N-benzyl-2-(4-methoxyphenyl)-4-(4-trifluoromethylphenyl)-5-phenylimidazole | 1401316-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-2-(4-methoxyphenyl)-4-(4-trifluoromethylphenyl)-5-phenylimidazole
• 英文别名: 1-Benzyl-2-(4-methoxyphenyl)-5-phenyl-4-[4-(trifluoromethyl)phenyl]imidazole；1-benzyl-2-(4-methoxyphenyl)-5-phenyl-4-[4-(trifluoromethyl)phenyl]imidazole
• CAS: 1401316-07-1
• 化学式: C₃₀H₂₃F₃N₂O
• 分子量: 484.521
• InChiKey: RATPGNOCHPDUBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-(4-methoxyphenyl)-4-(4-trifluoromethylphenyl)-5-phenylimidazole 在 Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 以100%的产率得到2-(4-methoxyphenyl)-5-phenyl-4-(4-trifluoromethylphenyl)-1H-imidazole
  参考文献：
  名称：

  One-pot Sequential Direct C–H Bond Arylation of Azoles Catalyzed by [Pd(phen)₂](PF₆)₂: Synthetic Methods for Triarylated Azoles

  摘要：

  Synthetic methods for triarylated azoles containing three different aryl groups via one-pot sequential multiple C-H bond arylations are described. The one-pot sequential diarylation of C5-monoarylated azoles was achieved by the simple sequential addition of two different aryl iodides with a [Pd(phen)(2)]PF6 catalytic system. The one-pot triarylation of N-methylimidazole was achieved by the combination of a previously reported Pd(OAc)(2)-P(2-furyl)(3) system and the present [Pd(phen)(2)]PF6 system. In this case, portionwise addition of aryl halide, base and the catalyst in the final step significantly improved the overall yield of the desired triarylated product These protocols led to triarylated azoles without a loss of efficiency compared to the corresponding previously reported stepwise syntheses via direct C-H bond arylation.

  DOI：

  10.1021/jo301621t
• 作为产物：
  描述：

  1-苄基-5-苯基咪唑 在 [Pd(phen)2](PF₆)2 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 N-benzyl-2-(4-methoxyphenyl)-4-(4-trifluoromethylphenyl)-5-phenylimidazole
  参考文献：
  名称：

  One-pot Sequential Direct C–H Bond Arylation of Azoles Catalyzed by [Pd(phen)₂](PF₆)₂: Synthetic Methods for Triarylated Azoles

  摘要：

  Synthetic methods for triarylated azoles containing three different aryl groups via one-pot sequential multiple C-H bond arylations are described. The one-pot sequential diarylation of C5-monoarylated azoles was achieved by the simple sequential addition of two different aryl iodides with a [Pd(phen)(2)]PF6 catalytic system. The one-pot triarylation of N-methylimidazole was achieved by the combination of a previously reported Pd(OAc)(2)-P(2-furyl)(3) system and the present [Pd(phen)(2)]PF6 system. In this case, portionwise addition of aryl halide, base and the catalyst in the final step significantly improved the overall yield of the desired triarylated product These protocols led to triarylated azoles without a loss of efficiency compared to the corresponding previously reported stepwise syntheses via direct C-H bond arylation.

  DOI：

  10.1021/jo301621t

文献信息

• One-pot Sequential Direct C–H Bond Arylation of Azoles Catalyzed by [Pd(phen)₂](PF₆)₂: Synthetic Methods for Triarylated Azoles
  作者：Fumitoshi Shibahara、Takayuki Yamauchi、Eiji Yamaguchi、Toshiaki Murai

  DOI：10.1021/jo301621t

  日期：2012.10.5

  Synthetic methods for triarylated azoles containing three different aryl groups via one-pot sequential multiple C-H bond arylations are described. The one-pot sequential diarylation of C5-monoarylated azoles was achieved by the simple sequential addition of two different aryl iodides with a [Pd(phen)(2)]PF6 catalytic system. The one-pot triarylation of N-methylimidazole was achieved by the combination of a previously reported Pd(OAc)(2)-P(2-furyl)(3) system and the present [Pd(phen)(2)]PF6 system. In this case, portionwise addition of aryl halide, base and the catalyst in the final step significantly improved the overall yield of the desired triarylated product These protocols led to triarylated azoles without a loss of efficiency compared to the corresponding previously reported stepwise syntheses via direct C-H bond arylation.