ethyl (trans-styryl)phosphinate | 33817-97-9

• 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: ethyl (trans-styryl)phosphinate
• 英文别名: (E)-ethyl(styryl)phosphinate；[(E)-2-[ethoxy(oxido)phosphaniumyl]ethenyl]benzene
• CAS: 33817-97-9
• 化学式: C₁₀H₁₃O₂P
• 分子量: 196.186
• InChiKey: HDVQVZVDVQOEJU-CMDGGOBGSA-N

物化性质

• 沸点：
  140-141 °C(Press: 0.08 Torr)
• 密度：
  1.1249 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  diethyl phenylethynylphosphoniteborane 在 乙醇 、 二异丁基氢化铝 作用下， 以 hexanes 为溶剂， 反应 100.0h， 生成 (Z)-ethyl(styryl)phosphinate 、 ethyl (trans-styryl)phosphinate
  参考文献：
  名称：

  Synthesis ofZ-Alkenyl Phosphorus Compounds through Hydroalumination and Carbocupration of Alkynyl Precursors

  摘要：

  The stereocontrolled synthesis of Z-alkenylphosphine-borane complexes is easily accomplished via the hydroalumination or carbocupration of alkynyl precursors. Z/E ratios are generally higher than 95/5. These reactions are stereocomplementary to our olefination approach.

  DOI：

  10.1021/ol2010374

文献信息

• Regiocontrol in the palladium-catalyzed hydrophosphinylation of terminal alkynes
  作者：Yamina Belabassi、Karla Bravo-Altamirano、Jean-Luc Montchamp

  DOI：10.1016/j.jorganchem.2010.08.018

  日期：2011.1

  The regioselectivity of the palladium-catalyzed hydrophosphinylation of terminal alkynes was investigated. Complementary conditions to achieve the predominant formation of either the linear or the branched alkenyl-H-phosphinate products were identified. With Pd/xantphos in acetonitrile, the linear isomer is generally obtained with good to excellent selectivity, and E-stereospecificity. On the other hand, by using Pd/dppf in the non-polar solvent toluene, good selectivity for the branched alkenyl-H-phosphinate is typically observed. The role of various reaction parameters is studied. (C) 2010 Elsevier B.V. All rights reserved.
• NiCl₂-Catalyzed Hydrophosphinylation
  作者：Patrice Ribière、Karla Bravo-Altamirano、Monika I. Antczak、Jennifer D. Hawkins、Jean-Luc Montchamp

  DOI：10.1021/jo050096l

  日期：2005.5.1

  A new nickel-based catalytic system has been developed for phosphorus-carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor substrates in our previously reported palladium-catalyzed hydrophosphinylation of alkyl phosphinates. The method is useful for the preparation of H-phosphinate esters and their derivatives. The one-pot synthesis of various important organophosphorus compounds is also demonstrated. The reaction can be conducted with microwave heating.