4-methyl-1,2,5-triphenylimidazole | 30234-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-1,2,5-triphenylimidazole
• 英文别名: 5-Methyl-2,3,4-phenyl-imidazol；4-methyl-1,2,5-triphenyl-1H-imidazole
• CAS: 30234-73-2
• 化学式: C₂₂H₁₈N₂
• 分子量: 310.398
• InChiKey: GWEXQEFGCDCCCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氯化铱(III) 水合物 、 4-methyl-1,2,5-triphenylimidazole 以 乙二醇乙醚 、 水 为溶剂， 生成
  参考文献：
  名称：

  Cyclometalated Iridium(III) Complexes Based on Phenyl-Imidazole Ligand

  摘要：

  Phenyl-imidazole-based ligands with various substitution patterns have been used as the main ligand for heteroleptic bis-cyclometalated Iridium complexes. Two series of complexes have been prepared and their photophysical and electrochemical properties were studied. The phosphorescence emission maxima range from about 490 to 590 nm, that is, from greenish-blue to orange. The first series is of the form Ir(L)(2)(acac) (L: a phenyl-imidazole based ligand; acac: acetylacetonate). In the first complex, la, L is 1,4,5-trimethyl-2-phenyl-1H-imidazole. Then, methyl groups are replaced with phenyl groups and chlorines are grafted on the cyclometalated phenyl ring. The second series is of the form Ir(4,5-dimethyl-1,2-diphenyl-1H-imidazole)(2)(L-a) (L-a: ancillary ligand being acetylacetonate, acac, N,N-dimethylamir o-picolinate, NPic, picolinate, Pic, or 2-(diphenylphosphino)acetic acid, P). These series show that modifying the substitution pattern on the ligands can alter the photophysical and electrochemical properties of the complexes. Overall, we show that compared to complexes containing phenyl-pyridine ligands, highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) are more delocalized over the entire main ligand in complexes containing phenyl-imidazole. Contrary to expectations, when chlorine atoms are used as strong acceptor substituents on the orthometalated phenyl, a red shift of the emission is observed. This behavior has been rationalized using theoretical calculations on the excited state of the chloro-substituted complex 3a compared to the model 1a.

  DOI：

  10.1021/ic901834v
• 作为产物：
  描述：

  在 溶剂黄146 、 锌 作用下， 反应 1.5h， 以10.48 g的产率得到4-methyl-1,2,5-triphenylimidazole
  参考文献：
  名称：

  Cyclometalated Iridium(III) Complexes Based on Phenyl-Imidazole Ligand

  摘要：

  Phenyl-imidazole-based ligands with various substitution patterns have been used as the main ligand for heteroleptic bis-cyclometalated Iridium complexes. Two series of complexes have been prepared and their photophysical and electrochemical properties were studied. The phosphorescence emission maxima range from about 490 to 590 nm, that is, from greenish-blue to orange. The first series is of the form Ir(L)(2)(acac) (L: a phenyl-imidazole based ligand; acac: acetylacetonate). In the first complex, la, L is 1,4,5-trimethyl-2-phenyl-1H-imidazole. Then, methyl groups are replaced with phenyl groups and chlorines are grafted on the cyclometalated phenyl ring. The second series is of the form Ir(4,5-dimethyl-1,2-diphenyl-1H-imidazole)(2)(L-a) (L-a: ancillary ligand being acetylacetonate, acac, N,N-dimethylamir o-picolinate, NPic, picolinate, Pic, or 2-(diphenylphosphino)acetic acid, P). These series show that modifying the substitution pattern on the ligands can alter the photophysical and electrochemical properties of the complexes. Overall, we show that compared to complexes containing phenyl-pyridine ligands, highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) are more delocalized over the entire main ligand in complexes containing phenyl-imidazole. Contrary to expectations, when chlorine atoms are used as strong acceptor substituents on the orthometalated phenyl, a red shift of the emission is observed. This behavior has been rationalized using theoretical calculations on the excited state of the chloro-substituted complex 3a compared to the model 1a.

  DOI：

  10.1021/ic901834v

文献信息

• TETRA-SUBSTITUTED HETEROARYL COMPOUNDS AND THEIR USE AS MDM2 AND/OR MDM4 MODULATORS
  申请人：Bold Guido

  公开号：US20120149661A1

  公开（公告）日：2012-06-14

  The invention relates to tetra-substituted heteroarylic compounds of the formula (I) wherein X 1 , X 3 and X 4 are independently C or N, Y is C—H, N—H or N, wherein the total number of nitrogen atoms represented by X 1 , X 3 , X 4 and Y is 1 or 2; rings A and B are independently selected from phenyl or pyridyl; R1, R4, R′, R″, n and m are as defined herein. Such compounds are suitable for the treatment of a disorder or disease which is mediated by the activity of MDM2 and/or MDM4, or variants thereof.

  本发明涉及公式（I）的四取代杂芳基化合物，其中X1、X3和X4独立地为C或N，Y为C-H、N-H或N，其中由X1、X3、X4和Y所代表的氮原子的总数为1或2；环A和环B独立地选自苯基或吡啶基；R1、R4、R'、R"、n和m如本文所定义。这些化合物适用于治疗由MDM2和/或MDM4或其变异体的活性介导的疾病或疾患。
• GOTO YOSHINOBU; HONJO NARIKO, CHEM. AND PHARM. BULL., 1978, 26, NO 12, 3798-3806
  作者：GOTO YOSHINOBU、 HONJO NARIKO

  DOI：——

  日期：——
• Cyclometalated Iridium(III) Complexes Based on Phenyl-Imidazole Ligand
  作者：Etienne Baranoff、Simona Fantacci、Filippo De Angelis、Xianxi Zhang、Rosario Scopelliti、Michael Grätzel、Md. Khaja Nazeeruddin

  DOI：10.1021/ic901834v

  日期：2011.1.17

  Phenyl-imidazole-based ligands with various substitution patterns have been used as the main ligand for heteroleptic bis-cyclometalated Iridium complexes. Two series of complexes have been prepared and their photophysical and electrochemical properties were studied. The phosphorescence emission maxima range from about 490 to 590 nm, that is, from greenish-blue to orange. The first series is of the form Ir(L)(2)(acac) (L: a phenyl-imidazole based ligand; acac: acetylacetonate). In the first complex, la, L is 1,4,5-trimethyl-2-phenyl-1H-imidazole. Then, methyl groups are replaced with phenyl groups and chlorines are grafted on the cyclometalated phenyl ring. The second series is of the form Ir(4,5-dimethyl-1,2-diphenyl-1H-imidazole)(2)(L-a) (L-a: ancillary ligand being acetylacetonate, acac, N,N-dimethylamir o-picolinate, NPic, picolinate, Pic, or 2-(diphenylphosphino)acetic acid, P). These series show that modifying the substitution pattern on the ligands can alter the photophysical and electrochemical properties of the complexes. Overall, we show that compared to complexes containing phenyl-pyridine ligands, highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) are more delocalized over the entire main ligand in complexes containing phenyl-imidazole. Contrary to expectations, when chlorine atoms are used as strong acceptor substituents on the orthometalated phenyl, a red shift of the emission is observed. This behavior has been rationalized using theoretical calculations on the excited state of the chloro-substituted complex 3a compared to the model 1a.

表征谱图