2,4,5-tris(furan-2-yl)-1H-imidazole | 92438-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4,5-tris(furan-2-yl)-1H-imidazole
• 英文别名: 2,4,5-tris(2-furyl)imidazoline；2.4.5-Tris-<α-furyl>-imidazol；2,4,5-tri(2-furyl)-1H-imidazole；TFI；2,4,5-tri-furan-2-yl-1H-imidazole；2,4,5-Tri-[2]furyl-1H-imidazol
• CAS: 92438-23-8
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: VGSZIZNQESLZJH-UHFFFAOYSA-N

物化性质

• 熔点：
  202 °C (decomp)
• 沸点：
  446.9±40.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,5-tris(furan-2-yl)-1H-imidazole 在 MgNi 氢气 作用下， 生成 2,4,5-tris-tetrahydrofuran-2-yl-1H-imidazole
  参考文献：
  名称：

  Schubert,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1962, vol. 17, p. 173 - 182

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 在 2-溴-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以96%的产率得到2,4,5-tris(furan-2-yl)-1H-imidazole
  参考文献：
  名称：

  Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazoles from Aromatic Aldehydes with HMDS Catalyzed by N-Bromosaccharin (NBSa)

  摘要：

  研究了一种在N-溴糖精(NBSa)存在下，通过六甲基二硅氮烷和芳香醛反应合成2,4,5-三芳基-1H-咪唑衍生物的一锅法高效合成工艺。这种新方法具有产率高、操作简单、反应时间短、工艺简便等优点。

  DOI：

  10.2174/15701786113106660091

文献信息

• Facile synthesis of trisubstituted imidazoles from 1,2-di(furan-2-yl)-2-oxoethyl carboxylates and their chemiluminescence
  作者：Baozhi Li、Qiang Gu、Yuanhui He、Tianqi Zhao、Shuaijun Wang、Jing Kang、Yumin Zhang

  DOI：10.1016/j.crci.2012.06.005

  日期：2012.9

  Résumé A facile synthesis of trisubstituted imidazoles containing furan rings was reported. Imidazoles were produced from 1,2-di(furan-2-yl)-2-oxoethyl carboxylates over solid alumina as solid support impregnated with ammonium acetate under solvent-free microwave-assisted conditions. The method possessed many remarkable advantages, such as the short reaction time (5–10 min), affording moderate to excellent yields and saving resources, conveniently operating process, which provided an attractive and environmentally-friendly approach for the synthesis of the important heterocyclic compounds. Moreover, the chemiluminescence property of some compounds synthesized has been investigated. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  简历 报告了一种简单合成含有呋喃环的三取代咪唑的方法。该方法以固态氧化铝为载体，浸渍醋酸铵，无需溶剂，在微波辅助条件下，从1,2-双(呋喃-2-基)-2-氧代乙基羧酸酯中生成咪唑。该方法有许多显著优点，如反应时间短（5-10分钟），产率从中等到优秀，节约资源，操作简便，为重要杂环化合物的合成提供了一种吸引人的、环境友好的途径。此外，还研究了部分合成化合物的化学发光性质。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.doc
• Directly Oxidized Chemiluminescence of 2-Substituted-4,5-di(2-Furyl)-1H -Imidazole by Acidic Potassium Permanganate and its Analytical Application for Determination of Albumin
  作者：Jing Kang、Yumin Zhang、Zhongxiu Huang、Lu Han、Jieli Tang、Shuaijun Wang、Yihua Zhang

  DOI：10.1007/s10895-011-0849-8

  日期：2011.7

  In the paper, 2,4,5-tri(2-furyl)-1H-imidazole (TFI) and 2-phenyl-4,5-di(2-furyl)-1H-imidazole (PDFI), were chosen to investigate chemiluminescence (CL) properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles. The directly oxidized CL of analytes by potassium permanganate (KMnO4) was in detail studied. The KMnO4 could directly oxidize TFI/PDFI to produce strong CL emission in acidic solution. The effects of experimental conditions were investigated. Under the optimal conditions, the effect of albumin on the TFI/PDFI-KMnO4 system was investigated. It was found that the addition of albumin into the system could induce enhancement of CL signal, and the enhanced CL intensity is linearly related to the logarithm of concentration of albumin. Based on this study, a novel CL method has been developed for the determination of albumin with high sensitivity and good selectivity. The method was applied to the determination of albumin in human serum samples, and the results were in agreement with those obtained by the bromcresol green (BCG) method. The relative errors for the analytical results were from −5.8% to 4.2%. These new phenomena would further enable people to exploit more CL analytical application of the heterocyclic imidazole derivatives.

