1,3-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)imidazolium bromide | 1399982-86-5

• 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-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)imidazolium bromide
• 英文别名: 1,3-di(p-methylbenzyl)-4,5-di(p-methoxyphenyl)imidazolium bromide
• CAS: 1399982-86-5
• 化学式: Br*C₃₃H₃₃N₂O₂
• 分子量: 569.541
• InChiKey: NRKXOJNTGXSSKT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.27
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1,3-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)imidazolium bromide 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以64.5%的产率得到[1,3-di(p-methylbenzyl)-4,5-di(p-methoxyphenyl)imidazol-2-ylidene](6-p-cymene)ruthenium(II) dichloride
  参考文献：
  名称：

  新型钌（II）和金（I）NHC配合物：合成，表征和其抗癌性能评估

  摘要：

  报道了新型Ru（II）-和Au（I）-N-杂环卡宾的合成，表征和生物学评估。所述NHC-钌（II）络合物（1 - 6）通过用银适当取代的咪唑鎓溴化物反应而合成2 O，形成NHC-溴化银原位随后用二聚转移金属化p -cymene钌（II）二氯化物。以类似方式将NHC-氯化金（I）络合物（NHC-Au（I）Cl）7 – 9用二甲基硫代氯化金（I）作金属转移剂合成了这些化合物。在NHC-金的配体交换（I）氯化物，通过或者与乙酸银络合物反应以得到NHC -金（I）乙酸盐（NHC -金（I）OAC）达到10 - 12或反应的NHC-金（I）在碱性条件下用2'，3'，4'，6'-四-O-乙酰基-1-硫代-β- d-吡喃葡萄糖（SR）氯化物得到NHC-金（I）-（2 '，3'，4'，6'-四-O-乙酰基-β- d-吡喃葡萄糖基-1-硫醇盐）络合物（NHC-Au（I）SR）13 – 15。Ru（II）-N

  DOI：

  10.1021/om400819p
• 作为产物：
  描述：

  4,5-bis(4-methoxyphenyl)-1H-imidazole 、 4-甲基苄溴 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以30.7%的产率得到1,3-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)imidazolium bromide
  参考文献：
  名称：

  Novel symmetrically p-benzyl-substituted 4,5-diaryl-imidazole N-heterocyclic carbene-silver(I) acetate complexes – Synthesis and biological evaluation

  摘要：

  Symmetrically substituted N-heterocyclic carbene (NHC) precursors 1a-e and 3a-e were synthesised by reacting 4,5-bisaryl-1H-imidazole with 2 equivalents of 4-benzyl bromide, 4-methylbenzyl bromide, 4-methoxybenzyl chloride, 4-methoxycarbonylbenzyl bromide or 4-cyanobenzyl bromide to give the 1,3-bis(p-benzyl substituted)-4,5-bisaryl-imidazolium halides. The NHC-silver(I) acetate complexes (1,3-bisbenzyl-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2a), (1,3-bis(4-methylbenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2b), (1,3-bis(4-methoxybenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2c), (1,3-bis(4-methoxycarbonylbenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2d), (1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2e), (1,3-bisbenzyl-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4a), (1,3-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4b), (1,3-bis(4-methoxybenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4c), (1,3-bis(4-methoxycarbonylbenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4d) and (1,3-bis(4-cyanobenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4e) were yielded by reacting these NHC precursors with silver(I) acetate. The silver(I) acetate complexes 2d, 2e and 4c were characterised by single crystal X-ray diffraction. Qualitative antibacterial studies against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus, using the Kirby-Bauer disc diffusion method were carried out on the ten NHC-silver(I) acetate complexes 2a-e and 4a-e. Also the IC50 values of these ten complexes were determined by an MTT-based assay against the human renal cancer cell line Caki-1 and the human breast cancer cell line MCF-7. The complexes 2a-e and 4a-e revealed the following IC50 values in mu M against Caki-1: 14 (+/- 1), 3.6 (+/- 1.0), 4.2 (+/- 0.5), 33 (+/- 2), 59 (+/- 4), 21 (+/- 1), 21 (+/- 2), 21 (+/- 1), 34 (+/- 2), 46 (+/- 2) and against MCF-7: 5.8 (+/- 0.6), 3.5 (+/- 0.4), 5.4 (+/- 0.3), 28 (+/- 1), 25 (+/- 2), 11 (+/- 2), 5.0 (+/- 0.3), 6.5 (+/- 0.4), 17 (+/- 1), 13 (+/- 1); respectively. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.006

文献信息

• Synthesis and cytotoxicity studies of p-benzyl substituted NHC–copper(I) bromide derivatives
  作者：Wojciech Streciwilk、Frauke Hackenberg、Helge Müller-Bunz、Matthias Tacke

  DOI：10.1016/j.poly.2013.11.039

  日期：2014.9