1-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)ethanone | 133992-62-8

• 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-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)ethanone
• 英文别名: 1-[5-Phenyl-1-(phenylmethyl)-1H-1,2,3-triazol-4-yl]ethanone；1-(1-benzyl-5-phenyltriazol-4-yl)ethanone
• CAS: 133992-62-8
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: VEYBKOXACWNJBF-UHFFFAOYSA-N

物化性质

• 沸点：
  500.9±60.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄基叠氮 、 苄叉丙酮 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 11.0h， 以92%的产率得到1-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)ethanone
  参考文献：
  名称：

  Regioselective synthesis of triazoles via base-promoted oxidative cycloaddition of chalcones with azides in aqueous solution

  摘要：

  使用无过渡金属条件下，开发了一种碱促进的氧化环加成反应，用于合成三取代三唑的区域选择性合成。

  DOI：

  10.1039/c5ra16974g

文献信息

• Regioselective synthesis of functionalized 1,2,3-triazoles via oxidative [3+2]-cycloaddition using Zn(OAc)2 - tBuOOH or ZnO nanoparticle as catalyst system in aqueous medium
  作者：Banoth Paplal、Sakkani Nagaraju、Balasubramanian Sridhar、Dhurke Kashinath

  DOI：10.1016/j.catcom.2017.05.006

  日期：2017.8

  The regioselective synthesis of functionalized pyrazole˗1,2,3-triazoles is reported via oxidative [3 + 2]-cycloaddition reactions of azides with β-nitrostyrenes and chalcone derivatives using Zn(OAc)2 - tBuOOH or ZnO nanoparticles as catalyst system in aqueous medium. The catalyst dependent product selectivity was observed with β-nitrostyrenes to give the triazoles with and without -NO2 group Zn(OAc)2

  官能pyrazole˗1,2,3三唑的区域选择性合成报道通过氧化[3 + 2]使用的Zn（OAc）β-硝基苯乙烯和查耳酮衍生物的叠氮化物-环反应2 -吨BuOOH或ZnO纳米颗粒作为催化剂体系在水性介质中。用β-硝基苯乙烯观察到催化剂依赖性的产物选择性，得到具有和不具有-NO 2基团Zn（OAc）2和ZnO纳米颗粒的三唑。查耳酮选择性地使三唑作为唯一产物具有良好的区域选择性。所得产物分别进一步转化为磺酰胺和恶唑。
• Another Example of Organo-Click Reactions: TEMPO-Promoted Oxidative Azide-Olefin Cycloaddition for the Synthesis of 1,2,3-Triazoles in Water
  作者：Dasari Gangaprasad、John Paul Raj、Tayyala Kiranmye、Kesavan Karthikeyan、Jebamalai Elangovan

  DOI：10.1002/ejoc.201601121

  日期：2016.12

  The water-mediated, metal-free, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) promoted oxidative [3+2] cycloaddition of organic azides with electron-deficient terminal and internal olefins was explored. A library of 1,4-disubstituted and 1,4,5-trisubstituted-1,2,3-triazoles were synthesized in moderate to excellent yields. This method was also found to be compatible not only with open-chain olefins

  探索了水介导的无金属 2,2,6,6-四甲基哌啶-1-氧基 (TEMPO) 促进了具有缺电子末端和内烯烃的有机叠氮化物的氧化 [3+2] 环加成。合成了 1,4-二取代和 1,4,5-三取代-1,2,3-三唑的文库，产率中等至极好。还发现该方法不仅与开链烯烃相容，而且与环烯烃相容。
• Synthesis of functionalized 1,2,3-triazoles using Bi₂WO₆ nanoparticles as efficient and reusable heterogeneous catalyst in aqueous medium
  作者：Banoth Paplal、Sakkani Nagaraju、Veerabhadraiah Palakollu、Sriram Kanvah、B. Vijaya Kumar、Dhurke Kashinath

  DOI：10.1039/c5ra09544a

  日期：——

  The regioselective synthesis of functionalized triazoles is achieved using a combination of Bi₂WO₆ nanoparticles (10 mol%) and click conditions from β-nitrostyrenes, phenylacetylene and chalcones with azides.

  功能化三唑的区域选择性合成是通过使用Bi₂WO₆纳米颗粒（10 mol％）和β-硝基苯乙烯、苯乙炔和查尔酮与叠氮化物的点击条件相结合实现的。
• Organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated ketones with azides through iminium catalysis
  作者：Wenjun Li、Zhiyun Du、Kun Zhang、Jian Wang

  DOI：10.1039/c4gc01929f

  日期：——

  1,3-Dipolar cycloaddition reaction of α,β-unsaturated ketones with azides through iminium catalysis has been developed. This method could furnish 1,4,5-trisubstituted 1,2,3-triazoles in good yields and high levels of regioselectivity.

  已经开发了亚胺催化的α，β-不饱和酮与叠氮化物的1，3-偶极环加成反应。该方法可以提供高产率和高区域选择性的1,4,5-三取代的1,2,3-三唑。
• Tunable Synthesis of 1,2,3‐Triazoles and Enamines through Deacylative Azide‐Alkene Cycloaddition
  作者：R. Rengasamy、J. Paul Raj、K. Vijayalakshmi、N. Punitha、M. Kesavan、M. Vajjiravel、Jebamalai Elangovan

  DOI：10.1002/ejoc.202101470

  日期：2022.4.27

  A [3+2] cycloaddition of activated olefins and organic azides leading to 1,4,5-trisubstituted 1,2,3-triazoles and enamines is reported. Triazoles were achieved in good yields from benzylidene diketones and organic azides by using copper oxide nanoparticles as catalyst while enamines were synthesized in good to excellent yields from benzylidene malonates and organic azides under solvent-free and catalyst-free

  报道了活化烯烃和有机叠氮化物的 [3+2] 环加成反应生成 1,4,5-三取代的 1,2,3-三唑和烯胺。通过使用氧化铜纳米颗粒作为催化剂，从亚苄基二酮和有机叠氮化物以良好的收率获得三唑，而在无溶剂和无催化剂条件下，从亚苄基丙二酸酯和有机叠氮化物以良好至优异的收率合成烯胺。