4,5-bis(4-methoxyphenyl)-2-p-tolyl-1H-imidazole | 36755-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-bis(4-methoxyphenyl)-2-p-tolyl-1H-imidazole
• 英文别名: 4,5-di(4-anisyl)-2-(4-tolyl)imidazole；4,5-bis(4-methoxyphenyl)-2-(4-methylphenyl)-1H-imidazole
• CAS: 36755-88-1
• 化学式: C₂₄H₂₂N₂O₂
• mdl: MFCD00997793
• 分子量: 370.451
• InChiKey: SFJOFRNEQLJWIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 4,5-bis(4-methoxyphenyl)-2-p-tolyl-1H-imidazole 在 sodium hydroxide 、 C₆H₅CH=C[CH₂N⁽¹⁺⁾Et₃Br^(1-)]2 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-ethyl-2-(4'-methylphenyl)-4,5-bis(p-methoxyphenyl) imidazole
  参考文献：
  名称：

  在 PTC 条件下使用新的相转移试剂对 2,4,5-三苯基咪唑衍生物进行 N-烷基化

  摘要：

  相转移催化 2,4,5-三苯基咪唑衍生物的 N-烷基化反应，使用一种新的相转移试剂，即 2-benzilidine-N,N,N,N',N',N'-hexaethyl propane-1,3 -二溴化二铵已被描述。所有 14 种化合物的结构均已通过光谱方法确定。

  DOI：

  10.1081/scc-100105320
• 作为产物：
  描述：

  对甲基苯甲醛 、 4,4'-二甲氧基苯酚酯 在 ammonium acetate 作用下， 反应 1.0h， 以92%的产率得到4,5-bis(4-methoxyphenyl)-2-p-tolyl-1H-imidazole
  参考文献：
  名称：

  二氧化硅键合的S-磺酸：无溶剂条件下合成三取代咪唑的可回收催化剂

  摘要：

  在二氧化硅键合的S-磺酸作为催化剂的存在下，高取代度合成了三取代的咪唑。反应在无溶剂条件下于130°C进行。反应后处理很简单，催化剂很容易通过过滤从产物中分离出来。

  DOI：

  10.1002/cjoc.201090129

文献信息

• Zinc (II) [tetra(4-methylphenyl)] Porphyrin: a Novel and Reusable Catalyst for Efficient Synthesis of 2,4,5-trisubstituted Imidazoles Under Ultrasound Irradiation
  作者：Javad Safari、Shiva Dehghan Khalili、Sayed Hossein Banitaba、Hossein Dehghani

  DOI：10.5012/jkcs.2011.55.5.787

  日期：2011.10.20

  An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or α-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) (tetra (4-methylphenyl)) porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, α-hydroxyketones as well as 1,2-diketones were

  使用锌（II）（四（4-甲基苯基））使1,2-二酮或α-羟基酮与芳族醛和乙酸铵缩合反应，可有效地三步合成2,4,5-三取代的咪唑描述了在室温下超声辐射下卟啉作为新型可重复使用的催化剂。在这种方法中，α-羟基酮以及1,2-二酮以优异的产率转化为它们相应的2,4,5-三取代的咪唑。
• l-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
  作者：Subhasis Samai、Ganesh Chandra Nandi、Pallavi Singh、M.S. Singh

  DOI：10.1016/j.tet.2009.10.019

  日期：2009.12

  A simple highly versatile and efficient synthesis of 2,4,5-trisubstituted imidazoles is achieved by three-component cyclocondensation of 1,2-dicarbonyl compound, aldehyde and ammonium acetate using l-proline as a catalyst in methanol at moderate temperature. To explore the utility of this method 1,2,4,5-tetrasubstituted imidazoles were also synthesized. The key advantages of this process are high yields

  在室温下，使用1-脯氨酸作为催化剂，通过1-脯氨酸作为催化剂，通过1,2-二羰基化合物，醛和乙酸铵的三组分环缩合，可以实现2,4,5-三取代的咪唑的简单高效且高效的合成。为了探索该方法的实用性，还合成了1,2,4,5-四取代的咪唑。该方法的主要优点是高产率，催化剂的成本效益，易于后处理和通过非色谱法纯化产物。
• Room temperature ionic liquid promoted improved and rapid synthesis of highly functionalized imidazole and evaluation of their inhibitory activity against human cancer cells
  作者：Chetan K. Jadhav、Amol S. Nipate、Asha V. Chate、Pratiksha M. Kamble、Ganesh A. Kadam、Vidya S. Dofe、Vijay M. Khedkar、Charansingh H. Gill

  DOI：10.1002/jccs.202000468

  日期：——

  advantage of this protocol for gram-scale synthesis adds to its practical applicability. Selected synthesized tetra- and trisubstituted imidazole scaffolds were screened for their in vitro antiproliferative properties against the human cancer cell lines EC-109, MCF-7, HGC-27, and PC-3. Compounds 4m, 5e, and 5v showed potent cytotoxic activity against the human breast cancer cell line PC-3, MCF-7, and HGC-27

  在这项研究中，我们报告了使用 1,8-二氮杂双环 [5.4.0]-undec-7-en-8-ium 咪唑盐离子液体作为催化剂以及用于快速多组分转化四-和三取代咪唑支架通过四组分和伪四组分反应制备，反应时间短，产率高，产物纯度高。离子液体价格便宜，可生物降解，并且可以回收和重复使用超过五个连续循环。该协议在克级合成方面的优势增加了其实际适用性。筛选了选定的合成四和三取代咪唑支架对人癌细胞系 EC-109、MCF-7、HGC-27 和 PC-3 的体外抗增殖特性。化合物4m、5e和5v 分别对人乳腺癌细胞系 PC-3、MCF-7 和 HGC-27 显示出有效的细胞毒活性。
• A highly efficient magnetic solid acid catalyst for synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation
  作者：Javad Safari、Zohre Zarnegar

  DOI：10.1016/j.ultsonch.2012.10.004

  日期：2013.3

  Fe3O4 nanoparticles were prepared by chemical coprecipitation method and subsequently coated with 3-aminopropyltriethoxysilane (APTES) via silanization reaction. Grafting of chlorosulfuric acid on the amino-functionalized Fe3O4 nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (SA-MNPs). SA-MNPs was found to be a mild and effective solid acid catalyst for the efficient, one-pot, three-component synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation. This protocol afforded corresponding imidazoles in shorter reaction durations, and in high yields. This green procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, short routine, and simplicity of the methodology. (C) 2012 Elsevier B.V. All rights reserved.
• Tandem Oxidation Process Using Ceric Ammonium Nitrate: Three-Component Synthesis of Trisubstituted Imidazoles Under Aerobic Oxidation Conditions
  作者：Ahmad Shaabani、Ali Maleki、Maryam Behnam

  DOI：10.1080/00397910802369661

  日期：2008.12.16

  By combining a ceric ammonium nitrate (CAN)-catalyzed aerobic oxidation of alpha-hydroxy ketones with a subsequent three-component condensation reaction using aldehydes and ammonium acetate, highly substituted imidazole derivatives can be assembled. This reaction is an important approach for the synthesis of highly substituted imidazole derivatives and was carried out in good to excellent yields in ethanol as an environmentally benign solvent.