diethyl 1-hydroxy-2-(4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl)ethylphosphonate | 1289220-78-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 1-hydroxy-2-(4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl)ethylphosphonate
• CAS: 1289220-78-5
• 化学式: C₁₂H₂₀N₃O₈P
• 分子量: 365.28
• InChiKey: KFVHLLCOXQLCRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  139.07
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  diethyl 1-hydroxy-2-(4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl)ethylphosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以91%的产率得到1-hydroxy-2-(4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl)ethylphosphonic acid
  参考文献：
  名称：

  Synthesis of Novel 1-Hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-Hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates

  摘要：

  Several new 1-hydroxy-2-(1,2,3-triazol-1-yl) ethylphosphonates and 2-hydroxy-3-(1,2,3-triazol-1-yl) propylphosphonates as well as the respective phosphonic acids were synthesized from diethyl 1,2-epoxyethylphosphonate and 2,3-epoxypropylphosphonate in the reaction sequence including the regioselective ring opening of the epoxide with azides followed by 1,3-dipolar cycloaddition of omega-azidophosphonates and selected alkynes and finally hydrolyses of the phosphonate esters.

  DOI：

  10.1080/10426507.2010.494646
• 作为产物：
  描述：

  epoxy-1,2 ethyl phosphonate de diethyle 在 ammonium sulfate 、 sodium azide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 8.0h， 生成 diethyl 1-hydroxy-2-(4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl)ethylphosphonate
  参考文献：
  名称：

  Synthesis of Novel 1-Hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-Hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates

  摘要：

  Several new 1-hydroxy-2-(1,2,3-triazol-1-yl) ethylphosphonates and 2-hydroxy-3-(1,2,3-triazol-1-yl) propylphosphonates as well as the respective phosphonic acids were synthesized from diethyl 1,2-epoxyethylphosphonate and 2,3-epoxypropylphosphonate in the reaction sequence including the regioselective ring opening of the epoxide with azides followed by 1,3-dipolar cycloaddition of omega-azidophosphonates and selected alkynes and finally hydrolyses of the phosphonate esters.

  DOI：

  10.1080/10426507.2010.494646

文献信息

• Design, synthesis, antiviral and cytotoxic evaluation of novel acyclic phosphonate nucleotide analogues with a 5,6-dihydro-1H-[1,2,3]triazolo[4,5-d]pyridazine-4,7-dione system
  作者：Emilia Bankowska、Jan Balzarini、Iwona E. Głowacka、Andrzej E. Wróblewski

  DOI：10.1007/s00706-013-1137-x

  日期：2014.4

  7-diones as phosphonate analogues of acyclic nucleosides having nucleobases replaced with substituted 1,2,3-triazoles. All compounds containing P-C-C-triazole or P-C-C-CH2-triazole moieties exist in single conformations in which the diethoxyphosphoryl and substituted 1,2,3-triazolyl or substituted (1,2,3-triazolyl)methyl groups are oriented anti. All phosphonates were evaluated in vitro for activity

  摘要：由ω-叠氮基烷基膦酸酯和乙炔二甲酸二甲酯合成了一系列2-（4,5-二甲氧基羰基-1H-1,2,3-三唑-1-基）烷基膦酸二乙酯，并将其进一步转化为相应的二酰胺，二酰肼，和5，6-二氢-1H- [1,2,3]三唑并[4,5-d]哒嗪-4,7-二酮作为无环核苷的膦酸酯类似物，其核碱基被取代的1,2,3-三唑取代。所有包含PCC-三唑或PCC-CH2-三唑部分的化合物都以单一构型存在，其中二乙氧基磷酰基和取代的1,2,3-三唑基或取代的（1,2,3-三唑基）甲基是反型的。在体外评估所有膦酸酯对多种DNA和RNA病毒的活性。没有一种化合物具有抗病毒活性。它们在100μM时没有抑制细胞生长的作用。