1-(2,4-dinitrophenyl)-3-nitro-1,2,4-triazole | 30595-51-8

• 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-(2,4-dinitrophenyl)-3-nitro-1,2,4-triazole
• 英文别名: 1-(2,4-dinitro-phenyl)-3-nitro-1H-[1,2,4]triazole；1-(2,4-Dinitrophenyl)-3-nitro-1,2,4-triazol
• CAS: 30595-51-8
• 化学式: C₈H₄N₆O₆
• 分子量: 280.156
• InChiKey: GQYAHPJQWTTXOA-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• 沸点：
  572.7±60.0 °C(Predicted)
• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2,4-dinitrophenyl)-3-nitro-1,2,4-triazole 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 73.0h， 生成 chloro[2-(2,4-dinitrophenyl)-4-methyl-5-nitro-3H-1,2,4-triazol-3-ylidene]-gold(I)
  参考文献：
  名称：

  1,2,4-Triazol-3-ylidenes with anN-2,4-Dinitrophenyl Substituent as Strongly π-Accepting N-Heterocyclic Carbenes

  摘要：

  AbstractThe synthesis and characterisation of a series of new Rh and Au complexes bearing 1,2,4‐triazol‐3‐ylidenes with a N‐2,4‐dinitrophenyl (N‐DNP) substituent are described. IR, NMR, single‐crystal X‐ray diffraction and computational analyses of the Rh complexes revealed that the N‐heterocyclic carbenes (NHCs) behaved as strong π acceptors and weak σ donors. In particular, a natural bond orbital (NBO) analysis revealed that the contributions of the Rh→Ccarbene π backbonding interaction energies (ΔEbb) to the bond dissociation energies (BDE) of the RhCcarbene bond for [RhCl(NHC)(cod)] (cod=1,5‐cyclooctadiene) reached up to 63 %. The Au complex exhibited superior catalytic activity in the intermolecular hydroalkoxylation of cyclohexene with 2‐methoxyethanol. The NBO analysis suggested that the high catalytic activity of the AuI complex resulted from the enhanced π acidity of the Au atom.

  DOI：

  10.1002/chem.201302567
• 作为产物：
  描述：

  2,4-二硝基氟苯 、 3-硝基-1,2,4-三氮唑 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以93%的产率得到1-(2,4-dinitrophenyl)-3-nitro-1,2,4-triazole
  参考文献：
  名称：

  1,2,4-Triazol-3-ylidenes with anN-2,4-Dinitrophenyl Substituent as Strongly π-Accepting N-Heterocyclic Carbenes

  摘要：

  AbstractThe synthesis and characterisation of a series of new Rh and Au complexes bearing 1,2,4‐triazol‐3‐ylidenes with a N‐2,4‐dinitrophenyl (N‐DNP) substituent are described. IR, NMR, single‐crystal X‐ray diffraction and computational analyses of the Rh complexes revealed that the N‐heterocyclic carbenes (NHCs) behaved as strong π acceptors and weak σ donors. In particular, a natural bond orbital (NBO) analysis revealed that the contributions of the Rh→Ccarbene π backbonding interaction energies (ΔEbb) to the bond dissociation energies (BDE) of the RhCcarbene bond for [RhCl(NHC)(cod)] (cod=1,5‐cyclooctadiene) reached up to 63 %. The Au complex exhibited superior catalytic activity in the intermolecular hydroalkoxylation of cyclohexene with 2‐methoxyethanol. The NBO analysis suggested that the high catalytic activity of the AuI complex resulted from the enhanced π acidity of the Au atom.

  DOI：

  10.1002/chem.201302567

文献信息

• Synthesis and anti-tuberculosis activity of N-aryl-C-nitroazoles
  作者：Krzysztof Walczak、Andrzej Gondela、Jerzy Suwiński

  DOI：10.1016/j.ejmech.2004.06.014

  日期：2004.10

  Twelve N-aryl derivatives of 4-nitroimidazole, 2-methyl-4-nitroimidazole, 4-nitropyrazole or 3-nitro-1,2,4-triazole have been synthesized either by a degenerated ring transformation reaction of 1,4-dinitroimidazoles with 4-substituted anilines or by a condensation of fluoronitrobenzenes with salts prepared from C-nitro-1H-azoles and 1,8-diazabicyclo[5.4.0]-7-undecene. The Tuberculosis Antimicrobial Acquisition and Coordinating Facility has provided anti-mycobacterial data concerning inhibition activity of 12 compounds. (C) 2004 Elsevier SAS. All rights reserved.
• 1,2,4-Triazol-3-ylidenes with an<i>N</i>-2,4-Dinitrophenyl Substituent as Strongly π-Accepting N-Heterocyclic Carbenes
  作者：Tetsuo Sato、Yoichi Hirose、Daisuke Yoshioka、Tsubasa Shimojo、Shuichi Oi

  DOI：10.1002/chem.201302567

  日期：2013.11.11

  AbstractThe synthesis and characterisation of a series of new Rh and Au complexes bearing 1,2,4‐triazol‐3‐ylidenes with a N‐2,4‐dinitrophenyl (N‐DNP) substituent are described. IR, NMR, single‐crystal X‐ray diffraction and computational analyses of the Rh complexes revealed that the N‐heterocyclic carbenes (NHCs) behaved as strong π acceptors and weak σ donors. In particular, a natural bond orbital (NBO) analysis revealed that the contributions of the Rh→Ccarbene π backbonding interaction energies (ΔEbb) to the bond dissociation energies (BDE) of the RhCcarbene bond for [RhCl(NHC)(cod)] (cod=1,5‐cyclooctadiene) reached up to 63 %. The Au complex exhibited superior catalytic activity in the intermolecular hydroalkoxylation of cyclohexene with 2‐methoxyethanol. The NBO analysis suggested that the high catalytic activity of the AuI complex resulted from the enhanced π acidity of the Au atom.