5-[anilino(dimethoxyphosphoryl)methyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione | 1245614-54-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-[anilino(dimethoxyphosphoryl)methyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1245614-54-3
• 化学式: C₁₈H₂₄N₃O₈P
• 分子量: 441.378
• InChiKey: STLLHQOMFMJSFE-HGJUEJOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  亚磷酸氢二甲酯 、 苯胺 、 1-((2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基)-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛 反应 3.0h， 以75%的产率得到5-[anilino(dimethoxyphosphoryl)methyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  无溶剂条件下高效，绿色制备5-氨基膦酸酯取代的嘧啶核苷

  摘要：

  开发了一种在无溶剂条件下对环境无害且高效的一锅法制备α-氨基膦酸酯的方法。通过使用该方法，以5-甲酰基-2'-脱氧尿苷，苯胺和亚磷酸二甲酯为起始原料，以良好的优良合成了5-氨基膦酸酯取代的嘧啶核苷。

  DOI：

  10.1016/j.cclet.2010.04.037

文献信息

• Solvent-Free Synthesis of Pyrimidine Nucleoside-Aminophosphonate Hybrids and Their Biological Activity Evaluation
  作者：Xinying Zhang、Yingying Qu、Xuesen Fan、C. Bores、Dong Feng、Graciela Andrei、Robert Snoeck、Erik De Clercq、Philippe M. Loiseau

  DOI：10.1080/15257770.2010.496281

  日期：2010.7.20

  A novel and highly efficient one-pot three-component synthesis of -aminophosphonates under neat condition was developed. By employing this method, hybrid compounds of aminophosphonate with pyrimidine nucleosides were synthesized in good to excellent yields starting from 5-formyl-2'-deoxyuridine, aniline and dimethyl phosphite. The antiviral and antileishmanial activities of these novel hybrid compounds were also studied but none were found to be active.
• An efficient and green preparation of 5-aminophosphonate substituted pyrimidine nucleosides under solvent-free conditions
  作者：Xin Ying Zhang、Ying Ying Qu、Xue Sen Fan

  DOI：10.1016/j.cclet.2010.04.037

  日期：2010.10

  An environmentally benign and highly efficient one-pot preparation of α-aminophosphonates under solvent-free conditions was developed. By employing this method, 5-aminophosphonate substituted pyrimidine nucleosides were synthesized in good to excellent yields starting from 5-formyl-2′-deoxyuridine, aniline and dimethylphosphite.

  开发了一种在无溶剂条件下对环境无害且高效的一锅法制备α-氨基膦酸酯的方法。通过使用该方法，以5-甲酰基-2'-脱氧尿苷，苯胺和亚磷酸二甲酯为起始原料，以良好的优良合成了5-氨基膦酸酯取代的嘧啶核苷。