2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-(thien-3-yl)pyrimidine | 1193313-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-(thien-3-yl)pyrimidine
• CAS: 1193313-39-1
• 化学式: C₂₃H₃₇N₂O₆PS
• 分子量: 500.596
• InChiKey: WWVFENXYIPVQDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  89.0
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-(thien-3-yl)pyrimidine 在 三甲基溴硅烷 、 三乙基碳酸氢铵缓冲液 作用下， 以 乙腈 、 水 为溶剂， 以33%的产率得到
  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
• 作为产物：
  描述：

  3-噻吩硼酸 、 5-bromo-2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]pyrimidine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 23.0h， 以45%的产率得到2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]-5-(thien-3-yl)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