1,3-bis(4-methoxybenzyl)-4,5-bisphenylimidazolium chloride | 1399982-80-9

• 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-methoxybenzyl)-4,5-bisphenylimidazolium chloride
• CAS: 1399982-80-9
• 化学式: C₃₁H₂₉N₂O₂*Cl
• 分子量: 497.036
• InChiKey: FLYQNXBNSQPEIP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1,3-bis(4-methoxybenzyl)-4,5-bisphenylimidazolium chloride 、 silver(I) acetate 以 二氯甲烷 为溶剂， 反应 168.0h， 以81.7%的产率得到(1,3-bis(4-methoxybenzyl)-4,5-bisphenylimidazole-2-ylidene)silver(I) acetate
  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
• 作为产物：
  描述：

  4,5-二苯基咪唑 、 4-甲氧基氯苄 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以43.3%的产率得到1,3-bis(4-methoxybenzyl)-4,5-bisphenylimidazolium chloride
  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

• Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the α-alkylation of ketones with primary alcohols
  作者：Mamajan Ovezova、Zafer Eroğlu、Önder Metin、Bekir Çetinkaya、Süleyman Gülcemal

  DOI：10.1039/d1dt01704g

  日期：——

  catalysts in the α-alkylation of ketones with primary alcohols using a borrowing hydrogen process and tandem Suzuki–Miyaura coupling/α-alkylation reactions. Among the synthesized Pd-PEPPSI complexes, complex 2c having 4-methoxyphenyl groups at the 4,5-positions and 4-methoxybenzyl substituents on the N-atoms of imidazole exhibited the highest catalytic activity in the α-alkylation of ketones with primary

  我们在此报告了四种具有骨架修饰的 N-杂环卡宾 (NHC) 配体的新型 Pd-PEPPSI 配合物的合成及其作为催化剂在使用借氢工艺和串联 Suzuki-Miyaura 偶联的酮与伯醇的 α-烷基化中的应用/α-烷基化反应。在合成的Pd-PEPPSI配合物中，在4,5-位具有4-甲氧基苯基和咪唑N-原子上具有4-甲氧基苄基取代基的配合物2c在酮与伯醇的α-烷基化中表现出最高的催化活性（ 18 个例子），产率高达 95%。此外，复杂的2c被证明是酮串联 Suzuki-Miyaura 偶联/α-烷基化以高产率得到联芳基酮的有效催化剂。通过汞中毒和热过滤实验验证了本催化系统的多相性质。此外，通过先进的分析技术确定了在 α-烷基化反应过程中 NHC 稳定的 Pd(0) 纳米粒子的形成。
• α-Alkylation of arylacetonitriles with primary alcohols catalyzed by backbone modified N-heterocyclic carbene iridium(<scp>i</scp>) complexes
  作者：Burcu Arslan、Süleyman Gülcemal

  DOI：10.1039/d0dt04082g

  日期：——

  backbone-modified N-heterocyclic carbene (NHC) complexes of iridium(I) (1d–f) have been synthesized and characterized. The electronic properties of the NHC ligands have been assessed by comparison of the IR carbonyl stretching frequencies of the in situ prepared [IrCl(CO)2(NHC)] complexes in CH2Cl2. These new complexes (1d–f), together with previously prepared 1a–c, were applied as catalysts for the α-alkylation

  合成并表征了一系列骨架修饰的铱（I）（1d–f）的N-杂环卡宾（NHC）配合物。通过比较在CH 2 Cl 2中原位制备的[IrCl（CO）2（NHC）]配合物的IR羰基拉伸频率，可以评估NHC配体的电子性质。这些新的配合物（1d–f）以及先前制备的1a–c将其用作等摩尔量的伯醇或2-氨基苄醇的芳基乙腈的α-烷基化催化剂。这些配合物的催化活性可以通过修饰NHC配体的N-取代基和主链来控制。NHC-Ir I络合物1f在N原子上带有4-甲氧基苄基取代基，在咪唑的4,5-位带有4-甲氧基苯基，在芳基乙腈与伯醇的α-烷基化反应中表现出最高的催化活性。在空气气氛中，在非常短的反应时间内，通过使用0.1 mol％1f和催化量的KOH（5 mol％），通过借用氢途径以高收率获得了各种α-烷基化的腈和氨基喹啉。