2-(anthracen-9-yl)-4,5-diphenyl-1H-imidazole | 6931-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(anthracen-9-yl)-4,5-diphenyl-1H-imidazole
• 英文别名: 2-(anthracen-10-yl)-4,5-diphenyl-1H-imidazole；ADPI；2-(Anthracen-9-yl)4,5-diphenylimidazole；2-anthracen-9-yl-4,5-diphenyl-1H-imidazole
• CAS: 6931-28-8
• 化学式: C₂₉H₂₀N₂
• 分子量: 396.491
• InChiKey: UBTQCXUORSAVEL-UHFFFAOYSA-N

物化性质

• 沸点：
  660.0±24.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(anthracen-9-yl)-4,5-diphenyl-1H-imidazole 在 四丁基溴化铵 、 溴 、 sodium hydroxide 作用下， 以 二硫化碳 、 水 、 丁酮 为溶剂， 反应 3.0h， 生成 2-(10-bromoanthr-9-yl)-1-n-dodecyl-4,5-diphenylimidazole
  参考文献：
  名称：

  Synthesis and optical behaviors of 2-(9-phenanthrenyl)-, 2-(9-anthryl)-, and 2-(1-pyrenyl)-1-alkylimidazole homologues

  摘要：

  Eight 2-(9-phenanthrenyl)-, 2-(9-anthryl)- and 2-(I-pyrenyl)-1-alkyl-benzimidazole compounds, three 2-(9-anthryl)-1-alkylphenanthroimidazole compounds and five 4,5-diphenyl-1-alkyl-2-(9-anthryl)imidazole compounds were synthesized by alkylation reactions of the corresponding benzimidazole, phenanthroimidazole or imidazole compounds. 2-(10-Bromo-9-anthryl)-1-alkyl-benzimidazole compounds were prepared by bromination reaction of 2-(9-anthryl)-1-alkylbenzimidazole compounds. All the synthesized compounds were characterized by elemental analysis, H-1 NMR, C-13 NMR, MS or HRMS; their absorption coefficients (epsilon), maximum absorption lambda(amax). fluorescence emission maximum lambda(em), Stokes shifts and fluorescence quantum yields (Phi(F)) in ethyl acetate were determined; their fluorescent lifetimes (T-1 and T-2) were measured in ethyl acetate and in solid state, respectively. The crystal structure of 2-(9-anthryl)-1-n-butyl-4,5-diphenylimidazole (12a) was determined to be triclinic, space group P-1 types, using single crystal X-ray crystallography technique. The results showed that these compounds exhibited moderate fluorescence-emission abilities and higher solubility in most organic solvents than their corresponding starting materials. The relationships between the optical behaviors and structures for these compounds were discussed. (C) 2009 Published by Elsevier B.V.

  DOI：

  10.1016/j.saa.2009.06.020
• 作为产物：
  描述：

  苯乙炔 在 ammonium acetate 、 氧气 、 cobalt(II) aceylacetonate 、 溶剂黄146 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(anthracen-9-yl)-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  钴（ii）催化炔烃与苯基肼的C（sp）–H键官能化：容易获得二芳基1,2-二酮† ‡

  摘要：

  已经描述了乙酰丙酮钴通过C（sp）–H键官能化催化炔烃的氧化二酮化反应。该反应涉及自由基机理，其中由苯基肼形成的苯基与Co（II）活化的炔烃偶合以产生1，2-二酮。反应在室温下在DMF中使用Ag 2 O /空气作为氧化体系进行。已证明该方案可用于合成一系列咪唑类化合物，其中包括有效的血小板凝集抑制剂曲非那格雷。

  DOI：

  10.1039/c5ob00419e

文献信息

• 2‐hydroxyethylammonium formate ionic liquid grafted magnetic nanoparticle as a novel heterogeneous catalyst for the synthesis of substituted imidazoles
  作者：Maryam Rajabzadeh、Hossein Eshghi、Reza Khalifeh、Mehdi Bakavoli

  DOI：10.1002/aoc.4052

  日期：2018.2

  acetate have been successfully carried out using 2‐hydroxyethylammonium formate (HEAF) grafted on a magnetic nanoparticles as a new heterogeneous catalyst. The as‐prepared catalyst was characterized by FT‐IR, TEM, FESEM, VSM, TGA and XRD. This catalyst indicated significant advantages, such as excellent yields, shorter reaction time, reusability of the catalyst and easy workup process.

