1-methyl-2,5-diphenylimidazole | 15994-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-2,5-diphenylimidazole
• 英文别名: 1-methyl-2,5-diphenyl-1H-imidazole；1-Methyl-2,5-diphenyl-imidazol
• CAS: 15994-89-5
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: IBOLHXVRVQJVJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1-methyl-2,5-diphenylimidazole 在 NaCl 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Suarez, Antonio; Vila, Jose Manuel; Pereira, Maria Teresa, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1990, vol. 20, p. 1425 - 1440

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl-2,5-diphenyl-1H-imidazole 3-oxide 在 溶剂黄146 、 锌 作用下， 反应 1.5h， 以4.11 g的产率得到1-methyl-2,5-diphenylimidazole
  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

• USE OF ARYL CHLORIDES IN PALLADIUM-CATALYZED C-H BOND FUNCTIONALIZATION
  申请人：Daugulis Olafs

  公开号：US20090012293A1

  公开（公告）日：2009-01-08

  A one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using chloroarenes and palladium catalysts is disclosed. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores.

  一种将氯代芳烃和钯催化剂高效地将碳氢键转化为碳碳键的一步法方法被揭示。该方法可以更快地引入复杂的分子实体，而这个过程通常需要更多的步骤。这一发明特别适用于有机合成复杂分子，例如但不限于药用分子。
• Nano CuO-catalyzed C–H functionalization of 1,3-azoles with bromoarenes and bromoalkenes
  作者：Wu Zhang、Yujie Tian、Na Zhao、Yuanyuan Wang、Jia Li、Zhenghua Wang

  DOI：10.1016/j.tet.2014.04.065

  日期：2014.9

  Copper oxide catalyzed direct C–H arylation and alkenylation of aromatic heterocycles using aryl and alkenyl bromides have been developed and have been applied to the C–H functionalization of a variety of 1,3-azoles like benzoxazole, benzothiazole, 1-methylbenzimidazole, and 1-methylimidazole, with moderate to excellent yields. The best performance has been achieved in the presence of PPh3 when average

  已经开发出使用芳基和烯基溴化物的氧化铜催化芳族杂环的直接C–H芳基化和烯基化反应，并将其应用于各种1,3-唑类的C–H官能化，如苯并恶唑，苯并噻唑，1-甲基苯并咪唑和1-甲基咪唑，具有中等至优异的收率。当Cuh纳米粒子的平均尺寸为6.5 nm时，在PPh 3的存在下已实现了最佳性能。该催化剂可以回收和再利用而不会显着降低其催化活性。
• Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the Use of Copper Iodide in the Reaction
  作者：Sommai Pivsa-Art、Tetsuya Satoh、Yoshiki Kawamura、Masahiro Miura、Masakatsu Nomura

  DOI：10.1246/bcsj.71.467

  日期：1998.2

  examined in the presence of catalytic amounts of Pd(OAc)2 and PPh3 in DMF using alkali metal carbonates as bases. It was found that the coupling products, 5-arylazoles, could be selectively produced in good yields by using Cs2CO3. In the case that their 2-position is unsubstituted, the site could also be arylated. In reactions using bromobenzene in place of iodobenzene, K2CO3 was also as effective as Cs2CO3

  使用碱金属碳酸盐作为碱，在 DMF 中存在催化量的 Pd(OAc)2 和 PPh3 的情况下，研究了碘苯与唑类化合物、1,2-二取代咪唑和 2-取代恶唑和噻唑的反应。发现使用 Cs2CO3 可以选择性地以良好的产率生产偶联产物 5-芳基唑。在它们的 2 位未被取代的情况下，该位点也可以被芳基化。在使用溴苯代替碘苯的反应中，K2CO3 也与 Cs2CO3 一样有效。添加化学计量量的 CuI 似乎特别促进了噻唑和噻吩衍生物的反应。2-未取代的唑类化合物与芳基碘化物的反应可以在一定程度上由 CuI 介导，而无需使用钯物质来生成 2-芳基唑类。
• Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: synthesis of imidazoles, pyrroles and pyrrolinones
  作者：Sergio Auricchio、Ada M. Truscello、Mirvana Lauria、Stefano V. Meille

  DOI：10.1016/j.tet.2012.06.069

  日期：2012.9

  the presence of metal salts. Imidazoles, pyrroles and new pyrrolinones derivatives are isolated in good overall yields. The role of metal salts was investigated as they can act as Lewis acids or electron donors. Mechanisms are proposed suggesting that imidazoles arise from addition of azirine to imines via radical or ionic mechanism; pyrroles and pyrrolinones are obtained from azirines with enamino

  发现在金属盐存在下，2 H- Azirines与亚胺，烯胺酮和烯胺酸酯反应。以良好的总收率分离出咪唑，吡咯和新的吡咯烷酮衍生物。研究了金属盐的作用，因为它们可以充当路易斯酸或电子给体。提出的机理表明，咪唑是通过自由基或离子机理将叠氮基添加到亚胺中而产生的。当该盐起路易斯酸的作用时，吡咯和吡咯烷酮是从带有烯氨基衍生物的叠氮中获得的。在后一种情况下，金属化合物的性质影响反应区域选择性。
• METATHESIS CATALYSTS AND METHODS THEREOF
  申请人：Massachusetts Institute of Technology

  公开号：US20140316088A1

  公开（公告）日：2014-10-23

  The present invention provides, among other things, novel compounds and methods for metathesis reactions. In some embodiments, a provided compound has the structure of formula I or II. In some embodiments, the present invention provides compounds and methods for Z-selective olefin metathesis.

  本发明提供了新颖的化合物和用于交换反应的方法，其中在一些实施例中，所提供的化合物具有公式I或II的结构。在一些实施例中，本发明提供了用于Z-选择性烯烃交换反应的化合物和方法。