diphenyl 1-phenylvinylphosphonate | 32187-40-9

• 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: diphenyl 1-phenylvinylphosphonate
• 英文别名: Diphenyl-(1-phenyl-vinyl)-phosphonat；Diphenyl (1-phenylethenyl)phosphonate；1-diphenoxyphosphorylethenylbenzene
• CAS: 32187-40-9
• 化学式: C₂₀H₁₇O₃P
• 分子量: 336.327
• InChiKey: VXRUYIAIPGSQRY-UHFFFAOYSA-N

物化性质

• 沸点：
  473.1±28.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diphenyl 1-phenylvinylphosphonate 在 <((t-Bu)2PH)PdP(t-Bu)2>2 (pretreated with oxygen) 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以80%的产率得到(1-Phenyl-ethyl)-phosphonic acid diphenyl ester
  参考文献：
  名称：

  Palladium Catalyzed Hydrogenation of .alpha.,.beta.-Unsaturated Sulfones and Phosphonates

  摘要：

  The binuclear palladium complex, [(Bu(2)(t)PH)-PdPBu(2)(t)](2), when treated with oxygen, catalyzes the hydrogenation of the double bond of alpha,beta-unsaturated sulfones and phosphonates in THF at room temperature and 1 atm of hydrogen pressure. Saturated sulfones and phosphonates were isolated in 49-93% yields.

  DOI：

  10.1021/jo00094a001
• 作为产物：
  描述：

  反式硝基苯乙烯 、 亚磷酸二苯酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到diphenyl 1-phenylvinylphosphonate
  参考文献：
  名称：

  Synthesis of Terminal Vinylphosphonates Via Dbu-Promoted Tandem Phospha-Michael/Elimination Reactions

  摘要：

  The terminal vinylphosphonates were prepared from various beta-nitroolefins and phosphites through tandem phospha-Michael/elimination reactions. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a variety of new vinylphosphonates were obtained in moderate to high yields under simple and mild condition. These new compounds were characterized by HRMS, H-1, C-13, and P-31 NMR techniques.

  DOI：

  10.1080/10426507.2014.906422

文献信息

• Preparation of Vinylphosphonates from Ketones Promoted by Tf₂O
  作者：Nana Xin、Yongzheng Lv、Yongjian Lian、Zhu Lin、Xian-Qiang Huang、Chang-Qiu Zhao、Yanlan Wang

  DOI：10.1021/acs.joc.2c02563

  日期：2023.3.3

  conditions. Both aryl and alkyl ketones could perform smoothly to give vinyl phosphonates in high to excellent yields. In addition, the reaction was easy to carry out and easy to scale up. Mechanistic studies suggested that this transformation might involve nucleophilic vinylic substitution or a nucleophilic addition–elimination mechanism.

  公开了一种有效促进酮磷酸化的三氟甲磺酸酐，并在无溶剂和无金属条件下制备了乙烯基磷化合物。芳基酮和烷基酮都可以顺利地以高收率得到膦酸乙烯酯。此外，该反应易于进行且易于放大。机理研究表明，这种转化可能涉及亲核乙烯基取代或亲核加成-消除机制。
• Palladium Catalyzed Hydrogenation of .alpha.,.beta.-Unsaturated Sulfones and Phosphonates
  作者：In Sik Cho、Howard Alper

  DOI：10.1021/jo00094a001

  日期：1994.7

  The binuclear palladium complex, [(Bu(2)(t)PH)-PdPBu(2)(t)](2), when treated with oxygen, catalyzes the hydrogenation of the double bond of alpha,beta-unsaturated sulfones and phosphonates in THF at room temperature and 1 atm of hydrogen pressure. Saturated sulfones and phosphonates were isolated in 49-93% yields.
• Synthesis of Terminal Vinylphosphonates Via Dbu-Promoted Tandem Phospha-Michael/Elimination Reactions
  作者：Hui-Xuan Chen、Lin-Jie Huang、Jin-Biao Liu、Jiang Weng、Gui Lu

  DOI：10.1080/10426507.2014.906422

  日期：2014.12.2

  The terminal vinylphosphonates were prepared from various beta-nitroolefins and phosphites through tandem phospha-Michael/elimination reactions. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a variety of new vinylphosphonates were obtained in moderate to high yields under simple and mild condition. These new compounds were characterized by HRMS, H-1, C-13, and P-31 NMR techniques.