1-amino-3,5-diphenyl-1,2,4-triazole | 34985-93-8

• 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-amino-3,5-diphenyl-1,2,4-triazole
• 英文别名: 3,5-diphenyl-[1,2,4]triazol-1-ylamine；1-Amino-3,5-diphenyl-1,2,4-triazol；1-Amino-3.5-diphenyl-1.2.4-triazol；3,5-Diphenyl-1H-1,2,4-triazol-1-amine；3,5-diphenyl-1,2,4-triazol-1-amine
• CAS: 34985-93-8
• 化学式: C₁₄H₁₂N₄
• mdl: MFCD03408160
• 分子量: 236.276
• InChiKey: YSJGEOFZICPMOC-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  471.4±28.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-3,5-diphenyl-1,2,4-triazole 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以1.3 g的产率得到1-dimethylamino-3,5-diphenyl-1,2,4-triazole
  参考文献：
  名称：

  1-烷基-3,6-二芳基-1,4-二氢-s-四嗪的末端重排为1-烷基氨基-3,5-二芳基-1,2,4-三唑

  摘要：

  小号具有无论是在3-或3,6-位上有烷基很容易反应或芳基格氏试剂芳基取代基-Tetrazines，得到1-烷基（或芳基）-1,4-二氢-小号-tetrazines。的1-烷基-1,4-二氢-小号-tetrazines重新排列甲醇氯化氢〜4 -烷基氨基-1,2,4-三唑，但thermolyse容易向较公知的，异构体的1-烷基氨基-1,2， 4-三唑。讨论了可能的反应途径，包括分解为腈和反应性中间体（例如1,3-偶极物质）。

  DOI：

  10.1039/p19840002779
• 作为产物：
  描述：

  3,5-二(苯基)-1H-1,2,4-三唑 在 2,4,6-三甲基苯磺酰羟胺 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-amino-3,5-diphenyl-1,2,4-triazole
  参考文献：
  名称：

  Radical Scavenging by N -Aminoazaaromatics

  摘要：

  N-Aminoazaaromatics were found to react with nitric oxide in the presence of oxygen to afford deaminated products in high yields. The reaction proceeded almost instantaneously in various solvents including water, and one to two equivalent of NO was consumed depending upon the amount of oxygen coexisted, and 1 equivalent of N2O was released in the reaction. In addition, N-aminoazoles were deaminated by potassium superoxide to give parent azoles in good yields. Two equivalents of superoxide was consumed, and about half equivalents of both nitrite and nitrate ion were released. The results demonstrated that N-aminoazoles have ability to protect the biological system against the oxidation promoted by radicals such as nitrogen oxides and superoxide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00118-8

文献信息

• Photoinduced Molecular Rearrangements. The Photochemistry of Some 1,2,4-Oxadiazoles in the Presence of Nitrogen Nucleophiles. Formation of 1,2,4-Triazoles, Indazoles, and Benzimidazoles
  作者：Silvestre Buscemi、Nicolò Vivona、Tullio Caronna

  DOI：10.1021/jo960765i

  日期：1996.1.1

  The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.
• HUNTER, D.;NEILSON, D. G., J. CHEM. SOC. PERKIN TRANS., 1984, N 12, 2779-2783
  作者：HUNTER, D.、NEILSON, D. G.

  DOI：——

  日期：——
• Radical Scavenging by N -Aminoazaaromatics
  作者：Takashi Itoh、Michiko Miyazaki、Hiromi Maeta、Yûji Matsuya、Kazuhiro Nagata、Akio Ohsawa

  DOI：10.1016/s0968-0896(00)00118-8

  日期：2000.8

  N-Aminoazaaromatics were found to react with nitric oxide in the presence of oxygen to afford deaminated products in high yields. The reaction proceeded almost instantaneously in various solvents including water, and one to two equivalent of NO was consumed depending upon the amount of oxygen coexisted, and 1 equivalent of N2O was released in the reaction. In addition, N-aminoazoles were deaminated by potassium superoxide to give parent azoles in good yields. Two equivalents of superoxide was consumed, and about half equivalents of both nitrite and nitrate ion were released. The results demonstrated that N-aminoazoles have ability to protect the biological system against the oxidation promoted by radicals such as nitrogen oxides and superoxide. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Termal rearrangement of 1-alkyl-3,6-diaryl-1,4-dihydro-s-tetrazines to 1-alkylamino-3,5-diaryl-1,2,4-triazoles
  作者：Daniel Hunter、Douglas G. Neilson

  DOI：10.1039/p19840002779

  日期：——

  having aryl substituents in either the 3- or 3,6-positions react readily with alkyl or aryl Grignard reagents to give 1-alkyl (or aryl)-1,4-dihydro-s-tetrazines. The 1-alkyl-1,4-dihydro-s-tetrazines rearrange in methanolic hydrogen chloride to 4-alkylamino-1,2,4-triazoles, but thermolyse readily to the less well known, isomeric 1-alkylamino-1,2,4-triazoles. Possible reaction pathways involving breakdown

  小号具有无论是在3-或3,6-位上有烷基很容易反应或芳基格氏试剂芳基取代基-Tetrazines，得到1-烷基（或芳基）-1,4-二氢-小号-tetrazines。的1-烷基-1,4-二氢-小号-tetrazines重新排列甲醇氯化氢〜4 -烷基氨基-1,2,4-三唑，但thermolyse容易向较公知的，异构体的1-烷基氨基-1,2， 4-三唑。讨论了可能的反应途径，包括分解为腈和反应性中间体（例如1,3-偶极物质）。