1-(2,5-dihydroxybenzyl)-3-methylimidazolium bromide | 1307314-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2,5-dihydroxybenzyl)-3-methylimidazolium bromide
• CAS: 1307314-79-9
• 化学式: Br*C₁₁H₁₃N₂O₂
• 分子量: 285.14
• InChiKey: YKOOICHIXJCXAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.22
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-(2,5-dimethoxybenzyl)imidazole 在 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(2,5-dihydroxybenzyl)-3-methylimidazolium bromide
  参考文献：
  名称：

  Palladium(II) complexes of imidazolin-2-ylidene N-heterocyclic carbene ligands with redox-active dimethoxyphenyl or (hydro)quinonyl substituents

  摘要：

  Four novel imidazolium salts, precursors to N-heterocyclic carbene (NHC) ligands, with 2,5-dimethoxybenzyl or 2,5-dihydroxybenzyl (i.e., p-hydroquinone) substituents have been prepared. The crystal structure of the hydroquinone-substituted imidazolium salt (H3LBr)-Br-3 reveals Br center dot center dot center dot H-O bridged chiral chains of alternating [H3L3](+) cations and Br counter-ions parallel to the x-axis. Palladium(II) complexes were accessible from reactions of the dimethoxyphenyl-substituted imidazolium precursors with palladium(II) acetate, but not from reactions of imidazolium cations with hydroquinonyl substituents. The crystal structure of the bis(dimethoxybenzyl)-substituted bis(NHC)Pd complex, cis-[PdBr2(L-2)] (2), is described. Puckering of the bis(NHC) ligand leads to a cleft in which an included molecule of dimethylformamide is situated. The cleft is closed by one of the dimethoxybenzyl groups which p-stacks with the dimethylformamide; the other dimethoxybenzyl group points away from the cleft and Pd(II) centre. Reaction of complex 2 with BBr3 afforded the targeted bis(hydroquinone)-substituted bis(NHC) Pd(II) complex 3 (97% yield) which, in turn, was oxidised by 2,3-dichloro-5,6-dicyano-benzoquinone to the corresponding p-benzoquinone-substituted bis(NHC) Pd(II) complex 4 (98% yield). The cyclic voltammograms of the Pd(II) complexes 2-4 reveal waves that are attributed to an admix of the anticipated ligand-centred and [Pd(C-NHC)(2)Br-2]-centred processes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.02.007