[2-(phenylthio)propyl]diphenylphosphane oxide | 1261158-14-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [2-(phenylthio)propyl]diphenylphosphane oxide
• 英文别名: [Phenyl(2-phenylsulfanylpropyl)phosphoryl]benzene；[phenyl(2-phenylsulfanylpropyl)phosphoryl]benzene
• CAS: 1261158-14-8
• 化学式: C₂₁H₂₁OPS
• 分子量: 352.437
• InChiKey: ODTWSXMEZNIQEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-二苯基1,2-丙烯基膦氧化物 、 苯硫酚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以77%的产率得到[2-(phenylthio)propyl]diphenylphosphane oxide
  参考文献：
  名称：

  Some synthetic applications of vinylphosphane oxides

  摘要：

  Vinylphosphane oxides have been used as Michael acceptors for the diastereoselective synthesis of anti alpha-functionalized-beta-silylated phosphane oxides and beta-stannyl-, beta-phenylthio- or beta-phosphanyl phosphane oxides. Although the utility of these substrates as dipolarophiles was more limited, we have obtained a mixture of 3- and 4-phosphanylpyrazoles in which the latter is the major regioisomer, by 1,3-cycloaddition with N-phenylsydnone. Moreover, vinylphosphane oxides reacted with aldehydes in the presence of LDA by a Baylis-Hillman type reaction, leading to (E)-beta-hydroxyphosphane oxides, which were readily converted in allenes. It is noteworthy that the application of this methodology to silylated substrates has permitted us to synthesize an interesting and more versatile silylallene. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.016

文献信息

• Some synthetic applications of vinylphosphane oxides
  作者：Ana M. Gonzalez-Nogal、Purificacion Cuadrado、Maria A. Sarmentero

  DOI：10.1016/j.tet.2010.10.016

  日期：2010.12

  Vinylphosphane oxides have been used as Michael acceptors for the diastereoselective synthesis of anti alpha-functionalized-beta-silylated phosphane oxides and beta-stannyl-, beta-phenylthio- or beta-phosphanyl phosphane oxides. Although the utility of these substrates as dipolarophiles was more limited, we have obtained a mixture of 3- and 4-phosphanylpyrazoles in which the latter is the major regioisomer, by 1,3-cycloaddition with N-phenylsydnone. Moreover, vinylphosphane oxides reacted with aldehydes in the presence of LDA by a Baylis-Hillman type reaction, leading to (E)-beta-hydroxyphosphane oxides, which were readily converted in allenes. It is noteworthy that the application of this methodology to silylated substrates has permitted us to synthesize an interesting and more versatile silylallene. (C) 2010 Elsevier Ltd. All rights reserved.