(1-(biphenyl-4-yl)ethenyl)phosphonic acid | 478490-56-1

• 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: (1-(biphenyl-4-yl)ethenyl)phosphonic acid
• 英文别名: 1-(4-diphenyl)ethenylphosphonic acid；1-(4-Phenylphenyl)ethenylphosphonic acid
• CAS: 478490-56-1
• 化学式: C₁₄H₁₃O₃P
• 分子量: 260.229
• InChiKey: PCIHINITXQHDAN-UHFFFAOYSA-N

物化性质

• 沸点：
  506.9±53.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-(biphenyl-4-yl)ethenyl)phosphonic acid 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 生成 diethyl (+/-)-1-(4-diphenyl)ethylphosphonate
  参考文献：
  名称：

  铱-膦基恶唑啉配合物对α，β-不饱和膦酸酯的高度对映选择性加氢：萘普生的磷类似物的合成

  摘要：

  通过[Ir（cod）（膦恶唑啉）] + [BAr F ] -在温和条件下，通过不对称氢化，以ee 92–95％合成了许多药学上感兴趣的光学活性的1-芳基乙基膦酸酯，包括萘普生的磷类似物-催化剂。

  DOI：

  10.1016/s0957-4166(03)00224-6
• 作为产物：
  描述：

  联苯单乙酮 在 三氯化磷 作用下， 以 溶剂黄146 为溶剂， 以60%的产率得到(1-(biphenyl-4-yl)ethenyl)phosphonic acid
  参考文献：
  名称：

  摘要：

  A convenient and inexpensive general preparation method for 1-arylethylphosphonic acids and their esters was developed involving in reduction of the corresponding 1-ethenylphosphonates by ammonium formate in the presence of palladium on carbon. A homogeneous enantioselective hydrogenation of 1-arylethenylphosphonic acids in the presence of chiral ruthenium catalysts provided optically active 1-arylethylphosphonic acids of enantiomeric purity up to 86%. The preliminary data on biological activity testing of the 1-arylethylphosphoic acids synthesized evidence that some among the compounds obtained are low-toxic substances with the properties of immunosuppressors of the central type of action.

  DOI：

  10.1023/a:1016511609369

文献信息

• Synthesis of 1-arylcyclopropylphosphonates
  作者：N. S. Gulyukina、A. V. Varakuta、I. P. Beletskaya

  DOI：10.1007/s11172-007-0290-y

  日期：2007.9

  A simple method for the synthesis of 1-arylcyclopropylphosphonates was proposed. The method involves treatment of 1-arylethenylphosphonic acids or their esters with diazomethane followed by thermolysis of intermediate 3-aryl-4,5-dihydro-3H-pyrazol-3-ylphosphonates.

  提出了一种合成 1-芳基环丙基膦酸盐的简单方法。该方法包括用重氮甲烷处理 1-芳基乙烯基膦酸或其酯，然后热解中间体 3-芳基-4,5-二氢-3H-吡唑-3-基膦酸盐。
• ——
  作者：N. S. Gulyukina、T. M. Dolgina、G. N. Bondarenko、I. P. Beletskaya、N. A. Bondarenko、J. -C. Henry、D. Lavergne、V. Ratovelomanana-Vidal、J. -P. Genet

  DOI：10.1023/a:1016511609369

  日期：——

  A convenient and inexpensive general preparation method for 1-arylethylphosphonic acids and their esters was developed involving in reduction of the corresponding 1-ethenylphosphonates by ammonium formate in the presence of palladium on carbon. A homogeneous enantioselective hydrogenation of 1-arylethenylphosphonic acids in the presence of chiral ruthenium catalysts provided optically active 1-arylethylphosphonic acids of enantiomeric purity up to 86%. The preliminary data on biological activity testing of the 1-arylethylphosphoic acids synthesized evidence that some among the compounds obtained are low-toxic substances with the properties of immunosuppressors of the central type of action.
• Highly enantioselective hydrogenation of α,β-unsaturated phosphonates with iridium–phosphinooxazoline complex: synthesis of a phosphorus analogue of naproxen
  作者：Natalia S Goulioukina、Tat'yana M Dolgina、Grigorii N Bondarenko、Irina P Beletskaya、Mikhail M Ilyin、Vadim A Davankov、Andreas Pfaltz

  DOI：10.1016/s0957-4166(03)00224-6

  日期：2003.5

  A number of pharmaceutically interesting optically active 1-arylethylphosphonates, including a phosphorus analogue of naproxen, has been synthesized with ee 92–95% via asymmetric hydrogenation under mild conditions using [Ir(cod)(phosphine oxazoline)]+ [BArF]− catalysts.

  通过[Ir（cod）（膦恶唑啉）] + [BAr F ] -在温和条件下，通过不对称氢化，以ee 92–95％合成了许多药学上感兴趣的光学活性的1-芳基乙基膦酸酯，包括萘普生的磷类似物-催化剂。