methyl (p-chlorophenyl)phosphonic acid | 131066-52-9

• 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 (p-chlorophenyl)phosphonic acid
• 英文别名: (4-Chlorophenyl)-methoxyphosphinic acid
• CAS: 131066-52-9
• 化学式: C₇H₈ClO₃P
• 分子量: 206.565
• InChiKey: CYXPZBHXDWLIFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (p-chlorophenyl)phosphonic acid 在 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 (2S)-2-[[(2S)-2-[(4-chlorophenyl)-hydroxyphosphoryl]oxy-4-methylpentanoyl]amino]-4-methylpentanoic acid
  参考文献：
  名称：

  Differential binding energy: a detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorus-containing inhibitors

  摘要：

  Two series of phosphorus-containing peptide analogues, 3 (Cbz-Gly-psi(PO2-CH2)Leu-Xaa) and 4 (Cbz-Gly-psi-(PO2-NH)Leu-psi[CO2]Xaa), have been synthesized and evaluated as inhibitors of the zinc endopeptidase thermolysin. In comparison with the previously reported phosphonamidates 1, the phosphinates 3 lose only 0.1 kcal/mol in binding affinity, whereas the depsipeptides 4 are bound 2.7 kcal/mol more weakly; these values are contrasted to the 4.0 kcal/mol reduction in binding affinity observed for the phosphonates 2 (Cbz-Gly-psi(PO2-O)Leu-Xaa) in comparison to 1 (Cbz-Gly-psi(PO2-NH)Leu-Xaa). The observed effects are interpreted through consideration of the differences in active-site and solvent interactions. For the comparison between the diamides 1 and the depsipeptides 4, a full accounting of the balance between these interactions can be approached. The arylphosphonates 5 (Aryl-psi(PO2-O)Leu-Leu) were synthesized and evaluated to investigate the importance of phosphonate basicity on the overall binding affinity of these zinc-coordinating inhibitors; the inhibitor K(i) values were found to be independent of phosphonate p(K)a, indicating that the basicity of the phosphonate moiety exerts counterbalancing effects on the energies of zinc coordination and solvation. For analysis of the influence of structural variations on observed affinity, the definition of "differential binding energy" is introduced as a practical alternative to the concept of "intrinsic binding energy".

  DOI：

  10.1021/ja00001a043
• 作为产物：
  描述：

  4-氯苯磷酸 、 原甲酸三甲酯 在 sodium hydroxide 作用下， 生成 methyl (p-chlorophenyl)phosphonic acid
  参考文献：
  名称：

  Differential binding energy: a detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorus-containing inhibitors

  摘要：

  Two series of phosphorus-containing peptide analogues, 3 (Cbz-Gly-psi(PO2-CH2)Leu-Xaa) and 4 (Cbz-Gly-psi-(PO2-NH)Leu-psi[CO2]Xaa), have been synthesized and evaluated as inhibitors of the zinc endopeptidase thermolysin. In comparison with the previously reported phosphonamidates 1, the phosphinates 3 lose only 0.1 kcal/mol in binding affinity, whereas the depsipeptides 4 are bound 2.7 kcal/mol more weakly; these values are contrasted to the 4.0 kcal/mol reduction in binding affinity observed for the phosphonates 2 (Cbz-Gly-psi(PO2-O)Leu-Xaa) in comparison to 1 (Cbz-Gly-psi(PO2-NH)Leu-Xaa). The observed effects are interpreted through consideration of the differences in active-site and solvent interactions. For the comparison between the diamides 1 and the depsipeptides 4, a full accounting of the balance between these interactions can be approached. The arylphosphonates 5 (Aryl-psi(PO2-O)Leu-Leu) were synthesized and evaluated to investigate the importance of phosphonate basicity on the overall binding affinity of these zinc-coordinating inhibitors; the inhibitor K(i) values were found to be independent of phosphonate p(K)a, indicating that the basicity of the phosphonate moiety exerts counterbalancing effects on the energies of zinc coordination and solvation. For analysis of the influence of structural variations on observed affinity, the definition of "differential binding energy" is introduced as a practical alternative to the concept of "intrinsic binding energy".

  DOI：

  10.1021/ja00001a043

文献信息

• Verfahren zur Herstellung von gegebenenfalls substituierten Benzaldehyd-dialkylacetalen
  申请人：BAYER AG

  公开号：EP0012240A2

  公开（公告）日：1980-06-25

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von gegebenenfalls substituierten Benzaldehyd-dialkylacetalen durch elektrochemische Oxidation von gegebenenfalls substituierten Toluolen in alkoholischer Lösung in Gegenwart eines Leitsalzes der Formel in der Y ein Alkalimetall oder gegebenenfalls substituiertes Ammonium bedeutet, A für -SO2- oder steht, wobei R6 Alkoxy, Aralkoxy, Aryloxy, Hydroxyl oder OY bedeutet, und R5 für Hydroxyl, OY, Alkyl, Aralkyl, Aryl, Alkoxy, Aralkoxy oder Aryloxy steht, unter Rückführung der entstehenden Nebenprodukte in das Ausgangsmaterial der elektrochemischen Oxidation.

  本发明涉及一种制备任选取代的苯甲醛二烷基乙缩醛的工艺，其方法是在酒精溶液中，在 式中导电盐的存在下，通过电化学氧化任选取代的甲苯来制备苯甲醛二烷基乙缩醛。 其中 Y 是碱金属或任选取代的铵、 A 是 -SO2- 或 其中 R6 是烷氧基、烷氧基、芳氧基、羟基或 OY，以及 R5 是羟基、OY、烷基、芳烷基、芳基、烷氧基、芳氧基或芳氧基、 将产生的副产物回收到电化学氧化的起始原料中。
• Differential binding energy: a detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorus-containing inhibitors
  作者：Bradley Morgan、John M. Scholtz、Marcus D. Ballinger、Ilan D. Zipkin、Paul A. Bartlett

  DOI：10.1021/ja00001a043

  日期：1991.1

  Two series of phosphorus-containing peptide analogues, 3 (Cbz-Gly-psi(PO2-CH2)Leu-Xaa) and 4 (Cbz-Gly-psi-(PO2-NH)Leu-psi[CO2]Xaa), have been synthesized and evaluated as inhibitors of the zinc endopeptidase thermolysin. In comparison with the previously reported phosphonamidates 1, the phosphinates 3 lose only 0.1 kcal/mol in binding affinity, whereas the depsipeptides 4 are bound 2.7 kcal/mol more weakly; these values are contrasted to the 4.0 kcal/mol reduction in binding affinity observed for the phosphonates 2 (Cbz-Gly-psi(PO2-O)Leu-Xaa) in comparison to 1 (Cbz-Gly-psi(PO2-NH)Leu-Xaa). The observed effects are interpreted through consideration of the differences in active-site and solvent interactions. For the comparison between the diamides 1 and the depsipeptides 4, a full accounting of the balance between these interactions can be approached. The arylphosphonates 5 (Aryl-psi(PO2-O)Leu-Leu) were synthesized and evaluated to investigate the importance of phosphonate basicity on the overall binding affinity of these zinc-coordinating inhibitors; the inhibitor K(i) values were found to be independent of phosphonate p(K)a, indicating that the basicity of the phosphonate moiety exerts counterbalancing effects on the energies of zinc coordination and solvation. For analysis of the influence of structural variations on observed affinity, the definition of "differential binding energy" is introduced as a practical alternative to the concept of "intrinsic binding energy".