1-(2-phenylethyl)benzimidazole | 22492-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-phenylethyl)benzimidazole
• 英文别名: 1-(2-phenylethyl)-1H-benzimidazole
• CAS: 22492-13-3
• 化学式: C₁₅H₁₄N₂
• mdl: MFCD00958410
• 分子量: 222.29
• InChiKey: GLKFHNCBBKKHGM-UHFFFAOYSA-N

物化性质

• 熔点：
  74-75 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  395.6±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 溶解度：
  29.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-phenylethyl)benzimidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 bis[1,3-di-(2-phenylethyl)benzimidazoline-2-ylidene]
  参考文献：
  名称：

  Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds

  摘要：

  New benzimidazole derivatives were synthesised by electron-rich olefines (7, 8 and 9) with appropriate reagents. The compounds synthesised were identified by 1H NMR, 13C NMR, FT-IR spectroscopic techniques and elemental analysis. All compounds studied in this work were screened for their in vitro antimicrobial activities against the standard strains: Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853) and the yeasts Candida albicans and Candida tropicalis. Eleven of the compounds inhibited the growth of gram-positive bacteria (E. faecalis and S. aureus) at MIC values between 50 and 400 microg/ml. None of the compounds exhibit antimicrobial activity against Gram-negative bacteria (E. coli and P. Aeruginosa) at the concentrations studied (6.25-800 microg/ml). Nine of the tested compounds showed an antifungal activity with a range of the MICs between 50 and 400 microg/ml.

  DOI：

  10.1016/s0014-827x(03)00068-5
• 作为产物：
  描述：

  苯并咪唑 、 乙基溴苯 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 1-(2-phenylethyl)benzimidazole
  参考文献：
  名称：

  结合新的苯并咪唑盐用于Sonogashira交叉偶联反应的高效绿色催化体系

  摘要：

  合成了许多新颖的苯并咪唑盐，并使用1 H NMR，13 C NMR和红外光谱技术以及元素分析确定了其结构。在Cs 2 CO 3存在下由Pd（OAc）2和铜纳米颗粒组成并在聚乙二醇溶剂中掺入新型苯并咪唑盐的催化剂体系显着提高了芳烃卤化物和苯乙炔在微波辐射下的Sonogashira反应的收率。 10分钟

  DOI：

  10.1002/aoc.3897

文献信息

• N‐Heterocyclic Carbene (NHC)‐Stabilized Ru ⁰ Nanoparticles: In Situ Generation of an Efficient Transfer Hydrogenation Catalyst
  作者：Lakshay Kathuria、Noor U. Din Reshi、Ashoka G. Samuelson

  DOI：10.1002/chem.202000142

  日期：2020.6.18

  untethered ruthenium half‐sandwich complexes were synthesized and characterized spectroscopically. X‐ray crystallographic analysis of three untethered and two tethered Ru N‐heterocyclic carbene (NHC) complexes were also carried out. These RuNHC complexes catalyze transfer hydrogenation of aromatic ketones in 2‐propanol under reflux, optimally in the presence of (25 mol %) KOH. Under these conditions, the

  束缚和未束缚的钌半三明治复合物通过光谱法表征。还进行了三个未束缚的和两个束缚的Ru N-杂环卡宾（NHC）配合物的X射线晶体学分析。这些RuNHC配合物可在回流条件下（2-5％的KOH）存在下，在2-丙醇中催化芳族酮的转移加氢反应。在这些条件下，形成2–3 nm大小的Ru 0通过TEM测量检测纳米颗粒。对纳米颗粒的固态NMR研究表明，NHC配体与Ru纳米颗粒（NPs）的表面结合。与以前已知的通向NHC稳定化的Ru纳米催化剂的途径相比，这种由碱促进的直接从芳族化的钌-NHC络合物和不受束缚的钌-NHC络合物到NHC稳定的钌纳米颗粒的途径更方便。[RuCl 2（p- cymene）] 2混合物的反应也产生了类似的催化活性RuNP。NHC前体与KOH在异丙醇中回流。这些经过NHC稳定的RuNP催化的转移氢化具有很高的周转率。如果纳米颗粒暴露于空气中或通过在反应期间冷却反应混合物而使其聚集和沉淀，则催化效率显着降低。
• Carbonylative Acetylation of Heterocycles
  作者：Youcan Zhang、Zhiping Yin、Xiao-Feng Wu

