1-(3-氨基-5-甲基-1H-吡唑-4-基)-乙酮 | 139111-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-氨基-5-甲基-1H-吡唑-4-基)-乙酮
• 中文别名: 1-(5-氨基-3-甲基-1H-吡唑-4-基)乙酮
• 英文名称: 4-acetyl-3-amino-5-methylpyrazole
• 英文别名: 1-(3-amino-5-methyl-1H-pyrazol-4-yl)ethanone
• CAS: 139111-42-5
• 化学式: C₆H₉N₃O
• mdl: MFCD19103630
• 分子量: 139.157
• InChiKey: XYPSOOKVMCUCIY-UHFFFAOYSA-N

物化性质

• 沸点：
  356.9±37.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  71.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-(3-氨基-5-甲基-1H-吡唑-4-基)-乙酮 以 丙酮 为溶剂， 生成 (di-μ-N(1),N(2)-(3-methyl-4-acetyl-5-aminopyrazolate)bis(dimethyl sulphoxide)dichlorodiplatinum(II))
  参考文献：
  名称：

  Dehydrohalogenation and dimeric complex formation proceeded at the solid-phase heating of trans-[Pt(3-methyl-4-acetyl-5- aminopyrazole)(dimethyl sulphoxide)Cl2]. X-ray structure of the DI-μ-N1,N2-(3-methyl-4-acetyl- 5-aminopyrazolate)bis(dimethyl sulphoxide)dichlorodiplatinum(II)

  摘要：

  The bridge-splitting reaction of [Pt(Me2SO)(mu-Cl)Cl]2 with 3-methyl-4-acetyl-5-aminopyrazol (R3PzH) in acetone leads to the formation and isolation of the trans-[Pt(Me2SO)R3PzH)Cl2] complex. On heating in the solid phase trans-[Pt(Me2SO) (R3PzH)Cl2] undergoes thermal conversion with the formation of [Pt2(R3Pz)2(Me2SO)2Cl2] and the abstraction of HCl. The structure of the complex [Pt2(R3Pz)2(Me2SO)2Cl2] was determined by X-ray diffraction analysis. The complex exhibits a head-to-tail dimeric structure with two bridged pyrazolate anions. The dimerization reaction studied represents an unusual type of the solid-phase conversion of platinum complexes, which can be considered as a variant of the "Anderson rearrangement".

  DOI：

  10.1016/s0277-5387(00)80240-5
• 作为产物：
  描述：

  5-hydroxy-3,5-dimethyl-1-S-methylisothiocarbamoyl-2-pyrazolinium iodide 以 水 为溶剂， 反应 15.0h， 生成 1-(3-氨基-5-甲基-1H-吡唑-4-基)-乙酮
  参考文献：
  名称：

  3-氨基吡唑衍生物合成的结构和机理方面的理论研究

  摘要：

  通过X射线分析和光谱技术确定了5-羟基-3，5-二甲基-1- S-甲基异硫代氨基甲酰基-2-吡唑啉碘化物（HDMCPI）的结构，其为3-氨基吡唑衍生物的环状中间体。在碱性水溶液中处理HDMCPI时，出乎意料地产生了4-乙酰基3（5）-氨基-5（3）-甲基吡唑（AAMP）。通过1 H和13监测HDMCPI的反应13 C NMR光谱。结果表明，酮亚胺互变异构体是唯一的互变异构形式。密度泛函理论解释了酮亚胺互变异构体的自发形成，其存在是在碱性介质中生成碳负离子的主要条件。碳负离子进一步进行环化并消除MeSH，从而产生AAMP。在乙酰丙酮与硫代氨基脲代替S-甲基异硫代氨基脲的反应中，没有痕量的AAMP。该结果可以归因于互变异构平衡中不存在酮亚胺形式，这将为亲核攻击和进一步环化提供碳负离子的形成。

