N-acetyl-2-phenylbenzimidazole | 63759-84-2

• 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: N-acetyl-2-phenylbenzimidazole
• 英文别名: 1-acetyl-2-phenyl-1H-benzoimidazole；1h-Benzo[d]imidazole,1-acetyl-2-phenyl-；1-(2-phenylbenzimidazol-1-yl)ethanone
• CAS: 63759-84-2
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: UDPKAXAWPNCYRA-UHFFFAOYSA-N

物化性质

• 沸点：
  423.6±28.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-acetyl-2-phenylbenzimidazole 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 [Pd(N-acetyl-2-phenylbenzimidazole)(μ-Br)]2
  参考文献：
  名称：

  A way to obtain cyclopalladation of unsubstituted 2-phenylimidazole derivatives

  摘要：

  This work shows the difficulties of obtaining cyclopalladated complexes with 2-phenylimidazole and 2-phenylbenzimidazole as ligands. The protection of the NH group in the heterocycle with an acetyl group allows the formation of several cyclopalladated complexes of both ligands. The X-ray structure of the dimeric acetate-bridge complex of N-acetyl-2-phenyl-benzimidazole is described. The subsequent displacement of the protective group affords a monomeric cyclopalladated complex of 2-phenylbenzimidazole, as well as a coordination complex of this ligand.

  DOI：

  10.1016/0022-328x(96)06148-7
• 作为产物：
  描述：

  乙酰氯 、 2-苯基苯并咪唑 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以95.5%的产率得到N-acetyl-2-phenylbenzimidazole
  参考文献：
  名称：

  A way to obtain cyclopalladation of unsubstituted 2-phenylimidazole derivatives

  摘要：

  This work shows the difficulties of obtaining cyclopalladated complexes with 2-phenylimidazole and 2-phenylbenzimidazole as ligands. The protection of the NH group in the heterocycle with an acetyl group allows the formation of several cyclopalladated complexes of both ligands. The X-ray structure of the dimeric acetate-bridge complex of N-acetyl-2-phenyl-benzimidazole is described. The subsequent displacement of the protective group affords a monomeric cyclopalladated complex of 2-phenylbenzimidazole, as well as a coordination complex of this ligand.

  DOI：

  10.1016/0022-328x(96)06148-7

文献信息

• Palladium-Catalyzed Synthesis of Aromatic Ketones and Isoindolobenzimidazoles<i>via</i>Selective Aromatic CH Bond Acylation
  作者：Juyou Lu、Hao Zhang、Xiaowu Chen、Hongxia Liu、Yuyang Jiang、Hua Fu

  DOI：10.1002/adsc.201200743

  日期：2013.1.9

  A convenient and efficient palladium-catalyzed synthesis of aromatic ketones and isoindolobenzimidazoles has been developed via selective aromatic CH bond acylation. The protocol uses palladium acetate as the catalyst, readily available carboxylic acids as the acylating reagents, trifluoroacetic anhydride as the activated agent of the acids, and the corresponding aromatic ketones and isoindolobenzimidazoles

  通过选择性芳族CH键的酰化反应，已经开发了一种便捷高效的钯催化芳族酮和异吲哚并苯并咪唑类化合物的合成方法。该方案使用乙酸钯作为催化剂，容易获得的羧酸作为酰化剂，三氟乙酸酐作为酸的活化剂，并以良好或优异的收率获得了相应的芳族酮和异吲哚并苯并咪唑。该发现应为合成芳族酮和异吲哚并苯并咪唑类化合物提供一种新的有用的策略。
• A way to obtain cyclopalladation of unsubstituted 2-phenylimidazole derivatives
  作者：Fèlix Zamora、Santiago Luna、Pilar Amo-Ochoa、Luis Alfonso Martínez-Cruz、Angel Vegas

  DOI：10.1016/0022-328x(96)06148-7

  日期：1996.9

  This work shows the difficulties of obtaining cyclopalladated complexes with 2-phenylimidazole and 2-phenylbenzimidazole as ligands. The protection of the NH group in the heterocycle with an acetyl group allows the formation of several cyclopalladated complexes of both ligands. The X-ray structure of the dimeric acetate-bridge complex of N-acetyl-2-phenyl-benzimidazole is described. The subsequent displacement of the protective group affords a monomeric cyclopalladated complex of 2-phenylbenzimidazole, as well as a coordination complex of this ligand.