1,4-Diphenyl-4-triphenylphosphoranylidenebut-1-yn-3-one | 96709-74-9

• 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: 1,4-Diphenyl-4-triphenylphosphoranylidenebut-1-yn-3-one
• 英文别名: 1,4-Diphenyl-but-3-in-2-on-yliden-triphenyl-phosphoran；1,4-Diphenyl-1-(triphenyl-lambda5-phosphanylidene)but-3-yn-2-one；1,4-diphenyl-1-(triphenyl-λ5-phosphanylidene)but-3-yn-2-one
• CAS: 96709-74-9
• 化学式: C₃₄H₂₅OP
• 分子量: 480.546
• InChiKey: XIFOSABPVXDKRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-Diphenyl-4-triphenylphosphoranylidenebut-1-yn-3-one 反应 -6.0h， 以70%的产率得到1，4-二苯基丁二炔
  参考文献：
  名称：

  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 8. Preparation of symmetrical and unsymmetrical 1,3-diynes from alkynoyl ylides and oxalyl diylides

  摘要：

  Seven examples of the alkynoyl phosphorus ylides 5 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 750 degrees C, to undergo extrusion of Ph(3)PO to give the unsymmetrical 1,3-diynes 9 in moderate yield. Six examples of the oxalyl diylides 6 have been prepared and their fully assigned C-13 NMR spectra are presented. Upon FVP, those with R = aryl undergo two-fold extrusion of Ph(3)PO to give symmetrical 1,3-diynes 13 but this requires the unusually severe temperature of 900 degrees C. In contrast those with R = CO(2)Me, CO(2)Et or COPh undergo complete reaction at 500 degrees C but afford only Ph(3)PO and fragmentation products.

  DOI：

  10.1039/p19960000485
• 作为产物：
  描述：

  phenylpropiolyl chloride 、 苯基次甲基三苯基膦烷 在 三乙胺 作用下， 生成 1,4-Diphenyl-4-triphenylphosphoranylidenebut-1-yn-3-one
  参考文献：
  名称：

  Gough,S.T.D.; Trippett,S., Journal of the Chemical Society, 1964, p. 543 - 544

  摘要：

  DOI：

文献信息

• Kinetics and mechanism of gas-phase pyrolysis of ylides. Part 3.¹Thermal reactivity of<i>α</i>-carbonyl- and thiocarbonyl-stabilized methylenetriphenylphosphoranes
  作者：Rasha F. Al-Bashir、Nouria A. Al-Awadi、Osman M. E. El-Dusouqui

  DOI：10.1002/poc.1752

  日期：2011.4

  Fourteen ketone/thione‐stabilized triphenylphosphonium methylides were subjected to conventional gas‐phase and flash vacuum pyrolysis (FVP). The kinetics of the first‐order thermal gas‐phase reactions of all these compounds were investigated over 360–653 K temperature range. The values of the Arrhenius log A and energy of activation of these ylides averaged 11.52 ± 0.34 s−1 and 133.20 ± 3.14 kJ mol−1

  十四种经酮/硫酮稳定的三苯基methyl亚甲基进行了常规气相和闪蒸热解（FVP）。在360–653 K的温度范围内研究了所有这些化合物的一级热气相反应的动力学。Arrhenius log A的值 和这些酰基的活化能分别平均为11.52±0.34 s -1和133.20±3.14 kJ mol -1。对密封管（静态）和FVP的产品进行了分析和比较。提出了一种机制来解释反应产物。速率常数[ k（s -1）]计算了500 K下的底物，并用于证实所提出的热解机理，并合理化了所研究化合物的热气相反应性。版权所有©2010 John Wiley＆Sons，Ltd.

表征谱图