Phosphat-monoethyl | 48028-75-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: Phosphat-monoethyl
• 英文别名: phosphoric acid monoethyl ester; deprotonated form；Phosphoric acid ethyl ester anion；Ethyl hydrogen phosphate
• CAS: 48028-75-7
• 化学式: C₂H₆O₄P
• 分子量: 125.041
• InChiKey: ZJXZSIYSNXKHEA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  生成 Phosphat-monoethyl
  参考文献：
  名称：

  Phosphorylimidazole Derivatives: Potentially Biosignaling Molecules

  摘要：

  The phosphorylation of imidazole by two activated phosphate diesters and a triester gives phosphorylimidazole derivatives that are stable enough in aqueous solution to be observed and identified by ESI-MS/MS and NMR Half-lives ranging from hours to days (in the case of the monoethyl ester) show that it is possible to design molecules with variable half-lives with potential to be used for biological intervention experiments as possible inhibitors of biosignaling processes or as haptens for the generation of antibodies.

  DOI：

  10.1021/jo2017394

文献信息

• Characterization of Transition States in Dichloro(1,4,7-triazacyclononane)copper(II)-Catalyzed Activated Phosphate Diester Hydrolysis
  作者：Kim A. Deal、Alvan C. Hengge、Judith N. Burstyn

  DOI：10.1021/ja952306p

  日期：1996.1.1

  The reaction mechanism for Cu[9]aneN3Cl2-catalyzed hydrolysis of ethyl 4-nitrophenyl phosphate was probed using kinetic isotope effects and isotope exchange experiments. The solvent deuterium isotope effect (Dk = 1.14), combined with the absence of 18O incorporation into 4-nitrophenol, suggests that hydrolysis proceeds through intramolecular attack of the metal-coordinated hydroxide at the phosphorus

  使用动力学同位素效应和同位素交换实验探讨了Cu[9]aneN3Cl2催化水解4-硝基苯基磷酸乙酯的反应机理。溶剂氘同位素效应 (Dk = 1.14) 与 18O 没有掺入 4-硝基苯酚相结合，表明水解是通过磷中心金属配位氢氧化物的分子内攻击进行的。次级 15N 同位素效应 (15k = 1.0013 ± 0.0002) 意味着离去基团的损失发生在限速步骤，在过渡态大约有 50% 的键断裂。这项研究是次级 15N 同位素效应首次应用于简单金属促进的水解反应，结果与协同键形成和裂解一致。
• Dephosphorylation Reactions of Mono-, Di-, and Triesters of 2,4-Dinitrophenyl Phosphate with Deferoxamine and Benzohydroxamic Acid
  作者：Michelle Medeiros、Elisa S. Orth、Alex M. Manfredi、Paulina Pavez、Gustavo A. Micke、Anthony J. Kirby、Faruk Nome

  DOI：10.1021/jo302374q

  日期：2012.12.7

  dephosphorylation reactions involving the exceptionally reactive nucleophilic group, hydroxamate. We compare results for hydroxamate groups anchored on the simple molecular backbone of benzohydroxamate (BHA) and on the more complex structure of the widely used drug, deferoxamine (DFO). BHA shows extraordinary reactivity toward the triester diethyl 2,4-dinitrophenyl phosphate (DEDNPP) and the diester ethyl 2,4-dinitrophenyl

  这项工作提出了生物学上有趣的脱磷酸化反应的详细动力学和机理研究，涉及异常反应性亲核基团异羟肟酸酯。我们比较了苯氧异羟肟酸酯（BHA）的简单分子骨架上锚固的异羟肟酸酯基团的结果以及广泛使用的药物去铁胺（DFO）的更复杂结构的结果。BHA对三酯2,4-二硝基苯基磷酸酯（DEDNPP）和二酯2,4-二硝基苯基磷酸二酯（EDNPP）具有非凡的反应性，但与单酯2,4-二硝基苯基磷酸酯（DNPP）的反应非常缓慢。通过检测形成的磷酸化中间体可以证实对磷的亲核攻击。这些经历了洛森型重排，导致亲核试剂的分解。DFO，在治疗上用于治疗急性铁中毒，它带有三个异羟肟酸酯基团，并且对三酯DEDNPP和二酯EDNPP均显示出较高的亲核活性。这一结果表明，在磷农药急性中毒的情况下，DFO可能具有潜在用途。
• Phosphorylimidazole Derivatives: Potentially Biosignaling Molecules
  作者：Elisa S. Orth、Eduardo H. Wanderlind、Michelle Medeiros、Pedro S. M. Oliveira、Boniek G. Vaz、Marcos N. Eberlin、Anthony J. Kirby、Faruk Nome

  DOI：10.1021/jo2017394

  日期：2011.10.7

  The phosphorylation of imidazole by two activated phosphate diesters and a triester gives phosphorylimidazole derivatives that are stable enough in aqueous solution to be observed and identified by ESI-MS/MS and NMR Half-lives ranging from hours to days (in the case of the monoethyl ester) show that it is possible to design molecules with variable half-lives with potential to be used for biological intervention experiments as possible inhibitors of biosignaling processes or as haptens for the generation of antibodies.