  DOI：10.1002/ejoc.201901728

  日期：2020.1.16

  A new procedure for the carbonylative acetylation of heterocycles has been developed. In this process, organic peroxide acts as the methyl source, various heterocycles were transformed into the corresponding methyl heterocyclic ketones in moderate to good yields.

  已经开发了杂环羰基乙酰化的新方法。在此过程中，有机过氧化物作为甲基来源，各种杂环以中等至良好的收率转化为相应的甲基杂环酮。
• Access to Aromatic Ring-Fused Benzimidazoles Using Photochemical Substitutions of the Benzimidazol-2-yl Radical
  作者：Fawaz Aldabbagh、Joanne O’Connell、Eoin Moriarty

  DOI：10.1055/s-0032-1316775

  日期：——

  onto the benzimidazole-2-position. Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution

  摘要 描述了从2-碘-1-（ω-芳烷基）-1 H-苯并咪唑的光化学五元，六元和七元环化。这种生产芳环稠合苯并咪唑的方法比使用化学引发剂的自由基方法明显更有效，尽管2-碘-1-（ω-吡啶-2-基烷基）-1H-苯并咪唑优先经历亲核性的ipso-取代反应。苯并咪唑-2-位。 描述了从2-碘-1-（ω-芳烷基）-1 H-苯并咪唑的光化学五元，六元和七元环化。这种生产芳环稠合苯并咪唑的方法比使用化学引发剂的自由基方法明显更有效，尽管2-碘-1-（ω-吡啶-2-基烷基）-1H-苯并咪唑优先经历亲核性的ipso-取代反应。苯并咪唑-2-位。
• Design and Synthesis of Polycyclic Imidazole‐Containing N‐ Heterocycles based on CH Activation/Cyclization Reactions
  作者：Viktor O. Iaroshenko、Dmytro Ostrovskyi、Mariia Miliutina、Aneela Maalik、Alexander Villinger、Andrei Tolmachev、Dmitriy M. Volochnyuk、Peter Langer

  DOI：10.1002/adsc.201200221

  日期：2012.9.17

  A new strategy for the synthesis of polycyclic imidazole‐containing N‐heterocycles, based on the two general synthetic ways, namely the Pd(II)‐catalyzed intramolecular arylation via CH/CHal and CH/CH coupling reactions, was developed. The method proposed here enables the synthesis of many fused N‐heterocycles containing purine, 1‐deazapurines and benzimidazole structural units.

  基于两种通用的合成方法，即通过CH / CHal和CH / CH偶联反应，Pd（II）催化的分子内芳基化反应，开发了一种合成多环咪唑N-杂环的新策略。本文提出的方法能够合成许多含有嘌呤，1-去氮杂嘌呤和苯并咪唑结构单元的稠合N-杂环。
• Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C–H bond functionalization
  作者：Peng-Yang Xin、Hong-Ying Niu、Gui-Rong Qu、Rui-Fang Ding、Hai-Ming Guo

  DOI：10.1039/c2cc32396f

  日期：——

  A novel protocol for nickel-catalyzed direct sp2 C–H bond alkylation of N-aromatic heterocycles has been developed. This new reaction proceeded efficiently at room temperature using a Grignard reagent as the coupling partner. This approach provides new access to a variety of alkylated N-aromatic heterocycles which are potentially of great importance in medicinal chemistry.

  一种新的协议已被开发用于镍催化的N-芳香族杂环直接sp² C–H键烷基化反应。该反应在室温下以格里尼亚试剂作为耦合伙伴高效进行。这种方法为获取各种烷基化的N-芳香族杂环提供了新的途径，这些化合物在药物化学中可能具有重要价值。