[3-(tert-butyl)-(1-acetic acid)]-imidazolium bromide | 1084725-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [3-(tert-butyl)-(1-acetic acid)]-imidazolium bromide
• CAS: 1084725-82-5
• 化学式: Br*C₉H₁₅N₂O₂
• 分子量: 263.134
• InChiKey: RIOWNXIXLLARTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.38
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.11
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [3-(tert-butyl)-(1-acetic acid)]-imidazolium bromide 在 氨 作用下， 反应 0.25h， 以58%的产率得到[3-(tert-butyl)-(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
• 作为产物：
  描述：

  甲硅烷基溴代乙酸三甲酯 、 1-叔丁基-1H-咪唑 在 甲醇 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.5h， 以56%的产率得到[3-(tert-butyl)-(1-acetic acid)]-imidazolium bromide
  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