2-甲基-1-苯基-1H-咪唑 | 60053-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-甲基-1-苯基-1H-咪唑
• 英文名称: 2-methyl-1-phenyl-1H-imidazole
• 英文别名: 1-phenyl-2-methyl-1H-imidazole；2-methyl-1-phenylimidazole
• CAS: 60053-07-8
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: ZQNVWAQNCHHONO-UHFFFAOYSA-N

物化性质

• 沸点：
  147 °C(Press: 20 Torr)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  2-甲基-1-苯基-1H-咪唑 在 potassium hydride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 24.0h， 生成 1-methyl-2-methylene-3-phenyl-2,3-dihydro-1H-imidazole
  参考文献：
  名称：

  溶液中N-杂环烯烃的Brönsted碱和亲核性：N-杂环碳烯与N-杂环的烯烃。哪个更基本，哪个更亲核？

  摘要：

  通过使用紫外可见光谱法测量相应的前体在DMSO中的平衡酸度，建立了包含9种代表性N-杂环烯烃（NHO）的布朗斯台德碱度标度。基本性（p K aH被调查的NHO的s）范围从14.7到24.1。不饱和NHO的碱性比其N-杂环卡宾（NHC）类似物的碱性强。但是，饱和盐的碱度比其NHC类似物的碱度弱得多，这在很大程度上是由于芳香化作用本质上影响NHC和NHO前体的酸离解。通过监测这些NHO与常用参比亲电试剂的反应动力学来光度法测量四个NHO的亲核性，以定量亲核反应性。通常，NHO的亲核性比常用的路易斯碱（例如Ph 3）强得多P或DMAP [4-（二甲氨基）吡啶]，但比其NHC类似物弱；然而，将这一结论推广到具有明显电子和结构特性的各种亲电子试剂时，应谨慎行事。

  DOI：

  10.1021/acs.joc.0c02838
• 作为产物：
  描述：

  3-甲基-1-苯基吡唑 以 乙腈 为溶剂， 生成 2-甲基-1-苯基-1H-咪唑
  参考文献：
  名称：

  Phototransposition chemistry of 1-phenylpyrazole. Experimental and computational studies

  摘要：

  Photophysical and photochemical properties of 1-phenylpyrazole and 3-,4-, and 5-methyl-1-phenylpyrazoles have been investigated. INDO/S calculations agree with experimental measurements which show that the S1 and T1 states of these compounds are pi,pi* in character. Upon S0 --> S1(pi,pi*) excitation, these 1-phenylpyrazoles undergo phototransposition via a P4 permutation pathway. This process is consistent with a mechanism involving initial N-N bond cleavage followed by a 1,2-shift and cyclization to form the 1-phenylimidazole product. The 1,2-shift may occur via an undetected azirine intermediate. Whereas the regioselectivity of the reaction may be due to the stability of the N-phenyl radical, the quantum efficiencies of reaction and fluorescence are remarkably dependent on the location of the methyl group in the pyrazole ring. AM1 calculations provide energy-minimized structures for the more reactive 1-phenylpyrazole and 4-methyl- and 5-methyl-1-phenylpyrazoles in which the phenyl and pyrazole rings are perpendicular as required to stabilize the transition state for N-N bond cleavage. In contrast, such a perpendicular energy minimized S1 structure could not be obtained for the least reactive S1(pi,pi*) 3-methyl-1-phenylpyrazole which undergoes mainly radiative return to the ground state.

  DOI：

  10.1021/ja00070a008

文献信息

• Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C–N and C–O coupling reactions
  作者：Arpi Majumder、Ragini Gupta、Mrinmay Mandal、Madhu Babu、Debashis Chakraborty

  DOI：10.1016/j.jorganchem.2014.11.018

  日期：2015.4

  N-arylation and O-arylation of aryl halides by Ullmann-type cross coupling reaction under mild reaction conditions in a short reaction time. Two phosphine sulphide ligands and their corresponding Pd(0) complexes namely [Pd(p2S2)(dba)] and [Pd(pp3S4)(dba)], were synthesized, where p2S2 is 1,2-bis(diphenylphosphino)ethane disulfide, pp3S4 is tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide and dba

  本文描述了在温和的反应条件下，在较短的反应时间内，钯（0）催化Ullmann型交叉偶联反应进行芳基卤化物的N-芳基化和O-芳基化的有效方法。合成了两个硫化膦配体及其相应的Pd（0）络合物，即[Pd（p 2 S 2）（dba）]和[Pd（pp 3 S 4）（dba）]，其中p 2 S 2为1， 2-双（二苯基膦基）乙烷二硫化物，pp 3 S 4是三[2-（二苯基膦基）乙基]膦四硫化物，dba是二亚苄基丙酮。通过改变温度，溶剂，碱和催化剂的负载量，确定了使用碘代苯和苯并咪唑进行芳基化反应的最佳反应条件。使用碘代苯/溴苯和具有不同空间和电子性质的各种取代的芳基胺/苯酚/醇进行交叉偶联反应，从而以良好或优异的收率得到所需的N-芳基胺/二芳基醚/烷基芳基醚（ 70–94％）。
• Unique copper–salen complex: an efficient catalyst for N-arylations of anilines and imidazoles at room temperature
  作者：Ankur Gogoi、Gayatri Sarmah、Anindita Dewan、Utpal Bora

  DOI：10.1016/j.tetlet.2013.10.084

  日期：2014.1

  activity of a unique Cu–salen type complex in N-arylation of anilines with arylboronic acids in water. The protocol is found to be applicable for a wide range of electronically diversified arylboronic acids and anilines with excellent yields of the isolated product. Further the scope of this protocol has been extended to the synthesis of various N-aryl imidazoles in iso-propanol.

