1,3-di(2-phenylethyl)imidazolium bromide | 1176202-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-di(2-phenylethyl)imidazolium bromide
• 英文别名: 1,3-Bis(2-phenylethyl)imidazol-1-ium;bromide；1,3-bis(2-phenylethyl)imidazol-1-ium;bromide
• CAS: 1176202-59-7
• 化学式: Br*C₁₉H₂₁N₂
• 分子量: 357.293
• InChiKey: JSKOJKFKIDVKOB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-di(2-phenylethyl)imidazolium bromide 、 nickelocene 以 四氢呋喃 为溶剂， 反应 6.0h， 以71%的产率得到[CpNiBr{Im((CH₂)₂Ph)₂}]
  参考文献：
  名称：

  使用新型CpNiBr（NHC）配合物轻松活化活化的芳基卤化物的Suzuki-Miyaura

  摘要：

  由镍茂和相应的对称或不对称烷基/-苄基/苯乙基咪唑鎓溴化配体合成了九种新的Ni（II）-NHC络合物[CpNiBr（NHC）]，产率较高。通过使咪唑去质子化，然后用烷基或芳基卤化物处理，随后使仲烷基-，苄基-，或苯基乙基卤化物。[CpNiBr（NHC）]系列在活化的芳基卤化物与苯基硼酸的Suzuki-Miyaura偶联中表现出催化活性，从而得到各自的含联苯和联苯的产物。一般来说，带有更多给电子体的带有NHC的Ni配合物显示出更高的活性，这些芳基卤化物带有带有吸电子功能的芳族卤化物，包括羧醛部分。所有复合物的特征是1 H和13 C NMR光谱，FT-IR光谱，CHN和MS分析以及此处报告的六种选定的单晶X射线结构。

  DOI：

  10.1016/j.jorganchem.2016.03.017
• 作为产物：
  描述：

  乙基溴苯 在 potassium tert-butylate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.33h， 生成 1,3-di(2-phenylethyl)imidazolium bromide
  参考文献：
  名称：

  Novel phenethylimidazolium based ionic liquids: Design, microwave synthesis, in-silico, modeling and biological evaluation studies

  摘要：

  An eco-friendly preparation method for the novel bioactive imidazolium ionic liquids halides (ILs) was developed under microwave-assisted conditions. Synthesized ILs were characterized by spectroscopic techniques. Selected Is were investigated for their antimicrobial activity against highly resistant Gram-positive and Gram-negative bacterial strains. Overall, 3-(2-chlorobenzyl)-1-phenethyl-1H-imidazol-3-iumchloride (4) showed high antimicrobial activity against the Staphylococcus aureus strain in the inhibition zone tests and displayed low MIC and MBC levels against almost all tested bacteria. Furthermore, the Its were screened in vitro against human hepatocellular carcinoma (HepG-2), human breast adenocardnoma (MCF-7), and human colon carcinoma (Caco-2) cell lines. The screening results showed excellent to moderate anticancer activity across the ILs. Among the synthesized ILs, Overall, 3-(2-chlorobenzyl)-1-phenethyl-1H-imidazol-3-ium chloride (4) and 1-phenethyl-3-(3phenoxypropyl)-1H-imidazol-3-ium bromide (7) were found to exhibit the most promising ant proliferative effects and had the lowest IC50 values. The docking study suggested strong interaction of ILs with DNA with binding energy ranging from -4.9 to -4.1 kcal/mol. ILs 4 and 7 were most strongly bonded with -4.9 and -4.8 kcal/mol binding energy: confirming in vitro anticancer results. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2020.113778

文献信息

• [EN] METHOD FOR TREATING FIBROSIS AND CANCER WITH IMIDAZOLIUM AND IMIDAZOLINIUM COMPOUNDS<br/>[FR] PROCÉDÉ DE TRAITEMENT DE LA FIBROSE ET DU CANCER AVEC DE L'IMIDAZOLIUM ET DES COMPOSÉS À BASE D'IMIDAZOLINIUM
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2009096905A1

  公开（公告）日：2009-08-06

  There is presently provided methods for delivering an anti-fibrotic or anti-cancer agent to a cell. The methods comprise contacting a cell with an effective amount of imidazolium and imidazolinium compounds as described herein, including imidazolium and imidazolinium salts.

