1H-benzimidazol-2-ylmethyl diethyl phosphate | 1428649-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1H-benzimidazol-2-ylmethyl diethyl phosphate
• CAS: 1428649-67-5
• 化学式: C₁₂H₁₇N₂O₄P
• 分子量: 284.252
• InChiKey: PYDHQQFKWKWUPP-UHFFFAOYSA-N

物化性质

• 沸点：
  455.9±28.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1H-benzimidazol-2-ylmethyl diethyl phosphate 、 silver nitrate 以 水 为溶剂， 反应 1.0h， 以72%的产率得到[Ag(1H-benzimidazol-2-ylmethyl diethyl phosphate)2]NO3
  参考文献：
  名称：

  吡啶和苯并咪唑的磷酸盐衍生物的银（I）和铜（II）配合物的合成，表征和抗菌活性

  摘要：

  两个银（I）配合物-{[Ag（4-pmOpe）] NO 3 } n和[Ag（2-bimOpe）2 ] NO 3-和三个铜（II）配合物-[Cu 4 Cl 6 O（2- bimOpe）4 ]，[CuCl 2（4-pmOpe）2 ]和[CuCl 2（2-bis（pm）Ope]-）是通过硝酸银（I）或氯化铜（II）与磷酸亚铁的磷酸酯衍生物反应合成的吡啶和苯并咪唑，即磷酸二乙酯（吡啶-4-基甲基）（4-pmOpe），1 H-苯并咪唑-2-酰基甲基二乙基磷酸（2-bimOpe）和双（吡啶-2-基甲基）磷酸乙基（2- bis（pm）Ope）。这些化合物的特征是1 H，13C和31 P NMR以及IR光谱，元素分析和ESIMS光谱。另外，通过单晶X射线衍射分析确定了[[Ag（4-pmOpe）] NO 3 } n和[Cu 4 Cl 6 O（2-bimOpe）4 ]的分子和晶体结构。确定了合成的复合物和游离

  DOI：

  10.1002/cmdc.201300333
• 作为产物：
  描述：

  2-羟甲基苯并咪唑 、 氯磷酸二乙酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以56%的产率得到1H-benzimidazol-2-ylmethyl diethyl phosphate
  参考文献：
  名称：

  Synthesis, acid–base and complexing properties with Cu(II), Co(II) and Zn(II) in aqueous solution of a novel 1H-benzimidazol-2-ylmethyl diethyl phosphate ligand: Comparison with other 2-substituted benzimidazole ligands

  摘要：

  1H-Benzimidazol-2-ylmethyl diethyl phosphate (2-BimOpe) was synthesized via condensation of phosphorochloridic acid diethyl ester with 2-benzimidazolemethanol in the presence of triethylamine. This phosphate derivative of benzimidazole was chosen because of its expected biological properties, indicated up to now for many other related compounds. The coordinating properties of 2-BimOpe towards Cu(II), Co(II) and Zn(II) in aqueous solution have been studied through a combined application of potentiometric and spectroscopic methods (electronic absorption for Cu(II) and Co(II) as well as EPR spectroscopy in the case of Cu(II)). It was shown that 2-BimOpe coordinates Cu(II) yielding CuL and CuL2 species (the CuL2 complex being confirmed only by EPR). The same measurements have been made with benzimidazole (Bim) and 2-(hydroxymethyl)benzimidazole (2-CH(2)OHBim), the latter ligand capable of bidentate {NO} coordination. Moreover, the potentiometric results for the novel diethyl phosphate derivative of 1H-benzimidazol-2-ylmethanol, 2-BimOpe, have been compared with the literature data reported recently for (1H-benzimidazol-2-yl-methyl)phosphonate (Bimp(2-)). The difference between complexation abilities of Bim and 2-BimOpe comes evidently from a bulky effect of the estrificated phosphoric groups preventing the benzimidazole fragment to be involved in the consecutive complexation steps. On the other hand the N(3) nitrogen is the most acidic one (pK(a) = 4.04) in 2-BimOpe among the compounds considered. The release of the N(3)H+ proton occurs at a relatively low pH for 2-BimOpe, most probably due to the known electron withdrawing effect of the phosphate group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.01.006

