salicyloyl cyclic phosphate monoanion | 400605-09-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: salicyloyl cyclic phosphate monoanion
• 英文别名: Salicylsaeure (cyclic) phosphat；2-Oxido-2-oxo-1,3,2lambda5-benzodioxaphosphinin-4-one；2-oxido-2-oxo-1,3,2λ5-benzodioxaphosphinin-4-one
• CAS: 400605-09-6
• 化学式: C₇H₄O₅P
• 分子量: 199.08
• InChiKey: NSTFEPASKPWACS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  salicyloyl cyclic phosphate monoanion 在 diclazuril 、 重水 作用下， 以 氘代乙腈 为溶剂， 生成 monosalicyl phosphate monoanion
  参考文献：
  名称：

  Participation of Two Carboxyl Groups in Phosphodiester Hydrolysis. 1. Hydrolysis of Bis(2-carboxyphenyl) Phosphate

  摘要：

  The energies of rotamer conformations of bis(2-carboxyphenyl) phosphate (2), where one o-carboxy group is ionized and the other is not, have been determined by semiempirical (SAM1, AM1/SM2.1) calculations in order to approximate the probability of the presence of conformations in which the o-CO2- is in position to act as a nucleophile toward phosphorus and the o-CO2H function can hydrogen bond to prostereogenic oxygens of the -(PO2-)(conformer B) or leaving phenoxide oxygen (conformer A). With simulated water phase, conformer B appears to be at the global energy minima and conformer A is somewhat less stable. The kinetics and the mechanism of hydrolysis of bis(2-carboxyphenyl) phosphate (2) have been elucidated by use of H-1 and P-31 NMR spectroscopy in acetonitrile/water 95:5 and D2O at pD up to 5.0 (39 degrees C). The hydrolysis of 2 is initiated by nucleophilic attack of the o-CO2- upon phosphate phosphorus resulting in the elimination of salicylic acid to provide salicyloyl cyclic phosphate (3) with a rate constant of 1-5 x 10(-3) s(-1) and 3 converts to salicyl monophosphate with rate constants varying between 1 and 5 x 10(-4) s(-1). The rapidity of the formation of 3 from 2 suggests the importance of both o-CO2- and o-CO2H participation {a subject of the following manuscript}.

  DOI：

  10.1021/ja00154a005
• 作为产物：
  描述：

  bis(2-carboxyphenyl) phosphate dianion 在 diclazuril 、 重水 作用下， 以 氘代乙腈 为溶剂， 生成 salicylate 、 salicyloyl cyclic phosphate monoanion
  参考文献：
  名称：

  Participation of Two Carboxyl Groups in Phosphodiester Hydrolysis. 1. Hydrolysis of Bis(2-carboxyphenyl) Phosphate

  摘要：

  The energies of rotamer conformations of bis(2-carboxyphenyl) phosphate (2), where one o-carboxy group is ionized and the other is not, have been determined by semiempirical (SAM1, AM1/SM2.1) calculations in order to approximate the probability of the presence of conformations in which the o-CO2- is in position to act as a nucleophile toward phosphorus and the o-CO2H function can hydrogen bond to prostereogenic oxygens of the -(PO2-)(conformer B) or leaving phenoxide oxygen (conformer A). With simulated water phase, conformer B appears to be at the global energy minima and conformer A is somewhat less stable. The kinetics and the mechanism of hydrolysis of bis(2-carboxyphenyl) phosphate (2) have been elucidated by use of H-1 and P-31 NMR spectroscopy in acetonitrile/water 95:5 and D2O at pD up to 5.0 (39 degrees C). The hydrolysis of 2 is initiated by nucleophilic attack of the o-CO2- upon phosphate phosphorus resulting in the elimination of salicylic acid to provide salicyloyl cyclic phosphate (3) with a rate constant of 1-5 x 10(-3) s(-1) and 3 converts to salicyl monophosphate with rate constants varying between 1 and 5 x 10(-4) s(-1). The rapidity of the formation of 3 from 2 suggests the importance of both o-CO2- and o-CO2H participation {a subject of the following manuscript}.

  DOI：

  10.1021/ja00154a005

文献信息

• Participation of Two Carboxyl Groups in Phosphodiester Hydrolysis. 1. Hydrolysis of Bis(2-carboxyphenyl) Phosphate
  作者：Thomas C. Bruice、Andrei Blasko、Mark E. Petyak

  DOI：10.1021/ja00154a005

  日期：1995.12

  The energies of rotamer conformations of bis(2-carboxyphenyl) phosphate (2), where one o-carboxy group is ionized and the other is not, have been determined by semiempirical (SAM1, AM1/SM2.1) calculations in order to approximate the probability of the presence of conformations in which the o-CO2- is in position to act as a nucleophile toward phosphorus and the o-CO2H function can hydrogen bond to prostereogenic oxygens of the -(PO2-)(conformer B) or leaving phenoxide oxygen (conformer A). With simulated water phase, conformer B appears to be at the global energy minima and conformer A is somewhat less stable. The kinetics and the mechanism of hydrolysis of bis(2-carboxyphenyl) phosphate (2) have been elucidated by use of H-1 and P-31 NMR spectroscopy in acetonitrile/water 95:5 and D2O at pD up to 5.0 (39 degrees C). The hydrolysis of 2 is initiated by nucleophilic attack of the o-CO2- upon phosphate phosphorus resulting in the elimination of salicylic acid to provide salicyloyl cyclic phosphate (3) with a rate constant of 1-5 x 10(-3) s(-1) and 3 converts to salicyl monophosphate with rate constants varying between 1 and 5 x 10(-4) s(-1). The rapidity of the formation of 3 from 2 suggests the importance of both o-CO2- and o-CO2H participation a subject of the following manuscript}.