diethyl 2-hydroxy-3-[4-(methoxycarbonyl)-1,2,3-triazol-1-yl]propylphosphonate | 1289220-60-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 2-hydroxy-3-[4-(methoxycarbonyl)-1,2,3-triazol-1-yl]propylphosphonate
• 英文别名: Methyl 1-(3-diethoxyphosphoryl-2-hydroxypropyl)triazole-4-carboxylate
• CAS: 1289220-60-5
• 化学式: C₁₁H₂₀N₃O₆P
• 分子量: 321.27
• InChiKey: CGSIDKPGMCBUSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 2-hydroxy-3-[4-(methoxycarbonyl)-1,2,3-triazol-1-yl]propylphosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到2-hydroxy-3-[4-(methoxycarbonyl)-1,2,3-triazol-1-yl]propylphosphonic 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：

  2,3-环氧丙基膦酸二乙基酯 在 ammonium sulfate 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 diethyl 2-hydroxy-3-[4-(methoxycarbonyl)-1,2,3-triazol-1-yl]propylphosphonate
  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

• Synthesis of a New Series of Phosphonylated 1,2,3-Triazoles as Acyclic Analogs of Ribavirin
  作者：Iwona E. Głowacka、Jan Balzarini、Andrzej E. Wróblewski

  DOI：10.1002/ardp.201300156

  日期：2013.9

  A novel series of phosphonylated 1,2,3‐triazoles as structural acyclic analogs of ribavirin, in which the 1,2,3‐triazole ring was substituted at C4′ with COOMe, CONH2, CONHOH, and CH2NHBoc groups, were synthesized from diethyl azidomethyl‐, 2‐azidoethyl‐, 3‐azidopropyl‐, 4‐azidobutyl‐, 2‐azido‐1‐hydroxyethyl‐, 3‐azido‐2‐hydroxypropyl‐, 2‐azidoethoxymethyl‐ and 2‐azidoethoxyethylphosphonate. The efficient

  一系列新型膦酰化 1,2,3-三唑作为利巴韦林的结构无环类似物，其中 1,2,3-三唑环在 C4' 处被 COOMe、CONH2、CONHOH 和 CH2NHBoc 基团取代，由二乙基合成叠氮甲基-、2-叠氮乙基-、3-叠氮丙基-、4-叠氮丁基-、2-叠氮基-1-羟乙基-、3-叠氮基-2-羟丙基-、2-叠氮基乙氧基甲基-和2-叠氮基乙氧基乙基膦酸酯。描述了使用原位形成的叠氮化物从 4-硝基苯磺酰基甲基膦酸二乙酯有效合成叠氮甲基膦酸二乙酯。所有合成的化合物都在体外评估了它们对多种 RNA 和 DNA 病毒的抑制活性。在 100 µM 下未观察到抗病毒活性。只有化合物 13g 对 HeLa 细胞的增殖表现出抑制作用 (IC50 = 169 ± 45 µM)。
• Synthesis of Novel 1-Hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-Hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates
  作者：Iwona E. Głowacka、Marcin Cieślak、Dorota G. Piotrowska

  DOI：10.1080/10426507.2010.494646

  日期：2011.2.28

  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.