2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)-methoxy]pyrimidine | 1193313-37-9

• 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]pyrimidine
• 英文别名: 4-[Di(propan-2-yloxy)phosphorylmethoxy]-2,6-bis[(2-methylpropan-2-yl)oxy]pyrimidine
• CAS: 1193313-37-9
• 化学式: C₁₉H₃₅N₂O₆P
• 分子量: 418.47
• InChiKey: PNASYXIGWWIXEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  89
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)-methoxy]pyrimidine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以99%的产率得到5-bromo-2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]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
• 作为产物：
  描述：

  5-bromo-2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)methoxy]pyrimidine 在 2-呋喃硼酸 、 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 7.0h， 以57%的产率得到2,6-di-tert-butyloxy-4-[(diisopropoxyphosphoryl)-methoxy]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