ethyl methyl-(1-propyl-pent-1-enyl)phosphinate

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦酸及其衍生物
• 英文名称: ethyl methyl-(1-propyl-pent-1-enyl)phosphinate
• 英文别名: (E)-4-[ethoxy(methyl)phosphoryl]oct-4-ene
• 化学式: C₁₁H₂₃O₂P
• 分子量: 218.276
• InChiKey: AYVGSHHBXIFZFE-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-辛炔 、 ethyl phosphinate 、 硫酸二甲酯 在 nickel dichloride 苯磺酰胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以62%的产率得到ethyl methyl-(1-propyl-pent-1-enyl)phosphinate
  参考文献：
  名称：

  NiCl₂-Catalyzed Hydrophosphinylation

  摘要：

  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.

  DOI：

  10.1021/jo050096l

文献信息

• 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.