5-氨基-2,4-二氢-[1,2,4]噻唑-3-酮 | 1003-35-6

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-2,4-二氢-[1,2,4]噻唑-3-酮
• 中文别名: 5-氨基-2,4-二氢-[1,2,4]三氮唑-3-酮
• 英文名称: 5-amino-2,4-dihydro-3H-1,2,4-triazol-3-one
• 英文别名: 5-amino-1,2,4-triazol-3-one；ATO；5-amino-2,4-dihydro-[1,2,4]triazol-3-one；3-Amino-Δ²-1,2,4-triazolon-(5)；3-Amino-1,2,4-triazolon-(5)；5-Amino-1,2,4-triazol-3-on；5-Amino-1H-1,2,4-triazol-3(2H)-one；3-amino-1,4-dihydro-1,2,4-triazol-5-one
• CAS: 1003-35-6
• 化学式: C₂H₄N₄O
• mdl: MFCD00970120
• 分子量: 100.08
• InChiKey: XOHBRLLZSIGHDE-UHFFFAOYSA-N

物化性质

• 熔点：
  286-290 °C (decomp)
• 密度：
  2.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存放在室温、密封且干燥的环境中。

反应信息

• 作为反应物：
  描述：

  5-氨基-2,4-二氢-[1,2,4]噻唑-3-酮 在 溶剂黄146 、 sodium nitrite 作用下， 反应 4.0h， 以74%的产率得到1,2-二氢-3H-1,2,4-三氮唑-3-酮
  参考文献：
  名称：

  Synthesis of [3-14C]- and [5-14C]-labelled 5-nitro-1,2,4-triazol-3-one (NTO) and study of its chemical decomposition

  摘要：

  The chemical decomposition of NTO 1 and its corresponding amine ATO 2 was investigated. To make easier the identification of the decomposition products, we synthesized C-14-labelled NTO and ATO. Our results confirmed the high stability of the NTO triazolone ring. Its scission can be achieved partially by sulfuric acid under intensive heat and pressure. The triazolone ring of ATO was cleaved in alkaline solution. Carbon dioxide is evolved leaving a polar compound assumed to be aminoguanidine. The deamination of ATO was achieved by nitrosation. In dilute HCl (0.15N), 2 equivalents of NO2- lead to the triazolone: Lb, through a radical de-diazotation of the diazo intermediate. With 3 to 10 equivalents of NO2-, the nitrosation leads exclusively to the azide 6.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1203::aid-jlcr276>3.0.co;2-f
• 作为产物：
  描述：

  (Z)-1,2-bis(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)diazene 1-oxide 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 生成 5-氨基-2,4-二氢-[1,2,4]噻唑-3-酮
  参考文献：
  名称：

  电化学还原水性介质中的硝基三唑类化合物，作为合成新型绿色高能材料的一种方法†

  摘要：

  在水性介质中，已经研究了通过硝基三唑类化合物的电化学还原合成新的偶氮和甲氧基化合物的方法，硝基三唑酮 （NTO）和 硝基三唑（NTr）作为代表基板。还原NTO时，主要生成的固体是氮杂三唑酮（AZTO），偶氮三唑酮（azoTO）和氨基三唑酮 （ATO）作为次要产品，而 3-羟氨基三唑是NTr形成的主要产品。AZTO和azoTO作为不敏感的高炸药（IHE）的新型绿色高氮化合物受到关注。已评估了各种反应条件（如pH值和底物浓度）的影响，并提出了一种解释实验结果的机制。特别地，固体产物中的偶氮氧基与偶氮的比率受pH和温度的影响，次要产物ATO不是通过直接还原NTO而是通过tri三唑酮中间体的新型热歧化反应。高底物浓度和低电池温度的条件使maximize氧基的产量最大化，并使次要产物的形成最小化。结果表明，这种绿色的电合成方法通常可用于从合适的底物合成新的偶氮和偶氮三唑。

  DOI：

  10.1039/c1nj20770a

文献信息

• Microwave Irradiation for Accelerating Synthesis of [1,2,4]Triazole[4,3-a]-pyrimidines Based on Isoflavones
  作者：Zun-Ting Zhang、Juan Xie、Mu-Lin Zhu、Dong Xue

  DOI：10.1055/s-0030-1258105

  日期：2010.7

  Microwave irradiation was used to accelerate the cyclocondensation of isoflavones and 3-amino-1,2,4-triazoles in the presence of sodium methoxide to produce 6,7-diphenyl[1,2,4]-triazolo[4,3-a]pyrimidines in good to moderate yields.

