4-(3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline
• 英文别名: 2-(4'-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine；DMAPIP-b；4-(3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylbenzenamine；4-(1H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline
• 化学式: C₁₄H₁₄N₄
• mdl: MFCD16239445
• 分子量: 238.292
• InChiKey: UTJAALOGNBZRBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline 、 溴代十六烷 反应 0.33h， 生成 N-(hexadecyl)-2-(4-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridinylium bromide
  参考文献：
  名称：

  2-（4'-的光物理的调制Ñ，Ñ -dimethylaminophenyl）咪唑并[4,5- b ]吡啶通过长链Ñ -alkylations †

  摘要：

  合成了2-（4'- N，N-二甲基氨基苯基）咪唑并[4,5- b ]吡啶（DMAPIP-b）的N-烷基化产物，以研究长烷基链对荧光团光物理性质的影响。合成了两种不同的化合物：在分子1中，烷基链连接到DMAPIP-b的吡啶氮上，在分子2中烷基链被取代在DMAPIP-b的咪唑氮上。采用吸收，稳态和时间分辨荧光技术研究了不同溶剂中的光谱性质。分别对基态和激发态进行了密度泛函理论（DFT）和单重约束构型（CIS）以及与时间有关的DFT（TDDFT）计算，以计算分子的几何性质和电子性质。与DMAPIP-b不同，后者在质子溶剂中观察到双重发射，它既起源于局部激发态，又起源于分子内电荷转移（ICT）态，吡啶氮烷基化产物（1）则从ICT态发射单发射，而咪唑氮烷基化分子（2）仅在 甲醇 和 水。

  DOI：

  10.1039/c0pp00278j
• 作为产物：
  描述：

  N³-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-pyridine-2,3-diamine 在 重铬酸吡啶 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以97%的产率得到4-(3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline
  参考文献：
  名称：

  Dubey; Kulkarni; Vinod Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 5, p. 361 - 367

  摘要：

  DOI：

文献信息

• Eco-friendly and facile synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine in aqueous medium by air oxidation
  作者：Rajesh P. Kale、Mohammad U. Shaikh、Ganesh R. Jadhav、Charansingh H. Gill

  DOI：10.1016/j.tetlet.2008.12.104

  日期：2009.4

  a new environmentally-benign, convenient, and facile methodology for the synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine. The reaction of 2,3-diaminopyridine with substituted aryl aldehydes in water under thermal conditions without the use of any oxidative reagent has been studied. The reaction has yielded 1H-imidazo[4,5-b]pyridine derivatives by an air oxidative cyclocondensation reaction in

  我们报告了一种新的环境友好，方便，简便的方法合成2-取代-1 H-咪唑并[4,5- b ]吡啶。研究了2,3-二氨基吡啶与取代的芳基醛在水中在热条件下不使用任何氧化剂的反应。反应产生1 H-咪唑并[4,5- b吡啶衍生物通过空气氧化环缩合反应一步一步即可获得极佳的收率。此外，合成了一系列化合物，并通过熔点，EI-MS，NMR和IR工具对其进行了表征。为了比较，参考样品通过报道的方法制备。从经济和环境的角度来看，利用水性介质，容易的反应条件，分离和纯化使这种操作非常有趣。
• Hit generation and exploration: Imidazo[4,5-b]pyridine derivatives as inhibitors of Aurora kinases
  作者：Vassilios Bavetsias、Chongbo Sun、Nathalie Bouloc、Jóhannes Reynisson、Paul Workman、Spiros Linardopoulos、Edward McDonald

  DOI：10.1016/j.bmcl.2007.09.076

  日期：2007.12

  A hit generation and exploration approach led to the discovery of 31 (2-(4-(6-chloro-2-(4-(dimethylamino) phenyl)-3H-imidazo[4,5-b] pyridin-7-yl) piperazin-1-yl)-N-(thiazol-2-yl) acetamide), a potent, novel inhibitor of Aurora-A, Aurora-B and Aurora-C kinases with IC50 values of 0.042, 0.198 and 0.227 mu M, respectively. Compound 31 inhibits cell proliferation and has good microsomal stability. (c) 2007 Elsevier Ltd. All rights reserved.
• Double Proton Transfer Induced Twisted Intramolecular Charge Transfer Emission in 2-(4′-<i>N</i>,<i>N</i>-Dimethylaminophenyl)imidazo[4,5-b]pyridine
  作者：Anasuya Mishra、Saugata Sahu、Nihar Dash、Santosh Kumar Behera、G. Krishnamoorthy

  DOI：10.1021/jp404472b

  日期：2013.8.15

  The spectral characteristics of N,N-dimethyl-4-(4-methyl-4H-imidazo[4,5-b]pyridin-2-yl)benzenamine (PyN-Me), 1-methyl-2-(4'-(N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine (ImNH-Me), and 2-phenylimidazo[4,5-b]pyridine (PIP) are investigated to understand the mechanism of protic solvent induced dual fluorescence of 2-(4'-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine (DMAPIP-b). No dual emission is observed from PyN-Me where pyridyl nitrogen blocked from hydrogen bonding with protic solvents confirms the importance of hydrogen bonding of protic solvents with the pyridyl nitrogen in dual emission of DMAPIP-b. Like DMAPIP-b, ImNH-Me also exhibits weak emission and has a shorter fluorescence lifetime in methanol. However, single emission is observed from ImNH-Me in all solvents including protic solvents. This suggests that the imidazole >NH hydrogen also plays a role in the dual emission process. The longer wavelength emission of DMAPIP-b in water increases with increase in pH of the solution owing to deprotonation of the imidazole >NH group. On the basis of these results, the mechanism for the dual emission of DMAPIP-b is proposed.
• Dubey; Kumar, R. Vinod; Kulkarni, Subhash M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 5, p. 952 - 956
  作者：Dubey、Kumar, R. Vinod、Kulkarni, Subhash M.、Sunder, G. Hema、Smith, Graham、Kennard, Collin H. L.

  DOI：——

  日期：——
• Hydrogen bond induced twisted intramolecular charge transfer in 2-(4′-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine
  作者：Nihar Dash、F.A.S. Chipem、R. Swaminathan、G. Krishnamoorthy

  DOI：10.1016/j.cplett.2008.05.092

  日期：2008.7

  Protic solvent induced dual fluorescence in 2-(4'-N,N-dimethylaminophenyl) imidazo[4,5-b] pyridine (DMAPIP-b) was studied by using steady-state and time resolved fluorescence measurements. The long wavelength emission is attributed to the formation of a twisted intramolecular charge transfer (TICT) state facilitated by H-bonding of the solvent with the pyridine nitrogen of DMAPIP-b. Ab initio calculation predict that the molecule is planar in the ground state. Time resolved measurements suggest that an equilibrium is not established between the locally excited (LE) state and the TICT state. In an acidic medium the imidazole nitrogen is protonated and a single emission is observed. (C) 2008 Elsevier B. V. All rights reserved.