2-(3-Methylimidazol-3-ium-1-yl)-1-(4-phenylphenyl)ethanone;bromide | 121704-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-Methylimidazol-3-ium-1-yl)-1-(4-phenylphenyl)ethanone;bromide
• CAS: 121704-65-2
• 化学式: Br*C₁₈H₁₇N₂O
• 分子量: 357.25
• InChiKey: JZRIZZBDCXAAFQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4-羟基-6-甲基-2-吡喃酮 、 二茂铁甲醛 、 2-(3-Methylimidazol-3-ium-1-yl)-1-(4-phenylphenyl)ethanone;bromide 在 N-甲基咪唑 作用下， 以 水 为溶剂， 反应 2.0h， 以86%的产率得到2-(biphenylcarbonyl)-3-ferrocenyl-6-methyl-2H-furo[3, 2-c]pyran-4(3H)-one
  参考文献：
  名称：

  级联[4 +1]通过更环保的环环相扣氮叶立德 在 水：双环和三环稠合二氢呋喃的合成

  摘要：

  描述了一种新颖的咪唑鎓叶立德活化的[4 +1]环化方法，用于双环和三环稠合的非对映选择性合成 二氢呋喃 在 水。这种级联环化大概是通过迈克尔反应触发的两性离子烯醇化物进行的，随后伴随分子内环化。该方法的独特之处在于，它是关于咪唑鎓叶立德介导的[4 +1]环空的第一个报道。水作为一种统一的绿色方法，涉及原位碱再生系统和吡啶叶立德的替代品。

  DOI：

  10.1039/c2gc36276g
• 作为产物：
  描述：

  联苯单乙酮 在 水 、 氢溴酸 、 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 2-(3-Methylimidazol-3-ium-1-yl)-1-(4-phenylphenyl)ethanone;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

• 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.