4,5-Bis(4-methoxyphenyl)-2-(2-pyridyl)imidazole | 134789-80-3

• 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-(2-pyridyl)imidazole
• 英文别名: 2-(4,5-bis(4-methoxyphenyl)-1H-imidazol-2-yl)pyridine；2-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-yl]pyridine
• CAS: 134789-80-3
• 化学式: C₂₂H₁₉N₃O₂
• 分子量: 357.412
• InChiKey: SICDLQZAILJXOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-Bis(4-methoxyphenyl)-2-(2-pyridyl)imidazole 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到C₂₂H₁₈BF₂N₃O₂
  参考文献：
  名称：

  Structure–property correlation of solid-emissive boron–fluorine derivatives

  摘要：

  A series of solid-emissive BOPIM (boron 2-(2-pyridyl)imidazole complex) dyes, bearing electron-donating or -withdrawing substituents (methoxy, hydrogen, or nitro), are facilely synthesized. The compounds were characterized by H-1 NMR, C-13 NMR and MS. X-ray single crystal diffractions of BOPIM 1 and 2 indicate that nonplanar rigid structures were formed through intermolecular non-covalent interactions. Due to these non-covalent interactions, these dyes exhibit intense fluorescence in solution and also in solid state. According to H-1 NMR analysis, electronic effect of the substitutes plays an important role in contribution to these BOPIMs' electronic states. The photophysical measurements reveal that electron-donating groups (methoxy) lead to significant bathochromism of the absorption and emission. In contrast, electron-withdrawing moieties (nitro) play the reverse role. However, BOPIM 3 bearing nitro groups emits long wavelength fluorescence in solid state, probably due to the formation of intermolecular hydrogen bond. This work elucidates the spectroscopic structure-property relationship of solid-emissive BOPIMs, which would be valuable for design of solid-emissive dyes. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.043
• 作为产物：
  描述：

  2-氰基吡啶 、 4-甲氧基苯甲醛 在 ammonium acetate 、 溶剂黄146 、 碳酸氢钠 作用下， 反应 10.0h， 以92%的产率得到4,5-Bis(4-methoxyphenyl)-2-(2-pyridyl)imidazole
  参考文献：
  名称：

  实用的多组分合成从简单的结构单元的二或三芳基（杂芳基）取代的2-（吡啶-2-基）咪唑

  摘要：

  已经开发了一种方便且高效的多组分方案，用于由2-氰基吡啶，相应的芳族醛和NH 4 OAc /伯胺合成各种多取代的2-（吡啶-2-基）咪唑。值得注意的是，当使用芳族伯胺作为底物时，三取代的2-（吡啶-2-基）咪唑的收率很高，但是在一锅中可以同时获得二取代和三取代的2-（吡啶-2-基）咪唑。当某些脂肪族伯胺用作底物时。

  DOI：

  10.1021/cc100079b

文献信息

• Mechanofluorochromism based on BOPIM complexes: The effect of substituents and regulation of the direction of the emission color changes
  作者：Yong Zhan、Xin Wang、Yunhan Wang、Yongnan Xu

  DOI：10.1016/j.dyepig.2019.04.001

  日期：2019.8

  Novel boron 2-(2′-pyridyl)imidazole (BOPIM) complexes T1, T2 and T3 with different substituents (including bromo, tert-butyl and methoxyl) on the benzene ring of BOPIM dyes have been designed and synthesized, and their optical properties in both solution and the solid state were investigated and compared. The three compounds exhibited typical intramolecular charge transfer (ICT) characteristics. Solvent-dependent

  设计并合成了在BOPIM染料的苯环上具有不同取代基（包括溴，叔丁基和甲氧基）的新型2-（2'-吡啶基）咪唑硼配合物T1，T2和T3研究并比较了溶液和固态下的溶液。这三种化合物表现出典型的分子内电荷转移（ICT）特性。溶剂依赖性的紫外可见吸收，荧光发射光谱和量子化学计算表明分子推挽式电子结构。他们的ICT程度随着T1  <  T2  <  T3的顺序而增加。X射线晶体结构的分析揭示了BOPIM染料的扭曲的分子构象。此外，它们在机械力作用下表现出显着的可逆机械荧光变色（MFC）功能。发现通过改变BOPIM染料上的取代基可以容易地调节MFC活性。在机械刺激下，T1的发射颜色从亮绿色变为黄绿色，光谱红移仅为22 nm，而T2和T3给出了36和30 nm的大光谱红移。事实证明，代用品的电子和空间效应在调节ICT效应和分子间相互作用方面起着重要作用。更重要的是，取代基对BOPIM染料的MFC行为的显着
• Synthesis and platelet aggregation inhibitory activity of diphenylazole derivatives. I. Thiazole and imidazole derivatives.
  作者：Norihiko SEKO、Kohichiro YOSHINO、Koichi YOKOTA、Goro TSUKAMOTO

  DOI：10.1248/cpb.39.651

  日期：——

  Diphenylimidazole and diphenylthiazole derivatives were synthesized and tested as inhibitors of platelet aggregation in in vitro experiments with the rabbit. Diphenylthiazole derivatives (10) were more potent than diphenylimidazole derivatives (4) in inhibiting arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. Two diphenylimidazole and eight diphenylthiazole derivatives were evaluated for ex vivo arachidonic acid and collagen-induced platelet aggregation inhibitory activity using guinea pigs. In these compounds, 4, 5-bis(4-methoxyphenyl)-2-(1, 5-dimethyl-2-pyrrolyl)thiazole (10n) showed strong activity in vitro and ex vivo. The ex vivo activity of 10n was 200 times stronger than that of aspirin. The mechanism of the activity of 10n was the inhibition of cyclo-oxygenase.

  合成了二苯基咪唑和二苯基噻唑衍生物，并在兔子的体外实验中将其作为血小板聚集抑制剂进行了测试。在抑制花生四烯酸诱导的兔子富血小板血浆血小板聚集方面，二苯基噻唑衍生物（10）比二苯基咪唑衍生物（4）更有效。用豚鼠评估了两种二苯基咪唑和八种二苯基噻唑衍生物对花生四烯酸和胶原蛋白诱导的血小板聚集的体内外抑制活性。在这些化合物中，4, 5-双（4-甲氧基苯基）-2-（1, 5-二甲基-2-吡咯基）噻唑（10n）在体外和体内均表现出很强的活性。10n 的体内外活性比阿司匹林强 200 倍。10n 的活性机制是抑制环氧化酶。
• Microwave Enabled Umpulong Mechanism Based Rapid and Efficient Four- and Six-Component Domino Formations of 2-(2′-Azaaryl)imidazoles and <i>anti</i>-1,2-Diarylethylbenzamides
  作者：Bo Jiang、Xiang Wang、Feng Shi、Shu-Jiang Tu、Teng Ai、Austin Ballew、Guigen Li

  DOI：10.1021/jo902204s

  日期：2009.12.18

  Concise and efficient six-component and four-component domino approaches to anti-1,2-diarylethylbenzamides and highly Substituted 2-(2'-azaaryl)imidazoles have been developed under solvent-free and microwave-irradiation conditions. The reactions showed a broad scope of substrates in which a wide range of common commercial aromatic aldehydes and heteroaryl nitriles can be used. The syntheses were Finished within short periods (15-34 min) with good to excellent chemical yields and stereoselectivity that avoided tedious workup isolations. New mechanisms involving an umpolung have been proposed for these two reaction processes.