2-苯基-3H-咪唑并[4,5-c]吡啶 | 75007-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-3H-咪唑并[4,5-c]吡啶
• 英文名称: 2-Phenylimidazo<4,5-c>pyridine
• 英文别名: 2-phenyl-1H-imidazo[4,5-c]pyridine；2-Phenyl-3H-imidazo[4,5-c]pyridine
• CAS: 75007-92-0
• 化学式: C₁₂H₉N₃
• mdl: MFCD18256895
• 分子量: 195.224
• InChiKey: HXHORNUQSDXBNW-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230℃
• 沸点：
  428.5±37.0 °C(Predicted)
• 密度：
  1.270

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• 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

安全信息

• 海关编码：
  2933990090
• 储存条件：
  储存温度应保持在2-8°C，并需密封保存。

反应信息

• 作为反应物：
  描述：

  2-苯基-3H-咪唑并[4,5-c]吡啶 在 盐酸 、 水 、 三乙胺 作用下， 反应 10.0h， 生成 2-Phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  摘要：

  Reduction of-substituted [1,2,3]triazolo[4,5-c]pyridines with nickel-aluminum alloy in aqueous alkali gave 2-azaspinaceamines. Reduction of imidazo[4,5-c]pyridine and [1,2,3]triazolo[4,5-c]pyridine derivatives with formic acid in the presence of triethylamine resulted in formation of 5-formylspinaceamines and 2-azaspinaceamines. The 5-formyl group in the latter can be removed by acid hydrolysis. Unsubstituted 2-azaspinaceamine, an aza analog of natural spinaceamine, was synthesized for the first time.

  DOI：

  10.1023/a:1016350629395
• 作为产物：
  描述：

  3-氨基-4-(苄氨基)吡啶 在 sulfur 作用下， 反应 18.0h， 以60%的产率得到2-苯基-3H-咪唑并[4,5-c]吡啶
  参考文献：
  名称：

  2-芳基取代的咪唑并[4,5-b]吡啶和咪唑并[4,5-c]吡啶的制备

  摘要：

  DOI：

  10.1007/bf00476381

文献信息

• Catalyst-free one-pot synthesis of benzimidazoles from 1,2-diaminoarenes and alcohols
  作者：Mahender Reddy Marri、Swamy Peraka、Arun Kumar Macharla、Naresh Mameda、Srujana Kodumuri、Narender Nama

  DOI：10.1016/j.tetlet.2014.09.081

  日期：2014.11

  A new and efficient protocol is described for the one-pot synthesis of benzimidazoles from a variety of aryl alcohols and 1,2-diaminoarenes. The yields were ranging from moderate to excellent. Moreover, the present method is utilizing alcohols instead of aldehydes and the reactions are carried out under solvent- and catalyst-free conditions, offering an environmentally benign process.

  描述了一种新的有效方案，用于从多种芳基醇和1,2-二氨基芳烃一锅合成苯并咪唑。产量从中等到极好。而且，本方法利用醇代替醛，并且反应在无溶剂和无催化剂的条件下进行，提供了对环境无害的方法。
• Oxidative Cyclization Approach to Benzimidazole Libraries
  作者：Eric P. Arnold、Prolay K. Mondal、Daniel C. Schmitt

  DOI：10.1021/acscombsci.9b00189

  日期：2020.1.13

  building blocks, providing limited chemical space coverage. We have developed an amidine formation/oxidative cyclization sequence that enables anilines as a diversity set for benzimidazole C4–C7 SAR generation in parallel format. The amidine annulation was achieved using PIDA or Cu-mediated oxidation to access both N–H and N–alkyl benzimidazoles. This library protocol has now been utilized for analog

