1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile | 162824-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile
• 英文别名: 1-[Phenyl-(4-phenylphenyl)methyl]imidazole-4,5-dicarbonitrile
• CAS: 162824-36-4
• 化学式: C₂₄H₁₆N₄
• 分子量: 360.418
• InChiKey: CFZARRXTVARVKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile 在 sodium hydroxide 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 24.5h， 生成 联苯苄唑
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023
• 作为产物：
  描述：

  4,5-二氰基咪唑 、 4-苯基-二苯基甲醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023

文献信息

• Robust late-stage benzylic C(sp3)–H aminations by using transition metal-free photoredox catalysis
  作者：Prakash Kumar Sahoo、Yu Zhang、Yuman Qin、Peng Ren、Robin Cauwenbergh、Gandhi Siva Raman、Shoubhik Das

  DOI：10.1016/j.jcat.2023.06.002

  日期：2023.9

  Herein we report a transition metal-free approach for the regioselective functionalization of benzylic C(sp3)H bonds in the presence of various heterocyclic amines as nucleophiles. This straightforward and general route has provided various benzylic amines, including twelve pharmaceutically relevant compounds.

  在此，我们报告了一种无过渡金属的方法，用于在各种杂环胺作为亲核试剂存在的情况下对苄基 C(sp 3 ) H 键进行区域选择性功能化。这种简单而通用的途径提供了各种苄基胺，包括十二种药学相关化合物。