4-amino-1-(5-hydroxy-5,6-dihydro-2H-pyran-2-yl)-1H-pyrimidin-2-one | 72946-53-3

• 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: 4-amino-1-(5-hydroxy-5,6-dihydro-2H-pyran-2-yl)-1H-pyrimidin-2-one
• 英文别名: 4-amino-1-[(3S,6R)-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]pyrimidin-2-one
• CAS: 72946-53-3
• 化学式: C₉H₁₁N₃O₃
• 分子量: 209.205
• InChiKey: JGNXHVUGJCGFSX-POYBYMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-1-(5-hydroxy-5,6-dihydro-2H-pyran-2-yl)-1H-pyrimidin-2-one 在 Pd/SrCO₃ 氢气 作用下， 以 乙醇 为溶剂， 以67%的产率得到pentopyranine B
  参考文献：
  名称：

  Glycosylation of N4-benzoylcytosine and N6-benzoyladenine with acetylated glycals

  摘要：

  DOI：

  10.1007/bf00513298
• 作为产物：
  描述：

  D-xylal 在 吡啶 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 4-amino-1-(5-hydroxy-5,6-dihydro-2H-pyran-2-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Easy Synthesis and Different Conformational Behavior of Purine and Pyrimidine .beta.-D-glycero-Pent-2'-enopyranosyl Nucleosides

  摘要：

  Condensation of 3,4-bis-O-(p-nitrobenzoyl)-D-xylal with purines and pyrimidines (A, C, 6-chloropurine, G, T, U) without externally added acid catalyst leads to the 2',3'-unsaturated pentopyranosyl nucleosides in preparatively acceptable yields of both beta and alpha anomers and near complete suppression of formation of the 3'-substituted 1',2'-unsaturated regioisomers. Anomeric configurations of these analogues of nucleosides have been established for the 4'-O-deprotected derivatives by way of C-13 NMR. In all nine anomeric pairs the signals of the carbon atoms C-5' in alpha anomers are shifted upfield when compared with the corresponding signals of the beta anomers. Coupling constants J(4'5'ax) indicate pseudoaxial positions of purines in 33-40, 45, and 46. This is rationalized in terms of a pi-o*(c-1'-N-9) resonance and represents a case where aglycons occupy pseudoaxial positions via a mechanism'different than the anomeric effect. The same coupling constants of the alpha-pyrimidines 30, 32, 42, and 44 indicate H-4(0)<->H-0(4) equilibrium with a marginal preference toward the H-0(4) form, whereas the beta-pyrimidines 29, 31, 41, and 43 show a preference toward H-0(4) probably due to steric interactions.

  DOI：

  10.1021/jo00129a035

文献信息

• Easy Synthesis and Different Conformational Behavior of Purine and Pyrimidine .beta.-D-glycero-Pent-2'-enopyranosyl Nucleosides
  作者：Bogdan Doboszewski、Norbert Blaton、Piet Herdewijn

  DOI：10.1021/jo00129a035

  日期：1995.12

  Condensation of 3,4-bis-O-(p-nitrobenzoyl)-D-xylal with purines and pyrimidines (A, C, 6-chloropurine, G, T, U) without externally added acid catalyst leads to the 2',3'-unsaturated pentopyranosyl nucleosides in preparatively acceptable yields of both beta and alpha anomers and near complete suppression of formation of the 3'-substituted 1',2'-unsaturated regioisomers. Anomeric configurations of these analogues of nucleosides have been established for the 4'-O-deprotected derivatives by way of C-13 NMR. In all nine anomeric pairs the signals of the carbon atoms C-5' in alpha anomers are shifted upfield when compared with the corresponding signals of the beta anomers. Coupling constants J(4'5'ax) indicate pseudoaxial positions of purines in 33-40, 45, and 46. This is rationalized in terms of a pi-o*(c-1'-N-9) resonance and represents a case where aglycons occupy pseudoaxial positions via a mechanism'different than the anomeric effect. The same coupling constants of the alpha-pyrimidines 30, 32, 42, and 44 indicate H-4(0)<->H-0(4) equilibrium with a marginal preference toward the H-0(4) form, whereas the beta-pyrimidines 29, 31, 41, and 43 show a preference toward H-0(4) probably due to steric interactions.
• Glycosylation of N4-benzoylcytosine and N6-benzoyladenine with acetylated glycals
  作者：N. B. Khripach、I. A. Mikhailopulo、A. A. Akhrem

  DOI：10.1007/bf00513298

  日期：1982.1