1-phenyl-1H-1,2,3-triazole-4,5-dicarboxylic acid diethyl ester | 1377302-35-6

• 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-phenyl-1H-1,2,3-triazole-4,5-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 1-phenyltriazole-4,5-dicarboxylate
• CAS: 1377302-35-6
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: SGUZEAUQCAELLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  叠氮苯 、 丁炔二酸二乙酯 在 copper nanoparticulates in Guar-gum 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以92%的产率得到1-phenyl-1H-1,2,3-triazole-4,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Copper nanoparticulates in Guar-gum: a recyclable catalytic system for the Huisgen [3 + 2]-cycloaddition of azides and alkynes without additives under ambient conditions

  摘要：

  研究人员首次研究了室温下瓜尔胶中的铜纳米颗粒作为有机合成中的可循环催化系统。在无添加剂的环境条件下，评估了这些材料在叠氮化物和炔烃的 Huisgen [3 + 2]-cycloaddition 反应中的催化潜力。

  DOI：

  10.1039/c2gc35070j

文献信息

• Aqueous bile salt accelerated cascade synthesis of 1,2,3-triazoles from arylboronic acids
  作者：Anirban Garg、Abdul Aziz Ali、Krishnaiah Damarla、Arvind Kumar、Diganta Sarma

  DOI：10.1016/j.tetlet.2018.09.064

  日期：2018.11

  A facile, efficient and mild copper catalyzed strategy for cascade synthesis of various 1,4-disubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and alkynes was developed by using aqueous bile salt NaDC solution as an accelerating medium. Low catalyst loading (only 1 mol% Cu source was sufficient for in situ generation of azide followed by azide–alkyne coupling), green solvent, use of

  通过使用胆汁盐NaDC水溶液作为促进介质，开发了一种简便，高效，温和的铜催化策略，用于从芳基硼酸，叠氮化钠和炔烃级联合成各种1,4-二取代的1,2,3-三唑。低催化剂负载量（仅1 mol％的铜源足以就地生成叠氮化物，然后进行叠氮化物-炔烃偶联反应），绿色溶剂，使用生物表面活性剂作为添加剂以及较短的反应时间使该方案高度可访问且对环境友好。
• Ag–NHC anchored on silica: an efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis
  作者：Anirban Garg、Nagesh Khupse、Ankur Bordoloi、Diganta Sarma

  DOI：10.1039/c9nj03892b

  日期：——

  A silica-supported silver complex, Ag–NHC@SiO₂, was prepared by an anchoring coordination technique, which was successfully employed for the click reaction under mild reaction conditions.

  一种硅支撑的银配合物Ag-NHC@SiO₂通过锚定协调技术制备，成功地应用于温和反应条件下的点击反应。
• Silica immobilized copper N‐heterocyclic carbene: An effective route to 1,2,3‐triazoles via azide‐alkyne cycloaddition and multicomponent click reaction
  作者：Anirban Garg、Nobomi Borah、Jasmin Sultana、Akshay Kulshrestha、Arvind Kumar、Diganta Sarma

  DOI：10.1002/aoc.6298

  日期：2021.9

  supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic

  制备了一种新型二氧化硅负载的铜 N-杂环卡宾 (Cu-NHC@SiO 2 ) 配合物，并通过扫描电子显微镜 (SEM)、能量色散 X 射线光谱 (EDX) 和 X 射线光电子能谱 (XPS) 分析表征。该配合物是一种有效且易于回收的催化剂，用于通过直接叠氮化物-炔烃环加成反应以及使用芳基硼酸的一锅反应合成 1,2,3-三唑。该催化体系也适用于从各种苯甲醛合成 4-芳基-NH-1,2,3-三唑。此外，对于通过直接叠氮化物-炔烃环加成和多组分反应合成 1,2,3-三唑的所有三种方法，催化剂可以有效地循环至第五次循环。
• Copper(<scp>ii</scp>)-catalyzed oxidative [3+2] cycloaddition reactions of secondary amines with α-diazo compounds: a facile and efficient synthesis of 1,2,3-triazoles
  作者：Yi-Jin Li、Xue Li、Shao-Xiao Zhang、Yu-Long Zhao、Qun Liu

  DOI：10.1039/c5cc02092a

  日期：——

  A novel copper-catalyzed [3+2] cycloaddition reaction of secondary amines with α-diazo compounds has been developed via a cross-dehydrogenative coupling process under very mild conditions with molecular oxygen as a co-oxidant.

  已开发出一种新颖的铜催化的次烷胺与α-重氮化合物的[3+2]环加成反应，通过交叉脱氢偶联过程在非常温和的条件下进行，分子氧作为共氧化剂。
• Cu(II) ionic liquid promoted Simple and Economical Synthesis of 1,4-disubstituted-1,2,3-triazoles with Low Catalyst Loading
  作者：Parmita Phukan、Akshay Kulshrestha、Arvind Kumar、Srijita chakraborti、Pronobesh Chattopadhyay、Diganta Sarma

  DOI：10.1007/s12039-021-01980-9

  日期：2021.12

  In this work, we have described a very simple and low metal loading copper-based ionic liquid as solvent and catalyst for regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles. The proposed protocol proved its efficiency by showing excellent tolerance to a large array of electronically diverse substrates without the use of the external base, solvent and ligands. Moreover, from cytotoxicity analysis the catalyst was found to be non-toxic in nature due to extremely low loading of copper metal (0.1 mol %). This work describes a very simple and low metal loading catalytic system for efficient synthesis of 1,4-disubstituted-1,2,3-triazoles. The synthesized copper based ionic liquid acted both as solvent and as catalyst. Cytotoxicity analysis indicates that the catalyst is non-toxic in nature due to extremely low loading of copper metal (0.1 mol%).

  在这项工作中，我们描述了一种非常简单的低金属负载铜基离子液体，作为溶剂和催化剂，用于1,4-二取代-1,2,3-三唑的位点选择性合成。所提出的方案证明了其有效性，它对大量电子差异底物表现出极好的耐受性，而无需使用外部碱、溶剂和配体。此外，从细胞毒性分析中可以看出，由于铜金属的负载量极低（0.1 mol %），该催化剂本质上是无毒的。这项工作描述了一种非常简单的低金属负载催化体系，用于1,4-二取代-1,2,3-三唑的高效合成。合成的铜基离子液体既作为溶剂又作为催化剂。细胞毒性分析表明，由于铜金属的负载量极低（0.1 mol %），该催化剂本质上是无毒的。