3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine | 61532-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine
• 英文别名: 3-benzyl-3H-imidazo[4,5-b]pyridine；3-benzylimidazo[4,5-b]pyridine；3-benzyl-4-azabenzimidazole；3-benzyl-3H-imidazo[4,5-b]pyridine；3-Benzyl-3H-imidazo<4,5-b>pyridin
• CAS: 61532-32-9
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: QEBUDKVYOQLSOC-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C(Solv: hexane (110-54-3))
• 沸点：
  402.7±47.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine 在 sulfur 作用下， 反应 0.5h， 以95%的产率得到3-benzylimidazo[4,5-b]pyridine-2-thione
  参考文献：
  名称：

  Thionation of imidazopyridines

  摘要：

  DOI：

  10.1007/bf00475602
• 作为产物：
  描述：

  3-benzyl-3H-imidazo[4,5-b]pyridine 4-oxide 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以70%的产率得到3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  Synthesis and modulation properties of imidazo[4,5-b]pyridin-7-one and indazole-4,7-dione derivatives towards the Cryptosporidium parvum CpABC3 transporter

  摘要：

  The syntheses of new N-polysubstituted imidazo[4,5-b]pyridine-7-one (IF, 5 and 8a-8f) and indazole-4,7-dione (ID, 9 and 10) derivatives are described. The binding affinity of IP and ID towards the recombinant Nucleotide Binding Domain NBD1 of Cryptosporidium parvum CpABC3 was evaluated by intrinsic fluorescence quenching. IP induced a moderate quenching of the intrinsic fluorescence of H6-NBD1 whereas IDs 9 and 10 showed a binding affinity comparable to the ATP analogue TNP-ATP. In addition, 8d, Se and 10 were shown to be competitive inhibitors of the ATPase activity, but with low affinity. These compounds could thus act like some flavonoid derivatives, which can partly overlap both the nucleotide-binding site and the adjacent hydrophobic steroid-binding region of mammalian P-glycoproteins.

  DOI：

  10.1016/j.ejmech.2010.02.033

文献信息

• Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues
  作者：Bhaskaran Savitha、Ayyiliath. M. Sajith、M. Nibin Joy、K.K. Abdul Khader、A. Muralidharan、M. Syed Ali Padusha、Yadav D. Bodke

  DOI：10.1071/ch15420

  日期：——

  In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products

  在本文中，我们报告了在三卤代脱氮嘌呤的Suzuki交叉偶联反应中有机三氟硼酸钾盐作为亲核有机硼试剂的用途。通过使用该方案以良好至优异的产率合成了区域异构的C-2-取代的咪唑并[4，5- b ]吡啶类似物。芳基和杂芳基三氟硼酸酯容易反应，以高收率得到偶联产物，而三氟硼酸烷基酯则反应性较低。发现乙酸四丁铵的利用在提高交叉偶联过程的反应速率中起重要作用。另外，在硼酸和有机三氟硼酸钾盐之间进行了比较研究。
• Rapid construction of imidazopyridines from ortho-haloaminopyridines
  作者：Chaomin Li、Lily Chen、Dietrich Steinhuebel、Andrew Goodman

  DOI：10.1016/j.tetlet.2016.04.118

  日期：2016.6

  A practical strategy for the preparation of imidazopyridine derivatives from ortho-haloaminopyridines utilizing a two-step C–N coupling/cyclization reaction sequence has been developed. This procedure provides rapid and efficient access to many medicinally interesting imidazopyridine compounds and related imidazopyrazine/purine heterocycles.

  已开发出一种利用两步C–N偶联/环化反应序列从邻卤代氨基吡啶制备咪唑并吡啶衍生物的实用策略。该程序可快速有效地获得许多具有医学意义的咪唑并吡啶化合物和相关的咪唑并吡嗪/嘌呤杂环。
• Microwave-Assisted C-2 Direct Alk­enylation of Imidazo[4,5-<i>b</i>]pyr­idines: Access to Fluorescent Purine Isosteres with Remarkably Large Stokes Shifts
  作者：Tom Baladi、Anton Granzhan、Sandrine Piguel

  DOI：10.1002/ejoc.201600166

  日期：2016.5

  We describe herein the first C-2 direct alkenylation of the valuable 3H-imidazo[4,5-b]pyridine promoted by microwave-assisted Pd/Cu co-catalysis. The reaction is rapid and compatible with a wide range of functional groups either on the imidazo[4,5-b]pyridine ring or on the styryl bromides thereby leading to the isolation of 23 compounds with moderate to good yields. The relevance of this method is

  我们在此描述了由微波辅助 Pd/Cu 共催化促进的有价值的 3H-咪唑并 [4,5-b] 吡啶的第一次 C-2 直接烯基化。该反应快速且与咪唑并[4,5-b]吡啶环或苯乙烯基溴上的各种官能团相容，从而以中等至良好的产率分离出23种化合物。该方法的相关性通过其在合成新的交叉共轭推拉 2-乙烯基和 2-炔基咪唑并[4,5-b] 吡啶中的应用而得到证明，其特征在于具有令人满意的荧光量子产率和显着的溶剂化荧光变色特性。
• Stereoselective annelation of 3-substituted imidazo[4,5-b]pyridines with cyanoacetylenic alcohols and domino rearrangement of the adducts
  作者：Boris A. Trofimov、Ludmila Andriyankova、Lina Nikitina、Kseniya Belyaeva、Anastasiya Malkina、Oleg Dyachenko、Olga Kazheva、Anatolii Chekhlov、Andrei Afonin

  DOI：10.3998/ark.5550190.0013.622

  日期：——

  cyanoacetylenic tertiary �-alcohols to give stereoselectively functionalized 1,3-oxazolo(3,2-a)imidazo(4,5- b)pyridines in 50-88% yields. The adducts undergo a facile stereoselective hydrolytic domino rearrangement to functionalized derivatives of 2,3-diaminopyridines.

  咪唑 (4,5-b) 吡啶很容易与氰基乙炔叔醇退火 (45-50 o C, 24-30 h, MeCN)，得到立体选择性功能化的 1,3-恶唑并 (3,2-a) 咪唑 ( 4,5-b) 吡啶，产率为 50-88%。加合物经过简单的立体选择性水解多米诺重排，生成 2,3-二氨基吡啶的功能化衍生物。
• Ethoxymethylenemalonates and Malononitriles (EMM reagents) as formic acid equivalents: Synthesis of fused-imidazoles under neutral or mildly acidic con
  作者：Barb E. Segelstein、Bert L. Chenard、John E. Macor、Ronald J. Post

  DOI：10.1016/s0040-4039(00)91957-9

  日期：1993.3

  The use of ethoxymethylenemalonates and malononitriles (EMM reagents)for the efficient synthesis of fused imidazoles and related compounds is described.