  微波辐射在甲醇钠存在下加速异黄酮和3-氨基-1,2,4-三唑环缩合反应生成6,7-二苯基[1,2,4]-三唑并[4,3-a] ]嘧啶的产率良好至中等。
• Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
  申请人：Gonzalez Javier

  公开号：US20060122399A1

  公开（公告）日：2006-06-08

  The present invention provides compounds of formula (4), and their pharmaceutically acceptable salts and solvates, which are useful as inhibitors of the Hepatitis C virus (HCV) polymerase enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals. The present invention also provides pharmaceutical compositions comprising compounds of formula (4), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formula (4).

  本发明提供了式（4）的化合物及其药学上可接受的盐和溶剂，它们可用作丙型肝炎病毒（HCV）聚合酶酶的抑制剂，并且对于治疗HCV感染的HCV感染的哺乳动物也有用。本发明还提供了包含式（4）的化合物、其药学上可接受的盐和溶剂的药物组合物。此外，本发明还提供了中间体化合物和用于制备式（4）化合物的有用方法。
• Inhibitors of Hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：US07151105B2

  公开（公告）日：2006-12-19

  The present invention provides compounds of formula (4), and their pharmaceutically acceptable salts and solvates, which are useful as inhibitors of the Hepatitis C virus (HCV) polymerase enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals. The present invention also provides pharmaceutical compositions comprising compounds of formula (4), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formula (4).

  本发明提供了公式（4）的化合物及其药学上可接受的盐和溶剂，它们可用作丙型肝炎病毒（HCV）聚合酶酶的抑制剂，并且对于治疗HCV感染的HCV感染哺乳动物也很有用。本发明还提供了包括公式（4）的化合物、其药学上可接受的盐和溶剂的制药组合物。此外，本发明还提供了制备公式（4）化合物的中间体化合物和有用方法。
• INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
  申请人：Gonzalez Javier

  公开号：US20070015764A1

  公开（公告）日：2007-01-18

  The present invention provides compounds of formula (4), and their pharmaceutically acceptable salts and solvates, which are useful as inhibitors of the Hepatitis C virus (HCV) polymerase enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals. The present invention also provides pharmaceutical compositions comprising compounds of formula (4), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formula (4).

  本发明提供了公式(4)的化合物及其药学上可接受的盐和溶剂，这些化合物可用作丙型肝炎病毒（HCV）聚合酶酶的抑制剂，并且还可用于治疗HCV感染的HCV感染哺乳动物。本发明还提供了包含公式(4)的化合物、其药学上可接受的盐和溶剂的制药组合物。此外，本发明还提供了中间体化合物和制备公式(4)的方法。
• Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase, and Compositions and Treatments Using the Same
  申请人：Gonzalez Javier

  公开号：US20090281122A1

  公开（公告）日：2009-11-12

  The present invention provides compounds of formula (4), and their pharmaceutically acceptable salts and solvates, which are useful as inhibitors of the Hepatitis C virus (HCV) polymerase enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals. The present invention also provides pharmaceutical compositions comprising compounds of formula (4), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formula (4).

  本发明提供了式（4）的化合物及其药学上可接受的盐和溶剂化物，它们可用作丙型肝炎病毒（HCV）聚合酶酶的抑制剂，并且也可用于治疗HCV感染的HCV感染的哺乳动物。本发明还提供了包含式（4）的化合物、它们的药学上可接受的盐和溶剂化物的制药组合物。此外，本发明还提供了用于制备式（4）的化合物的中间体和方法。