1-benzyl-4,5-dimethyl-2-phenyl-1H-imidazole | 61728-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4,5-dimethyl-2-phenyl-1H-imidazole
• 英文别名: 1-benzyl-4,5-dimethyl-2-phenylimidazole
• CAS: 61728-51-6
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: QPOZWKKPJAUYHI-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C(Solv: acetone (67-64-1))
• 沸点：
  459.7±55.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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-4,5-dimethyl-2-phenyl-1H-imidazole 、 碘甲烷 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 以50%的产率得到1-benzyl-3,4,5-trimethyl-2-phenylimidazolium 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-甲基-4-苯基-1,3-恶唑-5(2H)-酮 以32%的产率得到
  参考文献：
  名称：

  GAKIS N.; MAERKY M.; HANSEN H.-J.; HEIMGARTNER H.; SCHMID H.; OBERHAENSLI+, HELV. CHIM. ACTA , 1976, 59, NO 6, 2149-2167

  摘要：

  DOI：

文献信息

• Elemental Sulfur-Promoted Aerobic Cyclization of Ketones and Aliphatic Amines for Synthesis of Tetrasubstituted Imidazoles
  作者：Xiangui Chen、Zhen Wang、Huawen Huang、Guo-Jun Deng

  DOI：10.1002/adsc.201800765

  日期：2018.10.18

  Elemental sulfur‐promoted cyclization for the one‐pot synthesis of tetra‐substituted imidazoles from benzylamines and ketones is described. Elemental sulfur combined with molecular oxygen as the benign co‐oxidant was found to be the key for the high efficiency of this transformation under metal‐free conditions. A range of tetrasubstituted imidazoles were synthesized from simple ketones and amines with

  描述了元素硫促进的环化反应，用于由苄胺和酮一锅合成四取代的咪唑。发现元素硫与分子氧结合作为良性助氧化剂是在无金属条件下高效转化的关键。由简单的酮和具有良好官能团耐受性的胺合成了一系列四取代的咪唑。
• Catalytic procedures for multicomponent synthesis of imidazoles: selectivity control during the competitive formation of tri- and tetrasubstituted imidazoles
  作者：Dinesh Kumar、Damodara N. Kommi、Narendra Bollineni、Alpesh R. Patel、Asit K. Chakraborti

  DOI：10.1039/c2gc35277j

  日期：——

  based ionic liquids (organic salts) were investigated for the three component reaction (3-MCR) of 1,2-diketone, aldehyde, and ammonium salts to form 2,4,5-trisubstituted imidazoles and the four component reaction (4-MCR) involving 1,2-diketone, aldehyde, amine and ammonium acetate to form 1,2,4,5-tetrasubstituted imidazoles. The HBF4–SiO2 was found to be the stand out catalyst for both the 3-MCR and

  不同的氟硼酸衍生的催化剂体系的催化潜力，即。研究了HBF 4水溶液，固体负载的HBF 4，金属四氟硼酸盐（无机盐），固体负载的金属四氟硼酸盐和基于四氟硼酸盐的离子液体（有机盐）对1,2-二酮，醛的三组分反应（3-MCR）和铵盐形成2,4,5-三取代的咪唑，然后进行涉及1,2-二酮，醛，胺和乙酸铵的四组分反应（4-MCR），形成1,2,4,5-四取代的咪唑。发现HBF 4 -SiO 2是3-MCR和4-MCR工艺的杰出催化剂。其次最有效的催化剂是LiBF 4和Zn（BF 4）2分别通过3-MCR和4-MCR形成2,4,5-三取代和1,2,4,5-四取代的咪唑。这是有关4-MCR过程中涉及1,2-二酮，醛，胺和乙酸铵的2,4,5-三取代咪唑竞争形成的未解决问题的第一份报告，并着重指出了催化剂体系在控制催化剂中的影响。选择性形成四取代的咪唑。弱质子酸的金属盐以四氟硼酸盐>高氯酸盐>三氟甲磺酸酯的
• Ni(<scp>ii</scp>)–salt catalyzed activation of primary amine-sp³C_α–H and cyclization with 1,2-diketone to tetrasubstituted imidazoles
  作者：Srikanta Samanta、Dipanwita Roy、Saikat Khamarui、Dilip K. Maiti

  DOI：10.1039/c3cc48437h

  日期：——

  NiCl₂·6H₂O and Ni(OAc)₂·4H₂O were found as efficient catalysts for C–H activation of benzyl and aliphatic amines for an unprecedented multi C–N bond forming cyclization with 1,2-diketones under refluxing toluene to furnish highly substituted and polycyclic imidazoles.

  NiCl₂·6H₂O 和 Ni(OAc)₂·4H₂O 被发现是对苄胺和脂肪胺进行C-H活化的高效催化剂，利用1,2-二酮在回流甲苯条件下进行前所未有的多个C-N键形成环化反应，生成高度取代和多环咪唑。
• Silver-Mediated C_α(sp³)-H Functionalization of Primary Amines: An Oxidative C-N Coupling Strategy for the Synthesis of Two Different Types of 1,2,4,5-Tetrasubstituted Imidazoles
  作者：Rajib Sarkar、Chhanda Mukhopadhyay

  DOI：10.1002/ejoc.201403465

  日期：2015.2

  A new silver(I)-mediated Cα(sp3)–H bond functionalization of primary amines and subsequent oxidative C–N cross-coupling reaction has been demonstrated. This protocol provides a simple, highly efficient, and straightforward approach to form significantly diverse 1,2,4,5-tetrasubstituted imidazoles. In this course of the reaction, a stoichiometric amount of Ag2CO3 was employed. Upon completion of reaction

  已经证明了一种新的银（I）介导的伯胺的 Cα（sp3）-H 键官能化和随后的氧化 C-N 交叉偶联反应。该协议提供了一种简单、高效和直接的方法来形成显着不同的 1,2,4,5-四取代咪唑。在该反应过程中，使用化学计量量的 Ag2CO3。反应完成后，银物质被成功回收和再利用，而没有任何活性损失。通过使用这种选择性氧化 C-N 偶联，很容易实现产品的良好收率，这是由关键的银 (I) 盐促进的。
• 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。