  我们在这里报告了一种独特的Cu-salen型配合物在水中苯胺与芳基硼酸的N-芳基化反应中的催化活性。已发现该方案适用于多种电子多样化的芳基硼酸和苯胺，且分离出的产物收率极高。此外，该方案的范围已扩展到在异丙醇中合成各种N-芳基咪唑。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20190319199A1

  公开（公告）日：2019-10-17

  A compound comprising a ligand L A of Formulae I, II, or III wherein the ligand L A is coordinated to a transition metal M, and optionally, M is also coordinated to a ligand L B ; A is N, B, or CR 7 ; Y is absent, or selected from the group consisting of C(O), C(R ya )(R yb ), C═C(R ya )(R yb ), and Si(R ya )(R yb ), where if Y of Ring A is absent then ring carbon of R 2 is bonded to N; wherein for the compounds of formula III at least one of R 2 , R 3 , and R 4 is selected from N(Ar 1 )R N′ or aryloxy; wherein Ar 1 is selected from aryl or heteroaryl, each of which is optionally substituted. An OLED that includes an organic layer disposed between an anode and a cathode, and the organic layer includes a compound comprising a ligand L A of Formulae I, II, or III above. The OLED can be incorporated into one or more of a consumer product, e.g., an electronic component module, a flat panel display, e.g., a display for a phone, television, laptop, and/or a lighting panel for either commercial or residential applications.

  由公式I、II或III的配体L A 组成的化合物 其中配体L A 与过渡金属M配位，并且可选地，M也与配体L B 配位； A为N、B或CR 7 ； Y为缺失，或从由C(O)、C(R ya )(R yb )、C═C(R ya )(R yb )和Si(R ya )(R yb )组成的组中选择，如果环A的Y缺失，则R 2 的环碳与N键合；其中对于公式III的化合物，至少R 2 、R 3 和R 4 中的一个选自N(Ar 1 )R N′ 或芳氧基；其中Ar 1 选自芳基或杂芳基，其中每一个都可以被选地取代。一种OLED，包括位于阳极和阴极之间的有机层，并且有机层包括具有上述公式I、II或III的配体L A 的化合物。OLED可以集成到一个或多个消费品中，例如，电子组件模块，平板显示器，例如，电话、电视、笔记本电脑的显示器，以及/或用于商业或住宅应用的照明面板。
• A Facile and Efficient Oxalyldihydrazide/Ketone-Promoted Copper-Catalyzed Amination of Aryl Halides in Water
  作者：Xinhai Zhu、Li Su、Liye Huang、Gong Chen、Jinlong Wang、Huacan Song、Yiqian Wan

  DOI：10.1002/ejoc.200800940

  日期：2008.12.23

  A novel three-component catalyst CuO/oxalyldihydrazide/ hexane-2,5-dione was a very convenient, economic, and effective catalytic system for the Ullmann-type C–N coupling reaction in water. Both aryl bromides and aryl iodides could

  一种新型的三组分催化剂 CuO/草酰二酰肼/己烷-2,5-二酮是一种非常方便、经济且有效的催化体系，用于在水中进行 Ullmann 型 C-N 偶联反应。芳基溴化物和芳基碘化物都可以
• Carbothioamide as Highly Efficient Ligand for Copper-catalyzed Room Temperature Chan-Lam Cross-Coupling Reaction
  作者：Jayantajit Baruah、Kongkona Gogoi、Anindita Dewan、Geetika Borah、Utpal Bora

  DOI：10.1002/bkcs.11248

  日期：2017.10

  The catalytic activity of three N,S‐donor ligands, viz L1 [2‐(4‐methoxybenzylidene)‐N‐phenylhydrazinecarbothioamide], L2 [2,2′‐(1,2‐diphenylethane‐1,2‐diylidene)bis(hydrazinecarbothioamide)] and L3 [2‐(4‐methoxybenzylidene)hydrazinecarbothioamide] has been reported for N‐arylation of imidazoles with arylboronic acids in ethanol at room temperature. The method was found to be applicable in N‐arylation

  三个N，S-给体配体的催化活性，即L1 [2-（4-甲氧基亚苄基）-N-苯基肼甲硫代酰胺]，L2 [2,2'-（1,2-二苯基乙烷-1,2-二亚甲基）bis（据报道，在室温下，L3 [2-（4-甲氧基亚苄基）肼基甲硫基酰胺]可用于在乙醇中将咪唑与芳基硼酸进行N-芳基化反应。发现该方法适用于N-芳基化反应，使各种电子形式的芳基硼酸与咪唑的分离收率均中等至优异。发现原位生成的配体铜（II）络合物2-（4-甲氧基亚苄基）-N-苯基肼基碳硫代酰胺（L1）是N-芳基化反应的高效均相催化剂。