2-喹啉-2-基-1H-苯并[f]苯并咪唑 | 848474-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2-喹啉-2-基-1H-苯并[f]苯并咪唑
• 英文名称: 2-(naphtho[3,4]imidazol-2-yl)quinoline
• 英文别名: 2-(2-quinolyl)naphthol[b]imidazole；2-(2-quinolyl)naphto[b]imidazole；1H-Naphth[2,3-d]imidazole, 2-(2-quinolinyl)-；2-quinolin-2-yl-1H-benzo[f]benzimidazole
• CAS: 848474-90-8
• 化学式: C₂₀H₁₃N₃
• 分子量: 295.343
• InChiKey: IZRREVBJIYALJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  588.5±42.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-喹啉-2-基-1H-苯并[f]苯并咪唑 、 三苯基硼烷 以 四氢呋喃 为溶剂， 以35%的产率得到BPh2(2-(2-quinolyl)naphthol[b]imidazolato)
  参考文献：
  名称：

  Synthesis, characterization and electroluminescence of B(III) compounds: BPh2(2-(2-quinolyl)naphtho[b]imidazolato) and BPh2(2-(2-quinolyl)benzimidazolato)

  摘要：

  Two novel luminescent boron compounds, BPh2(2.-(2-quinolyl)naphtho[b]imidazolato) (1) and BPh2(2-(2-quinolyi)benzimidazolato) (2), have been synthesized by the reactions of triphenylboron with appropriate ligands, 2-(2-quinolyl)naphtho[b]imidazole (QNI) and 2(2-quinolyl)benzimidazole (QBI), respectively. The structure of 1 was determined by single crystal X-ray diffraction, while 2 by spectroscopic methods. The structure of 1 reveals that the boron center is four coordinated. Several types of OLED possessing different colors were fabricated by using 1 as emitter. For the three-layer OLED with the structure ITO/NPB/2/Alq(3)/Mg-Ag, an emission band covering the whole visible region from 400 to 750 nm with the maximum brightness of 320 cd/m(2) was observed, indicating a perfect white light OLED (CIE = 0.33, 0.37). Compounds 1 and 2 form a new family of organometallic emitting materials which could be of interest for practical application. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.12.060
• 作为产物：
  描述：

  喹哪啶酸 、 2,3-二氨基萘 在 polyphosphoric acid 作用下， 反应 4.0h， 生成 2-喹啉-2-基-1H-苯并[f]苯并咪唑
  参考文献：
  名称：

  苯并咪唑-2-基喹啉和苯并咪唑-2-基异喹啉的衍生物作为对人结肠运动具有刺激活性的选择性A1腺苷受体拮抗剂

  摘要：

  通过使用人A 1，A 2A和A 3 AR进行竞争实验，合成了许多以各种方式连接到取代的苯并咪唑-2-基系统的喹啉和异喹啉，并将其评价为新型腺苷受体（ARs）拮抗剂。新化合物是基于2-（苯并咪唑-2-基）喹喔啉的衍生物设计的，该衍生物以前被报道为A 1和A 3 AR的有效和选择性拮抗剂。其中，3- [4-（乙硫基）-1 H-苯并咪唑-2-基]异喹啉4b表现出对A 1 AR（K i = 1.4 n M）和对A 2A（K i > 10μm）， A 2B（K i > 10μm）和A 3 ARs（K i > 1μM）的选择性。在分离的人结肠的圆形平滑肌制剂中的功能实验表明，4b在该肠区域的神经肌肉区室中充当A 1 AR的有效和选择性拮抗剂。生物学和药理学数据表明4b是开发具有结肠活动刺激特性的新型药物的合适起点。

  DOI：

  10.1002/cmdc.201100284

文献信息

• A new imidazolylquinoline for organic thin film transistor
  作者：Tsun-Ren Chen、Anchi Yeh、Jhy-Der Chen