  DOI：

  10.1016/j.tet.2010.05.093

文献信息

• Coupling of C-amino aza-substituted heterocycles with an isocyanide ligand in palladium(ii) complex
  作者：M. A. Kinzhalov、K. V. Luzyanin、V. P. Boyarskiy、M. Haukka、V. Yu. Kukushkin

  DOI：10.1007/s11172-013-0103-4

  日期：2013.3

  6-xylylisocyanide)palladium(ii) with 2-aminopyrazine affords a binuclear palladium complex, in which one of the metal atoms is involved in the palladacyclic ligand. In the contrast, the coupling of isocyanide ligands in cis-dichlorobis-(2,6-xylylisocyanide)palladium(ii) with another C-amino aza-substituted heterocycle, viz.,4-acetyl-3-amino-5-methylpyrazole, gives a mononuclear cationic palladium diaminocarbene

  顺式二氯双（2,6-二甲苯异氰化物）钯 (ii) 与 2-氨基吡嗪反应生成双核钯配合物，其中金属原子之一参与钯环配体。相比之下，顺式二氯双-(2,6-二甲苯基异氰化物)钯(ii)中的异氰化物配体与另一个C-氨基氮杂取代的杂环，即，4-乙酰基-3-氨基-5-甲基吡唑的偶联，得到单核阳离子钯二氨基卡宾络合物。两种化合物均通过元素分析、IR 光谱、1H、13C1H}、DEPT90/DEPT135 和 1H、13C-HSQC/1H、13C-HMBC NMR 光谱、高分辨率电喷雾电离质谱和 X 射线衍射进行表征.
• Cation- and/or anion-directed reaction routes. Could the desolvation pattern of isostructural coordination compounds be related to their molecular structure?
  作者：Berta Holló、Marko V. Rodić、Oskar Bera、Mirjana Jovičić、Vukadin M. Leovac、Zoran D. Tomić、Katalin Mészáros Szécsényi

  DOI：10.1007/s11224-013-0270-9

  日期：2013.12

  potentially biologically active isostructural pairs of octahedral NiII and CoII compounds with ampf and dmpc (3,5-dimethyl-1H-pyrazole-1-carboxamidine) ligands are evaluated and compared with the desolvation of 1. The results of the thermal data are discussed on the basis of structural features of the compounds. The minor differences in structures of the related compounds cannot be straightforwardly connected

  [Cu(ampf)(ClO4)(MeOH)2] , (1), ampf = N,N'-双(4-乙酰-5-甲基吡唑-3-基)甲脒的晶体和分子结构，由下式确定描述了 X 射线晶体学，并与结构相关的铜 (II) 配合物进行了比较，这些配合物是在类似的实验条件下使用具有不同阴离子的 CuII 盐形成的。鉴于钴（II）和镍（II）配合物具有相同的有机配体和不同的阴离子，也在相似的反应条件下形成，讨论了配合物的形成。与中心原子配位的溶剂分子在生物系统中起着重要作用。为了更好地了解去溶剂化机制，本研究介绍了 1 的去溶剂化模式。正如文献中很少关注溶剂化物配合物的去溶剂化机制，评估了三对具有 ampf 和 dmpc（3,5-二甲基-1H-吡唑-1-甲脒）配体的八面体 NiII 和 CoII 化合物的潜在生物活性同构对的去溶剂化机制，并与 1 的去溶剂化进行了比较。根据化合物的结构特征讨论热数据。相关
• Synthesis, structure and thermokinetic studies on perchlorate salts of metal complexes containing a formamidine-type ligand
  作者：Berta Holló、Vladislav Jašo、Vukadin M. Leovac、Vladimir Divjaković、Attila Kovács、Katalin Mészáros Szécsényi

  DOI：10.1080/00958972.2012.761338

  日期：2013.2.1

  4-acetyl-3-amino-5-methylpyrazole (aamp) precursor in the presence of triethyl orthoformate. Compounds of composition [M(ampf)(H2O)3](ClO4)2·H2O (M = CoII, NiII) have been formed. The crystal and molecular structures of the compounds have been determined by X-ray crystallography. The complexes were characterized by IR spectroscopy. The thermal stability and the decomposition kinetics of the two potential explosives

