2-[(4-amino-3-methyl-5-nitroso-6-oxo-1,6-dihydro)pyrimidin-2-yl]aminoacetic acid | 215525-73-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(4-amino-3-methyl-5-nitroso-6-oxo-1,6-dihydro)pyrimidin-2-yl]aminoacetic acid
• 英文别名: N-(4-amino-1,6-dihydro-1-methyl-5-nitroso-6-oxo-pyrimidin-2-yl)glycine；N-(6-amino-3-methyl-5-nitroso-4-oxo-3,4-dihydropyrimidin-2-yl)glycine；2-[(4-amino-1-methyl-5-nitroso-6-oxopyrimidin-2-yl)amino]acetic acid
• CAS: 215525-73-8
• 化学式: C₇H₉N₅O₄
• 分子量: 227.18
• InChiKey: RWHQJHRWFRFTSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(4-amino-3-methyl-5-nitroso-6-oxo-1,6-dihydro)pyrimidin-2-yl]aminoacetic acid 、 cadmium(II) chloride 在 KOH 作用下， 以 水 为溶剂， 生成 (Cd(μ-L)Cl(H2O)2*H2O)n
  参考文献：
  名称：

  Solution and solid study of Zn(II) and Cd(II) complexes with N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxo-pyrimidin-2-yl)glycine as ligand. Crystal structures of [ZnL2(H2O)4]·6H2O and {[Cd(μ-L)Cl(H2O)2]·H2O}

  摘要：

  Reactions of N-(4-amino-1,6-dihydro-1-methyl-5-nitroso-6-oxo-pyrimidin-2-yl)glycine with Zn(II) and Cd(II) (1:1 and 1:4 metal/ligand ratios, in aqueous media at 35 degrees C and 0.1 M KCI ionic strength) were studied by potentiometric methods. This study has revealed a similar qualitative behaviour to that found by us for this family of N-pyrimidine aminoacids, the primary coordination site being either the pyrimidine or the carboxylate group depending on whether the ligand acts in neutral form or deprotonated, respectively. In solid state two complexes were obtained by working in 1:1 metal-to-ligand ratio: [Zn(L)(2)(H2O)(4)]. 6H(2)O and {[Cd(mu-L)Cl(H2O)(2)]. H2O)(n), which were characterised by IR and NMR spectroscopies, TG and DSC techniques and single crystal X-ray diffraction. The former complex is mononuclear with the Zn(II) ion hexacoordinated in a distorted octahedral geometry. The coordination sphere is formed by four water molecules and two ligands coordinating in a monodentate fashion through the carboxylate group. The Cd(II) complex consists of a 1D infinite chain, with the metal ion heptacoordinated in a distorted pentagonal bipyramid. The ligand bridges the metal ions coordinating in a bis-didentate fashion through the pyrimidine and the carboxylate group. The nature of these complexes is very different to that shown by the Zn(II) and Cd(II) complexes with the related methionine derivative, which is attributed to he effect of the R substituent on the aminoacid moiety. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00070-0
• 作为产物：
  描述：

  6-amino-3,4-dihydro-3-methyl-2-methoxy-5-nitroso-4-oxopyrimidine 、 聚甘氨酸 在 氢氧化钾 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以76%的产率得到2-[(4-amino-3-methyl-5-nitroso-6-oxo-1,6-dihydro)pyrimidin-2-yl]aminoacetic acid
  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。
• Solution and solid study of Zn(II) and Cd(II) complexes with N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxo-pyrimidin-2-yl)glycine as ligand. Crystal structures of [ZnL2(H2O)4]·6H2O and {[Cd(μ-L)Cl(H2O)2]·H2O}
  作者：P. Arranz-Mascarós、R. López-Garzón*、M.D. Gutierrez-Valero、M.L. Godino-Salido、J.M. Moreno*

  DOI：10.1016/s0020-1693(00)00070-0

  日期：2000.6

  Reactions of N-(4-amino-1,6-dihydro-1-methyl-5-nitroso-6-oxo-pyrimidin-2-yl)glycine with Zn(II) and Cd(II) (1:1 and 1:4 metal/ligand ratios, in aqueous media at 35 degrees C and 0.1 M KCI ionic strength) were studied by potentiometric methods. This study has revealed a similar qualitative behaviour to that found by us for this family of N-pyrimidine aminoacids, the primary coordination site being either the pyrimidine or the carboxylate group depending on whether the ligand acts in neutral form or deprotonated, respectively. In solid state two complexes were obtained by working in 1:1 metal-to-ligand ratio: [Zn(L)(2)(H2O)(4)]. 6H(2)O and [Cd(mu-L)Cl(H2O)(2)]. H2O)(n), which were characterised by IR and NMR spectroscopies, TG and DSC techniques and single crystal X-ray diffraction. The former complex is mononuclear with the Zn(II) ion hexacoordinated in a distorted octahedral geometry. The coordination sphere is formed by four water molecules and two ligands coordinating in a monodentate fashion through the carboxylate group. The Cd(II) complex consists of a 1D infinite chain, with the metal ion heptacoordinated in a distorted pentagonal bipyramid. The ligand bridges the metal ions coordinating in a bis-didentate fashion through the pyrimidine and the carboxylate group. The nature of these complexes is very different to that shown by the Zn(II) and Cd(II) complexes with the related methionine derivative, which is attributed to he effect of the R substituent on the aminoacid moiety. (C) 2000 Elsevier Science S.A. All rights reserved.

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