(2,2-dimesityl-1-phenylethenyl) diethyl phosphate | 184016-72-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2,2-dimesityl-1-phenylethenyl) diethyl phosphate
• 英文别名: diethyl [1-phenyl-2,2-bis(2,4,6-trimethylphenyl)ethenyl] phosphate
• CAS: 184016-72-6
• 化学式: C₃₀H₃₇O₄P
• 分子量: 492.595
• InChiKey: GTMGNDSFFRRBGC-UHFFFAOYSA-N

物化性质

• 沸点：
  543.3±50.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,2-dimesityl-1-phenylethenyl) diethyl phosphate 在 tris(p-nitrophenyl)aminium hexafluoroantimonate 作用下， 以 乙腈 为溶剂， 以41%的产率得到3-mesityl-2-phenyl-4,6,7-trimethylbenzo[b]furan
  参考文献：
  名称：

  One-electron oxidation of enol phosphates, enol phosphites and enol phosphinates. Evidence for an unprecedented P–O bond cleavage in phosphoenol radical cations in solution¹

  摘要：

  For the first time phosphoenol radical cations are generated in solution and monitored by cyclic voltammetry and EPR; the sterically congested radical cations undergo an unprecedented P-O bond cleavage, the kinetics of which are determined.

  DOI：

  10.1039/cc9960002349
• 作为产物：
  描述：

  1-苯基-2,2-二(2,4,6-三甲基苯基)乙烯醇 在 O₂⁽¹⁺⁾*AsF₆^(1-)=(O₂)AsF₆ 、 sodium hydride 作用下， 以 四氢呋喃 、 氟里昂-22 为溶剂， 反应 20.0h， 生成 (2,2-dimesityl-1-phenylethenyl) diethyl phosphate
  参考文献：
  名称：

  One-electron oxidation of enol phosphates, enol phosphites and enol phosphinates. Evidence for an unprecedented P–O bond cleavage in phosphoenol radical cations in solution¹

  摘要：

  For the first time phosphoenol radical cations are generated in solution and monitored by cyclic voltammetry and EPR; the sterically congested radical cations undergo an unprecedented P-O bond cleavage, the kinetics of which are determined.

  DOI：

  10.1039/cc9960002349

文献信息

• First Characterization of Phosphoenol Radical Cations in Solution and the Kinetics of the Mesolytic P--O Bond Cleavage in Sterically Shielded Enoxy-Phosphorus Compounds after One-Electron Oxidation.
  作者：Michael Schmittel、Jens-Peter Steffen、Armin Burghart、R. Daniel Little、Giuseppe Silvestri、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0781

  日期：——

  The new phosphoenols 1-6 and 9 have been synthesized starting from stable simple enols. Upon chemical or electrochemical oxidation, for the first time phosphoenol radical cations could be characterized in solution by cyclic voltammetry and EPR spectroscopy. The preparative one-electron oxidation of the model systems afforded the benzofurans indicating an unprecedented mesolytic P-O bond cleavage. Using cyclic voltammetry the kinetics of this step was determined in dichloromethane and acetonitrile. A rationale to account for the selectivity of the mesolytic P-O bond cleavage is given. Accordingly, reactive species P+(OEt)(2) (16) and P-.(=O)(OEt)(2) (18) can be generated selectively by mesolytic cleavage. At high scan rates, the partially reversible oxidation wave 1(.+)reversible arrow 1(++) could be monitored indicating that the dication of enol phosphate 1 is relatively stable.