  目前提供了一种将抗纤维化或抗癌药物输送到细胞的方法。该方法包括将细胞与本文所述的咪唑和咪唑啉化合物的有效量接触，包括咪唑和咪唑啉盐。
• Base-free glucose dehydration catalysed by NHC-stabilised heterohalo cyclopentadienyl Cr(<scp>iii</scp>) complexes
  作者：Frederick P. Malan、Eric Singleton、Petrus H. van Rooyen、Jeanet Conradie、Marilé Landman

  DOI：10.1039/c8nj04804e

  日期：——

  detailed conformational DFT analysis, which showed metal-centred redox behaviour. Furthermore, the Cr(III) complex salt (6) was electrochemically oxidised to Cr(IV) and electrochemically reduced to Cr(II) more readily than the related Cr(III)–NHC complexes (1–5). All complexes (1–6) were active (up to 81% conversion) as catalysts in the dehydration of glucose to form 5-hydroxymethylfurfural in moderate

  从发新世及其相应的咪唑鎓盐中合成了五种空气稳定的杂卤代Cr（III）-NHC配合物（1-5）。使用N -4-NO 2-苄基咪唑盐会导致副反应，发生C–N键断裂，形成咪唑Cr（III）络合物盐（6）。通过循环伏安法和详细的构象DFT分析研究了所有六个配合物的电化学过程，结果表明了以金属为中心的氧化还原行为。此外，将Cr（III）络合物盐（6）电化学氧化为Cr（IV），然后电化学还原为Cr（III）。II）比相关的Cr（III）-NHC配合物（1-5）更容易。所有复合物（1-6）都具有活性（转化率高达81％）作为葡萄糖脱水形成5-羟甲基糠醛的催化剂，产率中等（高达76％）。该均相体系不需要氧化剂或化学计量的强碱（例如KO t Bu），而这在相关的催化体系中通常是必需的，这对于开发使用天然丰富前体的绿色催化过程非常重要。
• Facile Suzuki-Miyaura coupling of activated aryl halides using new CpNiBr(NHC) complexes
  作者：Frederick P. Malan、Eric Singleton、Petrus H. van Rooyen、Marilé Landman

  DOI：10.1016/j.jorganchem.2016.03.017

  日期：2016.7

  subsequently followed with reaction of a secondary alkyl-, benzyl-, or phenylethyl halide. The series of [CpNiBr(NHC)] exhibited catalytic activity in the Suzuki-Miyaura coupling of activated aryl halides with phenylboronic acid to give the respective biphenyl and biphenyl-containing products. In general, the more electron-donating NHC-bearing Ni complexes showed higher activity with aryl halides bearing

  由镍茂和相应的对称或不对称烷基/-苄基/苯乙基咪唑鎓溴化配体合成了九种新的Ni（II）-NHC络合物[CpNiBr（NHC）]，产率较高。通过使咪唑去质子化，然后用烷基或芳基卤化物处理，随后使仲烷基-，苄基-，或苯基乙基卤化物。[CpNiBr（NHC）]系列在活化的芳基卤化物与苯基硼酸的Suzuki-Miyaura偶联中表现出催化活性，从而得到各自的含联苯和联苯的产物。一般来说，带有更多给电子体的带有NHC的Ni配合物显示出更高的活性，这些芳基卤化物带有带有吸电子功能的芳族卤化物，包括羧醛部分。所有复合物的特征是1 H和13 C NMR光谱，FT-IR光谱，CHN和MS分析以及此处报告的六种选定的单晶X射线结构。
• Method for treating neurological disorders with imidazolium and imidazolinium compounds
  申请人：Agency for Science, Technology and Research

  公开号：EP2803356A1

  公开（公告）日：2014-11-19

  There is presently provided methods for delivering a neuroprotective agent to a neural cell. The methods comprise contacting a neural cell with an imidazolium or imidazolinium compound as described herein, including an imidazolium or imidazolinium salt.

  目前提供了向神经细胞递送神经保护剂的方法。这些方法包括将神经细胞与本文所述的咪唑或咪唑啉化合物（包括咪唑盐或咪唑啉盐）接触。
• METHOD FOR TREATING FIBROSIS AND CANCER WITH IMIDAZOLIUM AND IMIDAZOLINIUM COMPOUNDS
  申请人：Agency for Science, Technology And Research

  公开号：EP2249832A1

  公开（公告）日：2010-11-17