4-苄氧基苯基羟甲基膦酸二乙酯 | 1414869-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-苄氧基苯基羟甲基膦酸二乙酯
• 英文名称: diethyl 4-benzyloxyphenylhydroxymethylphosphonate
• 英文别名: diethyl 1-hydroxy-1-(4-benzyloxyphenyl)methylphosphonate；Diethoxyphosphoryl-(4-phenylmethoxyphenyl)methanol；diethoxyphosphoryl-(4-phenylmethoxyphenyl)methanol
• CAS: 1414869-49-0
• 化学式: C₁₈H₂₃O₅P
• 分子量: 350.351
• InChiKey: ZTPFXHSZRCIXLT-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  502.5±50.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-苄氧基苯基羟甲基膦酸二乙酯 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以91%的产率得到diethyl (4-benzyloxybenzoyl)phosphonate
  参考文献：
  名称：

  Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane

  摘要：

  DOI：

  10.24820/ark.5550190.p011.213
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 亚磷酸二乙酯 在 potassium phosphate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以93%的产率得到4-苄氧基苯基羟甲基膦酸二乙酯
  参考文献：
  名称：

  Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst

  摘要：

  摘要 描述了一种极其简单、高产量、高速且无溶剂的醛类羟基磷化方法，使用磷酸钾作为催化剂。该可重复使用的催化剂易于商业获取，在常温下操作简单，并且避免了传统的后处理和纯化过程，使该无溶剂方案成为一种近乎理想的合成方法。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.pdf

  DOI：

  10.1016/j.crci.2012.10.009

文献信息

• Triflic acid mediated functionalization of α-hydroxyphosphonates: route for sulfonamide phosphonates
  作者：Gangaram Pallikonda、Manab Chakravarty

  DOI：10.1039/c3ra43823f

  日期：——

  An operationally simple synthetic method for (±)-α-aryl/methylsulfonamidomethylphosphonates and new (±)-γ-aryl/methyl sulfonamidomethylvinylphosphonates has been developed through straightforward reactions of (±)-α-hydroxyphosphonates with sulfonamides in the presence of triflic acid (TfOH) at room temperature in a vessel open to air. For γ-dimethylallylhydroxyphosphonate, the (E)-1,3-butadienylphosphonate was formed quantitatively using TfOH while FeCl3 afforded the expected product in moderate yield unpredictably. The favourable sulfonoamidation of benzyl alcohol is also observed when TfOH was used for α-hydroxyphosphonates having a benzyloxy group.

  通过在室温下，在三氟甲磺酸（TfOH）存在下，将（±）-α-羟基膦酸与磺酰胺在开放容器中进行简单反应，开发了一种用于合成（±）-α-芳基/甲基磺酰胺甲基膦酸酯和新型（±）-γ-芳基/甲基磺酰胺甲基乙烯基膦酸酯的操作简便的合成方法。对于γ-二甲基烯丙基羟基膦酸，TfOH定量地形成（E）-1,3-丁二烯基膦酸，而FeCl3则以中等产率不可预测地得到了预期产物。当TfOH用于含有苄氧基的α-羟基膦酸时，也观察到苄醇的有利磺酰胺化。
• Synthesis of α-Hydroxyphosphonates and Their Antioxidant Properties
  作者：Kalla Reddi Mohan Naidu、Krishnammagari Suresh Kumar、Palanisamy Arulselvan、Chinnappareddy Bhupendra Reddy、Ola Lasekan

  DOI：10.1002/ardp.201200192

  日期：2012.12

  synthesized from the reaction of aldehyde (1) with triethylphosphite (2) in the presence of oxone and evaluated for their antioxidant properties against lipid peroxidation, reduced glutathione, superoxide dismutase, and catalase. The majority of the compounds showed promising antioxidant activity. Diethyl anthracen‐9‐yl (hydroxy) methylphosphonate (3n) is the most potent and biologically active compound

  在 oxone 存在下，醛 (1) 与亚磷酸三乙酯 (2) 反应合成了一系列 α-羟基膦酸酯，并评估了它们对脂质过氧化、还原型谷胱甘肽、超氧化物歧化酶和过氧化氢酶的抗氧化性能。大多数化合物显示出有希望的抗氧化活性。二乙基蒽-9-基（羟基）甲基膦酸酯（3n）是对抗自由基最有效和生物活性的化合物。
• An easy access to α-aryl substituted γ-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with α-hydroxyphosphonates and tandem regioselective C–C bond cleavage
  作者：Gangaram Pallikonda、Manab Chakravarty、Manoj K. Sahoo

  DOI：10.1039/c4ob01091d

  日期：——

  The α-aryl substituted (±)-γ-ketophosphonates are produced by Lewis acid mediated reactions of α-hydroxyphosphonates with 1,3-diketones.

  α-芳基取代的(±)-γ-酮磷酸酯是通过Lewis酸介导的α-羟基磷酸酯与1,3-二酮的反应产生的。
• Aryl sulfonamidomethylphosphonates as new class of green corrosion inhibitors for mild steel in 1M HCl: Electrochemical, surface and quantum chemical investigation
  作者：Chandrabhan Verma、A. Singh、G. Pallikonda、M. Chakravarty、M.A. Quraishi、I. Bahadur、E.E. Ebenso

  DOI：10.1016/j.molliq.2015.06.013

  日期：2015.9

  Synthesis and corrosion inhibition property of five aryl sulfonamidomethylphosphonates in 1 M HCl are reported using chemical, electrochemical, scanning electron microscopy (SEM) and quantum chemical calculation methods. Experimental results show that aryl sulfonamidomethylphosphonates are good corrosion inhibitors for mild steel in 1 M HCl and their inhibition efficiency increases with concentration. Potentiodynamic polarization studies show that studied inhibitors act as mixed type and their adsorption on mild steel surface obeys the Langmuir's adsorption isotherm. The thermodynamic (E-a, Delta H*, Delta S*, Delta G(0) (ads)) and quantum chemical parameters were calculated and discussed to describe the mechanism of adsorption. (C) 2015 Elsevier B.V. All rights reserved.