diisopropyl 2-amino-6-isopropoxy-5-nitropyrimidin-4-ylphosphonate | 1353054-69-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: diisopropyl 2-amino-6-isopropoxy-5-nitropyrimidin-4-ylphosphonate
• 英文别名: 5-Nitro-4-[oxido-di(propan-2-yloxy)phosphaniumyl]-6-propan-2-yloxypyrimidin-2-amine；5-nitro-4-[oxido-di(propan-2-yloxy)phosphaniumyl]-6-propan-2-yloxypyrimidin-2-amine
• CAS: 1353054-69-9
• 化学式: C₁₃H₂₃N₄O₆P
• 分子量: 362.323
• InChiKey: DBSGROXCJDQOKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diisopropyl 2-amino-6-isopropoxy-5-nitropyrimidin-4-ylphosphonate 在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 以81%的产率得到2-amino-6-isopropoxy-5-nitropyrimidin-4-ylphosphonic acid
  参考文献：
  名称：

  An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids

  摘要：

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.040
• 作为产物：
  描述：

  三异丙基亚磷酸酯 、 2-氨基-4-氯-5-硝基-6-羟基嘧啶 反应 0.33h， 以80%的产率得到diisopropyl 2-amino-6-isopropoxy-5-nitropyrimidin-4-ylphosphonate
  参考文献：
  名称：

  An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids

  摘要：

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.040

文献信息

• An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids
  作者：Petr Jansa、Ondřej Hradil、Ondřej Baszczyňski、Martin Dračínský、Blanka Klepetářová、Antonín Holý、Jan Balzarini、Zlatko Janeba

  DOI：10.1016/j.tet.2011.11.040

  日期：2012.1

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.