1-benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole | 1202246-72-7

• 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-1-yl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole；1-benzyl-4-naphthalen-1-yltriazole
• CAS: 1202246-72-7
• 化学式: C₁₉H₁₅N₃
• 分子量: 285.348
• InChiKey: GIJKESLWAGECCW-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-1-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-(1-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 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 1-benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole
  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

文献信息

• Synthesis of heterogeneous Ru(<scp>ii</scp>)-1,2,3-triazole catalyst supported over SBA-15: application to the hydrogen transfer reaction and unusual highly selective 1,4-disubstituted triazole formation <i>via</i> multicomponent click reaction
  作者：Priti Sharma、Jayant Rathod、A. P. Singh、Pradeep Kumar、Yoel Sasson

  DOI：10.1039/c7cy02619f

  日期：——

  catalyst was screened for the multicomponent click cycloaddition reaction in water medium as a green solvent and it exhibited unusual and excellent selectivity for the formation of 1,4-disubstituted triazole product under mild reaction condition. In addition, SBA-15-Tz-Ru(II)TPP catalyst also catalyzed the hydrogen transfer reaction of various carbonyl compounds with excellent catalytic activity to

  在本研究中，我们展示了一种简单有效的配体形成方法，并通过点击反应将共价锚定到异质支持物上。锚固在SBA-15的点击修饰配体上的三氯化三（三苯基膦）钌（II）络合物[RuCl 2（PPh 3）3 ]形成了一种新型的高效多相SBA-15-Tz-Ru（II）TPP催化剂。固态13 C，29 Si和31 P CP-MAS NMR光谱为形成非均相催化剂提供了证据。SBA-15-Tz-Ru（II）TPP催化剂在水介质中作为绿色溶剂进行了多组分点击环加成反应的筛选，在温和的反应条件下，它对形成1,4-二取代的三唑产物表现出不同寻常的优异选择性。此外，SBA-15-Tz-Ru（II）TPP催化剂还催化了各种具有优异催化活性的羰基化合物的氢转移反应，得到了相应的醇。非均相催化剂可以循环使用多次（五次）而不会损失反应性。
• The Sequential Sonogashira-Click Reaction: A Versatile Route to 4-Aryl-1,2,3-triazoles
  作者：Zoltán Novák、Krisztián Lőrincz、Péter Kele

  DOI：10.1055/s-0029-1216985

  日期：2009.10

  Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira­-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.

  芳基卤化物可以通过一步法操作容易地转化为4-芳基-1,2,3-三氮唑，该过程利用了钯/铜催化的Sonogashira-点击反应序列，并以三甲基硅基乙炔作为乙炔替代物。
• One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides
  作者：Eli Zysman-Colman、Sébastien Ladouceur、Ahmed Soliman

  DOI：10.1055/s-0030-1260256

  日期：2011.11

  1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

  通过对应(芳基乙炔基)三甲基硅烷和烷基溴的多组分一锅法方案，已制备了1N-烷基-4-芳基-1,2,3-三唑类化合物。原位形成烷基叠氮化物和炔基去保护，然后通过铜(I)催化的点击环加成反应，通常以良好至优异的产率获得了所需的1,4-二取代-1,2,3-三唑，观察到的不期望的1,5-位异构环加成物仅有微量。该方案消除了对活性有机叠氮化物和末端炔烃的需求。
• Synthesis of Triazoles by Electro-Assisted Click Reaction Using a Copper Foil Electrode
  作者：Luceldi Carre-Rangel、Karla Espinoza、Mercedes Oropeza-Guzmán、Ignacio Rivero

  DOI：10.21577/0103-5053.20210035

  日期：——

  for the synthesis of triazoles using the well-known “click chemistry” assisted by the electrochemical oxidation of metallic Cu0. The click reaction is used to couple a wide range of biological interest compounds. In this case, faster and less polluting methods for a biological environment was achived by in situ Cu0 electrooxidation, providing the suitable quantity of catalyst required by click reaction

  本文提出了一种创新的途径，利用电化学氧化金属Cu0辅助“点击化学”合成三唑。点击反应用于耦合各种生物感兴趣的化合物。在这种情况下，通过原位Cu0电氧化实现了更快速和更少污染的生物环境方法，提供了点击反应所需的适量催化剂。电化学池由铜箔作为工作电极、铂丝作为对电极和Ag/AgCl丝作为参比电极组成。在叔丁醇-水介质（1:1）中进行线性阳极扫描伏安法，使用四丁基铵四氟硼酸盐（TBATFB）作为电解质，显示了Cu0电氧化的起始电位。在恒定电极电位下，使用相同的电极配置制备了三种不同的三唑，反应时间短（60分钟），产率高（78-90%）。这些结果表明，CuI的原位形成发生在铜箔表面。还实施了脉冲电位程序，实现了92%的产率，减少了电极钝化，从而提高了工艺效率。电辅助点击反应通过创新的电化学反应高效地产生三唑。产品通过红外（IR）、核磁共振（1H和13C NMR）和质谱（MS）进行表征。
• Conventional and microwave assisted synthesis of 1,4-disubstituted 1,2,3-triazoles from Huisgen cycloaddition
  作者：Juan Ignacio Sarmiento-Sanchez、Adrian Ochoa-Teran、Ignacio A. Rivero

  DOI：10.3998/ark.5550190.0012.913

  日期：——

  In this paper the synthesis of a library of new 1,4-disubstituted 1,2,3-triazoles 1, with a variety of additional functional groups on its structure, from an in situ generated benzyl azide 2 and different alkynes and dialkynes 3 is reported. Optimal experimental conditions were established for the conventional click chemistry and for the microwave-assisted synthesis of these 1,2,3triazoles. Comparing

  在本文中，从原位生成的叠氮化苄 2 和不同的炔烃和二炔烃 3 合成了一个新的 1,4-二取代 1,2,3-三唑 1 库，其结构上具有多种附加官能团。报道。为常规点击化学和这些 1,2,3 三唑的微波辅助合成建立了最佳实验条件。比较结果可以得出结论，在微波辅助条件下，可以在更短的时间内以更高的产率获得产品。