2(S)-(acetoxymethyl)-4-[3,4-dihydro-2-oxo-4-amino-1(2H)-pyrimidinyl]-2,5-dihydrofuran | 259137-64-9

• 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(S)-(acetoxymethyl)-4-[3,4-dihydro-2-oxo-4-amino-1(2H)-pyrimidinyl]-2,5-dihydrofuran
• CAS: 259137-64-9
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: XMGHDFMTKZZZOX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.44
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2(S)-(acetoxymethyl)-4-[3,4-dihydro-2-oxo-4-amino-1(2H)-pyrimidinyl]-2,5-dihydrofuran 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以45%的产率得到2(S)-(hydroxymethyl)-4-[3,4-dihydro-2-oxo-4-amino-1(2H)-pyrimidinyl]-2,5-dihydrofuran
  参考文献：
  名称：

  Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides

  摘要：

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.

  DOI：

  10.1080/07328319908044614
• 作为产物：
  描述：

  Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 potassium tert-butylate 、 三乙胺 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 7.5h， 生成 2(S)-(acetoxymethyl)-4-[3,4-dihydro-2-oxo-4-amino-1(2H)-pyrimidinyl]-2,5-dihydrofuran
  参考文献：
  名称：

  Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides

  摘要：

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.

  DOI：

  10.1080/07328319908044614