5-bromo-2-(4,5-diphenyl-1H-imidazol-2-yl)phenol | 193466-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-bromo-2-(4,5-diphenyl-1H-imidazol-2-yl)phenol
• CAS: 193466-92-1
• 化学式: C₂₁H₁₅BrN₂O
• 分子量: 391.267
• InChiKey: ZZYLXLGJGXJPFF-UHFFFAOYSA-N

物化性质

• 沸点：
  571.8±50.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4,5-diphenyl-1H-imidazol-2-yl)phenol 、 三甲基铝 以 甲苯 为溶剂， 反应 3.0h， 以83.2%的产率得到dimethylaluminium 5-bromo-2-(4,5-diphenyl-1H-imidazol-2-yl)phenolate
  参考文献：
  名称：

  Dialkylaluminium 2-imidazolylphenolates: Synthesis, characterization and ring-opening polymerization behavior towards lactides

  摘要：

  The stoichiometric reaction of the 2-imidazolylphenols (L1-L9) with the trialkylaluminium reagents AlR3 (R = Me, Et and iBu), afforded the corresponding dialkylaluminium 2-imidazolylphenolate complexes [R2Al(L1-L9)] (C1-C11), which were characterized by H-1/C-13 NMR spectroscopy and by elemental analysis. The molecular structures of the representative complexes C1, C2, C4, C6 and C11 were determined by single-crystal X-Ray diffraction, and revealed a distorted tetrahedral geometry at aluminum. These dialkylaluminium 2-imidazolylphenolates (C1-C11) could efficiently catalyze the ring-opening polymerization of lactides to afford high molecular weight polylactide, both in the presence and absence of BnOH, and as such represent rare examples of the use of bi-dentate ligation at aluminum in such lactide polymerization systems. On the basis of the polymerization results for L-lactide, D-lactide and rac-lactide, the nature of the ligands and the aluminum bound alkyls were found to significantly affect the catalytic activity as well as the properties of the resultant polylactides. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.11.002
• 作为产物：
  描述：

  联苯甲酰 、 5-溴水杨醛 在 aluminium nitride 、 水 作用下， 以 neat (no solvent) 为溶剂， 反应 8.0h， 以86%的产率得到5-bromo-2-(4,5-diphenyl-1H-imidazol-2-yl)phenol
  参考文献：
  名称：

  Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia

  摘要：

  采用纳米氮化铝实现了一种简单、绿色且经济高效的合成三/四取代-1H-咪唑和2,3-二氢喹唑啉-4(1H)-酮的新方法。反应在无催化剂的条件下进行，产物的收率良好到优秀。

  DOI：

  10.1007/s12039-015-0890-2

文献信息

• l-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
  作者：Subhasis Samai、Ganesh Chandra Nandi、Pallavi Singh、M.S. Singh

  DOI：10.1016/j.tet.2009.10.019

  日期：2009.12

  A simple highly versatile and efficient synthesis of 2,4,5-trisubstituted imidazoles is achieved by three-component cyclocondensation of 1,2-dicarbonyl compound, aldehyde and ammonium acetate using l-proline as a catalyst in methanol at moderate temperature. To explore the utility of this method 1,2,4,5-tetrasubstituted imidazoles were also synthesized. The key advantages of this process are high yields

  在室温下，使用1-脯氨酸作为催化剂，通过1-脯氨酸作为催化剂，通过1,2-二羰基化合物，醛和乙酸铵的三组分环缩合，可以实现2,4,5-三取代的咪唑的简单高效且高效的合成。为了探索该方法的实用性，还合成了1,2,4,5-四取代的咪唑。该方法的主要优点是高产率，催化剂的成本效益，易于后处理和通过非色谱法纯化产物。