  DOI：10.1016/j.tetlet.2004.12.139

  日期：2005.2

  A new active electronic material, 2-(naphtho[3,4]imidazol-2-yl)quinoline (NIQ), 1, has been synthesized and fully characterized. This compound exhibits field-effect carrier mobility and behaves as a p-type semiconductor (mu(FET) = 0.148 cm(2)/V s at V-DS = 10 V). NIQ and its related imidazolylquinoline compounds may have possible applications as active materials in organic thin film transistors. (C) 2005 Elsevier Ltd. All rights reserved.
• Derivatives of Benzimidazol-2-ylquinoline and Benzimidazol-2-ylisoquinoline as Selective A1 Adenosine Receptor Antagonists with Stimulant Activity on Human Colon Motility
  作者：Barbara Cosimelli、Sabrina Taliani、Giovanni Greco、Ettore Novellino、Annalisa Sala、Elda Severi、Federico Da Settimo、Concettina La Motta、Isabella Pugliesi、Luca Antonioli、Matteo Fornai、Rocchina Colucci、Corrado Blandizzi、Simona Daniele、Maria Letizia Trincavelli、Claudia Martini

  DOI：10.1002/cmdc.201100284

  日期：2011.10.4

  novel antagonists of adenosine receptors (ARs) by competition experiments using human A1, A2A, and A3 ARs. The new compounds were designed based on derivatives of 2‐(benzimidazol‐2‐yl)quinoxaline, previously reported as potent and selective antagonists of A1 and A3 ARs. Among these, 3‐[4‐(ethylthio)‐1H‐benzimidazol‐2‐yl]isoquinoline 4 b exhibited the best combination of potency toward the A1 AR (Ki=1

  通过使用人A 1，A 2A和A 3 AR进行竞争实验，合成了许多以各种方式连接到取代的苯并咪唑-2-基系统的喹啉和异喹啉，并将其评价为新型腺苷受体（ARs）拮抗剂。新化合物是基于2-（苯并咪唑-2-基）喹喔啉的衍生物设计的，该衍生物以前被报道为A 1和A 3 AR的有效和选择性拮抗剂。其中，3- [4-（乙硫基）-1 H-苯并咪唑-2-基]异喹啉4b表现出对A 1 AR（K i = 1.4 n M）和对A 2A（K i > 10μm）， A 2B（K i > 10μm）和A 3 ARs（K i > 1μM）的选择性。在分离的人结肠的圆形平滑肌制剂中的功能实验表明，4b在该肠区域的神经肌肉区室中充当A 1 AR的有效和选择性拮抗剂。生物学和药理学数据表明4b是开发具有结肠活动刺激特性的新型药物的合适起点。
• Synthesis, characterization and electroluminescence of B(III) compounds: BPh2(2-(2-quinolyl)naphtho[b]imidazolato) and BPh2(2-(2-quinolyl)benzimidazolato)
  作者：Tsun-Ren Chen、Rong-Hong Chien、Anchi Yeh、Jhy-Der Chen

  DOI：10.1016/j.jorganchem.2005.12.060

  日期：2006.4

  Two novel luminescent boron compounds, BPh2(2.-(2-quinolyl)naphtho[b]imidazolato) (1) and BPh2(2-(2-quinolyi)benzimidazolato) (2), have been synthesized by the reactions of triphenylboron with appropriate ligands, 2-(2-quinolyl)naphtho[b]imidazole (QNI) and 2(2-quinolyl)benzimidazole (QBI), respectively. The structure of 1 was determined by single crystal X-ray diffraction, while 2 by spectroscopic methods. The structure of 1 reveals that the boron center is four coordinated. Several types of OLED possessing different colors were fabricated by using 1 as emitter. For the three-layer OLED with the structure ITO/NPB/2/Alq(3)/Mg-Ag, an emission band covering the whole visible region from 400 to 750 nm with the maximum brightness of 320 cd/m(2) was observed, indicating a perfect white light OLED (CIE = 0.33, 0.37). Compounds 1 and 2 form a new family of organometallic emitting materials which could be of interest for practical application. (c) 2006 Elsevier B.V. All rights reserved.