文献信息

• Synthesis, acid–base and complexing properties with Cu(II), Co(II) and Zn(II) in aqueous solution of a novel 1H-benzimidazol-2-ylmethyl diethyl phosphate ligand: Comparison with other 2-substituted benzimidazole ligands
  作者：Aleksander Kufelnicki、Magdalena Woźniczka、Urszula Kalinowska-Lis、Julia Jezierska、Justyn Ochocki

  DOI：10.1016/j.poly.2013.01.006

  日期：2013.4

  1H-Benzimidazol-2-ylmethyl diethyl phosphate (2-BimOpe) was synthesized via condensation of phosphorochloridic acid diethyl ester with 2-benzimidazolemethanol in the presence of triethylamine. This phosphate derivative of benzimidazole was chosen because of its expected biological properties, indicated up to now for many other related compounds. The coordinating properties of 2-BimOpe towards Cu(II), Co(II) and Zn(II) in aqueous solution have been studied through a combined application of potentiometric and spectroscopic methods (electronic absorption for Cu(II) and Co(II) as well as EPR spectroscopy in the case of Cu(II)). It was shown that 2-BimOpe coordinates Cu(II) yielding CuL and CuL2 species (the CuL2 complex being confirmed only by EPR). The same measurements have been made with benzimidazole (Bim) and 2-(hydroxymethyl)benzimidazole (2-CH(2)OHBim), the latter ligand capable of bidentate NO} coordination. Moreover, the potentiometric results for the novel diethyl phosphate derivative of 1H-benzimidazol-2-ylmethanol, 2-BimOpe, have been compared with the literature data reported recently for (1H-benzimidazol-2-yl-methyl)phosphonate (Bimp(2-)). The difference between complexation abilities of Bim and 2-BimOpe comes evidently from a bulky effect of the estrificated phosphoric groups preventing the benzimidazole fragment to be involved in the consecutive complexation steps. On the other hand the N(3) nitrogen is the most acidic one (pK(a) = 4.04) in 2-BimOpe among the compounds considered. The release of the N(3)H+ proton occurs at a relatively low pH for 2-BimOpe, most probably due to the known electron withdrawing effect of the phosphate group. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis, Characterization, and Antimicrobial Activity of Silver(I) and Copper(II) Complexes of Phosphate Derivatives of Pyridine And Benzimidazole
  作者：Urszula Kalinowska-Lis、Eligia M. Szewczyk、Lilianna Chęcińska、Jakub M. Wojciechowski、Wojciech M. Wolf、Justyn Ochocki

  DOI：10.1002/cmdc.201300333

  日期：2014.1

  silver(I) complexes—[Ag(4‐pmOpe)]NO3}n and [Ag(2‐bimOpe)2]NO3—and three copper(II) complexes—[Cu4Cl6O(2‐bimOpe)4], [CuCl2(4‐pmOpe)2], and [CuCl2(2‐bis(pm)Ope]—were synthesized by reaction of silver(I) nitrate or copper(II) chloride with phosphate derivatives of pyridine and benzimidazole, namely diethyl (pyridin‐4‐ylmethyl)phosphate (4‐pmOpe), 1H‐benzimidazol‐2‐ylmethyl diethyl phosphate (2‐bimOpe)

  两个银（I）配合物-[Ag（4-pmOpe）] NO 3 } n和[Ag（2-bimOpe）2 ] NO 3-和三个铜（II）配合物-[Cu 4 Cl 6 O（2- bimOpe）4 ]，[CuCl 2（4-pmOpe）2 ]和[CuCl 2（2-bis（pm）Ope]-）是通过硝酸银（I）或氯化铜（II）与磷酸亚铁的磷酸酯衍生物反应合成的吡啶和苯并咪唑，即磷酸二乙酯（吡啶-4-基甲基）（4-pmOpe），1 H-苯并咪唑-2-酰基甲基二乙基磷酸（2-bimOpe）和双（吡啶-2-基甲基）磷酸乙基（2- bis（pm）Ope）。这些化合物的特征是1 H，13C和31 P NMR以及IR光谱，元素分析和ESIMS光谱。另外，通过单晶X射线衍射分析确定了[[Ag（4-pmOpe）] NO 3 } n和[Cu 4 Cl 6 O（2-bimOpe）4 ]的分子和晶体结构。确定了合成的复合物和游离