(E)-(2-methyl)styryl diphenylphosphine oxide | 1033853-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(2-methyl)styryl diphenylphosphine oxide
• 英文别名: (E)-1-(4-(2-(diphenylphosphoryl)vinyl)phenyl)ethanone；4-[(E)-2-(diphenylphosphinyl)ethenyl]acetophenone；1-[4-[(E)-2-diphenylphosphorylethenyl]phenyl]ethanone
• CAS: 1033853-05-2
• 化学式: C₂₂H₁₉O₂P
• 分子量: 346.365
• InChiKey: NXDXHDGKGZDLPG-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-acetylphenylethynyl)diphenylphosphine 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以62%的产率得到(E)-(2-methyl)styryl diphenylphosphine oxide
  参考文献：
  名称：

  Rhodium-Catalyzed Reaction of 1-Alkynylphosphines with Water Yielding (E)-1-Alkenylphosphine Oxides

  摘要：

  将1-炔基膦与铑催化剂在1,4-二氧六烷/水的回流条件下处理，可以高选择性且高产率地制得(E)-1-烯基膦氧化物。该反应过程如下：1-炔基膦的氧化加成到铑上，随后发生水解，生成相应的末端炔和二苯基膦氧化物。然后，铑催化的末端炔的氢膦化反应继续进行，生成(E)-1-烯基膦氧化物。

  DOI：

  10.1246/bcsj.81.502

文献信息

• Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes
  作者：Qingwen Gui、Liang Hu、Xiang Chen、Jidan Liu、Ze Tan

  DOI：10.1039/c5cc04826e

  日期：——

  An efficient and stereoselective synthesis of vinylphosphonates and phosphine oxides was developed starting from styrenes using AgNO3 as the catalyst and K2S2O8 as the oxidant. Various vinyl-phosphonates and phosphine oxides were synthesized in good yields with excellent regioselectivity.

  从苯乙烯开始，使用AgNO 3作为催化剂，K 2 S 2 O 8作为氧化剂，开发了一种有效的立体选择性合成乙烯基膦酸酯和氧化膦的方法。以良好的产率和优异的区域选择性合成了各种乙烯基膦酸酯和氧化膦。
• Copper-Catalyzed Decarboxylative C–P Cross-Coupling of Alkynyl Acids with <i>H</i>-Phosphine Oxides: A Facile and Selective Synthesis of (<i>E</i>)-1-Alkenylphosphine Oxides
  作者：Gaobo Hu、Yuxing Gao、Yufen Zhao

  DOI：10.1021/ol502009b

  日期：2014.9.5

  A novel and efficient copper-catalyzed decarboxylative cross-coupling of alkynyl acids for the stereoselective synthesis of E-alkenylphosphine oxides has been developed. In the presence of 10 mol % of CuCl without added ligand, base, and additive, various alkynyl acids reacted with H-phosphine oxides to afford E-alkenylphosphine oxides with operational simplicity, broad substrate scope, and the stereoselectivity for E-isomers.
• Rhodium-Catalyzed Reaction of 1-Alkynylphosphines with Water Yielding (<i>E</i>)-1-Alkenylphosphine Oxides
  作者：Azusa Kondoh、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1246/bcsj.81.502

  日期：2008.4.15

  Treatment of 1-alkynylphosphines with a rhodium catalyst in 1,4-dioxane/H2O at reflux provides (E)-1-alkenylphosphine oxides in good yields with perfect stereoselectivity. The reaction proceeds as follows. Oxidative addition of 1-alkynylphosphine to rhodium followed by hydrolysis yields the corresponding terminal alkyne and diphenylphosphine oxide. Rhodium-catalyzed hydrophosphinylation of the terminal alkyne then proceeds to afford (E)-1-alkenylphosphine oxide.

  将1-炔基膦与铑催化剂在1,4-二氧六烷/水的回流条件下处理，可以高选择性且高产率地制得(E)-1-烯基膦氧化物。该反应过程如下：1-炔基膦的氧化加成到铑上，随后发生水解，生成相应的末端炔和二苯基膦氧化物。然后，铑催化的末端炔的氢膦化反应继续进行，生成(E)-1-烯基膦氧化物。