1-(4-硝基苯基)-5-苯基-4,5-二氢三唑 | 10480-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-硝基苯基)-5-苯基-4,5-二氢三唑
• 英文名称: 1-(4-nitrophenyl)-5-phenyl-Δ²-1,2,3-triazoline
• 英文别名: 1-(4-Nitrophenyl)-5-phenyl-4,5-dihydrotriazole
• CAS: 10480-11-2
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: PUWUPGKGBRTMOT-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  443.5±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(4-硝基苯基)-5-苯基-4,5-二氢三唑 在 potassium permanganate 、 四丁基氯化铵 作用下， 以 水 、 苯 为溶剂， 反应 4.0h， 以53%的产率得到1-(4-nitrophenyl)-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Kadaba, Pankaja K., Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 5, p. 857 - 864

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯胺 在 盐酸 、 choline chloride–urea 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 10.0h， 生成 1-(4-硝基苯基)-5-苯基-4,5-二氢三唑
  参考文献：
  名称：

  热叠氮化物-烯烃环加成反应：简单的多克访问Δ 2 -1,2,3- triazolines在深共晶的溶剂

  摘要：

  据报道，在深共晶溶剂（DES）中通过叠氮化物-烯烃环加成反应可以合成多种1,2,3-三唑啉。使用实验/计算-DFT方法研究了DES在这种转变中的作用以及整个产品分销的起源。

  DOI：

  10.1039/c8gc01797b

文献信息

• Thermal azide–alkene cycloaddition reactions: straightforward multi-gram access to Δ²-1,2,3-triazolines in deep eutectic solvents
  作者：Filip Sebest、Luis Casarrubios、Henry S. Rzepa、Andrew J. P. White、Silvia Díez-González

  DOI：10.1039/c8gc01797b

  日期：——

  The multi-gram synthesis of a wide range of 1,2,3-triazolines via azide–alkene cycloaddition reactions in a Deep Eutectic Solvent (DES) is reported. The role of DES in this transformation as well as the origin of the full product distribution was studied with an experimental/computational-DFT approach.

  据报道，在深共晶溶剂（DES）中通过叠氮化物-烯烃环加成反应可以合成多种1,2,3-三唑啉。使用实验/计算-DFT方法研究了DES在这种转变中的作用以及整个产品分销的起源。
• Triazolines. XXIX. 1,5-diaryl-Δ²-1,2,3-triazolines as aphicides: Mechanism of action via aziridine formation
  作者：Pankaja K. Kadaba

  DOI：10.1002/ps.2780420407

  日期：1994.12

  AbstractThe aphicidal activity of 21 different 1,5‐diphenyl‐Δ2‐1,2,3‐triazolines, conveniently prepared utilizing the catalytic effect of water on the 1,3‐cyclo‐addition of diazomethane to Schiff bases in aqueous dioxane, was evaluated. Triazolines bearing an o‐Cl substituent on the C‐phenyl, either alone (4) or in combination with a m‐ and/or a p‐substituent on the N‐phenyl (14, 15, 17 and 18), showed significant activity, with a combined m‐, p‐ substitution on the N‐phenyl the most effective (17 and 18). While an o‐Cl substituent led to greater activity than an o‐NO2 group, the introduction of an additional p‐Cl substituent on the C‐phenyl eliminated activity (21).The aphicidal activity of triazoline 18 was found to be dependent on the presence of UV light. Since fluorescent lighting used in the testing procedure contains UV light and since triazolines undergo photolysis when exposed to UV light to yield aziridines, it was logical to conclude that the aphicidal activity of the triazolines was, in fact, derived from the aziridines formed during the testing procedure. This mechanism of action was confirmed by preparing the aziridines 22, 23 and 24 corresponding to the active triazolines 14, 15 and 18, and showing that they possessed aphicidal activity equal to or better than that of the triazolines, and by the activity observed in several other structurally related aziridine analogues (25–28). Unlike aziridinyl phosphorous compounds, the aziridines described here are not mutagenic in the Ames assay and thus afford a safer class of pesticides.
• KADABA, P. K., J. PRAKT. CHEM., 1982, 324, N 5, 857-864
  作者：KADABA, P. K.

  DOI：——

  日期：——
• Metal-Free 1,2,3-Triazole Synthesis in Deep Eutectic Solvents
  作者：Filip Sebest、Samuel Haselgrove、Andrew J. P. White、Silvia Díez-González

  DOI：10.1055/s-0039-1690736

  日期：2020.4

  The metal-free regioselective preparation of 1,5- and 1,4-disubstituted triazoles is reported through a cycloaddition–elimination sequence. Reactions were carried out in environmentally friendly deep eutectic solvent (DES) and pure products were isolated without the need for chromatographic techniques.

  报道了无金属催化的1,5-和1,4-二取代三唑的区域选择性制备，通过环加成-消除序列完成。反应在环境友好的深共融溶剂（DES）中进行，纯产品被分离出来，无需色谱技术。
• Kadaba, Pankaja K., Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 5, p. 857 - 864
  作者：Kadaba, Pankaja K.

  DOI：——

  日期：——