2,5-bis(triphenylphosphoranylidene)-1,6-diphenylhexane-1,3,4,6-tetraone

• 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: 2,5-bis(triphenylphosphoranylidene)-1,6-diphenylhexane-1,3,4,6-tetraone
• 英文别名: 1,6-Diphenyl-2,5-bis(triphenyl-lambda5-phosphanylidene)hexane-1,3,4,6-tetrone；1,6-diphenyl-2,5-bis(triphenyl-λ5-phosphanylidene)hexane-1,3,4,6-tetrone
• 化学式: C₅₄H₄₀O₄P₂
• 分子量: 814.857
• InChiKey: RNNVZZOOKPEWBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  60
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis(triphenylphosphoranylidene)-1,6-diphenylhexane-1,3,4,6-tetraone 在 二氧化氮 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到苯甲酰腈
  参考文献：
  名称：

  稳定的磷叶立德与二氧化氮反应

  摘要：

  室温下稳定的叶立德 14-23 与过量的 NO2 在 CH2Cl2 中的反应根据起始叶立德的结构给出不同的结果。单酰基叶立德 14-16 与 Ph3PO·HNO3 (24) 一起得到相应的 α-氧代腈 4，这是首次得到充分表征。在相同条件下，叶立德 18 得到 2,4-二硝基苯甲腈 (26)、Ph3PO 和苯甲酸。检查的其他叶立德与各种其他产品都给出了 24。

  DOI：

  10.1002/(sici)1099-0690(199901)1999:1<251::aid-ejoc251>3.0.co;2-m
• 作为产物：
  描述：

  草酰氯 、 苯甲酰基亚甲基三苯基膦 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以64%的产率得到2,5-bis(triphenylphosphoranylidene)-1,6-diphenylhexane-1,3,4,6-tetraone
  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

文献信息

• Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide
  作者：R. Alan Aitken、Nazira Karodia

  DOI：10.1002/(sici)1099-0690(199901)1999:1<251::aid-ejoc251>3.0.co;2-m

  日期：1999.1

  The reaction of the stabilised ylides 14–23 with an excess of NO2 in CH2Cl2 at room temperature gives different results depending on the structure of the starting ylide. The monacyl ylides 14–16 give the corresponding α-oxo nitriles 4 together with Ph3PO · HNO3 (24) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4-dinitrobenzonitrile (26), Ph3PO

  室温下稳定的叶立德 14-23 与过量的 NO2 在 CH2Cl2 中的反应根据起始叶立德的结构给出不同的结果。单酰基叶立德 14-16 与 Ph3PO·HNO3 (24) 一起得到相应的 α-氧代腈 4，这是首次得到充分表征。在相同条件下，叶立德 18 得到 2,4-二硝基苯甲腈 (26)、Ph3PO 和苯甲酸。检查的其他叶立德与各种其他产品都给出了 24。
• Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 8. Preparation of symmetrical and unsymmetrical 1,3-diynes from alkynoyl ylides and oxalyl diylides
  作者：R. Alan Aitken、Hugues Hérion、Caroline E. R. Horsburgh、Nazira Karodia、Shirley Seth

  DOI：10.1039/p19960000485

  日期：——

  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.