  N,N'-双(4-乙酰基-5-甲基吡唑-3-基)甲脒 (ampf) 的两种甲脒型过渡金属配合物已通过相应金属高氯酸盐和 4-乙酰基的甲醇溶液中的模板反应合成-3-氨基-5-甲基吡唑 (aamp) 前体，在原甲酸三乙酯存在下。已形成组成为 [M(ampf)(H2O)3](ClO4)2· （M = CoII，NiIII）的化合物。化合物的晶体和分子结构已通过 X 射线晶体学确定。配合物通过红外光谱表征。通过热法测定了两种潜在炸药的热稳定性和分解动力学。
• Reaction of copper(II) with 1-carboxamide-3,5-dimethylpyrazole, 1-carboxamidine-3,5-dimethylpyrazole, 4-acetyl-3-amino-5-methylpyrazole and 5-amino-4-carboxamide-1-phenylpyrazole
  作者：K Mészáros Szécsényi、V.M Leovac、V.I Češljević、A Kovács、G Pokol、Gy Argay、A Kálmán、G.A Bogdanović、Ž.K Jaćimović、A Spasojević-de Biré

  DOI：10.1016/s0020-1693(03)00231-7

  日期：2003.9

  Complex formation of copper(II) bromide and acetate with 1-carboxamide-3,5-dimethylpyrazole (HL3) and copper(II) bromide with 5-amino-4-carboxamide-1-phenylpyrazole (L-2), 4-acetyl-3-amino-5-methylpyrazole (HL4) and 1-carboxamidine-3,5-dimethylpyrazole (HL5), was studied. The obtained compounds, CuBr2(L-2)(2), Cu(L-3)(2), CuBr2(HL4)(2), CuBr2(HL5)(2) and [CuBr(HL1)(L-3)](2) (HL1 denotes the 3,5-dimethylpyrazole), are characterized by elemental analysis, FT-IR spectrometry, molar conductivity, TG-MS and DSC. The X-ray structure of [CuBr(HL1)(L-3)](2) and Cu(L-3)(2) is discussed. For [CuBr(HL1)(L-3)](2) a dimeric penta-co-ordinated structure has been found; the co-ordination around the metal in Cu(L-3)(2) is trans-square planar. To CuBr2(L-2)(2) and CuBr2(HL4)(2) a nearly tetrahedral, while for CuBr2(HL5)(2) an octahedral geometry may be assumed. It means that the geometry of the compounds in the first place depends on the ligand substituents. The course of the complex formation reaction is anion-dependent and may be explained on the basis of Pearson's theory, taking into account the steric factors. A low stability intermediate formation was observed in the thermal decomposition of Cu(L-3)(2). (C) 2003 Elsevier B.V. All rights reserved.
• Synthesis of 4-acetyl-5(3)-amino-3(5)-methylpyrazoles and pyrazolo[3,4-d]pyrimidines from diacetylketeneN,S-acetal
  作者：V. A. Dorokhov、A. V. Komkov、B. I. Ugrak

  DOI：10.1007/bf00699932

  日期：1993.8

  Isomeric 4-acetyl-5-amino-3-methyl- and 4-acetyl-3-amino-5-methylpyrazoles (2, 3) were formed in the reaction of hydrazines with 3-[amino(methylthio)methylene]pentan-2,4-dione (1) (diacetylketene NS-acetal). Pyrazolo[3,4-d]pyrimidines (5a,b) were synthesized by condensation of 4-acetyl-5-amino-1,3-dimethylpyrazole (2a) with amide dimethylacetals followed by treatment with ammonium acetate. The structures of the compounds obtained were confirmed by C-13 and N-15 NMR spectroscopy.