1-苄基-2-(4-甲氧基苯基)-5-苯基-1H-咪唑 | 1041845-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苄基-2-(4-甲氧基苯基)-5-苯基-1H-咪唑
• 英文名称: 1-benzyl-2-(4-methoxyphenyl)-5-phenyl-1H-imidazole
• 英文别名: 1-Benzyl-2-(4-methoxyphenyl)-5-phenylimidazole；1-benzyl-2-(4-methoxyphenyl)-5-phenylimidazole
• CAS: 1041845-46-8
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: AAJIRHNKMXLRDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄基-2-(4-甲氧基苯基)-5-苯基-1H-咪唑 在 palladium on activated charcoal HC(O)ONH₄ 作用下， 以 甲醇 为溶剂， 反应 69.0h， 以99%的产率得到2-(4-methoxyphenyl)-4-phenyl-1H-imidazole
  参考文献：
  名称：

  高度选择性的4（5） -芳基- ，2,4-（5）-diaryl-和4,5-二芳基-1-合成，ħ经由的1-苄基1 Pd催化的直接C-5的芳基化-咪唑ħ -咪唑

  摘要：

  为4（5）的制备高度选择性的，实用，高效的协议-芳基- 1 H ^ -咪唑2，2,4（5）-diaryl-1 ħ -咪唑3，和4,5-二芳基-1- ħ -描述了咪唑1。这些协议的关键步骤是通过Pd催化商用C 1-苄基1 H-咪唑（8）与芳基卤化物的直接C-5芳基化反应，选择性合成5-芳基-1-苄基1 H-咪唑9-区域选择性。。由8的化合物3的三步合成还涉及咪唑的Pd催化和Cu介导的直接C-2芳基化反应9在无碱和无配体条件下与芳基卤化物反应。另一方面，由8的四步合成咪唑1还涉及化合物9的区域选择性溴化和所得的5-芳基-1-苄基-4-溴-1 H-咪唑11与芳基硼酸的Suzuki反应。在相转移条件下为5，然后进行N-脱苄基作用。

  DOI：

  10.1016/j.tet.2008.01.051
• 作为产物：
  描述：

  溴苯 在 三(2-呋喃基)膦 、 [Pd(phen)2](PF₆)2 、 palladium diacetate 、 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 生成 1-苄基-2-(4-甲氧基苯基)-5-苯基-1H-咪唑
  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.
• Highly selective synthesis of 4(5)-aryl-, 2,4(5)-diaryl-, and 4,5-diaryl-1H-imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1H-imidazole
  作者：Fabio Bellina、Silvia Cauteruccio、Annarita Di Fiore、Chiara Marchetti、Renzo Rossi

  DOI：10.1016/j.tet.2008.01.051

  日期：2008.6

  direct C-2 arylation of imidazoles 9 with aryl halides under base-free and ligandless conditions. On the other hand, the four-step synthesis of imidazoles 1 from 8 also involves the regioselective bromination of compounds 9 and a Suzuki reaction of the resulting 5-aryl-1-benzyl-4-bromo-1H-imidazoles 11 with arylboronic acids 5 under phase-transfer conditions, followed by N-debenzylation.

  为4（5）的制备高度选择性的，实用，高效的协议-芳基- 1 H ^ -咪唑2，2,4（5）-diaryl-1 ħ -咪唑3，和4,5-二芳基-1- ħ -描述了咪唑1。这些协议的关键步骤是通过Pd催化商用C 1-苄基1 H-咪唑（8）与芳基卤化物的直接C-5芳基化反应，选择性合成5-芳基-1-苄基1 H-咪唑9-区域选择性。。由8的化合物3的三步合成还涉及咪唑的Pd催化和Cu介导的直接C-2芳基化反应9在无碱和无配体条件下与芳基卤化物反应。另一方面，由8的四步合成咪唑1还涉及化合物9的区域选择性溴化和所得的5-芳基-1-苄基-4-溴-1 H-咪唑11与芳基硼酸的Suzuki反应。在相转移条件下为5，然后进行N-脱苄基作用。