2-(1-CH2An-1H-1,2,3-triazol-4-yl)pyridine | 1019336-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(1-CH2An-1H-1,2,3-triazol-4-yl)pyridine
• 英文别名: 2-[1-(Anthracen-9-ylmethyl)triazol-4-yl]pyridine；2-[1-(anthracen-9-ylmethyl)triazol-4-yl]pyridine
• CAS: 1019336-18-5
• 化学式: C₂₂H₁₆N₄
• 分子量: 336.396
• InChiKey: SMUGCARCMOYCIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)palladium(II) tetrafluoroborate 、 2-(1-CH2An-1H-1,2,3-triazol-4-yl)pyridine 以 乙腈 为溶剂， 以94%的产率得到Pd(2-(1-CH2An-1H-1,2,3-triazol-4-yl)pyridine)2(BF4)2
  参考文献：
  名称：

  Palladium(II) Complexes of Readily Functionalized Bidentate 2-Pyridyl-1,2,3-triazole “Click” Ligands: A Synthetic, Structural, Spectroscopic, and Computational Study

  摘要：

  The Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes, the CuAAC "click" reaction is currently receiving considerable attention as a mild, modular method for the generation of functionalized ligand scaffolds. Herein we show that mild one-pot "click" methods can be used to readily and rapidly synthesize a family of functionalized bidentate 2-pyridyl-1,2,3-triazole ligands, containing electrochemically, photochemically, and biologically active functional groups in good to excellent yields (47-94%). The new ligands have been fully characterized by elemental analysis, HR-ESI-MS, IR, H-1 and C-13 NMR and in three cases by X-ray crystallography. Furthermore we have demonstrated that this family of functionalized "click" ligands readily form bis-bidentate Pd(II)/complexes. Solution studies, X-ray crystallography, and density functional theory (DFT) calculations indicate that the Pd(II) complexes formed with the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine series of ligands are more stable than those formed with the [4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine "click" ligands.

  DOI：

  10.1021/ic200789b
• 作为产物：
  描述：

  2-乙炔基吡啶 、 9-(azidomethyl)anthracene 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以78%的产率得到2-(1-CH2An-1H-1,2,3-triazol-4-yl)pyridine
  参考文献：
  名称：

  双杂配 Ru(II) 探针的三唑取代基对磷酸二氢盐选择性检测的影响

  摘要：

  一系列七个新的双杂配 Ru(II) 探针 ( 1[PF 6 ] 2 – 7[PF 6 ] 2 ) 以及两个先前报道的探针 ( 8[PF 6 ] 2和9[PF 6 ] 2 ) 包含使用各种取代基功能化的类似阴离子结合三唑单元（氢键供体）用于详细的比较研究，以开发针对 H 2 PO 4 –的优异选择性探针。各种溶液和固态研究，例如1H-DOSY NMR，动态光散射（DLS），单晶X射线晶体学，和透射电子显微镜（TEM），已经建立了H的选择性传感2 PO 4 -通过这一系列的探针的主要是由于超分子聚合驱动增强3 MLCT 发射。Intestingly，1 [PF 6 ] 2和7 [PF 6 ] 2，具有缺电子（π-酸性）芳族五氟苯基取代基被发现是用于h优越探针2 PO 4 -相比于其他芳基-和聚芳族-取代的类似物（2[PF 6] 2 – 6[PF 6 ] 2、8[PF 6 ] 2和9[PF 6 ]

  DOI：

  10.1021/acs.inorgchem.1c01084

文献信息

• A fluorogenic ‘click’ reaction of azidoanthracene derivatives
  作者：Fang Xie、Krishnamoorthy Sivakumar、Qingbing Zeng、Michael A. Bruckman、Blake Hodges、Qian Wang

  DOI：10.1016/j.tet.2008.01.080

  日期：2008.3

  Fluorogenic reactions have broad applications in biolabeling, combinatorial synthesis of fluorescent dyes, and materials development. It was recently reported that the highly selective and efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction can be employed in designing new types of fluorogenic reactions. In this study, we report a fluorogenic reaction using anthracene azides as starting materials. The fluorescence of the anthryl core can be greatly inhibited upon introducing electron-donating azido groups in the proximity. Such weakly fluorescent anthracene azides demonstrate high reactivity with a variety of alkynes under the CuAAC conditions producing a strongly fluorescent triazole product with high quantum yields. This reaction can be used in the synthesis and screening of fluorescent dyes combinatorially. Compared with most existing methods, the fluorogenic CuAAC reaction is a much milder and simpler technique to prepare large libraries of fluorescent dyes without further purification. In order to demonstrate the efficiency of using anthracene azides for biolabeling applications, both small molecules and biomolecules including the multialkyne-derivatized cowpea mosaic virus and tobacco mosaic virus had been studied. (C) 2008 Elsevier Ltd. All rights reserved.