diethyl (2-hydroxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propyl)phosphonate | 1289220-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl (2-hydroxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propyl)phosphonate
• 英文别名: diethyl 2-hydroxy-3-(4-phenyl-1,2,3-triazol-1-yl)propylphosphonate；1-Diethoxyphosphoryl-3-(4-phenyltriazol-1-yl)propan-2-ol
• CAS: 1289220-62-7
• 化学式: C₁₅H₂₂N₃O₄P
• 分子量: 339.331
• InChiKey: RWEBGXINBYVCNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (2-hydroxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propyl)phosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到2-hydroxy-3-(4-phenyl-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：

  烯丙基磷酸二乙酯 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 氯化铵 、 sodium ascorbate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 diethyl (2-hydroxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propyl)phosphonate
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Novel 1-(Diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl Carboxylic Esters

  摘要：

  一系列新化合物，即1-(二乙氧基磷酰基)-3-(4-酮-1H-1,2,3-三唑-1-基)丙-2-基羧酸酯，基于咪唑甘油磷酸脱水酶（IGPD）的二氮芴烯中间体和IGPD的高活性抑制剂进行设计，并合成为针对植物IGPD的抑制剂。其结构通过1H-NMR、13C-NMR、31P-NMR和高分辨率质谱（HR-MS）进行了确认。通过培养皿法进行的除草剂评价显示，大多数化合物具有中等至良好的除草活性。选定六个化合物进行了进一步的盆栽实验，对稻田草进行除草剂评价。1-(二乙氧基磷酰基)-3-(4-苯基-1H-1,2,3-三唑-1-基)丙-2-基-2-(萘-1-基)乙酸酯（5-A3）和乙基1-(2-乙酰氧基-3-(二乙氧基磷酰基)丙基)-1H-1,2,3-三唑-4-羧酸酯（5-B4）表现出良好的除草活性。与以往报道的最佳除草活性化合物相比，5-A3和5-B4在250 g/hm2浓度下对稻田草生长的抑制效果，提高了近4倍的除草效力。然而，在盆栽实验中，它们的除草活性低于乙草胺（62.5 g/hm2）。

  DOI：

  10.3390/molecules20011088

文献信息

• 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.
• Synthesis and Herbicidal Activity of Novel 1-(Diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl Carboxylic Esters
  作者：Yan Jin、Hanqing Zhao、Huizhe Lu、Colleen Kuemmel、Jianjun Zhang、Daoquan Wang

  DOI：10.3390/molecules20011088

  日期：——

  A series of novel compounds, namely 1-(diethoxyphosphoryl)-3-(4-ones-1H-1,2,3-triazol-1-yl)propan-2-yl carboxylic esters, were designed on the basis of the diazafulvene intermediate of imidazole glycerol phosphate dehydratase (IGPD) and high-activity inhibitors of IGPD, and synthesized as inhibitors targeting IGPD in plants. Their structures were confirmed by 1H-NMR, 13C-NMR, 31P-NMR and HR-MS. The herbicidal evaluation performed by a Petri dish culture method showed that most compounds possessed moderate to good herbicidal activities. Six compounds were chosen for further herbicidal evaluation on barnyard grass by pot experiments. 1-(Diethoxyphosphoryl)-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propan-2-yl 2-(naphthalen-1-yl)acetate (5-A3) and ethyl 1-(2-acetoxy-3-(diethoxyphosphoryl)propyl)-1H-1,2,3-triazole-4-carboxylate (5-B4) showed good herbicidal activities. Compared with the compounds with the best herbicidal activity ever reported, both compounds 5-A3 and 5-B4, which can inhibit the growth of barnyard grass at the concentration of 250g/hm2, efficiently gave rise to a nearly 4-fold increase of the herbicidal potency. However, their herbicidal activities were lower than that of acetochlor (62.5 g/hm2) in the pot experiments.

  一系列新化合物，即1-(二乙氧基磷酰基)-3-(4-酮-1H-1,2,3-三唑-1-基)丙-2-基羧酸酯，基于咪唑甘油磷酸脱水酶（IGPD）的二氮芴烯中间体和IGPD的高活性抑制剂进行设计，并合成为针对植物IGPD的抑制剂。其结构通过1H-NMR、13C-NMR、31P-NMR和高分辨率质谱（HR-MS）进行了确认。通过培养皿法进行的除草剂评价显示，大多数化合物具有中等至良好的除草活性。选定六个化合物进行了进一步的盆栽实验，对稻田草进行除草剂评价。1-(二乙氧基磷酰基)-3-(4-苯基-1H-1,2,3-三唑-1-基)丙-2-基-2-(萘-1-基)乙酸酯（5-A3）和乙基1-(2-乙酰氧基-3-(二乙氧基磷酰基)丙基)-1H-1,2,3-三唑-4-羧酸酯（5-B4）表现出良好的除草活性。与以往报道的最佳除草活性化合物相比，5-A3和5-B4在250 g/hm2浓度下对稻田草生长的抑制效果，提高了近4倍的除草效力。然而，在盆栽实验中，它们的除草活性低于乙草胺（62.5 g/hm2）。