  描述了一种从苯胺平行合成苯并咪唑的有效方法。改变苯并咪唑的N1和C2载体的文库方法已经很成熟。但是，C4–C7变体传统上依赖于1,2-二苯胺结构单元，因此化学空间覆盖范围有限。我们已经开发了an形成/氧化环化序列，使苯胺能够作为苯并咪唑C4-C7 SAR平行生成形式的多样性集。通过使用PIDA或Cu介导的氧化作用来获得N和烷基烷基苯并咪唑的idine环化反应。该库协议现已用于四个药物化学项目的模拟生产。另外，通过类似的序列从氨基吡啶合成氮杂苯并咪唑。
• Selective autoxidation of benzylamines: application to the synthesis of some nitrogen heterocycles
  作者：Thanh Binh Nguyen、Ludmila Ermolenko、Ali Al-Mourabit

  DOI：10.1039/c3gc41186a

  日期：——

  A green and remarkably simple synthesis of nitrogen heterocycles from benzylamines and anilines o-substituted by a cyclizable group has been developed based on selective uncatalyzed autoxidation of benzylamines.

  绿色和非常简单的合成 氮 苄胺和 苯胺 基于苄基胺的选择性未催化的自氧化，已经开发了被可环化基团取代的邻位。
• A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
  作者：Sonu Kumar、Manash P. Sarmah、Yella Reddy、Ashish Bhatt、Ravi Kant

  DOI：10.1080/00397911.2021.2001658

  日期：2022.1.2

  Abstract Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation

  摘要 取代的苯并咪唑类和嘧唑类化合物是药物化学领域中一类重要的杂环芳香族有机化合物。已经描述了取代苯并和吡啶稠合的 1H-咪唑的一步微波加速合成。从机理上讲，该反应通过取代的 2-氟硝基苯和取代的芳基胺通过形成 N-羟基中间体进行反应，该中间体在较高温度下裂解得到所需的产物。与先前描述的合成方法相比，这种方法实现了反应时间的减少、更高的产率、更清洁的反应。
• Relay proton transfer triggered twisted intramolecular charge transfer
  作者：Santosh Kumar Behera、G. Krishnamoorthy

  DOI：10.1039/c5pp00339c

  日期：2015.12

  The mechanism for the dual emission of 2-(4’-N,N-dimethylaminophenyl)imidazo[4,5-c]pyridine (DMAPIP-c) in protic solvents was investigated by synthesizing and studying its analogues. Theoretical calculations were carried out to corroborate the experimental findings. The deprotonation studies suggest that the enhancement in the TICT emission of anionic forms of DMAPIP-c is limited to a protic environment. The spectral characteristics of DMAPIP-c were also studied in a methanol–acetonitrile binary solvent mixture. Unlike DMAPIP-c, the methyl derivatives do not emit dual fluorescence in protic solvents. The relative intensity of the TICT emission (with respect to that of normal emission) rises with the methanol amount in the acetonitrile—methanol binary solvent mixture. The studies also show that a 1 : 3 hydrogen bonded complex is formed between DMAPIP-c and methanol and it is responsible for the TICT emission. Based on the results a relay proton transfer tiggered TICT emission is proposed. TDDFT calculations were performed to predict the emission energies.

  通过合成和研究 2-(4'-N,N-二甲基氨基苯基)咪唑并[4,5-c]吡啶（DMAPIP-c）的类似物，研究了其在质子溶剂中的双发射机制。为证实实验结果，还进行了理论计算。去质子化研究表明，阴离子形式的 DMAPIP-c 的 TICT 发射增强仅限于质子环境。还研究了 DMAPIP-c 在甲醇-乙腈二元混合溶剂中的光谱特性。与 DMAPIP-c 不同，甲基衍生物在原生溶剂中不会发出双重荧光。在乙腈-甲醇二元溶剂混合物中，TICT 发射（相对于正常发射）的相对强度随甲醇量的增加而增加。研究还表明，DMAPIP-c 和甲醇之间形成了 1 : 3 的氢键复合物，它是 TICT 发射的原因。根据研究结果，提出了一种中继质子转移触发 TICT 发射的方法。通过 TDDFT 计算预测了发射能量。