1-(2-bromophenyl)-2-phenylpropan-2-ol | 1179616-19-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2-bromophenyl)-2-phenylpropan-2-ol
• CAS: 1179616-19-3
• 化学式: C₁₅H₁₅BrO
• mdl: MFCD12723233
• 分子量: 291.187
• InChiKey: UQWFMVSRSOCGDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-bromophenyl)-2-phenylpropan-2-ol 在 硫酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.17h， 以95%的产率得到(E)-1-bromo-2-(2-methyl-2-phenylethenyl)benzene
  参考文献：
  名称：

  苯乙烯与芳基重氮盐的热诱导碳羟基化。

  摘要：

  苯乙烯与芳基重氮盐的自由基碳羟基化已在温和的热条件下实现。可以耐受多种芳基重氮盐，并且基于自由基-极性交叉机制的反应原理可以扩展到碳醚化以及产生茋的Meerwein芳基化的两步、无金属变体。

  DOI：

  10.1002/anie.201601656
• 作为产物：
  描述：

  2-溴苯基丙酮 、 苯基溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以74%的产率得到1-(2-bromophenyl)-2-phenylpropan-2-ol
  参考文献：
  名称：

  Manganese Catalysts for C−H Activation: An Experimental/Theoretical Study Identifies the Stereoelectronic Factor That Controls the Switch between Hydroxylation and Desaturation Pathways

  摘要：

  We describe competitive C-H bond activation chemistry of two types, desaturation and hydroxylation, using synthetic manganese catalysts with several substrates. 9,10-Dihydrophenanthrene (DHP) gives the highest desaturation activity, the final products being phenanthrene (P1) and phenanthrene 9,10-oxide (P3), the latter being thought to arise from epoxidation of some of the phenanthrene. The hydroxylase pathway also occurs as suggested by the presence of the dione product, phenanthrene-9,10-dione (P2), thought to arise from further oxidation of hydroxylation intermediate 9-hydroxy-9,10-dihydrophenanthrene. The experimental work together with the density functional theory (DFT) calculations shows that the postulated Mn oxo active species, [Mn(O)(tpp)(Cl)] (tpp = tetraphenylporphyrin), can promote the oxidation of dihydrophenanthrene by either desaturation or hydroxylation pathways. The calculations show that these two competing reactions have a common initial step, radical H abstraction from one of the DHP sp(3) C-H bonds. The resulting Mn hydroxo intermediate is capable of promoting not only OH rebound (hydroxylation) but also a second H abstraction adjacent to the first (desaturation). Like the active Mn-V=O species, this Mn-IV-OH species also has radical character on oxygen and can thus give H abstraction. Both steps have very low and therefore very similar energy barriers, leading to a product mixture. Since the radical character of the catalyst is located on the oxygen p orbital perpendicular to the Mn-IV-OH plane, the orientation of the organic radical with respect to this plane determines which reaction, desaturation or hydroxylation, will occur. Stereoelectronic factors such as the rotational orientation of the OH group in the enzyme active site are thus likely to constitute the switch between hydroxylase and desaturase behavior.

  DOI：

  10.1021/ja908744w