1,2-diphenylimidazole | 52179-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-diphenylimidazole
• 英文别名: 1,2-diphenyl-1H-imidazole；1,2-Diphenylimidazol
• CAS: 52179-66-5
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: JNZXFLAEEPPCSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  1,2-diphenylimidazole 在 四(三苯基膦)钯 、 溴 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 4,5-bis(2-methylbenzo[b]thiophen-3-yl)-1,2-diphenyl-1H-imidazole
  参考文献：
  名称：

  咪唑二芳基乙烯开关：酸门控光致变色的替代方法

  摘要：

  我们准备了五个含有2-芳基咪唑作为乙烯桥（L1-L5）的二芳烃，并在咪唑中而不是在传统的附加芳基单元中引入了响应位点，以调节它们在酸刺激下的光致变色和热稳定性。结果表明，我们可以将热稳定性从P型转变为T型，并通过酸化阻止其光活性，并且可以证明，酸越强或添加的酸越多，二芳基乙烯光稳定性的衰减速度越快。此外，可以通过用等摩尔量的碱中和来恢复被禁止的光活性。

  DOI：

  10.1039/d0nj00606h
• 作为产物：
  描述：

  2-苯基咪唑 在 盐酸 、 potassium carbonate 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 1,2-diphenylimidazole
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm049120y

文献信息

• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：UNIVERSAL DISPLAY CORPORATION

  公开号：US20190051845A1

  公开（公告）日：2019-02-14

  A compound having a structure of the formula Ir(L A )(L B ), in which L A is a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand and L B is a monodentate, bidentate, tridentate, or tetradentate ligand, or not present, and where the total denticity of L A plus L B is 6, and L A includes at least one structure of Formula I: is disclosed as a useful phosphorescent emitter compound.

  一种具有Ir(LA)(LB)分子结构的化合物被披露为一种有用的磷光发射剂，其中LA是双齿、三齿、四齿、五齿或六齿配体，LB是单齿、双齿、三齿或四齿配体，或者不存在，LA和LB的总配位数为6，LA至少包括一个I式结构。
• NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME
  申请人：SFC CO., LTD.

  公开号：US20180072753A1

  公开（公告）日：2018-03-15

  The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R 1 to R 8 , and R 11 to R 20 are as defined in the specification.

  本发明涉及一种由[化学公式A]表示的有机发光化合物以及一种有机发光器件。在化学公式中，A、X、Y、Z以及取代基R1至R8和R11至R20如说明书中所定义。
• Diversity Synthesis via C−H Bond Functionalization:  Concept-Guided Development of New C-Arylation Methods for Imidazoles
  作者：Bengü Sezen、Dalibor Sames

  DOI：10.1021/ja036157j

  日期：2003.9.1

  systematic and comprehensive arylation of the 2-phenylimidazole core was feasible, and in the context of this study new arylation methods were developed. The direct 4-arylation of free 2-phenylimidazole was achieved with iodoarenes as the aryl donors in the presence of palladium catalyst (Pd/Ph(3)P) and magnesium oxide as the base. A complete switch from C-4 to C-2' arylation was accomplished using a ruthenium

  在此，我们提出了通过 CH 键功能化对结构基序进行系统衍生化的概念。这一概念不仅可以作为多样性合成新策略的蓝图，而且还可以为识别未解决的重要合成挑战提供系统指导。为了说明这一点，本研究选择了 2-苯基咪唑作为核心基序，这一选择受到了许多基于唑的合成物的启发，包括药物（化合物 SB 202190）以及荧光和化学发光探针。我们能够证明 2-苯基咪唑核的系统和全面的芳基化是可行的，并且在本研究的背景下开发了新的芳基化方法。在钯催化剂 (Pd/Ph(3)P) 和氧化镁作为碱的存在下，以碘代芳烃作为芳基供体实现了游离 2-苯基咪唑的直接 4-芳基化。使用钌催化剂 [CpRu(Ph(3)P)(2)Cl] 和 Cs(2)CO(3) 完成了从 C-4 到 C-2' 芳基化的完全转换。(N,2)-二苯基咪唑 (C-5 和 C-2' 芳基化) 的相应转化是通过基于钯的方法 [Pd(OAc)(2)/Ph(3)P/Cs(2)CO
• Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes
  作者：Can Liu、Zhiming Wang、Lei Wang、Pinhua Li、Yicheng Zhang

  DOI：10.1039/c9ob01883b

  日期：——

  A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

  使用1-芳基三氮烯作为芳基试剂，开发了一种高效的钯在C2-位上的唑催化芳基化反应。恶唑，噻唑，咪唑，1,3,4-恶二唑和恶唑啉等恶唑可与1-芳基三氮杂苯平稳地反应生成相应的产物，收率良好至极好，并且各种取代方式都可耐受该反应。
• Regioselective Synthesis of 1,5-Diaryl-1<i>H</i>-imidazoles by Palladium-Catalyzed Direct Arylation of 1-Aryl-1<i>H</i>-imidazoles
  作者：Fabio Bellina、Silvia Cauteruccio、Luisa Mannina、Renzo Rossi、Stéphane Viel

  DOI：10.1021/jo050274a

  日期：2005.5.1

  A variety of 1,5-diaryl-1H-imidazoles have been regioselectively synthesized by direct coupling of 1-aryl-1H-imidazoles with aryl iodides or bromides in DMF in the presence of CsF as the base and a catalyst precursor consisting of a mixture of Pd(OAc)2 and AsPh3. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium(II) halide species

  在CsF作为碱和由以下成分组成的催化剂前体的存在下，通过在DMF中将1-芳基-1 H-咪唑与芳基碘化物或溴化物直接偶联，已选择性地合成了多种1,5-二芳基-1 H-咪唑。 Pd（OAc）2和AsPh 3的混合物。在这项综合研究中获得的数据支持了涉及芳基钯（II）卤化物物种对咪唑环的亲电攻击的反应机理。有趣的是，已经发现在该研究中合成的一些咪唑衍生物对人肿瘤细胞系表现出显着的细胞毒性活性。