3-(2-(4-chlorophenyl)-2-oxoethyl)-1-methyl-1H-imidazol-3-ium bromide | 59349-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-(4-chlorophenyl)-2-oxoethyl)-1-methyl-1H-imidazol-3-ium bromide
• 英文别名: 3-[2-(4-chlorophenyl)-2-oxoethyl]-1-methyl-1H-imidazol-3-ium bromide；1-(4-chlorophenyl)-2-(3-methylimidazol-3-ium-1-yl)ethanone;bromide
• CAS: 59349-29-0
• 化学式: Br*C₁₂H₁₂ClN₂O
• 分子量: 315.597
• InChiKey: KXIKUNMXRCNYGK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.15
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-(4-chlorophenyl)-2-oxoethyl)-1-methyl-1H-imidazol-3-ium bromide 在 iron(II) chloride tetrahydrate 、 三乙胺 、 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 生成 2-(4-chlorophenyl)-5-methoxycarbonyl-3-(1-methyl-1H-imidazol-3-ium-3-yl)-4-phenylpyrrol-1-ide
  参考文献：
  名称：

  Fe（II）/ Et3N-中继催化的异恶唑与咪唑鎓盐的多米诺反应，用于合成4-咪唑基吡咯烷-2-羧酸甲酯，其内酯和甜菜碱衍生物。

  摘要：

  开发了一种简单的方法，用于在混合Fe（II）/ Et3N中继催化下，从容易获得的化合物，5-甲氧基异恶唑和苯并咪唑鎓盐合成4-咪唑基吡咯烷-2-羧酸甲酯。将产物容易地转化成相应的3-（5-甲氧基羰基-1H-咪唑-3-基-3-基）吡咯-1-化物，其又可以在碱性条件下水解成相应的甜菜碱。通过在非常温和的条件下与硫反应捕获4-甲氧基羰基取代的咪唑基吡咯烷的卡宾互变异构形式，得到相应的咪唑硫酮。

  DOI：

  10.3762/bjoc.11.189
• 作为产物：
  描述：

  对氯苯乙酮 在 水 、 氢溴酸 、 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 3-(2-(4-chlorophenyl)-2-oxoethyl)-1-methyl-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study

  摘要：

  The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (Plms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of Plms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by Plm was studied by laser flash photolysis and theoretical OFT computation. These time-resolved results showed that the triplet excited states of Plms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that Plm is involved in the photocycloaddition process through the (3)(DHP center dot center dot center dot Plm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.05.013

文献信息

• A simple approach to pyrrolylimidazole derivatives by azirine ring expansion with imidazolium ylides
  作者：Alexander F. Khlebnikov、Olesya A. Tomashenko、Liya D. Funt、Mikhail S. Novikov

  DOI：10.1039/c4ob00865k

  日期：——

  A domino reaction of 2H-azirines with 1-alkyl-3-phenacyl-1H-imidazolium bromides in the presence of Et3N provides a facile route to 1-alkyl-3-(1H-pyrrol-3-yl)-1H-imidazol-3-ium bromides. 1-Benzyl derivatives can be reduced to 1-(1H-pyrrol-3-yl)-1H-imidazoles with HCO2NH4 on Pd/C. The action of KOH on pyrrolylimidazolium salts leads to a new type of stable ylide, 3-(1H-imidazol-3-ium-3-yl)-pyrrol-1-ides

  在Et 3 N存在下2 H-叠氮基与1-烷基-3-苯甲酰基-1 H-咪唑鎓溴化物的多米诺反应提供了通往1-烷基-3-（1 H-吡咯-3-基）的简便方法-1 H-咪唑-3-溴化铵。1-苄基衍生物可以在Pd / C上用HCO 2 NH 4还原为1-（1 H-吡咯-3-基）-1 H-咪唑。KOH对吡咯基咪唑盐的作用产生了一种新型的稳定内立物3-（1 H-咪唑-3-基-3-基）-吡咯-1-化物，其原则上可以与以下物质处于互变异构平衡：相应的N杂环卡宾。虽然，根据DFT B3LYP / 6-31G（d）计算在真空中，2-芳基中的供电子取代基导致互变异构平衡移至卡宾侧，所研究的化合物以叶立德形式存在于溶液中并呈固态，这与相对稳定性相对应。用PCM溶剂模型计算出的种类。
• Oral hypoglycemic agents. Discovery and structure-activity relationships of phenacylimidazolium halides
  作者：Samuel J. Dominianni、Terence T. Yen

  DOI：10.1021/jm00130a013

  日期：1989.10

  Blood glucose levels in viable, yellow, obese, diabetic mice are reduced following oral administration of phenacylimidazolium halides. Compounds 2 and 3 produced reductions of ca. 40% 2 h after doses of 100 mg/kg po. Since these mice do not respond to sulfonylureas, the glucose-lowering activity of phenacylimidazolium salts in this model suggests a mechanism other than that of stimulating insulin secretion. Only phenacylimidazolium halides with electron-donating groups were active; other azolium salts or variations in the phenacyl portion (alterations in the keto function; chain lengthening or extensive branching) produced inactive compounds.
• Imidazolium ylide mediated tandem Knoevenagel–Michael–<i>O</i>-cyclization sequence for the synthesis of multi-substituted 4,5-dihydrofurans
  作者：Sivakumar Sathiyamoorthi、Abdulrahman I. Almansour、Suresh Kumar Raju、Arumugam Natarajan、Raju Ranjith Kumar

  DOI：10.1080/00397911.2020.1821226

  日期：2021.1.17

  The stereoselective syntheses of noveltrans-5-aroyl-2,4-diaryl-4,5-dihydrofuran-3-carbonitriles have been achievedviaa one-pot, three-component tandem protocol involving aroyl acetonitriles, aromatic aldehydes, and imidazolium ylide in the presence of Et3N.
• Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study
  作者：Xiaohe Zhu、Weipeng Li、Hong Yan、Rugang Zhong

  DOI：10.1016/j.jphotochem.2012.05.013

  日期：2012.8

  The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (Plms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of Plms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by Plm was studied by laser flash photolysis and theoretical OFT computation. These time-resolved results showed that the triplet excited states of Plms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that Plm is involved in the photocycloaddition process through the (3)(DHP center dot center dot center dot Plm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers. (C) 2012 Elsevier B.V. All rights reserved.
• Fe(II)/Et₃N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives
  作者：Ekaterina E Galenko、Olesya A Tomashenko、Alexander F Khlebnikov、Mikhail S Novikov、Taras L Panikorovskii

  DOI：10.3762/bjoc.11.189

  日期：——

  for the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates from easily available compounds, 5-methoxyisoxazoles and phenacylimidazolium salts under hybrid Fe(II)/Et3N relay catalysis. The products were easily transformed into the corresponding 3-(5-methoxycarbonyl-1H-imidazol-3-ium-3-yl)pyrrol-1-ides, which in turn can be hydrolyzed under basic conditions into the corresponding betaines. A carbene

  开发了一种简单的方法，用于在混合Fe（II）/ Et3N中继催化下，从容易获得的化合物，5-甲氧基异恶唑和苯并咪唑鎓盐合成4-咪唑基吡咯烷-2-羧酸甲酯。将产物容易地转化成相应的3-（5-甲氧基羰基-1H-咪唑-3-基-3-基）吡咯-1-化物，其又可以在碱性条件下水解成相应的甜菜碱。通过在非常温和的条件下与硫反应捕获4-甲氧基羰基取代的咪唑基吡咯烷的卡宾互变异构形式，得到相应的咪唑硫酮。