4-amino-5-(4-nitrobenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one | 147440-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-5-(4-nitrobenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
• 英文别名: 4-amino-3-[(4-nitrophenyl)methyl]-1H-1,2,4-triazol-5-one
• CAS: 147440-66-2
• 化学式: C₉H₉N₅O₃
• 分子量: 235.202
• InChiKey: FTZJIUOQQYVPPI-UHFFFAOYSA-N

物化性质

• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-5-(4-nitrobenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 在 盐酸 、 sodium nitrite 作用下， 反应 1.0h， 以91%的产率得到3-p-Nitrobenzyl-4,5-dihydro-1,2,4-triazol-5-one
  参考文献：
  名称：

  一些 4,5-dihydro-1,2,4-triazol-5-ones 的 1H NMR 谱

  摘要：

  合成了 30 个 3-取代和 3,4-二取代-4,5-二氢-1,2,4-三唑-5-酮（7 个是新化合物），并在三氟乙酸（TFA）中测量了它们的质子磁共振谱）。在 DMSO-d6 和 TFA 中运行的光谱比较时观察到的质子化位移归因于酸性介质中所得阳离子的脒型共振。

  DOI：

  10.1002/mrc.1260311211
• 作为产物：
  描述：

  碳酰肼 、 以 水 为溶剂， 反应 7.0h， 生成 4-amino-5-(4-nitrobenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Ikizler, Aykut A.; Ikizler, Aysun; Serdar, Mevluet, Acta poloniae pharmaceutica, 1997, vol. 54, # 5, p. 363 - 370

  摘要：

  DOI：

文献信息

• Reaction of 4-Amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 2,5-Dimethoxytetrahydrofuran
  作者：Aykut A. Ikizler、Haydar Yüksek

  DOI：10.1135/cccc19940731

  日期：——

  A number of studies involving some reactions of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones have been made in recent years. On the other hand, the reactions of some N-aminoheteroaryls with 1,4-diketones or 1,4-dialdehydes to give N,N'-linked biheteroaryls have also been reported. In the present study, a series of 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones I were condensed in good yields with the succinaldehyde equivalent, 2,5-dimethoxytetrahydrofuran to give N,N'-bis(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-1,4-butanediimines II or 1-(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)pyrroles III in nitrobenzene or acetic acid medium, respectively. To obtain more information on type II compounds, 3-methyl-4-ethylidenamino-4,5-dihydro-1H-1,2, 4-triazol-5-one (IV) was synthesized.

  近年来进行了一些涉及4-氨基-4,5-二氢-1H-1,2,4-三唑-5-酮的反应研究。另一方面，已经报道了一些N-氨基杂环芳烃与1,4-二酮或1,4-二醛反应形成N,N'-偶联的双杂环芳烃的反应。在本研究中，一系列3-烷基-4-氨基-4,5-二氢-1H-1,2,4-三唑-5-酮I与琥珀醛等价物2,5-二甲氧基四氢呋喃反应，在硝基苯或乙酸介质中得到N,N'-双(3-烷基-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)-1,4-丁二亚胺II或1-(3-烷基-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)吡咯III，收率良好。为了获得更多关于II型化合物的信息，合成了3-甲基-4-乙烯基氨基-4,5-二氢-1H-1,2,4-三唑-5-酮IV。
• Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity
  作者：HAKAN BEKTAŞ、AHMET DEMİRBAŞ、NESLİHAN DEMİRBAŞ、ŞENGÜL ALPAY KARAOĞLU

  DOI：10.3906/kim-0905-36

  日期：——

  2-3-(4-Substitutedbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5- dihydro-1H-1,2,4-triazol-1-yl}-N'-(aryl-methylene)acetohydrazides (5a-g), 4-amino-2--(4-substitutedbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol- 1-yl}-N'-(arylmethylene)acetohydrazides (6a,b), and 4-[2-(1H-indol- 3-yl)ethyl]-5-(4-substitutedbenzyl)-2-5-(phenylamino)-1,3,4-thiadiazol- 2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a,b) were synthesized starting from 4-alkyl-5-(4-substitutedbenzyl)-2,4-dihydro- 3H-1,2,4-triazol-3-ones (2a-c) by several steps and their structures were well characterized by elemental analyses, IR, ^1H-NMR, ^13}C-NMR, and mass spectral studies. They were also screened for their microbial activities. The obtained antimicrobial activity results revealed that 12 among the 24 compounds tested displayed variable growth inhibition effects on the tested gram-positive and gram-negative bacterial strains. None of the compounds showed antifungal activity against yeast-like fungi.

  2-3-(4-Substitutedbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5- dihydro-1H-1,2,4-triazol-1-yl}-N'-(aryl-methylene)acetohydrazides (5a-g), 4-amino-2--(4-substitutedbenzyl)-5-oxo-4,5-二氢-1H-1,2,4-三唑-1-基}-N'-(芳基亚甲基)乙酰肼 (6a,b)，以及 4-[2-(1H-吲哚-3-基)乙基]-5-(4-取代苄基)-2-5-(苯基氨基)-1、4-烷基-5-(4-取代苄基)-2,4-二氢-3H-1,2,4-三唑-3-酮(2a-c)为起点，经多个步骤合成了 2,4-二氢-3H-1,2,4-三唑-3-酮(8a,b)，并通过元素分析、红外光谱、^1H-NMR、^13}C-NMR 和质谱研究对其结构进行了表征。 此外，还对它们进行了微生物活性筛选。 所获得的抗菌活性结果显示，24 种受测化合物中有 12 种对受测的革兰氏阳性和革兰氏阴性细菌菌株具有不同的生长抑制作用。 没有一种化合物显示出对酵母类真菌的抗真菌活性。
• Ikizler, Aykut A.; Yueksek, Haydar, Revue Roumaine de Chimie, 1996, vol. 41, # 7-8, p. 585 - 590
  作者：Ikizler, Aykut A.、Yueksek, Haydar

  DOI：——

  日期：——
• Ikizler, Aykut A.; Ikizler, Aysun; Serdar, Mevluet, Acta poloniae pharmaceutica, 1997, vol. 54, # 5, p. 363 - 370
  作者：Ikizler, Aykut A.、Ikizler, Aysun、Serdar, Mevluet、Yildirim, Nuri

  DOI：——

  日期：——
• 1H NMR spectra of some 4,5-dihydro-1,2,4-triazol-5-ones
  作者：A. Aykut Ikizler、Aysun Ikizler、Haydar Yüksek

  DOI：10.1002/mrc.1260311211

  日期：1993.12

  3‐substituted‐ and 3,4‐disubstituted‐4,5‐dihydro‐1,2,4‐triazol‐5‐ones (seven being new compounds) were synthesized and their proton magnetic resonance spectra were measured in trifluoroacetic acid (TFA). The protonation shifts observed on comparison of the spectra run in DMSO‐d6 and TFA were attributed to an amidinium‐type resonance of the resulting cations in the acidic medium.

  合成了 30 个 3-取代和 3,4-二取代-4,5-二氢-1,2,4-三唑-5-酮（7 个是新化合物），并在三氟乙酸（TFA）中测量了它们的质子磁共振谱）。在 DMSO-d6 和 TFA 中运行的光谱比较时观察到的质子化位移归因于酸性介质中所得阳离子的脒型共振。