1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide | 59349-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide
• 英文别名: 2-(3-Methylimidazol-3-ium-1-yl)-1-(4-methylphenyl)ethanone;bromide
• CAS: 59349-28-9
• 化学式: Br*C₁₃H₁₅N₂O
• 分子量: 295.179
• InChiKey: SXFHGNOMYIJTOX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.49
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-4'-甲基苯乙酮 在 N-甲基咪唑 作用下， 以 乙醚 为溶剂， 以72%的产率得到1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide
  参考文献：
  名称：

  Imidazolium hypoglycemic agents

  摘要：

  咪唑盐在给哺乳动物施用后能有效降低血糖水平。

  公开号：

  US04609670A1

文献信息

• 3-(2-Aryl-2-oxoethyl)-imidazolium salts as hypoglycemic agents
  申请人：ELI LILLY AND COMPANY

  公开号：EP0182533A2

  公开（公告）日：1986-05-28

  The invention relates to imidazolium salts which are effective in lowering blood glucose levels in mammals. In particular, there is provided a compound of formula (I) which is useful in lowering blood glucose levels: in which: R1 is C1-C4 alkyl; R2 and R3, independently, are hydrogen or C1-C4 alkyl; each R4, independently is, -OR5, -NR6R7, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethyl, or C1-C4 alkylthio; R5 is hydrogen or R6 is hydrogen, C1-C4 alkyl, or -C-R8; R7 is hydrogen or C1-C4 alkyl; each R8, independently, is C1-C4 alkyl or phenyl; Z is oxygen or sulfur; X is a therapeutically acceptable anion; and m is 0, 1 or 2.

  本发明涉及可有效降低哺乳动物血糖水平的咪唑盐。 特别是提供了一种有助于降低血糖水平的式 (I) 化合物：其中： R1为C1-C4烷基；R2和R3独立地为氢或C1-C4烷基；每个R4独立地为-OR5、-NR6R7、C1-C4烷基、C1-C4烷氧基、三氟甲基或C1-C4烷硫基；R5为氢或R6为氢、C1-C4烷基或-C-R8；R7为氢或C1-C4烷基；每个R8独立地为C1-C4烷基或苯基；Z为氧或硫；X为治疗上可接受的阴离子；m为0、1或2。
• 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.
• 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.
• DOMINIANNI, SAMUEL J.;YEN, TERENCE T.
  作者：DOMINIANNI, SAMUEL J.、YEN, TERENCE T.

  DOI：——

  日期：——
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  作者：DOMINIANNI S. J.、 YEN T. T.

  DOI：——

  日期：——