butyl (1-propyl-pent-1-enyl)phosphinate | 853411-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butyl (1-propyl-pent-1-enyl)phosphinate
• CAS: 853411-29-7
• 化学式: C₁₂H₂₅O₂P
• 分子量: 232.303
• InChiKey: NZICOMXPZLTMQZ-ZRDIBKRKSA-N

物化性质

• 沸点：
  300.2±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  15.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  butyl (1-propyl-pent-1-enyl)phosphinate 、 5-溴-1-戊烯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到pent-4-enyl-(1-propyl-pent-1-enyl)-phosphinic acid butyl ester
  参考文献：
  名称：

  Alkylation of H-Phosphinate Esters under Basic Conditions

  摘要：

  An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.

  DOI：

  10.1021/jo062436o
• 作为产物：
  描述：

  正硅酸丁酯 、 4-辛炔 在 nickel dichloride 亚膦酸 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以100%的产率得到butyl (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

• Palladium-catalyzed phosphorus–carbon bond formation: cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates
  作者：Karla Bravo-Altamirano、Zhihong Huang、Jean-Luc Montchamp

  DOI：10.1016/j.tet.2005.03.107

  日期：2005.6

  palladium catalysis. This full paper examines the scope and some mechanistic aspects of this phosphorus–carbon bond forming reaction. The reactions of alkenyl and allylic halides are also described for the first time. This novel cross-coupling provides a convenient access to a variety of substituted H-phosphinates.

  H-芳基次膦酸酯和相关化合物的直接形成可以使用钯催化来完成。这篇全文探讨了这种磷-碳键形成反应的范围和一些机理方面。还首次描述了烯基和烯丙基卤化物的反应。这种新颖的交叉偶联可方便地获得各种取代的H-次膦酸酯。