methyl 3-(1H-benzo[d]imidazol-1-yl)-benzoate | 1381947-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: methyl 3-(1H-benzo[d]imidazol-1-yl)-benzoate
• 英文别名: Methyl 3-(1h-benzo[d]imidazol-1-yl)benzoate；methyl 3-(benzimidazol-1-yl)benzoate
• CAS: 1381947-81-4
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: WCCSRCPLXQKEPK-UHFFFAOYSA-N

物化性质

• 沸点：
  442.7±47.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(1H-benzo[d]imidazol-1-yl)-benzoate 在 氯化亚砜 、 caesium carbonate 作用下， 以 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of Novel N-Heterocyclic Carbene-Oxazoline Palladium Complexes and Their Applications in Suzuki-Miyaura Cross-Coupling Reaction

  摘要：

  A series of novel N-heterocyclic carbene-oxazoline ligands were synthesized in six steps. Palladium complexes were obtained by deprotonation of the benzimidazole salts and subsequent ligation with Pd(OAc)(2) in THF. Different types of cyclic bis- and tetrapalladium complexes were achieved by modifying substituent of oxazoline group. The structures of these palladium complexes were characterized by NMR and X-ray diffraction analysis. Catalytic properties of these Pd-complexes were tested by Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1055/s-0033-1338848
• 作为产物：
  描述：

  3-氨基苯甲酸甲酯 在 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 caesium carbonate 、 对甲苯磺酸 、 双(2-二苯基磷苯基)醚 作用下， 以 甲醇 、 甲苯 为溶剂， 60.0~100.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 methyl 3-(1H-benzo[d]imidazol-1-yl)-benzoate
  参考文献：
  名称：

  Synthesis of Novel N-Heterocyclic Carbene-Oxazoline Palladium Complexes and Their Applications in Suzuki-Miyaura Cross-Coupling Reaction

  摘要：

  A series of novel N-heterocyclic carbene-oxazoline ligands were synthesized in six steps. Palladium complexes were obtained by deprotonation of the benzimidazole salts and subsequent ligation with Pd(OAc)(2) in THF. Different types of cyclic bis- and tetrapalladium complexes were achieved by modifying substituent of oxazoline group. The structures of these palladium complexes were characterized by NMR and X-ray diffraction analysis. Catalytic properties of these Pd-complexes were tested by Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1055/s-0033-1338848

文献信息

• Cu(I)–N-heterocyclic carbene-catalyzed base free C–N bond formation of arylboronic acids with amines and azoles
  作者：Maoyuan Zhang、Zengbing Xu、Dabin Shi

  DOI：10.1016/j.tet.2020.131861

  日期：2021.1

  A new N-heterocyclic carbene (NHC) precursor of imidazolium chloride and its corresponding Cu(I)–NHC complex 1 was synthesized. The complex 1 was found to be a highly effective catalyst for Chan-Evans-Lam coupling of arylboronic acid with amines and azoles (including imidazole, pyrazole and triazole), without addition of base at room temperature. Various substituents on three substrates can be tolerated

  合成了一种新的氯化咪唑鎓的N-杂环卡宾（NHC）前驱体及其相应的Cu（I）-NHC配合物1。发现在室温下不添加碱的情况下，络合物1是用于芳基硼酸与胺和唑类（包括咪唑，吡唑和三唑）的Chan-Evans-Lam偶联的高效催化剂。可以耐受三种底物上的各种取代基，从而以良好至极好的收率（62–94％）提供所需的偶联产物。该方法是实用的，并为构建C–N键提供了相应的铜催化Chan-Evans-Lam方法的替代方法。