methyl phenoxycarbonylphosphonate sodium salt | 83877-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl phenoxycarbonylphosphonate sodium salt
• 英文别名: Sodium methyl phenoxycarbonylphosphonate；sodium;methoxy(phenoxycarbonyl)phosphinate
• CAS: 83877-29-6
• 化学式: C₈H₈O₅P*Na
• 分子量: 238.112
• InChiKey: DHJNMYFYRKJNNP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.61
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl (phenoxycarbonyl)phosphonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以80%的产率得到methyl phenoxycarbonylphosphonate sodium salt
  参考文献：
  名称：

  金属阳离子介导的膦甲酸二酯水解：化学选择性和催化作用1

  摘要：

  Ce(IV)、Th(IV) 显着加速二甲基 (7)、甲基苯基 (8)、苯基甲基 (9) 和二苯基 (10) 膦酰甲酸二酯在 D(2)O (pD 1.7-3.1) 中的水解)、Zr(IV) 和 Hf(IV) 阳离子。观察到化学选择性，其中 Zr(IV) 和 Hf(IV) 主要指导 P-OR 水解，而 Th(IV) 和 Ce(IV) 主要指导 C-OR 水解。离开组效率（OMe 与 OPh）调节化学选择性。金属阳离子还介导了最初生成的膦酰甲酸酯单酯 14、15、18 和 20 的进一步水解反应。 P-OR/C-OR 选择性的起源根据可能存在于溶液和反应动力学。

  DOI：

  10.1021/ja030437h

文献信息

• Synthesis of esters of phosphonoformic acid and their antiherpes activity
  作者：Jan O. Noren、Erik Helgstrand、Nils G. Johansson、Alfons Misiorny、Goeran Stening

  DOI：10.1021/jm00356a028

  日期：1983.2

  Aliphatic and aromatic mono-, di-, and triesters of phosphonoformic acid (foscarnet) were synthesized. The triesters were prepared by the Michaelis-Arbuzov reaction and were hydrolyzed to di- and monoesters. The compounds were tested for antiviral activity on isolated herpes simplex virus type 1 (HSV-1) DNA polymerase, in a HSV-1 plaque reduction assay, and on a cutaneous HSV-1 infection in guinea pigs. None of the esters inhibited the activity of isolated HSV-1 polymerases. Monoesters with a free carboxylic group and diesters with an aromatic carboxylic ester function were active against the cutaneous herpes infection. Mono- and diesters with an aromatic phosphonic ester group also showed activity in the plaque-reduction assay. However, mono- and diesters with an aromatic phosphonic ester group also showed activity in the plaque-reduction assay. However, mono- and diesters with aliphatic carboxylic ester groups were inactive in all test systems. The results show that all three acidic groups of phosphonoformic acid must be free in order to get antiviral activity at the enzyme level. However, certain esters of this acid may be biotransformed to the acid itself to give antiherpes activity.
• NOREN, J. O.;HELGSTRAND, E.;JOHANSSON, N. G.;MISIORNY, A.;STENING, G., J. MED. CHEM., 1983, 26, N 2, 264-270
  作者：NOREN, J. O.、HELGSTRAND, E.、JOHANSSON, N. G.、MISIORNY, A.、STENING, G.

  DOI：——

  日期：——
• Metal-Cation-Mediated Hydrolysis of Phosphonoformate Diesters:  Chemoselectivity and Catalysis¹
  作者：Robert A. Moss、Hugo Morales-Rojas、Saketh Vijayaraghavan、Jingzhi Tian

  DOI：10.1021/ja030437h

  日期：2004.9.1

  methyl (9), and diphenyl (10) phosphonoformate diesters are substantially accelerated by Ce(IV), Th(IV), Zr(IV), and Hf(IV) cations. Chemoselectivity is observed, whereby Zr(IV) and Hf(IV) principally direct P-OR hydrolysis, whereas Th(IV) and Ce(IV) mainly direct C-OR hydrolysis. Leaving group efficiency (OMe vs OPh) modulates the chemoselectivity. The metal cations also mediate further hydrolytic reactions

  Ce(IV)、Th(IV) 显着加速二甲基 (7)、甲基苯基 (8)、苯基甲基 (9) 和二苯基 (10) 膦酰甲酸二酯在 D(2)O (pD 1.7-3.1) 中的水解)、Zr(IV) 和 Hf(IV) 阳离子。观察到化学选择性，其中 Zr(IV) 和 Hf(IV) 主要指导 P-OR 水解，而 Th(IV) 和 Ce(IV) 主要指导 C-OR 水解。离开组效率（OMe 与 OPh）调节化学选择性。金属阳离子还介导了最初生成的膦酰甲酸酯单酯 14、15、18 和 20 的进一步水解反应。 P-OR/C-OR 选择性的起源根据可能存在于溶液和反应动力学。