d,l-2,4-diphenylpentan-3-one | 84454-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: d,l-2,4-diphenylpentan-3-one
• 英文别名: (2R,4R)-2,4-diphenylpentan-3-one
• CAS: 84454-39-7
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: OWDHNYUHCPSQFR-ZIAGYGMSSA-N

物化性质

• 沸点：
  333.3±11.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  d,l-2,4-diphenylpentan-3-one 在 2,2,6,6-四甲基哌啶氧化物 作用下， 以 苯 为溶剂， 生成 meso-2,4-diphenylpentan-3-one
  参考文献：
  名称：

  三重自由基对与氮氧自由基的顺磁性相互作用：“抗清除”效应

  摘要：

  d,l-2,4-diphenylpentan-3-one (d,l-DPP) 在苯中的光解中产生的三重 sec-phenethyl/sec-phenethylacyl 自由基对 (RP) 的重组概率 Pr 从 0.033 增加随着稳定自由基 TEMPO 的浓度从 0 m 增加到 0.146 M，增加到 0.098。 假定的自由基清除剂的不寻常效果可以用两个过程之间的竞争来解释：硝基氧对双生自由基的化学清除，以及Genate 自由基和氮氧自由基之间的自旋交换。第二个过程显然更快，并增强了双三线态 RP 的三线态到单线态系统间的交叉。因此，随着自由基清除剂 TEMPO 浓度的增加，P 增加。这些结果揭示了一种特殊情况，即顺磁性清道夫，通过物理加速系统间交叉比清除速度更快，增强了三重双生对接近时的反应性。新的结果是“笼子效应”或成对自由基对的重组效率的增加。这些结果让我们可以从全新的视角看待双胞胎在均质、非粘性溶液中的笼子效应。

  DOI：

  10.1021/ja00091a059
• 作为产物：
  描述：

  meso-2,4-diphenylpentan-3-one 在 SDS micelles 作用下， 以 水 为溶剂， 生成 d,l-2,4-diphenylpentan-3-one
  参考文献：
  名称：

  Photostereoisomerization and the magnetic isotope effect

  摘要：

  The photodiastereomerization of meso- and d,1-2,4-diphenylpentan-3-one (meso-DPP and d,/-DPP, labeled and unlabeled with C-13 at the carbonyl carbon) was investigated in micellar solution to determine the probabilities of recombination of the micellized primary geminate radical pair toward formation of different combination products. A mathematical analysis is developed and employed to investigate the probabilities of formation of the combination products from the primary geminate radical pair produced by photochemical alpha-cleavage. The extent of chemical conversion, the chemical yields of combination products, and the dependence of these two observables on the application of external magnetic fields are employed to arrive at conclusions concerning the probabilities of formation of combination products from the primary radical pair. An experimental parameter, S, which is determined by the extent of diastereoisomerization as a function of conversion, was shown to be constant and obtainable with high experimental accuracy. The values of S were found to depend on the initial stereochemistry of the starting DPP. The constancy of S and the observation of different values of S for different initial substrates place strong constraints on the relationships which are possible between the probabilities of combination of the geminate radical pair. Within these constraints, several limiting cases are analyzed concerning the relationships between probabilities for combination. Further information was obtained experimentally from the measurement of C-13 isotope separation efficiencies due to the magnetic isotope effect and due to a classical (mass) isotope effect in the reaction of photodissociation at different magnetic fields. The results allow, within the confidence provided by highly accurate experimental data, the conclusion that primary geminate radical pairs of sec-phenethylacyl/sec-phenethyl radicals recombine, in micelle solutions, to regenerate the precursor substrate structure and diastereomer structure with equal probability.

  DOI：

  10.1021/j100178a002

文献信息

• Photochemistry of diastereomeric 2,4-diphenylpentan-3-ones and related ketones in "super-cage" environments provided by micelles, porous glass, and porous silica: temperature and magnetic field effects
  作者：Bruce H. Baretz、Nicholas J. Turro

  DOI：10.1021/ja00343a039

  日期：1983.3

  temperature effects (in the range 25 to -77 "C) on the product of DPP are small for photolysis in homogeneous solution, substantial variations in product ratios with variation in temperature can be achieved when the photolyses are conducted in super-cage environments. Similarly, although magnetic field effects on the product distributions are negligibly small for photolysis in homogeneous solutions, significant

  2,4-diphenylpentan-3-one (DPP)、1,3,4-triphenylbutan-2-one (TPB) 和 1,3-diphenylbutan-2- 的内消旋和 d,l 异构体的光化学一种（a-MeDBK）已在均质溶剂和“超级笼”环境中进行了研究，这些环境对双自由基对的组分的扩散位移施加了限制，从而提高了双自由基对笼反应的效率。含有胶束、多孔玻璃和多孔二氧化硅的离子去污剂溶液提供了这种超笼环境的例子。DPP 在戊烷或苯中光解的主要反应过程是脱羰，然后是 PhCHCH3 自由基的偶联 (-93%) 或歧化 (N 3%)。在超笼环境中，歧化程度显着增加，非对映异构体相互转化也是如此。C) DPP 的产物在均相溶液中的光解作用很小，当在超笼环境中进行光解时，随着温度的变化，产物比的显着变化可以实现。类似地，尽管磁场对均匀溶液中光解的产物分布的影响小到可以忽略不计，但发现在超级笼环境中