methyl (3S,5S)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidine-5-carboxylate | 1050517-95-7

• 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: methyl (3S,5S)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidine-5-carboxylate
• CAS: 1050517-95-7
• 化学式: C₁₆H₁₆FN₃O₅
• 分子量: 349.319
• InChiKey: NONORBPWSYHTJA-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.63
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (3S,5S)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidine-5-carboxylate 在 红铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以61%的产率得到(3S,5S)-(-)-[5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidin-5-yl]methanol
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

  摘要：

  A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2.3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

  DOI：

  10.1021/jo800769m
• 作为产物：
  描述：

  甲醇 、 (3S,5S,3'R)-4,4-dimethyk-2-oxo-1-phenylpyrrolidin-3-yl 5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidine-5-carboxylate 在 potassium carbonate 作用下， 反应 3.0h， 以55%的产率得到methyl (3S,5S)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

  摘要：

  A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2.3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

  DOI：

  10.1021/jo800769m