2-(4-methoxyphenyl)-4,5-diphenyl-1-(p-tolyl)-1H-imidazole | 1414944-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxyphenyl)-4,5-diphenyl-1-(p-tolyl)-1H-imidazole
• 英文别名: 2-(4-Methoxyphenyl)-1-(4-methylphenyl)-4,5-diphenylimidazole
• CAS: 1414944-19-6
• 化学式: C₂₉H₂₄N₂O
• 分子量: 416.522
• InChiKey: ZCYOAMYNOHDXAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 在 ammonium acetate 、 1,3-bis(octylbenzimidazolium)bromide 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.16h， 生成 2-(4-methoxyphenyl)-4,5-diphenyl-1-(p-tolyl)-1H-imidazole
  参考文献：
  名称：

  ONE-POT SYNTHESIS OF POLYSUBSTITUTED IMIDAZOLES FROM ARYLALDEHYDES IN WATER CATALYZED BY NHC USING MICROWAVE IRRADIATION

  摘要：

  A simple, high yielding synthesis of tri (3a-i) and tetrasubstituted (4a-g) imidazols from aldehydes is described. The cornerstone of this methodology involves the condensation of NH4OAc, substituted aldehydes, and benzoin, which is synthesized in situ from aldehydes catalyzed by N-heterocyclic carbine (NHC), under microwave irradiation in water to afford trisubstituted imidazoles (3a-i). If arylamine is added in the solution, tetrasubstituted imidazoles (4a-g) can be obtained. Lepidilines B and trifenagrel are also synthesized in high yield using this procedure. All the experiment deta are in agreement with the literature.

  DOI：

  10.4067/s0717-97072012000300002

文献信息

• One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus–Radziszewski Reaction
  作者：Wei Sun、Mingjuan Zhang、Peilang Li、Yiqun Li

  DOI：10.1055/s-0037-1611835

  日期：2019.9

  Abstract A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids

  抽象的 通过Pd（OAc）2 / Ce（SO 4）2 / Bi（NO 3）3从α-羟基苯基乙酸，二苯乙炔和胺中合成新颖高效的一锅合成咪唑三金属催化体系。一系列对照实验表明，整个反应是通过一锅级联过程完成的，该过程结合了α-羟基苯基乙酸的脱羧步骤，二苯基乙炔的Wacker型氧化步骤以及原位生成的芳基醛和苯的Debus-Radziszewski环合反应，以及胺。该反应代表使用α-羟基苯基乙酸和二苯乙炔作为芳基醛和β-二酮的来源的新颖的多组分反应。该方法具有宽泛的底物范围和良好的官能团耐受性，可在温和条件下以优异的收率（72–88％）组装相应的多取代的咪唑。 通过Pd（OAc）2 / Ce（SO 4）2 / Bi（NO 3）3从α-羟基苯基乙酸，二苯乙炔和胺中合成新颖高效的一锅合成咪唑三金属催化体系。一系列对照实验表明，整个反应是通过一锅级联过程完成的，该过程结合了α-羟基苯基乙酸的脱羧步骤，二
• (Carboxy-3-oxopropylamino)-3-propylsilylcellulose as a novel organocatalyst for the synthesis of substituted imidazoles under solvent-free conditions
  作者：Mehri Salimi、Mohammad Ali Nasseri、Tayyebeh Daliran Chapesshloo、Batol Zakerinasab

  DOI：10.1039/c5ra01909e

  日期：——

  organocatalyst, has been prepared by a synthesis grafting of –COOH functionalized organosilanes on a cellulose using surface hydroxyl groups as anchor points. The –CO2H group-functionalized cellulose was synthesized via the consecutive surface functionalization with 3-aminopropyltriethoxysilane (3-APTES) followed by the condensation of the surface –NH2 groups with succinic anhydride. COPAPSC is used as a catalyst

  （羧基-3-氧代丙基氨基）-3-丙基甲硅烷基纤维素（COPAPSC）是一种新型的有机催化剂，它是通过将-COOH官能化的有机硅烷合成接枝到纤维素上而使用表面羟基作为锚定点而制备的。通过用3-氨丙基三乙氧基硅烷（3-APTES）进行连续的表面官能化，然后缩合表面-NH 2，合成了–CO 2 H基团官能化的纤维素。与琥珀酸酐基团。COPAPSC用作催化剂，可在无溶剂条件下由苯甲腈，芳族醛，乙酸铵和胺反应合成三取代和四取代的咪唑。该方法的主要优点是高产率，易于后处理，通过非色谱法纯化产物和催化剂的可重复使用性。
• Appel reagent as novel promoter for the synthesis of polysubstituted imidazoles
  作者：Mehdi Khoshneviszadeh、Mohammad Mahdavi

  DOI：10.24820/ark.5550190.p010.039

  日期：——

  in the presence of Appel reagent (Ph3P/CCl4). Tri-substituted imidazoles is synthesized via condensation of aldehydes, benzil and ammonium acetate, and tetra-substituted imidazole is prepared via condensation of aldehydes, benzil, ammonium acetate and primary amines. These protocols allow the simple preparation of the desired products using readily available reagent instead of complex, expensive and

  摘要 我们提出了一种在 Appel 试剂 (Ph3P/CCl4) 存在下合成多取代咪唑的有效方法。三取代咪唑是由醛、苄基和乙酸铵缩合合成的，四取代咪唑是由醛、苄基、乙酸铵和伯胺缩合制备的。这些协议允许在温和的反应条件下使用现成的试剂而不是复杂、昂贵和有毒的试剂以优异的产率简单地制备所需的产品。
• Covalently anchored organic carboxylic acid on porous silica nano particle: A novel organometallic catalyst (PSNP-CA) for the chromatography-free highly product selective synthesis of tetrasubstituted imidazoles
  作者：Suman Ray、Paramita Das、Asim Bhaumik、Arghya Dutta、Chhanda Mukhopadhyay

  DOI：10.1016/j.apcata.2013.03.024

  日期：2013.5

  A novel organometallic catalyst (PSNP-CA) has been prepared by post synthesis grafting of -COOH functionalized organosilane on porous silica nano particle by using surface hydroxyl groups as anchor point. It was characterized by using an array of sophisticated analytical techniques like 13C CP MAS NMR, 29Si MAS NMR, CHN analysis, BET, HR TEM, XRD, TGA, FTIR and pH measurement. The leaching of the active site is greatly avoided as the organic moieties are covalently attached to the inorganic support. This is the first example of organocatalysis promoted by a -COOH functionalized porous silica nano particle for the chemoselective synthesis of densely substituted imidazoles. The molecular scaffolds which assimilate bio-active imidazole moiety may be worthwhile molecule from the biological point of view. All the other reported procedures led to the mixture of tri and tetra substituted imidazoles and their proportions were successfully evaluated from crude H-1 NMR spectra. Greenness of the process was well instituted as water was exploited as reaction medium. This catalyst retained its activity after having it exposed to ambient atmosphere for 10 days. There was no deteriorating effect of aerial oxygen or moisture towards the activity of the catalyst. (C) 2013 Elsevier B.V. All rights reserved.