ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate | 91396-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate
• 英文别名: ethyl 5-methyl-1-(4-chlorophenyl)-1H-1,2,3-triazole-4-carboxylate；ethyl 1-(p-chlorophenyl)-5-methyl-1,2,3-triazol-4-carboxylate；ethyl 1-p-chlorophenyl-5-methyl-1,2,3-triazol-4-carboxylate；1-(4-chloro-phenyl)-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester；1-(4-Chlor-phenyl)-5-methyl-1,2,3-triazol-carbonsaeure-(4)-aethylester；ethyl 1-(4-chlorophenyl)-5-methyltriazole-4-carboxylate
• CAS: 91396-26-8
• 化学式: C₁₂H₁₂ClN₃O₂
• 分子量: 265.699
• InChiKey: DRUYKNWEYPHLEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate 在 一水合肼 作用下， 生成 1-(p-chlorophenyl)-5-methyl-1,2,3-triazol-4-carboxyhydrazide
  参考文献：
  名称：

  Wang, Yan-Fei; Dong, Hong-Ru; Li, Rong-Shan, Indian Journal of Heterocyclic Chemistry, 2012, vol. 22, # 1, p. 81 - 84

  摘要：

  DOI：
• 作为产物：
  描述：

  1-叠氮-4-氯苯 、 乙酰乙酸乙酯 在 1-butyl-3-methylimidazolium hydroxide 作用下， 反应 0.58h， 以85%的产率得到ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  Efficient, green and regioselective synthesis of 1,4,5-trisubstituted-1,2,3-triazoles in ionic liquid [bmim]BF4 and in task-specific basic ionic liquid [bmim]OH

  摘要：

  据报道，通过在离子液体[bmim]BF4中，以L-脯氨酸为催化剂，以及在特定任务基础性离子液体[bmim]OH中，将芳基叠氮化合物与活性亚甲基化合物反应合成1,4,5-三取代的1,2,3-三唑的方法简便且环境友好。这里定义的方法避免了早期现有方法所要求的苛刻条件，并且在产率高、操作简便、后续处理容易和反应时间短等方面表现得非常高效。

  DOI：

  10.1007/s13738-013-0224-6

文献信息

• Efficient TMG catalyzed synthesis of 1,2,3-triazoles
  作者：Fereshteh Ahmadi、Zeinab Noroozi Tisseh、Minoo Dabiri、Ayoob Bazgir

  DOI：10.1016/j.crci.2013.05.006

  日期：2013.12

  Résumé A practical and efficient method for the synthesis of 1,2,3-triazoles via the cycloaddition reaction of azides and CH-acids in the presence of 1,1,3,3-tetramethylguanidine (TMG) in ethanol at 30 °C has been reported. The simple experimental procedure, short reaction times, and good yields are the advantages of the present method.

  摘要 一种实用且高效的合成1,2,3-三氮唑的方法，通过叠氮化合物与CH-酸在1,1,3,3-四甲基胍（TMG）存在下于30°C的乙醇中进行环加成反应得以报道。该方法的简单实验步骤、较短的反应时间以及良好的产率是其优势所在。
• Synthesis of biologically as well as industrially important 1,4,5-trisubstituted-1,2,3-triazoles using a highly efficient, green and recyclable DBU–H2O catalytic system
  作者：Harjinder Singh、Jayant Sindhu、Jitender M. Khurana

  DOI：10.1039/c3ra44440f

  日期：——

  Substituted 1,2,3-triazoles are important heterocyclic molecules with applications in diverse research areas. 1,3-Dipolar cycloaddition reaction of azides and enolizable compounds is an important method of generating substituted 1,2,3-triazoles. However, the reported methods in the literature for 1,3-cycloaddition of aryl azides involve long reaction time, use of hazardous/volatile reagents, and toxic organic solvents. In this paper we have reported the novel environment friendly protocols for the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by reaction of various aryl azides with active methylene compounds in a DBU–water system under conventional heating, ultrasonic and microwave irradiation. The methodologies defined herein showed synthetic advantages in terms of high atom economy, low environmental impact, mild reaction conditions and good yields in shorter reaction time and recyclability of the reaction medium.

