1-(2,6-diisopropylphenyl)-3-benzyl imidazolium bromide | 1003570-22-6

• 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-(2,6-diisopropylphenyl)-3-benzyl imidazolium bromide
• 英文别名: 3-benzyl-1-(2,6-diisopropylphenyl)-1H-imidazol-3-ium bromide
• CAS: 1003570-22-6
• 化学式: Br*C₂₂H₂₇N₂
• 分子量: 399.374
• InChiKey: QOSIJNGGDSIJRA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(2,6-diisopropylphenyl)-3-benzyl imidazolium bromide 以 二氯甲烷 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  以钯双（N-杂环卡宾）配合物为催化剂的Heck偶联反应在核心官能化的聚（苄基醚）树状聚合物

  摘要：

  双（imidazolylidene）钯络合物9 - 12含有空间位阻的芳基（均三甲苯基或2,6-二异丙基）和聚（苯醚）树枝状作为NHC配体的N-取代基是可访问到第三代通过的转移金属化相应的银配合物。配合物9 – 12在Heck反应条件下是可溶，活性和非常稳定的催化剂。NHC配体在催化过程中似乎与Pd稳定配位。催化活性随世代数的增加而增加，尽管是不规则的。X射线衍射，荧光和DOSY-NMR光谱以及MD模拟研究证实，由于树枝状取代基尺寸的增加，钯位点在反应溶剂中不会明显拥塞。这是聚（苄基醚）树突的构象半柔韧性以及这些树突与N-杂环配体之间的苄基连接的结果。

  DOI：

  10.1021/acs.inorgchem.5b02629
• 作为产物：
  描述：

  溴甲苯 、 1-(2,6-二异丙基苯基)-1H-咪唑 在 碳酸氢钠 作用下， 反应 1.5h， 以93%的产率得到1-(2,6-diisopropylphenyl)-3-benzyl imidazolium bromide
  参考文献：
  名称：

  Noels型NHC-钌配合物的机械合成及其在开环易位聚合中的应用

  摘要：

  球磨机的使用使各种N-芳基，N-烷基咪唑鎓盐和相应的NHC银（I）络合物的有效机械合成成为可能。钌通过机械化学进行重金属化可以快速进入（从1.5分钟到1小时）到与Noels型预催化剂具有相似结构的络合物。评估降冰片烯在不同溶剂（包括无毒溶剂）中的开环易位聚合反应中的配合物，发现其中一种与Noels催化剂相比具有很高的催化活性。

  DOI：

  10.1021/acs.organomet.0c00013

文献信息

• Solving the challenging synthesis of highly cytotoxic silver complexes bearing sterically hindered NHC ligands with mechanochemistry
  作者：Audrey Beillard、François Quintin、Jérémie Gatignol、Pascal Retailleau、Jean-Luc Renaud、Sylvain Gaillard、Thomas-Xavier Métro、Frédéric Lamaty、Xavier Bantreil

  DOI：10.1039/d0dt00410c

  日期：——

  straightforward synthesis of a variety of silver(I) complexes featuring challenging NHC ligands. Sterically hindered including electron-poor or with very low solubility imidazolium salts were ground with silver(I) oxide to furnish heteroleptic or homoleptic complexes in high yields and short reaction times. The synthesis of heteroleptic bis-NHC silver(I) complexes was also performed for the first time in a

  使用球磨机可以直接合成具有挑战性NHC配体的各种银（I）配合物。包括电子贫乏或溶解度非常低的受阻位咪唑鎓盐与氧化银（I）一起研磨，以高收率和较短的反应时间提供杂配或均配的配合物。杂合双-NHC银的合成（I）复合物也是第一次在球磨机中进行。机械化学方法的效率和快速性使得能够生成空前的NHC银复合物文库，评估了其对HCT116结肠直肠癌细胞系的细胞毒性，为药物机械化学提供了一个罕见的例子。发现阳离子银配合物比中性类似物更有效，IC 50值低至21 nM，且比顺铂强256倍。
• Piano‐Stool Ruthenium <i>N</i>‐Heterocyclic Carbene Complexes for <i>gem</i>‐Specific Catalytic Dimerization of Terminal Alkynes
  作者：Kasumi Hayashi、Qiuming Liang、Franka Philippi、Datong Song

  DOI：10.1002/ejic.202300168

  日期：2023.7.25

  A series of piano-stool Ru-NHC (NHC=N-heterocyclic carbene) complexes with various levels of steric congestion have been used as precatalysts in the catalytic dimerization of terminal alkynes. The most congested complexes of this series give 100 % gem-enyne products at ambient temperature when activated with a base.

  一系列具有不同空间拥挤程度的钢琴凳Ru-NHC（NHC= N-杂环卡宾）配合物已被用作末端炔烃催化二聚反应的预催化剂。当用碱激活时，该系列中最稠密的配合物在环境温度下可产生 100%宝石-烯炔产品。
• Allylic alkylation and amination using mixed (NHC)(phosphine) palladium complexes under biphasic conditions
  作者：Alexandre Flahaut、Sylvain Roland、Pierre Mangeney

  DOI：10.1016/j.jorganchem.2007.10.012

  日期：2007.12

  A dramatic improvement of the catalytic activity was observed when a phosphine was added in allylic alkylation reactions catalyzed by (NHC)Pd(eta(3)-C3H5)Cl complexes. Consequently, several palladium complexes, generated in situ from different NHC-silver complexes, [Pd(eta 3-C3H(5))Cl](2) and PPh3, were tested in this reaction to evaluate their potential. High reaction rates and conversions could be obtained with this catalytic system in the alkylation of allylic acetates with dimethylmalonate, particularly under biphasic conditions using water/dichloromethane and KOH 1 M as the base. These conditions are experimentally more convenient and gave higher reaction rates than the classical anhydrous conditions (NaH/THF). In this system, the phosphine is essential since no conversion was obtained when it is not present. The steric hindrance of the carbene ligand has a great influence on the activity and the stability of the catalytic system. The best NHC ligands for this reaction are either 1-mesityl-3-methyl-imidazol-2-ylidene or 1-(2,6-diisopropylphenyl)-3-methylimidazol- 2-ylidene which are less bulky among the NHC tested. These two ligands led in 5 min to a complete conversion at 20 degrees C. The Pd-catalyzed allylic amination reaction using (E)-1,3-diphenylprop-3-en-yl acetate and benzylamine was also tested with (NHC)(PPh3)Pd complexes and under the biphasic conditions. This reaction was found to be slower than the alkylation with dimethylmalonate but a ;complete conversion could be reached in 6 h at 20 degrees C using K2CO3 1 M as the base. NMR experiments indicated that mixed (NHC)(PPh3) Pd complexes are formed in situ but their structure could not be established exactly. (C) 2007 Elsevier B.V. All rights reserved.