesis of the key starting material 4‐amino‐3,5‐diisopropylphenol is also described. Etherification of hydroxy‐decorated ligand intermediates before formation of the imidazolium core and subsequent modification, or direct etherification of the versatile synthon IPrOH⋅HCl, allowed access to various linker types including triethoxysilyl, primary amino and norbornenyl, which are not accessible by other methods. An IPrOR–palladium(II) complex was prepared, and its catalytic activity was evaluated in challenging Buchwald–Hartwig aminations of aryl chlorides. This precatalyst displayed excellent activity and selectivity under mild reaction conditions, achieving in some cases a 10‐fold improvement in TOF relative to the IPr‐based version. An unexpected activity profile was observed wherein sterically demanding anilines were coupled more easily than those lacking ortho‐substitution.magnified image

  DOI：

  10.1002/adsc.201300903