2-(2,3,4,5,6-pentamethylbenzyl)-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-2-ium bromide | 1009637-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-(2,3,4,5,6-pentamethylbenzyl)-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-2-ium bromide
• 英文别名: 2-[(2,3,4,5,6-Pentamethylphenyl)methyl]-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-2-ium；2-[(2,3,4,5,6-pentamethylphenyl)methyl]-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-2-ium;bromide
• CAS: 1009637-05-1
• 化学式: Br*C₁₉H₂₉N₂
• 分子量: 365.357
• InChiKey: CBPYXXZWCUKJJC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 2-(2,3,4,5,6-pentamethylbenzyl)-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-2-ium bromide 以 甲苯 为溶剂， 以53%的产率得到
  参考文献：
  名称：

  Annulated N-Heterocyclic Carbene Ligands Derived from 2-Methylaminopiperidine: Their Complexes and Catalytic Applications

  摘要：

  A new type of carbene precursor, 1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine (1), has been prepared from 2-(aminomethyl)piperidine and N,N-dimethylformamide dimethylacetal. The reactions of three imidazolidinium salts with [Rh(acac)(COD)] and [Ir(u-OMe)(COD)](2) were found to afford rhodium and iridium complexes of N-heterocyclic carbenes, respectively. These complexes have been tested as catalysts in the transfer hydrogenation of cyclohexanone and acetophenone using 2-propanol as hydrogen source.

  DOI：

  10.1021/om701105y
• 作为产物：
  描述：

  1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine 、 2,3,4,5,6,-pentamethylbenzyl bromide 以 甲苯 为溶剂， 反应 4.0h， 生成 2-(2,3,4,5,6-pentamethylbenzyl)-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-2-ium bromide
  参考文献：
  名称：

  Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents

  摘要：

  Variously substituted benzyl bromides were employed to quaternize hexahydrobenzylimidazo[1,5-a] pyridine (A) and the resulting bromides (1-11) were evaluated for their in vitro antimicrobial activity against 10 pathogenic microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Micrococcus luteus, Proteus vulgaris, Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia, Candida albicans and Candida krusei. Antimicrobial activities were surprisingly high (MIC: 0.78-400 mu g/mL) and the sensitivity of the salts tested has been found to depend strongly both on the benzyl substituents and the microorganisms used. However, the correlation observed between antimicrobial activity and calculated partition coefficient (ClogP) was poor. Acute toxicity assessment of these salts showed LD50 of 757-2000 mg/kg, after oral administration in mice in 24 h. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.012

文献信息

• Synthesis, characterization, and reactivity of palladium(II) complexes containing piperidoimidazolin-2-ylidene
  作者：Hayati Türkmen、İbrahim Kani

  DOI：10.1002/aoc.3015

  日期：2013.8

  series of Pd–N‐heterocyclic carbene (Pd‐NHC) complexes with pyrazine (1) or pyridine (2) and NHC (3) were synthesized and characterized by elemental analysis and spectroscopic methods. In addition, the molecular structure of 3 was determined by X‐ray diffraction studies. The effects of these ligands on catalyst activation and the performance of complexes 1, 2, 3 were studied on Suzuki–Miyaura reactions

  合成了一系列Pd- N杂环卡宾（Pd-NHC）与吡嗪（1）或吡啶（2）和NHC（3）的配合物，并通过元素分析和光谱法对其进行了表征。此外，3的分子结构是通过X射线衍射研究确定的。上催化剂活化这些配体和配合物的性能的影响1，2，3进行了研究与芳基氯的苯基硼酸铃木-宫浦反应。最后，我们证明了复合物1非常擅长重构Kumada–Tamao–Corriu交叉偶联反应。版权所有©2013 John Wiley＆Sons，Ltd.
• Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents
  作者：Hayati Türkmen、Nur Ceyhan、N. Ülkü Karabay Yavaşoğlu、Güven Özdemir、Bekir Çetinkaya

  DOI：10.1016/j.ejmech.2011.04.012

  日期：2011.7

  Variously substituted benzyl bromides were employed to quaternize hexahydrobenzylimidazo[1,5-a] pyridine (A) and the resulting bromides (1-11) were evaluated for their in vitro antimicrobial activity against 10 pathogenic microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Micrococcus luteus, Proteus vulgaris, Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia, Candida albicans and Candida krusei. Antimicrobial activities were surprisingly high (MIC: 0.78-400 mu g/mL) and the sensitivity of the salts tested has been found to depend strongly both on the benzyl substituents and the microorganisms used. However, the correlation observed between antimicrobial activity and calculated partition coefficient (ClogP) was poor. Acute toxicity assessment of these salts showed LD50 of 757-2000 mg/kg, after oral administration in mice in 24 h. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Annulated N-Heterocyclic Carbene Ligands Derived from 2-Methylaminopiperidine: Their Complexes and Catalytic Applications
  作者：Hayati Türkmen、Tania Pape、F. Ekkehardt Hahn、Bekir Çetinkaya

  DOI：10.1021/om701105y

  日期：2008.2.1

  A new type of carbene precursor, 1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine (1), has been prepared from 2-(aminomethyl)piperidine and N,N-dimethylformamide dimethylacetal. The reactions of three imidazolidinium salts with [Rh(acac)(COD)] and [Ir(u-OMe)(COD)](2) were found to afford rhodium and iridium complexes of N-heterocyclic carbenes, respectively. These complexes have been tested as catalysts in the transfer hydrogenation of cyclohexanone and acetophenone using 2-propanol as hydrogen source.