diethyl 4H-1,2,4-triazol-4-yl methylphosphonate | 1279637-93-2

• 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 4H-1,2,4-triazol-4-yl methylphosphonate
• 英文别名: diethyl 4H-1,2,4-triazol-4-ylmethylphosphonate；4-[[Diethoxy(oxido)phosphaniumyl]methyl]-1,2,4-triazole；4-[[diethoxy(oxido)phosphaniumyl]methyl]-1,2,4-triazole
• CAS: 1279637-93-2
• 化学式: C₇H₁₄N₃O₃P
• 分子量: 219.18
• InChiKey: PFIWUIRYNPNDBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 4H-1,2,4-triazol-4-yl methylphosphonate 、 zinc(II) acetate dihydrate 以 氘代氯仿 为溶剂， 生成 Zn(acetate)2(diethyl 4H-1,2,4-triazol-4-yl methylphosphonate)2
  参考文献：
  名称：

  Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and β-lactamase assay

  摘要：

  Coordinating abilities of 4R-1,2,4-triazole derivatives (R = glycine ethyl ester (L1), glycine (L2), diethylamino malonate (L3), methionine (L4) and diethyl aminomethylphosphonate (L5)) towards Zn-II ions have been studied in solution, in solid state and versus three zinc-beta-lactamases. The crystal structure of [Zn-3(L-4)(6)(H2O)(6)] (6) is described; it is the first crystal structure involving a 1,2,4-triazole functionalized methionine. It forms a trinuclear complex with central zinc octahedrally coordinated by only L4, whereas terminal zinc ions coordination sphere is completed by three water molecules. L4 exhibits a dual functionality of a bridging bidentate ligand as well as an anion. A dense hydrogen bonding network connects these trinuclear entity into a 3D supramolecular network. The Zn-II ions in 6 are held at equidistance (3.848 angstrom) which coincidently matches with the corresponding Zn center dot center dot center dot Zn distance in the binuclear zinc enzyme from Bacillus cereus (3.848 and 4.365 angstrom). Among L1-L5 screened for beta-lactamase assay, L4 shows modest inhibition for BcII enzyme. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.12.017
• 作为产物：
  描述：

  N,N'-bis(dimethylaminomethylene)hydrazine 、 二乙基氨基甲烷膦酸酯 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 diethyl 4H-1,2,4-triazol-4-yl methylphosphonate
  参考文献：
  名称：

  Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and β-lactamase assay

  摘要：

  Coordinating abilities of 4R-1,2,4-triazole derivatives (R = glycine ethyl ester (L1), glycine (L2), diethylamino malonate (L3), methionine (L4) and diethyl aminomethylphosphonate (L5)) towards Zn-II ions have been studied in solution, in solid state and versus three zinc-beta-lactamases. The crystal structure of [Zn-3(L-4)(6)(H2O)(6)] (6) is described; it is the first crystal structure involving a 1,2,4-triazole functionalized methionine. It forms a trinuclear complex with central zinc octahedrally coordinated by only L4, whereas terminal zinc ions coordination sphere is completed by three water molecules. L4 exhibits a dual functionality of a bridging bidentate ligand as well as an anion. A dense hydrogen bonding network connects these trinuclear entity into a 3D supramolecular network. The Zn-II ions in 6 are held at equidistance (3.848 angstrom) which coincidently matches with the corresponding Zn center dot center dot center dot Zn distance in the binuclear zinc enzyme from Bacillus cereus (3.848 and 4.365 angstrom). Among L1-L5 screened for beta-lactamase assay, L4 shows modest inhibition for BcII enzyme. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.12.017

文献信息

• Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and β-lactamase assay
  作者：Anil D. Naik、Joséphine Beck、Marinela M. Dîrtu、Carine Bebrone、Bernard Tinant、Koen Robeyns、Jacqueline Marchand-Brynaert、Yann Garcia

  DOI：10.1016/j.ica.2010.12.017

  日期：2011.3

  Coordinating abilities of 4R-1,2,4-triazole derivatives (R = glycine ethyl ester (L1), glycine (L2), diethylamino malonate (L3), methionine (L4) and diethyl aminomethylphosphonate (L5)) towards Zn-II ions have been studied in solution, in solid state and versus three zinc-beta-lactamases. The crystal structure of [Zn-3(L-4)(6)(H2O)(6)] (6) is described; it is the first crystal structure involving a 1,2,4-triazole functionalized methionine. It forms a trinuclear complex with central zinc octahedrally coordinated by only L4, whereas terminal zinc ions coordination sphere is completed by three water molecules. L4 exhibits a dual functionality of a bridging bidentate ligand as well as an anion. A dense hydrogen bonding network connects these trinuclear entity into a 3D supramolecular network. The Zn-II ions in 6 are held at equidistance (3.848 angstrom) which coincidently matches with the corresponding Zn center dot center dot center dot Zn distance in the binuclear zinc enzyme from Bacillus cereus (3.848 and 4.365 angstrom). Among L1-L5 screened for beta-lactamase assay, L4 shows modest inhibition for BcII enzyme. (C) 2010 Elsevier B.V. All rights reserved.