1-萘-2-基苯并咪唑 | 127603-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-萘-2-基苯并咪唑
• 英文名称: 1-(naphthalen-2-yl)-1H-benzo[d]imidazole
• 英文别名: 1-(Naphthalen-2-yl)-1H-benzimidazole；1-naphthalen-2-ylbenzimidazole
• CAS: 127603-35-4
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: MKKKQIFJTFRBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-萘-2-基苯并咪唑 在 ammonium hexafluorophosphate 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 mono(3,3'-(anthracene-9,10-diylbis(methylene))bis(1-(naphthalen-2-yl)-1H-benzo[d]imidazol-3-ium)) monoacetate
  参考文献：
  名称：

  1-(2-Naphthalenyl)benzimidazolium based fluorescent probe for acetate ion in 90% aqueous buffer

  摘要：

  A new fluorescent probe 9,10-bis[1-(2-naphthalenylbenzimidazolium)-3-methyl]anthracene 1 has been synthesized which shows highly selective fluorescence quenching with only acetate ions in 90% aqueous buffer at pH 7.4. The structure optimization (DFT) of probe 1 and its 1:1 complex with acetate anion, shows that probe 1 is pre-organized and has to undergo minimal spatial reorganization during complexation with acetate anion. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.084
• 作为产物：
  描述：

  苯并咪唑 、 2-萘硼酸 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到1-萘-2-基苯并咪唑
  参考文献：
  名称：

  Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound

  摘要：

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.

  DOI：

  10.3987/com-14-s(k)18

文献信息

• A Chemoselective and Desulfurative Chan-Lam Coupling: C-N Bond Formation between Benzimidazoline-2-Thiones and Arylboronic Acids
  作者：Jin-Quan Chen、Xing Liu、Jia Guo、Zhi-Bing Dong

  DOI：10.1002/ejoc.202000075

  日期：2020.5.3

  An efficient method for the chemoselective and desulfurative Chan–Lam cross‐coupling was developed. By modulating the amount of the catalyst Cu(OAc)2·H2O, alkali, temperature, and solvent, the desulfurative C–N bond formation product (N‐arylbenzimidazoles) could be selectively furnished smoothly. This protocol shows potential synthetic value for the preparation of a diversity of arylbenzoheterocyclic

  开发了一种化学选择性和脱硫Chan-Lam交叉偶联的有效方法。通过调节催化剂Cu（OAc）2 · H 2 O的量，碱，温度和溶剂，可以选择性地平稳地提供脱硫C–N键形成产物（N-芳基苯并咪唑）。该方案显示了潜在的合成价值，可用于制备在药物和农用化学品中可能具有活性的各种芳基苯并杂环化合物。
• Synthesis of cationic π-extended imidazolium salts by sequential Cu-catalyzed arylation/annulation and photocyclization
  作者：Tianbao Wang、Qinze Zheng、Linhua Wang、Zhenmei Huang、Huaxing Zhang、Yuming Zhang、Cheng Zhang、Ge Gao

  DOI：10.1039/d1cc06194a

  日期：——

  A series of cationic π-extended imidazolium salts were synthesized by a sequential Cu-catalyzed arylation/annulation and photocyclization strategy in a simple but efficient way. Among them, a nine-fused-ring compound with a doubly aza[5]helical geometry is by far the largest cationic polycyclic heteroaromatic with a central imidazolium core.

  通过连续的铜催化芳基化/环化和光环化策略以简单但有效的方式合成了一系列阳离子 π 扩展咪唑鎓盐。其中，具有双氮杂[5]螺旋几何结构的九稠环化合物是迄今为止最大的具有中心咪唑鎓核的阳离子多环杂芳族化合物。
• <i>N</i>-Heterocyclic Carbenes: Versatile Second Cyclometalated Ligands for Neutral Iridium(III) Heteroleptic Complexes
  作者：Tian-Yi Li、Xiao Liang、Liang Zhou、Chen Wu、Song Zhang、Xuan Liu、Guang-Zhao Lu、Li-Sha Xue、You-Xuan Zheng、Jing-Lin Zuo

  DOI：10.1021/ic501949h

  日期：2015.1.5

  With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)(2)Ir(NHC), were synthesized efficiently. The obtained Ir(III) complexes display typical phosphorescence of 455-485 nm with quantum yields up to 0.73. By modifying the phenyl moiety in the NHCs with electron-withdrawing substituents (e.g., -F or -CF3) or replacing it with N-heteroaromatic rings (pyridine or pyrimidine), the HOMO-LUMO gaps are broadened, and the emissions shift to the more blue region accordingly. Furthermore, to extend the application scope of NHCs as the second cyclometalated ligands, five other Ir(III) complexes from blue to red were synthesized with different first cyclometalated ligands. Finally, the organic light-emitting diodes using one blue emitter exhibit a maximum current efficiency of 37.83 cd A(-1), an external quantum efficiency of 10.3%, and a maximum luminance of 8709 cd m(-2). Our results demonstrate that NHCs as the second cyclometalated ligands are good candidates for the achievement of efficient phosphorescent Ir-III complexes and corresponding devices.
• Photophysical processes of some benzimidazole derivatives
  作者：Zhaobin Chen、Caihong Zhang、Liheng Feng

  DOI：10.1016/j.saa.2005.01.028

  日期：2005.11

  The photophysical properties of N-(alpha-naphthyl)-benzimidazole (alpha-NABI), N-(beta-naphthyl)-benzimidazole (beta-NABI) and N-(alpha-pyridyl)-benzimidazole (alpha-PYBI) were studied and alpha-NYBI exhibit intramolecular charge transfer fluorescence in polar solvents. The fluorescence of benzimidazoles can be quenched by acetic acid and the existence of exciplexes was observed between the benzimidazole derivatives and acetic acid. Particularly, the maximum emission peak of solution of alpha-PYBI in mixed solvent, ether and acetic acid, presents obvious red-shift with the increase of concentration of acetic acid in the mixed solvent. (c) 2005 Elsevier B.V. All rights reserved.
• 1-(2-Naphthalenyl)benzimidazolium based fluorescent probe for acetate ion in 90% aqueous buffer
  作者：Sandeep Kumar、Prabhpreet Singh、Subodh Kumar

  DOI：10.1016/j.tetlet.2012.02.084

  日期：2012.4

  A new fluorescent probe 9,10-bis[1-(2-naphthalenylbenzimidazolium)-3-methyl]anthracene 1 has been synthesized which shows highly selective fluorescence quenching with only acetate ions in 90% aqueous buffer at pH 7.4. The structure optimization (DFT) of probe 1 and its 1:1 complex with acetate anion, shows that probe 1 is pre-organized and has to undergo minimal spatial reorganization during complexation with acetate anion. (c) 2012 Elsevier Ltd. All rights reserved.