1-benzyl-4-(naphthalen-2-yl)-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4-(naphthalen-2-yl)-1H-1,2,3-triazole
• 英文别名: 4-(2-Naphthalenyl)-1-(phenylmethyl)-1H-1,2,3-triazole；1-benzyl-4-naphthalen-2-yltriazole
• 化学式: C₁₉H₁₅N₃
• 分子量: 285.348
• InChiKey: XRWKCSUOQIPSGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  1-benzyl-4-(naphthalen-2-yl)-1H-1,2,3-triazole 、 iridium(III) chloride trihydrate 以 乙二醇乙醚 、 水 为溶剂， 反应 6.0h， 生成 [Ir(1-benzyl-4-(2-naphthyl)triazole)₂(Cl)]₂
  参考文献：
  名称：

  New cyclometalated iridium(III) dye chromophore complexes for n-type dye-sensitised solar cells

  摘要：

  The synthesis of seven iridium complexes where aryl-1,2,3-triazole (Ar-tz) moieties act as cyclometalating ligands with 2,2'-bipyridyl-4,4'-dicarboxylic acid (dcb) as a N<^>N ancillary/anchoring ligand, is described. The new dye complexes [Ir(Ar-tz)(2)(dcb)1[PF6] (AS1-7) were prepared in a two stage procedure with iridium-chloride dimer isolation. DFF analysis together with photophysical investigations reveal how using different substituents on the phenyl ring, or a different aryl system, lead to the tuning of the absorption and emission properties of these complexes. Computational studies therefore demonstrate an ideal HOMO-LUMO directionality for the [Ir(Ar-tz)(2)(dcb)(+) framework, promoting a favourable electron transfer into the TiO2 conduction band upon photoexcitation. Preliminary unoptimized tests on TiO2 DSSCs have been carried out which show similar photovoltaic performance to the [lr(PPY)(2)(deb)] [PF6] (ppy = 2-phenylpyridine) benchmark. (C) 2016 Published by Elsevier B.V.

  DOI：

  10.1016/j.ica.2016.12.003
• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-benzyl-4-(naphthalen-2-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  芳基三唑衍生物及其羟基次甲基同系物对B16黑色素瘤细胞系的合成及细胞毒性评估。

  摘要：

  在这份手稿中，我们描述了一些三唑衍生物对B16黑色素瘤细胞系的合成和细胞毒性评估。为此，我们使用Besthmann-Ohira试剂将一组芳香醛转化为末端炔烃，并通过乙炔格氏试剂制备了相应的羟甲基同化炔烃。然后使用固体负载的催化剂（Amberlyst A-21 CuI）将这些生成的两组炔烃进行铜（I）催化的炔烃-叠氮化物环加成反应（CuAAC），第三组由有机叠氮化物组成。然后在体外针对B16黑色素瘤细胞系测试了合成的三唑。其中，化合物a1b1（R1 =对硝基苯基，R2 =苄基），a4b1（R1 =萘基，R2 =苄基）和a4b5（R1 =萘基，R2 =（R / S）-二氧戊环）表现出对B16的最佳活性黑色素瘤细胞

  DOI：

  10.1016/j.ejmech.2016.06.057

文献信息

• Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy
  作者：Zheng‐Guang Wu、Xiang‐Ji Liao、Li Yuan、Yi Wang、You‐Xuan Zheng、Jing‐Lin Zuo、Yi Pan

  DOI：10.1002/chem.202000252

  日期：2020.5.4

  Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI -catalyzed azide-alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate

