2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-[(E)-2-phenylvinyl]pyrimidine | 1193313-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-[(E)-2-phenylvinyl]pyrimidine
• CAS: 1193313-46-0
• 化学式: C₂₇H₄₁N₂O₆P
• 分子量: 520.606
• InChiKey: XTUFVKSNGPMFOI-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  89.0
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  5-bromo-2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]pyrimidine 、 反式-BETA-苯乙烯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以25%的产率得到2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-[(E)-2-phenylvinyl]pyrimidine
  参考文献：
  名称：

  Use of Pd-catalyzed Suzuki–Miyaura coupling reaction in the rapid synthesis of 5-aryl-6-(phosphonomethoxy)uracils and evaluation of their inhibitory effect towards human thymidine phosphorylase

  摘要：

  A number of new 5-aryl substituted pyrimidine acyclic nucleoside phosphonates were synthesized and tested for their ability to inhibit human TP. Their rapid synthesis using Pd-catalyzed Suzuki-Miyaura coupling reactions of various arylboronic acids with 5-bromo-4-(phosphonomethoxy)-2,6-dibutoxypyrimidine was successfully applied. For a series of 5-aryl-6-phosphonomethoxyuracils, an increased inhibitory effect was determined. This effect is supported by the results found for 4-fluorophenyl (K-i(dThd)=4.89 +/- 0.62) and 3-nitrophenyl (K-i(dThd)=3.98 +/- 0.46) substituents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.039