1,3-bis(2,6-diisopropyl-4-hydroxyphenyl)imidazolium chloride | 1620922-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(2,6-diisopropyl-4-hydroxyphenyl)imidazolium chloride
• CAS: 1620922-83-9
• 化学式: C₂₇H₃₇N₂O₂*Cl
• 分子量: 457.056
• InChiKey: DHRBZQGHTMDLSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(2,6-diisopropyl-4-hydroxyphenyl)imidazolium chloride 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1,3-bis[4-(octadecyloxy)-2,6-diisopropylphenyl]imidazolium tetrafluoroborate
  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 、 氯化铵 作用下， 以 乙醚 、 乙醇 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 73.67h， 生成 1,3-bis(2,6-diisopropyl-4-hydroxyphenyl)imidazolium chloride
  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

文献信息

• Cooperative NHC‐based Catalytic System Immobilised onto Carbon Materials for the Cycloaddition of CO ₂ to Epoxides
  作者：Myriam Y. Souleymanou、Fatima El‐Ouahabi、Anna M. Masdeu‐Bultó、Cyril Godard

  DOI：10.1002/cctc.202001816

  日期：2021.4.9

  as organocatalysts in the cycloaddition of CO2 with epoxides. The best performing organocatalyst was then non‐covalently immobilised onto carbon materials (carbon nanotubes (CNTs), reduced graphene oxide (rGO) and carbon beads (CBs)) via π‐π stacking interactions and their activity and recoverability in the cycloaddition reaction were studied. The heterogenised catalyst onto reduced graphene oxide (4 a@rGO)

  合成了新的pyr标记的咪唑鎓盐及其相应的羧酸盐，并将其作为有机催化剂在环氧化物与CO 2的环加成反应中进行了测试。然后，通过π-π堆积相互作用将性能最佳的有机催化剂非共价固定在碳材料上（碳纳米管（CNTs），还原氧化石墨烯（rGO）和碳珠（CBs）），并研究它们在环加成反应中的活性和可回收性。 。所述heterogenised催化剂上还原的石墨烯氧化物（4尽管观察到活性损失@rGO）被回收数次。该催化剂还用于在温和条件下转化一系列环氧化物。