2-(2,3-dimethylphenyl)imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,3-dimethylphenyl)imidazole
• 英文别名: 2-(2,3-dimethylphenyl)-1H-imidazole
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: NXUCETYUQFSJBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 2-(2,3-dimethylphenyl)imidazole 以 乙醚 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones

  摘要：

  A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (1-11) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (12-20) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol-1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC] = 3.13 mu g) was equipotent as standard drug ciprofloxacin and [2-(4-Nitrophenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC = 1.56 mu g) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC = 0.002 mu g) was two times more effective than standard drug ciprofloxacin (MIC = 0.004 mu g) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)-imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC = 0.005 mu g) was equipotent to the reference compound, fluconazole against tested fungal strains.

  DOI：

  10.3109/14756366.2010.548331
• 作为产物：
  描述：

  咪唑 、 2,3-二甲基苯胺 在 盐酸 、 sodium azide 、 sodium acetate 作用下， 以 水 为溶剂， 反应 51.0h， 生成 2-(2,3-dimethylphenyl)imidazole
  参考文献：
  名称：

  Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones

  摘要：

  A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (1-11) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (12-20) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol-1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC] = 3.13 mu g) was equipotent as standard drug ciprofloxacin and [2-(4-Nitrophenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC = 1.56 mu g) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC = 0.002 mu g) was two times more effective than standard drug ciprofloxacin (MIC = 0.004 mu g) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)-imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC = 0.005 mu g) was equipotent to the reference compound, fluconazole against tested fungal strains.

  DOI：

  10.3109/14756366.2010.548331

文献信息

• 2,5-DIAZACYCLOPENTADIENYUDENE: A STANDARD CARBENE OR A HIGHLY REACTIVE DIRADICAL ?
  作者：Núria Bru、Jaume Vilarrasa

  DOI：10.1246/cl.1980.1489

  日期：1980.12.5

  2,5-Diazacyclopentadienylidene (2H-imidazolylidene), generated either by photolysis or thermolysis from 2-diazo-2H-imidazole, reacts with benzene derivatives to give mainly a mixture of o-, m-, and p-substituted 2-phenylimidazoles. The carbene shows a strong diradical character, in sharp contrast with the well-known behavior of cyclopentadienylidene.

  2,5-二氮杂环戊二烯炔（2H-咪唑氮烯）通过光解或热解从2-二氮-2H-咪唑生成，与苯衍生物反应，主要生成o-、m-和p-取代的2-苯基咪唑混合物。该卡宾表现出强烈的双自由基特性，与众所周知的环戊二烯基炔的行为形成鲜明对比。
• [EN] PROCESS FOR PREPARATION OF MEDETOMIDINE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE MÉDÉTOMIDINE
  申请人：TECH AB I

  公开号：WO2011070069A1

  公开（公告）日：2011-06-16

  The present disclosure relates to a process for the preparation of medetomidine, 4-[1-(2,3-Dimethylphenyl)ethyl]- 1H-imidazoIe in an environmentally favourable and commercially feasible manner. Previous methods for the preparation of medetomidine use expensive 4-substituted imidazole derivatives as starting material. A practical way of synthesis is provided in which the imidazole ring is built up during a multi-step process starting from commercially affordable, 2,3-dimethylbenzoic. Mild reaction conditions are used throughout the process.

  本公开涉及一种以环境友好和商业可行的方式制备美地托嗪（medetomidine），即4-[1-(2,3-二甲基苯基)乙基]-1H-咪唑的过程。以前制备美地托嗪的方法使用昂贵的4-取代咪唑衍生物作为起始物质。提供了一种实用的合成方法，其中咪唑环是在从商业可负担的2,3-二甲基苯甲酸开始的多步过程中构建的。整个过程中使用温和的反应条件。
• Continuous fermentation process which is useful for the simultaneous optimal production of propionic acid and vitamin B12
  申请人：Gesellschaft für Biotechnologische Forschung mbH (GBF)

  公开号：EP0668359A1

  公开（公告）日：1995-08-23

  The present invention relates to a fermentation process which is useful for the simultaneous production of propionic acid and vitamin 812, characterized in that it employs the culturing, on a suitable culture medium, of at least one microorganism suitable for the production of vitamin B12 and propionic acid, and in that the corresponding fermentation is carried out in continuous fashion and involves at least two successive stages, a first stage associated with the optimal production of propionic acid, and a second with the optimal production of vitamin B12.

  本发明涉及一种有助于同时生产丙酸和维生素 812 的发酵工艺，其特征在于它采用了至少一种适于生产维生素 B12 和丙酸的微生物在合适的培养基上进行培养，相应的发酵以连续的方式进行，至少包括两个连续的阶段，第一阶段与丙酸的最佳生产有关，第二阶段与维生素 B12 的最佳生产有关。
• Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives
  作者：Deepika Sharma、Balasubramanian Narasimhan、Pradeep Kumar、Vikramjeet Judge、Rakesh Narang、Erik De Clercq、Jan Balzarini

  DOI：10.1016/j.ejmech.2008.08.010

  日期：2009.6

  In the present study, we have synthesized 2-(substituted phenyl)-1H-imidazole (1-12) and (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanone (13-26) analogues and screened them for their antimicrobial activity against Gram positive, Gram negative and fungal species. The results of antibacterial study indicated that compounds 15,17 and 24 showed appreciable antibacterial activity and compound 26 emerged as the most potential antifungal agent. The results of SAR studies indicated that the presence of electron withdrawing groups is necessary for the antimicrobial activity of the synthesized compounds. The results of the present study indicated that compounds 15, 17 and 24 might be of interest for the identification of new antimicrobial molecules as their antibacterial activity is equivalent to the standard drug norfloxacin. Further, the antiviral screening of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13-26) against a panel of viral strains indicated that compounds 16 and 19 can be selected as lead compounds for the development of novel antiviral agents. (C) 2008 Elsevier Masson SAS. All rights reserved.
• BRU N.; VILARRASA J., CHEM. LETT., 1980, NO 12, 1489-1492
  作者：BRU N.、 VILARRASA J.

  DOI：——

  日期：——