N,N'-bis(2,2-diethoxyethyl)imidazolium bromide | 1095571-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,N'-bis(2,2-diethoxyethyl)imidazolium bromide
• CAS: 1095571-82-6
• 化学式: Br*C₁₅H₂₉N₂O₄
• 分子量: 381.31
• InChiKey: ZCKIUFFXEHHJST-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.42
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  45.73
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,2-diethoxyethyl)imidazolium bromide 在 ammonium hexafluorophosphate 作用下， 以 丙酮 为溶剂， 以85%的产率得到N,N'-bis(2,2-diethoxyethyl)imidazolium hexafluorophosphate
  参考文献：
  名称：

  Novel Ag(I), Pd(II), Ni(II) complexes of N,N′-bis-(2,2-diethoxyethyl)imidazole-2-ylidene: Synthesis, structures, and their catalytic activity towards Heck reaction

  摘要：

  Tetra-ether substituted imidazolium salts, LHX ( where LH = N,N'-bis(2,2-diethoxyethyl) imidazolium cation and X = Br, BF4, PF6, BPh4, NO3 and NTf2 anions) were derived from imidazole. Attempts to produce aldehyde functionalized imidazolium salt through acid hydrolysis of LHBr resulted an unexpected tetra-hydroxy compound LAHBr and the dialdehyde compound LBHBr. Reaction of LHBr with Ag2O afforded [L2Ag][AgBr2] (1). Mononuclear Pd-complex trans-[L2PdCl2] (2) and dinuclear Pd- complex [(LPdCl2)(2)] ( 3) were obtained by 1: 1 and 1: 2 reaction of in situ generated Ag-carbene with Pd(CH3CN)(2)Cl-2. cis-[LPdPPh3Cl2] (4) was synthesized from reaction of PPh3 with dinuclear complex 3. Hydrolysis of 3 under acidic conditions also generates a hydroxy derivative 3A and the aldehyde derivative 3B. Direct heating of LHBr with Ni(OAc)(2)center dot 4H(2)O at 120 degrees C under vacuum generated trans-[L2NiBr2] (5). These complexes were characterized by NMR, mass, elemental analysis, and X-ray single crystal diffraction analysis. Pd- Pd interaction was observed in 3. All the Pd complexes exhibited excellent catalytic activity in Heck reaction. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.017
• 作为产物：
  描述：

  咪唑 、 2-溴-1,1-二乙氧基乙烷 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以80%的产率得到N,N'-bis(2,2-diethoxyethyl)imidazolium bromide
  参考文献：
  名称：

  Novel Ag(I), Pd(II), Ni(II) complexes of N,N′-bis-(2,2-diethoxyethyl)imidazole-2-ylidene: Synthesis, structures, and their catalytic activity towards Heck reaction

  摘要：

  Tetra-ether substituted imidazolium salts, LHX ( where LH = N,N'-bis(2,2-diethoxyethyl) imidazolium cation and X = Br, BF4, PF6, BPh4, NO3 and NTf2 anions) were derived from imidazole. Attempts to produce aldehyde functionalized imidazolium salt through acid hydrolysis of LHBr resulted an unexpected tetra-hydroxy compound LAHBr and the dialdehyde compound LBHBr. Reaction of LHBr with Ag2O afforded [L2Ag][AgBr2] (1). Mononuclear Pd-complex trans-[L2PdCl2] (2) and dinuclear Pd- complex [(LPdCl2)(2)] ( 3) were obtained by 1: 1 and 1: 2 reaction of in situ generated Ag-carbene with Pd(CH3CN)(2)Cl-2. cis-[LPdPPh3Cl2] (4) was synthesized from reaction of PPh3 with dinuclear complex 3. Hydrolysis of 3 under acidic conditions also generates a hydroxy derivative 3A and the aldehyde derivative 3B. Direct heating of LHBr with Ni(OAc)(2)center dot 4H(2)O at 120 degrees C under vacuum generated trans-[L2NiBr2] (5). These complexes were characterized by NMR, mass, elemental analysis, and X-ray single crystal diffraction analysis. Pd- Pd interaction was observed in 3. All the Pd complexes exhibited excellent catalytic activity in Heck reaction. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.017