ethyl 3,4-dioxo-4-phenyl-2-triphenylphosphoranylidenebutanoate | 152126-77-7

• 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: ethyl 3,4-dioxo-4-phenyl-2-triphenylphosphoranylidenebutanoate
• 英文别名: Ethyl 3,4-dioxo-4-phenyl-2-(triphenyl-lambda5-phosphanylidene)butanoate；ethyl 3,4-dioxo-4-phenyl-2-(triphenyl-λ5-phosphanylidene)butanoate
• CAS: 152126-77-7
• 化学式: C₃₀H₂₅O₄P
• 分子量: 480.5
• InChiKey: NFNSVEYNSUQACI-UHFFFAOYSA-N

物化性质

• 沸点：
  628.3±38.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-dioxo-4-phenyl-2-triphenylphosphoranylidenebutanoate 以23%的产率得到
  参考文献：
  名称：

  Aitken R. Alan, Herion Hugues, Janosi Amaya, Karodia Nazira, Raut Swati V+, J. Chem. Soc. Perkin Trans. 1, (1994) N 17, S 2467-2472

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基乙醛酸钠 在 草酰氯 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 ethyl 3,4-dioxo-4-phenyl-2-triphenylphosphoranylidenebutanoate
  参考文献：
  名称：

  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 5. Selective extrusion of PH₃PO from β,γ,β′-trioxo ylides to give diacylalkynes

  摘要：

  Sixteen examples of the previously unknown trioxo ylides 7 have been prepared by acylation of stabilised phosphorus ylides 8 with alpha-oxo acid chlorides 9. Extrusion of Ph(3)PO from these is readily achieved using FVP at 500 degrees C in most cases, to afford the diacylalkynes 10 in moderate yield. Three examples failed to give the expected alkynes and the nature of the processes involved in these cases is uncertain. Fully assigned C-13 NMR spectra are presented for the ylides and an unexpected pattern is observed in the value of J(p-c) for the three carbonyl carbons depending on the nature of the substituents present. There is some correlation between the value of (2)J(p-c) for the central carbonyl carbon and the success of the pyrolysis although this is not complete. The method has been used to prepare a specifically C-13 labelled acetylenic diester 14.

  DOI：

  10.1039/p19940002467

文献信息

• Pyrolysis of β,γ,β′-trioxo phosphorus ylides: Convenient synthesis of symmetrical and unsymmetrical diacylalkynes
  作者：R.Alan Aitken、Hugues Hérion、Amaya Janosi、Swati V. Raut、Shirley Seth、Ian J. Shannon、Fiona C. Smith

  DOI：10.1016/s0040-4039(00)73898-6

  日期：1993.8

  Flash vacuum pyrolysis of a series of 1,2,4-trioxo-3-triphenylphosphoranylidene-butane derivatives, formed by acylation of β-oxo-phosphorus ylides with α-oxo-acid chlorides, results in extrusion of Ph3PO exclusively across the 2,3-position to give diacylalkynes.

  快速真空热解一系列1,2,4-三氧代-3-三苯基磷酰亚芳基-丁烷衍生物，该衍生物是通过将β-氧代磷酰基化物与α-氧代酰氯酰化而形成的，导致Ph 3 PO仅在整个反应釜中挤出。2,3-位生成二酰基炔烃。
• Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 5. Selective extrusion of PH₃PO from β,γ,β′-trioxo ylides to give diacylalkynes
  作者：R. Alan Aitken、Hugues Hérion、Amaya Janosi、Nazira Karodia、Swati V. Raut、Shirley Seth、Ian J. Shannon、Fiona C. Smith

  DOI：10.1039/p19940002467

  日期：——

  Sixteen examples of the previously unknown trioxo ylides 7 have been prepared by acylation of stabilised phosphorus ylides 8 with alpha-oxo acid chlorides 9. Extrusion of Ph(3)PO from these is readily achieved using FVP at 500 degrees C in most cases, to afford the diacylalkynes 10 in moderate yield. Three examples failed to give the expected alkynes and the nature of the processes involved in these cases is uncertain. Fully assigned C-13 NMR spectra are presented for the ylides and an unexpected pattern is observed in the value of J(p-c) for the three carbonyl carbons depending on the nature of the substituents present. There is some correlation between the value of (2)J(p-c) for the central carbonyl carbon and the success of the pyrolysis although this is not complete. The method has been used to prepare a specifically C-13 labelled acetylenic diester 14.
• Aitken R. Alan, Herion Hugues, Janosi Amaya, Karodia Nazira, Raut Swati V+, J. Chem. Soc. Perkin Trans. 1, (1994) N 17, S 2467-2472
  作者：Aitken R. Alan, Herion Hugues, Janosi Amaya, Karodia Nazira, Raut Swati V+

  DOI：——

  日期：——