  在本论文中，选择了2，4，5-三(2-呋喃基)-1H-咪唑(TFI)和2-苯基-4，5-二(2-呋喃基)-1H-咪唑(PDFI)来探讨2-取代-4，5-二(2-呋喃基)-1H-咪唑类化合物的化学发光(CL)性质。详细研究了高锰酸钾(KMnO4)对分析物的直接氧化CL反应。KMnO4可以在酸性溶液中直接氧化TFI/PDFI并产生强的CL发射。研究了试验条件的影响。在最佳条件下，考察了清蛋白对该体系的影响。结果表明:体系中加入清蛋白能诱导CL信号增强，增强的CL强度与清蛋白浓度的对数值有线性关系。基于此，建立了一种高灵敏度和良好选择性的测定清蛋白的新的CL方法。应用于人血清中清蛋白的测定，结果与溴甲酚绿(BCG)法的测定结果一致，分析结果的相对误差在-5.8%到4.2%之间。这些新现象将进一步促进人们开发更多的杂环咪唑衍生物的CL分析应用。
• Convenient One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with HMDS in the Presence of Molecular Iodine
  作者：Hojat Veisi、Ardashir Khazaei、Leila Heshmati、Saba Hemmati

  DOI：10.5012/bkcs.2012.33.4.1231

  日期：2012.4.20

  A one-pot efficient procedure for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in the presence of molecular iodine has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, and the availability of reagents.

  已经开发了一种通过六甲基二硅氮烷与芳基醛、苯甲醇、苄基卤在分子碘存在下反应以良好至优异产率合成 2,4,5-三芳基-1H-咪唑衍生物的一锅高效方法。该方法的显着优点是后处理程序简单，产品产量高，试剂可用。
• Efficient synthesis of 1-R1-2-R-4,5-di(furan-2-yl)-1H-imidazoles and their luminescence properties
  作者：Yao Chen、Qiang Gu、Baozhi Li、Qiu Chen、Xiaodong Chen、Yumin Zhang、Jinxin Liu

  DOI：10.1016/j.crci.2013.05.014

  日期：2013.12

  Résumé In this study, a series of 1-R1-2-R-4,5-di(furan-2-yl)-1H-imidazole derivatives were synthesized in better yield 59.0%∼89.8% by the treatment of purified imidazole compounds with benzyl chloride or allyl chloride in the presence of sodium hydride, and were characterized by FT–IR, HRMS, 1H NMR and 13C NMR spectroscopy. Furthermore, the luminescence properties of the synthesized products were investigated. It was found that N-substituted groups of imidazole have little influence on the absorption bands in a 0.1 N H2SO4 aqueous solution containing 0.5 mL of dissolved CH3OH. However, the emission of some compounds in solution was sensitive to the polarity of the solvents. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  摘要 在本研究中，通过在氢化钠存在下用苄基氯或烯丙基氯处理纯化的咪唑化合物，合成了一系列1-R1-2-R-4,5-二(furan-2-基)-1H-咪唑衍生物，产率提高至59.0%~89.8%。这些化合物通过FT-IR、HRMS、1H NMR和13C NMR光谱进行了表征。此外，还研究了合成产品的发光特性。研究发现，咪唑的N取代基对含有0.5 mL溶解的CH3OH的0.1 N H2SO4水溶液中的吸收带影响不大。然而，某些化合物在溶液中的发射对溶剂的极性敏感。 补充材料： 本文的补充材料作为单独文件提供： mmc1.doc
• One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with Hexamethyldisilazane in Molten Tetrabutylammonium Bromide
  作者：Javad Salehi、Mohammad Khodaei、Ahmad Khosropour

  DOI：10.1055/s-0030-1258393

  日期：2011.2

  A simple and efficient method for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in molten tetrabutylammonium bromide as an inexpensive and non toxic solvent has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, the use of an ionic liquid as a green solvent, and the availability of reagents.

  通过六甲基二硅氮烷与芳基醛、苄醇、苄基卤化物在作为廉价无毒溶剂的熔融四丁基溴化铵中的反应，开发出了一种简单高效的 2,4,5-三芳基-1H-咪唑衍生物的合成方法，产率从良好到极佳。这种方法的显著优点是操作过程简单、产品收率高、使用离子液体作为绿色溶剂以及试剂易得。