[3-(2,6-di-isopropylphenyl)-(1-α-acetate)]imidazolium | 1084725-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [3-(2,6-di-isopropylphenyl)-(1-α-acetate)]imidazolium
• 英文别名: 3-(2,6-di-isopropylphenyl)-1-(α-acetato)-imidazolium；2-[3-[2,6-Di(propan-2-yl)phenyl]imidazol-1-ium-1-yl]acetate
• CAS: 1084725-85-8
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: VQTAJTUYTIRJKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [3-(2,6-di-isopropylphenyl)-(1-α-acetate)]imidazolium 、 palladium diacetate 在 LiN(i-Pr)2 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到
  参考文献：
  名称：

  Copper and palladium complexes with N-heterocyclic carbene ligands functionalised with carboxylate groups

  摘要：

  The new imidazolium salts functionalised with the trimethylsilyl ester group 1a-c, were easily obtained by quaternisation of alkyl- or aryl-imidazoles with trimethylsilyl bromoacetate. Salt 1a was isolated and fully characterised. It reacted with mesityl copper (Cu(5)Mes(5)) under trimethylsilyl abstraction to form the complex 2. Methanolysis of 1a-c gave good yields of the carboxylic acid functionalised imidazolium salts 3a-c. Deprotonation of the latter in liquid ammonia led to the zwitterionic imidazolium carboxylates 4a-c. Reaction of 4a with (Cu(5)Mes(5)) gave solutions from which the insoluble polymeric 5a crystallised slowly. Generation of the carboxylate-functionalised NHC in situ followed by reaction with Pd(OOCCH3)(2) gave the new complex 6a in which the NHC-carboxylate ligand is chelate bidentate. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.07.017
• 作为产物：
  描述：

  [3-(2,6-di-isopropylphenyl)-(1-acetic acid)]-imidazolium bromide 在 氨 作用下， 反应 0.25h， 以82%的产率得到[3-(2,6-di-isopropylphenyl)-(1-α-acetate)]imidazolium
  参考文献：
  名称：

  Copper and palladium complexes with N-heterocyclic carbene ligands functionalised with carboxylate groups

  摘要：

  The new imidazolium salts functionalised with the trimethylsilyl ester group 1a-c, were easily obtained by quaternisation of alkyl- or aryl-imidazoles with trimethylsilyl bromoacetate. Salt 1a was isolated and fully characterised. It reacted with mesityl copper (Cu(5)Mes(5)) under trimethylsilyl abstraction to form the complex 2. Methanolysis of 1a-c gave good yields of the carboxylic acid functionalised imidazolium salts 3a-c. Deprotonation of the latter in liquid ammonia led to the zwitterionic imidazolium carboxylates 4a-c. Reaction of 4a with (Cu(5)Mes(5)) gave solutions from which the insoluble polymeric 5a crystallised slowly. Generation of the carboxylate-functionalised NHC in situ followed by reaction with Pd(OOCCH3)(2) gave the new complex 6a in which the NHC-carboxylate ligand is chelate bidentate. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.07.017