2,6-diamino-3-methyl-5-nitrosopyrimidin-4(3H)-one | 31469-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,6-diamino-3-methyl-5-nitrosopyrimidin-4(3H)-one
• 英文别名: 2,4-diamino-1-methyl-5-nitroso-6-oxopyrimidine；2,4-diamino-5-nitroso-6-oxo-pyrimidine；2,6-diamino-3-methyl-5-nitroso-3H-pyrimidin-4-one；InChI=1/C5H7N5O2/c1-10-4(11)2(9-12)3(6)8-5(10)7/h6H2,1H3,(H2,7,8；2,6-diamino-3-methyl-5-nitrosopyrimidin-4-one
• CAS: 31469-63-3
• 化学式: C₅H₇N₅O₂
• 分子量: 169.143
• InChiKey: AEANNQKPRCDUBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-diamino-3-methyl-5-nitrosopyrimidin-4(3H)-one 、 zinc(II) chloride 以 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and structural characterization of Zn (II), Ag (I) and Pd (II) complexes with 2,4-diamino-5-nitroso-6-oxopyrimidine. Crystal and molecular structure of [ZnCl2 (L) (H2O)] and [Ag (NO3) (L)2]

  摘要：

  Three complexes of formula [ZnCl2(L)(H2O)], [Ag(NO3)(L)(2)] and [PdCl2(L)]. 2H(2)O have been obtained by reacting the ligand 2,4-diamino-5-nitroso-6-oxo-pyrimidine with the corresponding metal salt. The complexes have been characterized by thermal and spectroscopic techniques and, for the two former, by single crystal X-ray diffraction. [ZnCl2(L)(H2O)]: C5H9N5O3Cl2Zn, a=9.197(5), b=11.663(6), c=10.166(7)Angstrom, beta=90.66(3), monoclinic, P2(1)/n, Z=4. [Ag(NO3)(L)(2)]: C10H14N11O7Ag, a=15.920(5), b=7.395(5), c= 14.408(5) Angstrom, beta = 97.678(5), monoclinic, C2/c, Z=4. In all of them the ligand coordinates in a neutral bidentate fashion through the exocyclic nitroso and oxo groups, in the two former complexes through the N(5)/O(6) atoms whereas in the latter the donor atoms are the O(5)/O(6). These coordination modes are connected with the fact that the ligand is able to adopt two conformations depending on the intramolecular N(4)H ... O(5) hydrogen bond. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(98)00340-4
• 作为产物：
  描述：

  6-amino-3,4-dihydro-3-methyl-2-methoxy-5-nitroso-4-oxopyrimidine 在 ammonium hydroxide 作用下， 反应 1.75h， 以96%的产率得到2,6-diamino-3-methyl-5-nitrosopyrimidin-4(3H)-one
  参考文献：
  名称：

  嘧啶衍生物中甲氧基的氨解。通过5-亚硝基激活

  摘要：

  通过在嘧啶环上引入5-亚硝基将强烈激活嘧啶衍生物中2-甲氧基的亲核取代。几种2-甲氧基-5-亚硝基嘧啶衍生物的氨解反应可在室温下在羟基以及具有不同伯胺的非羟基介质中进行，且时间短且收率高。氨基裂解的底物包括6-[[（- O-乙酰基）糖基]氨基嘧啶，其提供相应的2-氨基嘧啶而不损害糖部分的乙酰基保护基。

  DOI：

  10.1002/jhet.5570390114

文献信息

• Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5-nitroso
  作者：Group M. Melguizo、A. Marchal、M. Nogueras、A. Sánchez、J. N. Low

  DOI：10.1002/jhet.5570390114

  日期：2002.1

  The nucleophilic substitution of 2-mefhoxy groups in pyrimidine derivatives was strongly activated by introduction of a 5-nitroso group on to the pyrimidine ring. The aminolysis of several 2-methoxy-5-nitrosopyrimidine derivatives was performed at room temperature in hydroxylic as well as in non-hydroxylic media with different primary amines in short time and good yields. The aminolysed substrates

  通过在嘧啶环上引入5-亚硝基将强烈激活嘧啶衍生物中2-甲氧基的亲核取代。几种2-甲氧基-5-亚硝基嘧啶衍生物的氨解反应可在室温下在羟基以及具有不同伯胺的非羟基介质中进行，且时间短且收率高。氨基裂解的底物包括6-[[（- O-乙酰基）糖基]氨基嘧啶，其提供相应的2-氨基嘧啶而不损害糖部分的乙酰基保护基。
• Synthesis and coordination properties of a new ligand designed for surface functionalization of carbon substrates
  作者：Matteo Savastano、Carlotta Zoppi、Antonio Bianchi、Carla Bazzicalupi

  DOI：10.1016/j.ica.2020.119793

  日期：2020.10

  Abstract The new ligand H2L, constituted by a tetraethylenepentamine functionalized with terminal 6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidine groups, has been synthesized with the ultimate goal of preparing Pd2+-containing heterogeneous single metal ion catalysts based on multi-walled carbon nanotubes (MWCNT-L-Pd) and graphene (G-L-Pd) for catalytic applications. In this paper, we report

  摘要合成了由末端被6-氨基-3,4-二氢-3-甲基-5-亚硝基-4-氧代嘧啶基团官能化的四亚乙基五胺构成的新配体H2L，其最终目的是制备含Pd2 +的异质单分子。基于多壁碳纳米管（MWCNT-L-Pd）和石墨烯（GL-Pd）的金属离子催化剂，用于催化应用。在本文中，我们报告了配体的合成及其通过使用Zn2 +和Cu2 +作为测试阳离子进行的配位性能的初步表征。确定了与这些金属离子在水溶液中的配合物的高稳定性常数，
• Synthesis and structural characterization of Zn (II), Ag (I) and Pd (II) complexes with 2,4-diamino-5-nitroso-6-oxopyrimidine. Crystal and molecular structure of [ZnCl2 (L) (H2O)] and [Ag (NO3) (L)2]
  作者：P Arranz-Mascarós、M.L Godino-Salido、R López-Garzón、M.D Gutiérrez-Valero、J.M Moreno

  DOI：10.1016/s0277-5387(98)00340-4

  日期：1999.1

  Three complexes of formula [ZnCl2(L)(H2O)], [Ag(NO3)(L)(2)] and [PdCl2(L)]. 2H(2)O have been obtained by reacting the ligand 2,4-diamino-5-nitroso-6-oxo-pyrimidine with the corresponding metal salt. The complexes have been characterized by thermal and spectroscopic techniques and, for the two former, by single crystal X-ray diffraction. [ZnCl2(L)(H2O)]: C5H9N5O3Cl2Zn, a=9.197(5), b=11.663(6), c=10.166(7)Angstrom, beta=90.66(3), monoclinic, P2(1)/n, Z=4. [Ag(NO3)(L)(2)]: C10H14N11O7Ag, a=15.920(5), b=7.395(5), c= 14.408(5) Angstrom, beta = 97.678(5), monoclinic, C2/c, Z=4. In all of them the ligand coordinates in a neutral bidentate fashion through the exocyclic nitroso and oxo groups, in the two former complexes through the N(5)/O(6) atoms whereas in the latter the donor atoms are the O(5)/O(6). These coordination modes are connected with the fact that the ligand is able to adopt two conformations depending on the intramolecular N(4)H ... O(5) hydrogen bond. (C) 1999 Elsevier Science Ltd. All rights reserved.

表征谱图