3-(1-p-tolyl-1H-1,2,3-triazol-4-yl)pyridine | 1345842-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(1-p-tolyl-1H-1,2,3-triazol-4-yl)pyridine
• 英文别名: 3-[1-(4-methylphenyl)-1,2,3-triazol-4-yl]pyridine；3-[1-(4-tolyl)-1H-1,2,3-triazol-4-yl]pyridine；3-[1-(4-Methylphenyl)triazol-4-yl]pyridine；3-[1-(4-methylphenyl)triazol-4-yl]pyridine
• CAS: 1345842-09-2
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: ZIRHSTOYUAEUOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氰基吡啶 、 p-叠氮甲苯 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 3-(1-p-tolyl-1H-1,2,3-triazol-4-yl)pyridine
  参考文献：
  名称：

  Design and combinatorial synthesis of a novel kinase-focused library using click chemistry-based fragment assembly

  摘要：

  Fragment-based lead discovery is a new approach for lead generation that has emerged in the past decade. Because the initial fragments identified in the fragment screening typically show weak binding affinity, an intensive medicinal chemistry effort would be required to grow initial fragments into a potential lead compound. Here we demonstrate a kinase focused evolved fragment (KFEF) library, constructed by click chemistry-based fragment assembly, that is a valuable source of kinase inhibitors. This combinatorial assembly of two fragments, kinase-privileged alkyne fragments and diversified azide fragments, by two cycloaddition reactions shows a unique potential for the one-step synthesis of structurally diverse evolved fragments. The screening of this triazole-based KFEF library allowed the rapid identification of potent lead candidates for FLT3 and GSK3 beta kinase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.076

文献信息

• Eight-membered-ring diaminocarbenes bearing naphthalene moiety in the backbone: DFT studies, synthesis of amidinium salts, generation of free carbene, metal complexes, and solvent-free copper catalyzed azide–alkyne cycloaddition (CuAAC) reaction
  作者：Gleb A. Chesnokov、Maxim A. Topchiy、Pavel B. Dzhevakov、Pavel S. Gribanov、Aleksandr A. Tukov、Victor N. Khrustalev、Andrey F. Asachenko、Mikhail S. Nechaev

  DOI：10.1039/c6dt04484k

  日期：——

  eight-membered ring N-heterocyclic carbene (NHC) bearing a rigid naphthalene moiety in the backbone is reported for the first time. Stereoelectronic properties of 4,5-dihydro-1H-naphtho[1,8-ef][1,3]diazocin-3(2H)-ylidene (NaphtDHD) and smaller ring NHCs were theoretically studied at the DFT level. Amidinium salts were prepared from corresponding amidines and dibromides. Free carbene NaphtDHD-Dipp (Dipp

  首次报道了在骨架中带有刚性萘部分的新型八元环N-杂环卡宾（NHC）。理论上在DFT水平上研究了4,5-二氢-1 H-萘[1,8- ef ] [1,3]二唑-3（2 H）-亚烷基（NaphtDHD）和较小的环NHC的立体电子性质。由相应的salts和二溴化物制备盐。通过用LiHMDS处理相应的盐，在溶液中生成了游离的卡宾NaphtDHD-Dipp（Dipp = 2,6-二异丙基苯基）。它在低温下在溶液中稳定，而在室温下则迅速分解。银（I）和铜（I合成了复合物，并在固态下对其结构进行了表征。铜（I）络合物[（NaphtDHD-Mes）CuBr]（Mes =甲基1,2,4,6-三甲基苯基）在炔烃-叠氮化物环加成（CuAAC）反应中在无溶剂条件下表现出高催化活性。
• Copper(I) Iodide Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from anti-3-Aryl-2,3-dibromopropanoic Acids and Organic Azides
  作者：Chunxiang Kuang、Qing Yang、Xuezhi Cheng、Yiwen Yang

  DOI：10.1055/s-0030-1261030

  日期：2011.9

  A series of 1,4-disubstituted 1,2,3-triazoles were synthesized in a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides in dimethyl sulfoxide with inexpensive copper (I) iodide as the catalyst. cyclizations - heterocycles - azides - triazoles

  一锅法由抗-3-芳基-2,3-二溴丙酸和有机叠氮化物在二甲亚砜中以廉价的碘化铜（I）为原料，合成了一系列1,4-二取代的1,2,3-三唑。催化剂。 环化-杂环-叠氮化物-三唑
• Design and combinatorial synthesis of a novel kinase-focused library using click chemistry-based fragment assembly
  作者：Takayuki Irie、Ikuo Fujii、Masaaki Sawa

  DOI：10.1016/j.bmcl.2011.10.076

  日期：2012.1

  Fragment-based lead discovery is a new approach for lead generation that has emerged in the past decade. Because the initial fragments identified in the fragment screening typically show weak binding affinity, an intensive medicinal chemistry effort would be required to grow initial fragments into a potential lead compound. Here we demonstrate a kinase focused evolved fragment (KFEF) library, constructed by click chemistry-based fragment assembly, that is a valuable source of kinase inhibitors. This combinatorial assembly of two fragments, kinase-privileged alkyne fragments and diversified azide fragments, by two cycloaddition reactions shows a unique potential for the one-step synthesis of structurally diverse evolved fragments. The screening of this triazole-based KFEF library allowed the rapid identification of potent lead candidates for FLT3 and GSK3 beta kinase. (C) 2011 Elsevier Ltd. All rights reserved.