1-benzyl-4-(3-nitrophenyl)-1H-1,2,3-triazole | 1355996-78-9

• 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-(3-nitrophenyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(3-nitrophenyl)triazole；1-benzyl-4-(3-nitrophenyl)triazole
• CAS: 1355996-78-9
• 化学式: C₁₅H₁₂N₄O₂
• 分子量: 280.286
• InChiKey: WYDHFQPKWPNJFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  73.85
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride trihydrate 、 1-benzyl-4-(3-nitrophenyl)-1H-1,2,3-triazole 以 乙二醇乙醚 、 水 为溶剂， 反应 6.0h， 生成 [Ir(1-benzyl-4-(3-nitrophenyl)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-(3-nitrophenyl)-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

• 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。
• 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‐Catalyzed Four‐Component Cascade Reaction for the Construction of Triazoles Bearing β‐Hydroxy Chalcogenides
  作者：Xiang‐Xiang Wang、Bo‐Xun Sun、Zhi‐Wei Zhao、Xin Chen、Wen‐Jin Xia、Yuehai Shen、Ya‐Min Li

  DOI：10.1002/adsc.202100938

  日期：2022.1.4

  A copper-catalyzed four-component cascade reaction for the preparation of triazoles bearing β-hydroxy chalcogenides from terminal alkynes, azides, epoxides, and Se/K2S is reported. The present reaction proceeds under mild conditions, and exhibits a good functional group compatibility. A possible mechanism is proposed.

  报道了一种铜催化的四组分级联反应，用于从末端炔烃、叠氮化物、环氧化物和 Se/K 2 S制备带有 β-羟基硫属元素化物的三唑。本反应在温和的条件下进行，并表现出良好的官能团相容性。提出了一种可能的机制。
• 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。
• Ultrasmall Cu ^I Nanoparticles Stabilized on Surface of HPMC: An Efficient Catalyst for Fast and Organic Solvent‐Free Tandem Click Chemistry in Water
  作者：Sudripet Sharma、Jacek B. Jasinski、Wilfried M. Braje、Sachin Handa

  DOI：10.1002/cssc.202201826

  日期：2023.2.8

  Click chemistry: Ultrasmall CuI nanoparticles stabilized by hydroxypropyl methylcellulose (HPMC) enable fast, completely organic solvent-free, and tandem click chemistry in water. The reaction time is between 10–45 min with the spontaneous crashing of pure products from hydrophobic pockets of HPMC, avoiding organic solvents for product extraction and purification.

  点击化学：由羟丙基甲基纤维素 (HPMC) 稳定的超小 Cu I纳米粒子可在水中实现快速、完全无有机溶剂的串联点击化学。反应时间在 10-45 分钟之间，纯产品从 HPMC 的疏水口袋中自发破碎，避免了用于产品提取和纯化的有机溶剂。