4-methyl-1,2-diphenyl-1H-imidazole | 82672-31-9

• 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-diphenyl-1H-imidazole
• 英文别名: 4-Methyl-1,2-diphenylimidazole
• CAS: 82672-31-9
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: VUCKNACICSUGPI-UHFFFAOYSA-N

物化性质

• 熔点：
  89 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  418.1±38.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

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：

  4-甲基-2-苯基噻唑 在 马来酸酐 、 双氧水 、 镍 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 130.0h， 生成 4-methyl-1,2-diphenyl-1H-imidazole
  参考文献：
  名称：

  Honjo, Noriko; Niiya, Tokihiro; Goto, Yoshinobu, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 5, p. 1722 - 1730

  摘要：

  DOI：

文献信息

• Ln[N(SiMe₃)₂]₃-Catalyzed Cross-Diinsertion of CN/CC into an NH Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles
  作者：Longcheng Hong、Yinlin Shao、Lixin Zhang、Xigeng Zhou

  DOI：10.1002/chem.201402701

  日期：2014.7.7

  A lanthanide‐catalyzed sequential insertion of CN and CC into an NH bond is presented. The convenient reaction, which proceeds under mild conditions, is an efficient method for preparing 1,2,4‐trisubstituted imidazoles directly from readily available propargylamines and nitriles.

  CN和CC的镧系元素催化的顺序插入到一个N  H键被呈现。在温和的条件下进行的便捷反应是直接从容易获得的炔丙基胺和腈制备1,2,4-三取代的咪唑的有效方法。
• Unusual 1,4-methylene transfer from a Simmons-Smith reagent to 1,3-diazabuta-1,3-dienes
  作者：S. Jayakumar、M.P.S. Ishar、Mohinder P. Mahajan

  DOI：10.1016/s0040-4039(98)01365-3

  日期：1998.9

  Novel 1,4 methylene transfer from a Simmons-Smith reagent to 1-aryl-4-secondary amino-4-methylthio or methyl-2-phenyl-1,3-diazabuta-1,3-dienes leading to 1-aryl-2-phenyl-4-secondary amino or methyl -imidazoles are described.

  从Simmons-Smith试剂向1，芳基-4-仲氨基-4-甲硫基或甲基-2-苯基-1,3-二氮杂丁1,3-二烯的甲基1,2-4亚甲基转移导致1-芳基-2描述了-苯基-4-仲氨基或甲基-咪唑。
• IMIDAZOLE BASED LXR MODULATORS
  申请人：Exelixis Patent Company LLC

  公开号：US20140038964A1

  公开（公告）日：2014-02-06

  Methods of using compounds of the invention, such as compounds of Formulae IIa, IIb, IIc, or IId and pharmaceutically acceptable salts thereof are disclosed. The compounds are useful in treating, preventing, inhibiting or ameliorating the symptoms of a disease or disorder that is modulated or otherwise affected by nuclear receptor activity, or in which nuclear receptor activity is implicated.

  本发明公开了使用本发明化合物，例如公式IIa、IIb、IIc或IId及其药学上可接受的盐的方法。这些化合物在治疗、预防、抑制或改善受核受体活性调节或受核受体活性牵涉的疾病或疾病症状方面具有用途。
• 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。
• Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles
  作者：Battistina Asproni、Giuseppe Talani、Fabio Busonero、Amedeo Pau、Sebastiano Sanna、Riccardo Cerri、Maria Paola Mascia、Enrico Sanna、Giovanni Biggio

  DOI：10.1021/jm049120y

  日期：2005.4.1

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.