methyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate | 15922-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate
• 英文别名: 4-Methoxycarbonyl-5-methyl-1-(p-nitrophenyl)-1,2,3-triazole；5-methyl-1-(4-nitro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid methyl ester；Methyl-5-methyl-1-(p-nitrophenyl)-(1H)-triazol-4-carboxylat；methyl 5-methyl-1-(4-nitrophenyl)triazole-4-carboxylate
• CAS: 15922-67-5
• 化学式: C₁₁H₁₀N₄O₄
• 分子量: 262.225
• InChiKey: MTCJTYXBCYMGTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate 在 氯化亚砜 、 sodium hydroxide 作用下， 反应 24.0h， 生成 5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbonyl chloride
  参考文献：
  名称：

  Synthesis and mesomorphic properties of novel [1,2,3]-triazole mesogenic based compounds

  摘要：

  A series of five-membered heterocyclic 1,2,3-triazole derivatives with different substituents in N1 position was synthesized. The heterocyclic moiety was connected through an ester function to a p-decyloxyphenyl or p-decyloxybiphenyl tails Polarized microscopy studies, X-ray scattering and differential scanning calorimetry (DSC) analysis revealed that the target compounds exhibit enantiotropic liquid crystalline properties. Their mesomorphic behavior is closely related to the nature of the substituent X present in N1 position of the heterocycle. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.020
• 作为产物：
  描述：

  methyl (E)-3-(2-phenylpyrazolidin-1-yl)but-2-enoate 、 4-nitrophenyl azide 生成 methyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  DALLA CROCE P., ANN. CHIM., (ITAL) 1973, 63, NO 7-8, 29-35

  摘要：

  DOI：

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。
• A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes
  作者：Sarah Zeghada、Ghenia Bentabed-Ababsa、Aïcha Derdour、Safer Abdelmounim、Luis R. Domingo、José A. Sáez、Thierry Roisnel、Ekhlass Nassar、Florence Mongin

  DOI：10.1039/c1ob05176h

  日期：——

  β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower activation energy). The effect of non-conventional activation methods on the degradation of 1,2,3-triazolines was next studied experimentally. Finally, some of the 1,2,3-triazoles such synthesized were evaluated for their bactericidal and

  一方面是由芳基叠氮化物进行反应，另一方面是由β-二羰基化合物或丙二腈衍生的活化烯烃，通过常规加热或微波活化，得到1-芳基-1 H-1,2,3-三唑 理论上已经使用DFT方法在B3LYP / 6-31G *水平上研究了涉及β-二羰基化合物的反应机理和区域选择性：它们是包含β-二羰基化合物及其烯醇形式的互变异构平衡的多米诺过程。烯醇的1，3-偶极环加成与芳基叠氮化物（高活化能）和脱水过程（较低活化能）形成。接下来通过实验研究非常规活化方法对1,2,3-三唑啉降解的影响。最后，评估了这样合成的一些1,2,3-三唑的杀菌和细胞毒性活性。
• 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。
• Self condensation of enamines mediated by acetylation. A novel approach to 1-(azol-5-yl)-(1E,3Z)-butadiene-4-N,N-dimethylamines
  作者：Yuri Shafran、Yuri Rozin、Tetyana Beryozkina、Sergei Zhidovinov、Oleg Eltsov、Julia Subbotina、Johann Leban、Rashida Novikova、Vasiliy Bakulev

  DOI：10.1039/c2ob25331c

  日期：——

  Novel self-condensation of 3-(azol-5-yl)-1,1-dimethylenamines has been found to form new C–C bonds leading to 2,4-(1,2,3-triazole-1,2,3-thiadiazole-3-phenylisothiazole)-(1E,3Z)-5-yl-butadiene-1-amines. The discovered reaction represents a new example of C–H functionalization in unsaturated systems and can serve an efficient synthetic approach to rational design of new 2,4-(diazole-5-yl)-dieneamines

  已发现3-（azol-5-yl）-1,1-二甲基亚胺的新型自缩合形成新的C–C键，从而导致2,4-（1,2,3-三唑-1,2,3 -噻二唑-3-苯基异噻唑）-（1 E，3 Z）-5-基丁二烯-1-胺。所发现的反应代表了不饱和体系中C–H官能化的新实例，可为合理设计新的2,4-（二唑-5-基）-二烯胺提供有效的合成方法。