1-benzyl-2-methyl-4,5-diphenyl-1H-imidazole | 95434-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-2-methyl-4,5-diphenyl-1H-imidazole
• 英文别名: 1-Benzyl-2-methyl-4,5-diphenylimidazole；1-benzyl-2-methyl-4,5-diphenylimidazole
• CAS: 95434-70-1
• 化学式: C₂₃H₂₀N₂
• 分子量: 324.425
• InChiKey: YQJKAMGLEMIFRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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-benzyl-2-methyl-4,5-diphenyl-1H-imidazole 、 碘甲烷 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 以36%的产率得到1-benzyl-2,3-dimethyl-4,5-diphenylimidazolium iodide
  参考文献：
  名称：

  Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

  摘要：

  Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD3OH at 80 degrees C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. We report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD3OH at 80 degrees C.

  DOI：

  10.1021/jacs.5b02879
• 作为产物：
  描述：

  2-methyl-4,5-diphenyl-1H-imidazole 、 氯化苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到1-benzyl-2-methyl-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives

  摘要：

  In this study, derivatives of 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole were synthesized and their analgesic activity assayed in two tests. 1,2,4,5-Tetrasubstituted imidazole compounds were obtained by the treatment of purified imidazole compounds with benzyl chloride in the presence of sodium hydride. The structure elucidation of the compounds was performed by IR, H-1-NMR and mass spectroscopic data and elemental analysis results. Generally the prepared compound exhibited only moderate analgesic activity in mice at the dose of 100 mg/kg i.p.; however, a few of them exhibited good activity, almost equivalent to that of morphine at 1 mg/kg i.p. was observed. At the above dosage, no toxicity was observed for all compounds. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01076-x

文献信息

• An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3·3H2O
  作者：Saikat Das Sharma、Parasa Hazarika、Dilip Konwar

  DOI：10.1016/j.tetlet.2008.02.053

  日期：2008.3

  InCl3·3H2O was found to be a mild and effective catalyst for the efficient, one-pot, three component synthesis of 2,4,5-trisubstituted imidazoles at room temperature. Moreover, the utility of this protocol was further explored conveniently for the one-pot, four component synthesis of 1,2,4,5-tetrasubstituted imidazoles in high yields.

  发现InCl 3 ·3H 2 O是在室温下高效，一锅，三组分合成2,4,5-三取代的咪唑的温和有效的催化剂。此外，可以方便地进一步探索该方案的实用性，以高产率一锅，四组分合成1,2,4,5-四取代的咪唑。
• Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds
  作者：Jenifer J. Gabla、Dharmesh R. Lathiya、Akash A. Revawala、Kalpana C. Maheria

  DOI：10.1007/s11164-018-3707-3

  日期：2019.4

  The SBA-15–Pr–SO3H catalyst was found to be an efficient and recyclable solid acid catalyst and this solvent-free MW protocol afforded products in good to excellent yields of both, tri and tetra imidazoles (> 95%) within shorter reaction time (3 min) at 600 W as compared to the SBA-15 and other existing protocols. The applicability of this protocol was further explored by conducting the experiments

  摘要 通过介孔SBA-15的表面改性，通过一锅共缩聚法合成了原磺酸磺酸官能化的Santa Barbara Amorphous-15（SBA-15-Pr-SO 3 H）催化剂。合成的SBA-15 – Pr – SO 3 H已通过特殊的表征技术进行了表征，例如小角度和广角XRD，SEM – EDX，TEM，TG – DTA，酸度，FT-IR，Py-FT-IR和BET表面积分析。研究了合成催化剂对无溶剂微波辐射的催化活性，用于绿色快速合成多取代的咪唑，[2,4,5-三苯基-1（H）-咪唑（三咪唑）和1-苄基-2,4,5-三苯基-1 H-咪唑（四咪唑）]。SBA-15-Pr-SO 3发现H催化剂是一种有效且可循环使用的固体酸催化剂，这种无溶剂的MW方案在600 W的较短反应时间（3分钟）内提供了三咪唑和四咪唑（> 95％）的良好至优异收率的产物。与SBA-15和其他现有协议相比。通过在各种溶剂和取
• SbCl5.SiO2: an efficient alternative for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles in solvent or under solvent-free condition
  作者：B. Sadeghi、B. B. F. Mirjalili、S. Bidaki、M. Ghasemkhani

  DOI：10.1007/bf03245896

  日期：2011.9

  In a one-pot four-component reaction, an aldehyde, an amine, benzil and ammonium acetate were condensed for the synthesis of 1,2,4,5-tetrasubstituted imidazoles in the presence of silica supported antimony pentachloride (SbCl5.SiO2) in improved yields. The catalyst is recoverable by simple filtration and can be used in the subsequent reactions.

  在单锅四组分反应中，在二氧化硅负载的五氯化锑（SbCl 5 .SiO 2）存在下，将醛，胺，苄基和乙酸铵进行缩合以合成1,2,4,5-四取代的咪唑。）以提高产量。该催化剂可通过简单过滤回收，并可用于随后的反应中。
• IMIDAZOLIUM CATIONS WITH EXCEPTIONAL ALKALINE STABILITY
  申请人：Cornell University

  公开号：EP4108691A1

  公开（公告）日：2022-12-28

  The invention provides a compound of formula (II): wherein: R1 is wherein ∗ represents the point of attachment to the nitrogen atom at position 1 of the imidazolium ring; m is 0 or 1; n is 1-8, provided that the sum of m + n does not exceed 8; R2 is phenyl substituted with 0 to 3 substituents R6 individually selected from C1-C3 alkyl; R3 is selected from C2-C16 hydrocarbyl; R4 and R5 are individually selected from C1-C16 hydrocarbyl, or taken together R4 and R5, together with the carbon atoms to which they are attached, form a ring selected from benzene, cyclooctene and norbornene; and X- is a counterion.

  本发明提供了一种式 (II) 的化合物： 其中 R1 是 其中 ∗ 代表与咪唑环位置 1 的氮原子的连接点； m 为 0 或 1； n 为 1-8，但 m+n 之和不超过 8； R2 是被 0 至 3 个单独选自 C1-C3 烷基的取代基 R6 取代的苯基； R3 选自 C2-C16 烃基； R4 和 R5 单独选自 C1-C16 碳氢基，或 R4 和 R5 与它们所连接的碳原子一起形成一个选自苯、环辛烯和降冰片烯的 环；以及 X- 是反离子。
• Imidazoles and imidazolium cations with exceptional alkaline stability
  申请人：CORNELL UNIVERSITY

  公开号：US11242432B2

  公开（公告）日：2022-02-08

  The invention provides: imidazole and imidazolium compounds of formulas (I) and (II): polymers containing a plurality of imidazolium-containing repeating units of formula (III′): and membranes and devices comprising the polymers. Also provided are methods of making the inventive compounds and polymers.

  本发明提供：式 (I) 和 (II) 的咪唑和咪唑鎓化合物： 含有多个式（III′）含咪唑重复单元的聚合物： 以及包含这些聚合物的膜和装置。此外，还提供了制造本发明化合物和聚合物的方法。