  取代的1,2,3-呫唑是重要的杂环分子，在多个研究领域具有应用。叠氮化物与可烯醇化合物的1,3-极性环加成反应是一种生成取代1,2,3-呫唑的重要方法。然而，文献中报道的芳香叠氮化物的1,3-环加成方法涉及较长的反应时间、使用危险/挥发性试剂以及有毒的有机溶剂。在本文中，我们报道了通过在DBU-水体系中对各种芳香叠氮化物与活性亚甲基化合物进行反应，合成1,4,5-三取代-1,2,3-呫唑的新型环保合成方法，反应条件为传统加热、超声波和微波照射。这里定义的方法在合成上具有高原子经济、低环境影响、温和反应条件以及在较短反应时间内获得良好产率和反应介质的可回收性等优点。
• Organocatalytic Enamide–Azide Cycloaddition Reactions: Regiospecific Synthesis of 1,4,5‐Trisubstituted‐1,2,3‐Triazoles
  作者：Lee Jin Tu Danence、Yaojun Gao、Maoguo Li、Yuan Huang、Jian Wang

  DOI：10.1002/chem.201002775

  日期：2011.3.21

  Heterocycles in one click: A novel organocatalytic enamide–azide cycloaddition reaction has been developed. This synthetic procedure represents a new method for the efficient construction of 1,4,5‐trisubstituted‐1,2,3‐triazoles under mild reaction conditions. Most significantly, the investigated process is highly regiospecific (see scheme).

  一键杂环：已开发出一种新型的有机催化的酰胺-叠氮环加成反应。该合成方法代表了一种在温和的反应条件下有效构建1,4,5-三取代-1,2,3-三唑的新方法。最重要的是，所研究的过程具有高度的区域特异性（请参阅方案）。
• Efficient, green and regioselective synthesis of 1,4,5-trisubstituted-1,2,3-triazoles in ionic liquid [bmim]BF4 and in task-specific basic ionic liquid [bmim]OH
  作者：Harjinder Singh、Jayant Sindhu、Jitender M. Khurana

  DOI：10.1007/s13738-013-0224-6

  日期：2013.10

  Convenient and environmentally benign procedures have been reported for the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by the reaction of aryl azides with active methylene compounds in ionic liquid [bmim]BF4 in the presence of l-proline as a catalyst and also in task-specific basic ionic liquid [bmim]OH. The methodologies defined herein avoid the severe conditions as posed by earlier existing methods and proved to be efficient in terms of good yields, operational simplicity, easy workup and short reaction time.

  据报道，通过在离子液体[bmim]BF4中，以L-脯氨酸为催化剂，以及在特定任务基础性离子液体[bmim]OH中，将芳基叠氮化合物与活性亚甲基化合物反应合成1,4,5-三取代的1,2,3-三唑的方法简便且环境友好。这里定义的方法避免了早期现有方法所要求的苛刻条件，并且在产率高、操作简便、后续处理容易和反应时间短等方面表现得非常高效。
• Regiospecific Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles via Enolate–Azide Cycloaddition between 1,3-Dicarbonyl Compounds and Aryl Azides
  作者：Ronald Nelson、Víctor Kesternich、Marcia Pérez-Fehrmann、Sally Jaldin、Laurence Marcourt、Philippe Christen

  DOI：10.3184/174751916x14656662266973

  日期：2016.8

  A cycloaddition reaction at room temperature between aryl azides and 1,3-dicarbonyl compounds in the presence of potassium carbonate in dimethylsulphoxide yielded 10 4-ethoxycarbonyl-1-aryl-5-methyl-1H-1,2,3-triazoles and seven other closely-related compounds. The 1,2,3-triazoles, nine of which are new, were obtained in good to high yields and only the 1,4-regioisomers were formed.

  在碳酸钾的存在下，芳基叠氮化物和 1,3-二羰基化合物在二甲基亚砜中的室温环加成反应产生 10 4-乙氧基羰基-1-芳基-5-甲基-1H-1,2,3-三唑和其他七种密切相关的化合物。1,2,3-三唑，其中九个是新的，以良好到高产率获得并且仅形成了1,4-区域异构体。