methyl (p-methylphenyl)phosphonic acid | 131066-53-0

• 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-methylphenyl)phosphonic acid
• 英文别名: Methoxy-(4-methylphenyl)phosphinic acid
• CAS: 131066-53-0
• 化学式: C₈H₁₁O₃P
• 分子量: 186.147
• InChiKey: ANYLJMIIASXDAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-methylphenyl)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-[hydroxy-(4-methylphenyl)phosphoryl]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：

  1-(4-methylphenyl)-3-methyl-2,5-dihydro-1H-phosphole 1-oxide 在 TEA 、 溴 、 间氯过氧苯甲酸 、 3-氯苯甲酸 作用下， 以 氯仿 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 0.83h， 生成 methyl (p-methylphenyl)phosphonic acid
  参考文献：
  名称：

  芳基-2,3-氧杂磷双环[2.2.2]辛烯衍生物—氧代芳基膦氧化物（芳基偏膦酸酯）的前体

  摘要：

  7- phosphanorbornene -7-氧化物的拜尔-维利格氧化，在磷原子空间要求的取代基（4A - d）由米氯过苯甲酸，得到标题产物（5A - d），为两种区域异构体的混合物（阿和乙） 。热力学控制的结果异构体A是稳定的，而动力学控制的产物异构体B则发生分解和/或环氧化。的单晶X射线分析P - （2,4,6-三异丙基）oxaphosphabicyclooctene（5AC）不仅可用于评估其结构，而且在文献中首次可检测到X射线辐照碎裂形成的低配位芳基偏膦酸酯（15c）。前体（5Aa - c）用于醇的热诱导和紫外光介导的断裂相关磷酸化。除了通过间膦酸酯中间体（15）的众所周知的消除-加成机理外，还证实了涉及具有五价五配位磷原子的物种（16）的新颖的消除成膜途径。

  DOI：

  10.1016/j.tet.2004.01.069

文献信息

• Aryl-2,3-oxaphosphabicyclo[2.2.2]octene derivatives—the precursors of oxoarylphosphine oxides (aryl metaphosphonates)
  作者：Stefan Jankowski、György Keglevich、Tomasz Nonas、Henrietta Forintos、Marek Główka、Juliusz Rudziński

  DOI：10.1016/j.tet.2004.01.069

  日期：2004.3

  The Baeyer–Villiger oxidation of 7-phosphanorbornene 7-oxides with sterically demanding substituents on the phosphorus atom (4a–d) by m-chloroperbenzoic acid afforded the title products (5a–d) as a mixture of two regioisomers (A and B). Isomer A, the result of thermodynamic control, was stable, while isomer B, the product of kinetic control, underwent decomposition and/or epoxidation. Single crystal

  7- phosphanorbornene -7-氧化物的拜尔-维利格氧化，在磷原子空间要求的取代基（4A - d）由米氯过苯甲酸，得到标题产物（5A - d），为两种区域异构体的混合物（阿和乙） 。热力学控制的结果异构体A是稳定的，而动力学控制的产物异构体B则发生分解和/或环氧化。的单晶X射线分析P - （2,4,6-三异丙基）oxaphosphabicyclooctene（5AC）不仅可用于评估其结构，而且在文献中首次可检测到X射线辐照碎裂形成的低配位芳基偏膦酸酯（15c）。前体（5Aa - c）用于醇的热诱导和紫外光介导的断裂相关磷酸化。除了通过间膦酸酯中间体（15）的众所周知的消除-加成机理外，还证实了涉及具有五价五配位磷原子的物种（16）的新颖的消除成膜途径。
• 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".