  使用接枝在磁性纳米粒子上的甲酸2-羟乙基铵（HEAF）作为新型多相催化剂，已经成功进行了苯，醛和乙酸铵的催化一锅缩合反应。制备的催化剂通过FT-IR，TEM，FESEM，VSM，TGA和XRD表征。该催化剂显示出显着的优点，例如优异的收率，较短的反应时间，催化剂的可重复使用性和后处理工艺容易。
• Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by [Hmim]HSO₄ as a powerful Brönsted acidic ionic liquid
  作者：Ahmad R Khosropour

  DOI：10.1139/v08-009

  日期：2008.3.1

  An efficient and green procedure for the synthesis of 2,4,5-trisubstituted imidazoles with various aldehydes using a catalytic amount of 1-methylimidazolium hydrogenesulfate as an active and low cost Brönsted acidic room temperature ionic liquid has been developed. The ionic liquid was easily separated from the reaction mixture and was recycled five times without any loss in activity.Key words: ionic liquid, 2,4,5-trisubstituted imidazoles, [Hmim]HSO₄, aldehyde, benzil.

  利用催化量的 1-甲基咪唑硫酸氢盐作为活性低、成本低的勃氏酸性室温离子液体，开发了一种高效、绿色的 2,4,5-三取代咪唑与各种醛的合成方法。该离子液体很容易从反应混合物中分离出来，并且可以循环使用五次，活性没有任何损失。关键词：离子液体、2,4,5-三取代咪唑、[Hmim]HSO4、醛、苯齐尔。
• Co(II) anchored glutaraldehyde crosslinked magnetic chitosan nanoparticles (MCS) for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
  作者：Harminder Singh、Jaspreet Kaur Rajput

  DOI：10.1002/aoc.3989

  日期：2018.1

  A simple, highly efficient and green synthesis of 2,4,5‐trisubsituted and 1,2,4,5‐tetrasubstituted imidazoles was developed using a novel MCS‐GT@Co(II) magnetically recoverable and recyclable catalyst under refluxing conditions with ethanol as a solvent. The catalyst was prepared by immobilization of chitosan onto Fe3O4 using glutaraldehyde as crosslinker followed by Co(II) ion immobilization via cobalt

  使用新型MCS-GT @ Co（II）磁性可回收和可循环利用的催化剂，在乙醇回流条件下，开发了一种简单，高效且绿色的2,4,5-三取代和1,2,4,5-四取代的咪唑合成方法作为溶剂。通过使用戊二醛作为交联剂将壳聚糖固定在Fe 3 O 4上，然后通过乙酸钴固定Co（II）离子来制备催化剂。使用多种技术表征催化剂。对于有机产物的测定，1 H NMR，13使用13 C NMR和傅立叶变换红外光谱。还尝试了用催化剂的各个组分进行反应，但是在制备的催化剂中组分的协同作用显示出最高的产率和最短的反应时间。
• Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia
  作者：MARYAM HAJJAMI、ARASH GHORBANI-CHOGHAMARANI、ZAKIEH YOUSOFVAND、MASOOMEH NOROUZI

  DOI：10.1007/s12039-015-0890-2

  日期：2015.7

  A simple, green and cost-effective protocol was achieved for the synthesis of tri/tetrasubstituted-1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride. The reaction was carried out under catalyst-free conditions and the products were isolated in good to excellent yield.

  采用纳米氮化铝实现了一种简单、绿色且经济高效的合成三/四取代-1H-咪唑和2,3-二氢喹唑啉-4(1H)-酮的新方法。反应在无催化剂的条件下进行，产物的收率良好到优秀。
• NiO nanocomposites/rGO as a heterogeneous catalyst for imidazole scaffolds with applications in inhibiting the DNA binding activity
  作者：Gyanendra Kumar、Navin Kumar Mogha、Manish Kumar、Subodh、Dhanraj T. Masram

  DOI：10.1039/c9dt04416g

  日期：——

  nano-catalyst for the synthesis of imidazole derivatives. Consequently, a series of imidazole derivatives were synthesized, catalyzed by rGO-NiO-NCs, in 60 min with high yields (86% to 96%) under green conditions. Furthermore, the present synthetic methodology was used for the synthesis of highly aromatic imidazole derivatives (B1-B3) whose calf thymus-DNA binding affinities suggest their superior

  本文中，我们报告了一种简便的方法，该方法可通过基于固定在表面功能化的还原氧化石墨烯片材上的氧化镍纳米复合材料的自发空中氧化来合成新型高度通用的多相催化剂。NiO纳米复合/还原氧化石墨烯（rGO-NiO-NC）是一种高效，成本效益高，可重复使用，选择性且环保的纳米催化剂，即使经过五个反应周期也不会失去任何活性。发现在rGO-NiO纳米复合材料上的镍负载量为3.3 at％，这有助于将rGO-NiO-NCs用作合成咪唑衍生物的纳米催化剂而得到有效利用。因此，在绿色条件下，rGO-NiO-NC在60分钟内以高收率（86％至96％）合成了一系列咪唑衍生物。此外，本合成方法用于合成高度芳香的咪唑衍生物（B1-B3），其小牛胸腺DNA结合亲和力表明它们具有取代溴化乙锭（EB）的优异抑制能力，这已通过分子对接研究得到了进一步证实。此外，发现合成反应的绿色化学矩阵非常接近理想值，例如碳效率（82.32％），电子因子（0