1-methyl-3-phenacylimidazolium bromide | 19748-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-3-phenacylimidazolium bromide
• 英文别名: 1-methyl-3-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium bromide；3-phenacyl-1-methylimidazolium bromide；3-Methyl-1-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium bromide；2-(3-methylimidazol-3-ium-1-yl)-1-phenylethanone;bromide
• CAS: 19748-13-1
• 化学式: Br*C₁₂H₁₃N₂O
• 分子量: 281.152
• InChiKey: LQFSSOYDVYBCDV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  16
• 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：

  1-methyl-3-phenacylimidazolium bromide 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 ammonium hydroxide 、 碳酸氢钠 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 56.0h， 生成 4,6-二苯基-2(1H)-吡啶酮
  参考文献：
  名称：

  带有Ynals的Y环的N杂环碳环催化环空：直接获得α-Pyrones

  摘要：

  我们在此报告了N-杂环卡宾（NHC）催化的带有芳基的酰基化物环化，提供了制备4,6-二取代的α-吡喃酮的有效方法。该方法可提供高产率到高产率的各种α-吡喃酮，以及广泛的底物范围和良好的官能团耐受性。

  DOI：

  10.1002/asia.201800595
• 作为产物：
  描述：

  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 1-methyl-3-phenacylimidazolium 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
• 作为试剂：
  描述：

  3,5-diethyl 1,4-dihydropyridine-3,5-dicarboxylate 在 1-methyl-3-phenacylimidazolium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以41%的产率得到tetraethyl 3,9-diazahexacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
  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

• Synthesis and antimicrobial action of aminoketones
  作者：A. F. Popov、Zh. P. Piskunova、V. N. Matvienko、G. P. Kondratenko、Yu. I. Nikolenko

  DOI：10.1007/bf00764817

  日期：1989.10

  chemical preparations among the pathogens of infectious diseases renders very urgent the search for chemotherapeutic agents, particularly in the series of aminoketones and their salts. With the object of the further (cf. [i-4]) determination of the dependence of the structure-biological activity of aminoketones, we synthesized a series of hydrogen halides of aminoketones (1)-(VII) (Table i) and carried

  传染病病原体中对许多抗生素和化学制剂的抗性广泛分布，使得寻找化学治疗剂，特别是氨基酮及其盐系列变得非常紧迫。为了进一步（参见[i-4]）确定氨基酮的结构-生物活性的依赖性，我们合成了一系列氨基酮（1）-（VII）的卤化氢（表i）并进行了对它们对革兰氏阳性和革兰氏阴性微生物的五种参考菌株的抗菌作用的研究（表 2）。
• Method for treating fibrotic diseases or other indications IC
  申请人：Alteon, Inc.

  公开号：US20020068729A1

  公开（公告）日：2002-06-06

  Provided, among other things, is a method of treating or ameliorating or preventing an indication of the invention in an animal, including a human comprising administering an effective amount of a compound of the formula I: 1

  提供了一种处理、改善或预防动物包括人类发明的指示的方法，包括给予公式I的化合物的有效量：1
• Method for treating fibrotic diseases or other indications with imidazolium agents
  申请人：Alteon, Inc.

  公开号：US20030176426A1

  公开（公告）日：2003-09-18

  Provided is a method of treating or ameliorating an indication of the invention in an animal, including a human, by administering an effective amount of a compound of the formula I: 1 wherein R 1 , R 2 , M, X and Z are as described supra. Also provided are certain imidazolium compounds and pharmaceutical compositions containing the imidazolium compounds.

  提供了一种治疗或改善动物（包括人类）发明的征兆的方法，通过给予公式I的有效量的化合物： 1 其中R 1 ，R 2 ，M，X和Z如上所述。还提供了一些咪唑啉化合物和包含咪唑啉化合物的药物组合物。
• DABCO-catalyzed multi-component domino reactions for the one-pot efficient synthesis of diverse and densely functionalized benzofurans in water
  作者：Sajedeh Golchin、Mohammad Hossein Mosslemin、Afshin Yazdani-Elah-Abadi、Nasim Shams

  DOI：10.1007/s11164-016-2726-1

  日期：2017.3

  An efficient, three-component strategy for the improved synthesis of a pharmaceutically interesting diverse kind of multi-functionalized benzofurans via one-pot two-step domino protocol with high diastereoselectivity in excellent yields has been established. The synthesis was achieved by reacting phenacyl bromides, N -heterocycles, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds in the presence

  已经建立了一种有效的三组分策略，该方法可通过一锅两步多米诺协议以高非对映选择性，优良收率改善药学上令人关注的各种多功能苯并呋喃的合成。合成是通过使苯甲酰溴 N 催化量的DABCO（1,4-二氮杂双环[2.2.2]辛烷）存在下，作为廉价，令人印象深刻且易于获得的催化剂，在回流下的水中存在-杂环，芳族醛和环状1,3-二羰基化合物。在此过程中，一锅中总共形成了三个新的键（两个C–C和一个C–O）。反应时间短，出众的收率，无需色谱纯化以及在整个反应过程中避免使用对环境有害或有毒的催化剂和有机溶剂，可能会使该方案对学术界和工业界非常有用。
• 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。