(E)-N-tert-butyl-3-diphenylphosphanyl-3-phenylprop-2-en-1-imine | 1151694-12-0

• 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: (E)-N-tert-butyl-3-diphenylphosphanyl-3-phenylprop-2-en-1-imine
• CAS: 1151694-12-0
• 化学式: C₂₅H₂₆NP
• 分子量: 371.462
• InChiKey: LONWVNLKIMDFGT-PEVVOWSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  、 二苯基(三甲基硅基)膦 在 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以74.6%的产率得到(E)-N-tert-butyl-3-diphenylphosphanyl-3-phenylprop-2-en-1-imine
  参考文献：
  名称：

  A Versatile Methodology for the Synthesis of α,β-Unsaturated 3-Iminophosphines

  摘要：

  AbstractPhorteen phine phosphines: Fourteen new α,β‐unsaturated β‐chloroimines were synthesized from inexpensive ketones by using the Vilsmeier–Haack reagent followed by Schiff‐base condensation. Each imine was subsequently converted to an α,β‐unsaturated 3‐iminophosphine through either late‐metal‐catalyzed phosphorus–carbon cross‐coupling or through an addition–elimination sequence (see scheme). This high‐yield protocol serves as a general means to produce α,β‐unsaturated 3‐iminophosphines.magnified imageFourteen new α,β‐unsaturated β‐chloroimines were synthesized from commercially available ketones using the Vilsmeier–Haack reagent, followed by Schiff‐base condensation. Each imine was subsequently converted to an α,β‐unsaturated 3‐iminophosphine through either late‐metal‐catalyzed phosphorus–carbon cross‐coupling or through an addition–elimination sequence. Depending on the substituents present on the vinyl group, the resultant phosphines were isolated as either E or Z diastereomers with successful isolation of predominately single diastereomers for all fourteen new phosphines investigated. Full synthetic and spectroscopic details, as well as several X‐ray crystal structures of these new imines and phosphines, are reported in addition to X‐ray crystal structures of related palladium complexes.

  DOI：

  10.1002/chem.200802310

文献信息

• A Versatile Methodology for the Synthesis of α,β-Unsaturated 3-Iminophosphines
  作者：Andrew R. Shaffer、Joseph A. R. Schmidt

  DOI：10.1002/chem.200802310

  日期：2009.3.2

  AbstractPhorteen phine phosphines: Fourteen new α,β‐unsaturated β‐chloroimines were synthesized from inexpensive ketones by using the Vilsmeier–Haack reagent followed by Schiff‐base condensation. Each imine was subsequently converted to an α,β‐unsaturated 3‐iminophosphine through either late‐metal‐catalyzed phosphorus–carbon cross‐coupling or through an addition–elimination sequence (see scheme). This high‐yield protocol serves as a general means to produce α,β‐unsaturated 3‐iminophosphines.magnified imageFourteen new α,β‐unsaturated β‐chloroimines were synthesized from commercially available ketones using the Vilsmeier–Haack reagent, followed by Schiff‐base condensation. Each imine was subsequently converted to an α,β‐unsaturated 3‐iminophosphine through either late‐metal‐catalyzed phosphorus–carbon cross‐coupling or through an addition–elimination sequence. Depending on the substituents present on the vinyl group, the resultant phosphines were isolated as either E or Z diastereomers with successful isolation of predominately single diastereomers for all fourteen new phosphines investigated. Full synthetic and spectroscopic details, as well as several X‐ray crystal structures of these new imines and phosphines, are reported in addition to X‐ray crystal structures of related palladium complexes.