1,5-bis(4-nitrophenyl)-1H-1,2,3-triazole | 31802-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-bis(4-nitrophenyl)-1H-1,2,3-triazole
• 英文别名: 1,5-bis-(4-nitro-phenyl)-1H-[1,2,3]triazole；1,5-Bis<4-Nitrophenyl>-1,2,3-triazol；1,5-Di-p-nitrophenyl-1,2,3-triazol；1,5-Bis(4-nitrophenyl)triazole
• CAS: 31802-49-0
• 化学式: C₁₄H₉N₅O₄
• 分子量: 311.257
• InChiKey: KEWRJGWVAWHNQI-UHFFFAOYSA-N

物化性质

• 熔点：
  198-199 °C
• 沸点：
  564.9±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-nitrophenyl azide 在 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 copper(II) sulfate 、 sodium ascorbate 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.25h， 生成 1,5-bis(4-nitrophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Pd-Catalyzed Regioselective Arylation on the C-5 Position ofN-Aryl 1,2,3-Triazoles

  摘要：

  We herein report a highly efficient method for the arylation at the C-5 position of N-aryl 1,2,3-triazoles via a direct palladium catalyzed arylation reaction. The optimal reaction conditions required a combination of Pd(OAc)(2) and tris(o-tolyl)phosphine as catalyst, and Cs2CO3 as the base under inert atmosphere. A variety of C-5 substituted N-aryl 1,2,3-triazoles were prepared using these conditions with yields in the 70-88% range. Regioselective C-5 arylations were also performed on 1,4-disubstituted 1,2,3-triazoles. The regioselectivity in triazole substitution at the C-5 position was confirmed by single crystal XRD. In addition, computational investigations of key steps of the catalytic cycle using the density functional theory have provided a rationalization to the selective C-5 arylation of N-aryl 1,2,3-triazoles.

  DOI：

  10.1021/jo5026145

文献信息

• Design and applications of new phosphine-free tetradentate Pd-catalyst: Regioselective C–H activation on 1-substituted 1,2,3-triazoles and indoles(NH-Free)
  作者：Sarma V. Markandeya、Ch. Renuka、Parvathi K. Lakshmi、A. Rajesh、Chidara Sridhar、Korupolu Raghu Babu

  DOI：10.1080/00397911.2017.1381260

  日期：2018.1.17

  ABSTRACT This article describes the synthesis of a new phosphine free tetradentate Pd catalyst using dl-2,3-diaminopropionic acid. The complex was characterized by Mass, IR, and 1H NMR. The catalyst is air stable at room temperature and non-hygroscopic. Application of this new catalyst to regioselective C–H activation on 1-substituted 1,2,3-triazole and indoles with aryl iodides to get corresponding

  摘要 本文描述了使用 dl-2,3-二氨基丙酸合成一种新的无膦四齿 Pd 催化剂。该配合物通过质谱、红外和 1 H NMR 表征。该催化剂在室温下对空气稳定且不吸湿。应用这种新催化剂对 1-取代的 1,2,3-三唑和吲哚与芳基碘进行区域选择性 C-H 活化，得到相应的 C-5 和 C-2 芳基化产物，收率令人满意。所有产品均通过光谱研究表征。图形概要
• Kadaba, Pankaja K., Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 5, p. 857 - 864
  作者：Kadaba, Pankaja K.

  DOI：——

  日期：——
• KADABA, P. K., J. PRAKT. CHEM., 1982, 324, N 5, 857-864
  作者：KADABA, P. K.

  DOI：——

  日期：——
• KADABA PANKAJA K., SYNTHESIS, 1978, NO 9, 694-695
  作者：KADABA PANKAJA K.

  DOI：——

  日期：——
• Pd-Catalyzed Regioselective Arylation on the C-5 Position of<i>N</i>-Aryl 1,2,3-Triazoles
  作者：K. Durga Bhaskar Yamajala、Mahendra Patil、Shaibal Banerjee

  DOI：10.1021/jo5026145

  日期：2015.3.20

  We herein report a highly efficient method for the arylation at the C-5 position of N-aryl 1,2,3-triazoles via a direct palladium catalyzed arylation reaction. The optimal reaction conditions required a combination of Pd(OAc)(2) and tris(o-tolyl)phosphine as catalyst, and Cs2CO3 as the base under inert atmosphere. A variety of C-5 substituted N-aryl 1,2,3-triazoles were prepared using these conditions with yields in the 70-88% range. Regioselective C-5 arylations were also performed on 1,4-disubstituted 1,2,3-triazoles. The regioselectivity in triazole substitution at the C-5 position was confirmed by single crystal XRD. In addition, computational investigations of key steps of the catalytic cycle using the density functional theory have provided a rationalization to the selective C-5 arylation of N-aryl 1,2,3-triazoles.