  Click化学专注于使用简单的前体进行分子的精细合成的高选择性反应的开发。毋庸置疑，CuI催化的叠氮化物-炔烃环加成（CuAAC）是点击化学最有价值的例子之一，但由于需要额外的还原剂和配体以及细胞毒性铜，因此受到一些限制。在这里，我们展示了一种新颖的叠氮化物-炔烃环加成反应的策略，该策略涉及光氧化还原电子转移自由基机理，而不是传统的金属催化配位过程。这种新开发的光催化的叠氮化物-炔烃环加成反应可以在室温下，在空气和可见光存在的条件下，在温和条件下进行，显示出良好的官能团耐受性，优异的原子经济性，高达99％的高收率，和绝对的区域选择性，提供了各种1,4-二取代的1,2,3-三唑衍生物，包括生物活性分子和药物。使用可回收的光催化剂，太阳能和水作为溶剂，使该光催化系统具有可持续性和环境友好性。此外，叠氮化物-炔烃环加成反应可以在具有优异区域选择性的无金属催化剂的存在下进行光催化，这代表了点击化学
• CuO-Nanoparticles Catalyzed Synthesis of 1,4-Disubstituted-1,2,3-Triazoles from Bromoalkenes
  作者：John Paul Raj、Dasari Gangaprasad、Murugesan Vajjiravel、Kesavan Karthikeyan、Jebamalai Elangovan

  DOI：10.1007/s12039-018-1452-1

  日期：2018.5

  A novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles. A library of 1,4-disubstituted 1,2,3-triazoles has been constructed with good to excellent yields. SynopsisA novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles. A library of 1,4-disubstituted 1,2,3-triazoles has been constructed with good to excellent yields.

  开发了一种新颖高效的协议，涉及使用市售的CuO纳米颗粒（CNP）作为催化剂，用于合成1,2,3-三氮唑。已构建了一系列1,4-二取代的1,2,3-三氮唑，产率从良好到优秀。摘要：开发了一种新颖高效的协议，涉及使用市售的CuO纳米颗粒（CNP）作为催化剂，用于合成1,2,3-三氮唑。已构建了一系列1,4-二取代的1,2,3-三氮唑，产率从良好到优秀。
• A novel route to 1,4-disubstituted-1,2,3-triazoles through metal-free decarboxylative azide-alkene cycloaddition
  作者：R. Rengasamy、K. Vijayalakshmi、N. Punitha、J. Paul Raj、K. Karthikeyan、J. Elangovan

  DOI：10.1016/j.tetlet.2021.153440

  日期：2021.11

  A collection of 1,4-disubstituted 1,2,3-triazoles was achieved by decarboxylative [3 + 2] cycloaddition of organic azides and cinnamic acids. Metal-free condition, high regioselectivity and easy accessibility of starting materials are the salient attributes of this protocol.

  通过有机叠氮化物和肉桂酸的脱羧 [3 + 2] 环加成反应获得了 1,4-二取代的 1,2,3-三唑。无金属条件、高区域选择性和易于获取起始材料是该协议的显着属性。
• Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides
  作者：Li Zhang、Xinguo Chen、Peng Xue、Herman H. Y. Sun、Ian D. Williams、K. Barry Sharpless、Valery V. Fokin、Guochen Jia

  DOI：10.1021/ja054114s

  日期：2005.11.23

  Cp*RuCl(PPh3)2 is an effective catalyst for the regioselective "fusion" of organic azides and terminal alkynes, producing 1,5-disubstituted 1,2,3-triazoles. Internal alkynes also participate in this catalysis, resulting in fully substituted 1,2,3-triazoles.
• 4-Organochalcogenoyl-1H-1,2,3-triazoles: synthesis and functionalization by a nickel-catalyzed Negishi cross-coupling reaction
  作者：Hélio A. Stefani、Daiana M. Leal、Flávia Manarin

  DOI：10.1016/j.tetlet.2012.09.062

  日期：2012.11

  A general method for the synthesis of triazoles containing selenium and tellurium was accomplished via a CuCAAC reaction between organic azides and a terminal triple bond, generated by in situ deprotection of the silyl group. The reaction tolerates alkyl and arylazides, with alkyl and aryl substituents directly bonded to the chalcogen atom. The products were readily functionalized by a nickel-catalyzed Negishi cross-coupling reaction, furnishing the aryl-heteroaryl products at the 4-position in good yields. (C) 2012 Elsevier Ltd. All rights reserved.