2-methyl-1, 4-diphenyl-1H-imidazole | 82672-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-1, 4-diphenyl-1H-imidazole
• 英文别名: 2-methyl-1,4-diphenyl-1H-imidazole；1,4-diphenyl-2-methylimidazole；2-Methyl-1,4-diphenylimidazole
• CAS: 82672-35-3
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: MNHBUUYQHWINBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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

• 作为产物：
  描述：

  苯胺基乙腈 在 吡啶 、 palladium(II) trifluoroacetate 、 三氟乙酸铵 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 2-methyl-1, 4-diphenyl-1H-imidazole
  参考文献：
  名称：

  通过钯（II）催化的CC偶联和CN缩合级联反应可控制地访问多取代的咪唑

  摘要：

  通过级联钯催化的CC偶合反应，然后形成分子内CN键，可随意合成各种2,4-二取代，1,2,4-三取代和1,2,4,5-四取代的咪唑的新颖有效的方法发展了。首先报道了容易获得的硼酸和N-取代的2-氨基乙腈，是制备二，三和四取代的咪唑的起始原料，其产率高至优异。

  DOI：

  10.1039/c7cc05315k

文献信息

• One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using<i>N</i>-Bromosuccinimide
  作者：Sachin D. Pardeshi、Pratima A. Sathe、Kamlesh S. Vadagaonkar、Atul C. Chaskar

  DOI：10.1002/adsc.201700900

  日期：2017.12.11

  N‐bromosuccinimide (NBS)‐mediated one‐pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N‐arylbenzamidines and o‐phenylenediamines, respectively, in a water:1,4‐dioxane mixture. The reaction involves formation of an α‐bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with

  N-溴代琥珀酰亚胺（NBS）介导的苯乙烯，N-芳基苯甲m和邻苯二胺的单锅，绿色，高效，实用合成取代咪唑和喹喔啉已在水中：1,4-二恶烷混合物。该反应包括在NBS和水存在下形成α-溴代酮作为中间体，然后与N-芳基苯甲m和邻苯二酚缩合。苯二胺。使用廉价的NBS作为溴源以及氧化剂，水作为溶剂和易于获得的起始原料，可以使该方案在环境上无害且在经济上可行。得到的咪唑和喹喔啉取代基的收率好至极好，并具有广泛的官能团相容性。
• Unusual methylene transfer in reactions of Simmons–Smith reagent with 1,3-diazabuta-1,3-dienes: synthesis of functionalised imidazole derivatives
  作者：S Jayakumar、Mohinder P Mahajan

  DOI：10.1016/s0040-4020(02)00127-8

  日期：2002.4

  The reactions of Simmons–Smith reagent with 1-aryl-2-phenyl-4-methylthio-4-secondary amino 1,3-diazabuta-1,3-dienes 1 underwent an unusual 1,4-methylene transfer resulting in the formation of 1-aryl-2-phenyl-4-secondary amino imidazoles 4. Whereas, its reactions with 1-aryl-2-phenyl-4-secondary amino-1,3-diazabuta-1,3-dienes 8 underwent an initial 1,2-methylene transfer leading to an aziridine intermediate

  Simmons–Smith试剂与1-芳基-2-苯基-4-甲硫基-4-仲氨基1,3-二氮杂丁-1,3-二烯1的反应经历了异常的1,4-亚甲基转移，导致形成1-芳基-2-苯基-4-仲氨基咪唑4。然而，其与1-芳基-2-苯基-4-仲氨基-1,3-二氮杂丁-1,3-二烯8的反应进行了初始的1,2-亚甲基转移，导致氮丙啶中间体重新排列为1-芳基-4-苯基咪唑11。
• Pyrazole or Triazole Compounds and Their Use for the Manufacture of a Medicament for Treating Somatic Mutation-Related Diseases
  申请人：Almstead Neil

  公开号：US20080280869A1

  公开（公告）日：2008-11-13

  The present invention relates to methods, compounds, and compositions for treating or preventing diseases associated with nonsense mutations in an mRNA by administering the compounds or compositions of the present invention. More particularly, the present invention relates to methods, compounds, and compositions for suppressing premature translation termination associated with a nonsense mutation in an mRNA.

  本发明涉及通过给予本发明的化合物或组合物来治疗或预防与mRNA中无意义突变相关的疾病的方法、化合物和组合物。更具体地说，本发明涉及用于抑制与mRNA中无意义突变相关的早期翻译终止的方法、化合物和组合物。
• PYRAZOLE OR TRIAZOLE COMPOUNDS AND THEIR USE FOR THE MANUFACTURE OF A MEDICAMENT FOR TREATING SOMATIC MUTATION-RELATED DISEASES
  申请人：PTC THERAPEUTICS, INC.

  公开号：US20150274674A1

  公开（公告）日：2015-10-01

  The present invention relates to methods, compounds, and compositions for treating or preventing diseases associated with nonsense mutations in an mRNA by administering the compounds or compositions of the present invention. More particularly, the present invention relates to methods, compounds, and compositions for suppressing premature translation termination associated with a nonsense mutation in an mRNA.

  本发明涉及使用本发明中的化合物或组合物治疗或预防与mRNA中的无义突变相关的疾病的方法、化合物和组合物。更具体地说，本发明涉及用于抑制与mRNA中的无意义突变相关的早期翻译终止的方法、化合物和组合物。
• 10.1021/acs.orglett.4c01534
  作者：Li, Zhi、He, Zhengjun、Huang, Qiang、Kan, Mei、Li, Hongji

  DOI：10.1021/acs.orglett.4c01534

  日期：——

  amidines in the absence of any transition metal catalyst is first reported. This methodology involves sequential addition/cyclization that is perfectly tuned by stepwise addition of K2CO3, affording a plethora of valuable 1,2,4- and 1,2,5-trisubstituted imidazoles in good yields with high regioselectivity. Importantly, trapping and isolation of the reactive intermediate unveiled the reaction mechanism

  首次报道了在不存在任何过渡金属催化剂的情况下炔基锍盐与双亲核N-芳基脒的可调反应流形。该方法涉及顺序添加/环化，通过逐步添加K 2 CO 3进行完美调整，以良好的产率和高区域选择性提供大量有价值的1,2,4-和1,2,5-三取代咪唑。重要的是，反应中间体的捕获和分离揭示了[3 + 2]环加成反应中三键β-攻击的反应机制。