2',5'-difluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one

• 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'-difluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one
• 英文别名: 3-(2,5-Difluorophenyl)cyclohex-2-en-1-one
• 化学式: C₁₂H₁₀F₂O
• 分子量: 208.208
• InChiKey: FRBDYLOCRLXKHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2',5'-difluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 在 氢溴酸 、 氧气 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以97%的产率得到2',5'-diuorobiphenyl-3-ol
  参考文献：
  名称：

  在分子氧下，在存在溴化氢的催化下，铜催化的2-环己烯-1-酮的氧化芳构化为苯酚†

  摘要：

  在分子氧下，在催化量的铜盐和HBr水溶液存在下，使用2-环己烯-1-酮实现了催化氧化芳构化，从而获得了苯酚衍生物。HBr的量已成功减少到催化量，并且不需要其他添加剂（例如配体和氧化剂）以及惰性条件。可以在廉价和简单的条件下合成在所需位置具有取代基的各种单，二和三取代的苯酚。还证明了氧化芳构化/溴化顺序可得到具有过量HBr的溴酚。

  DOI：

  10.1039/c3ra43071e
• 作为产物：
  描述：

  2',5'-difluoro-2,3,4,5-tetrahydro-1,1'-biphenyl 在 eosin 作用下， 以 乙腈 为溶剂， 反应 2.33h， 以76%的产率得到2',5'-difluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one
  参考文献：
  名称：

  Visible Light Promoted Allylic C–H Oxidation

  摘要：

  A mild and efficient one-pot visible light-induced method has been developed for the allylic oxidation. The oxidation of allylic systems has played a prominent role in this context as possibly the most widely applied C-H functionalization, owing to the utility of enones. The allylic C-H oxidation is relatively simple and predictable, even on a preparative scale, because active species generated at the allylic position are stabilized by the double bond.

  DOI：

  10.5562/cca3126

文献信息

• Palladium-Catalyzed Oxidative Heck Coupling of Cyclic Enones with Simple Arenes by CH Activation
  作者：Leung Gulice Yiu Chung、Nur Asyikin Binte Juwaini、Jayasree Seayad

  DOI：10.1002/cctc.201500079

  日期：2015.4.20

  A simple catalyst system consisting of Pd(OAc)2 and 3‐nitropyridine for the aerobic oxidative Heck coupling of cyclic enones, in particular challenging unsubstituted cyclic enones, with simple arenes by CH activation was investigated. This novel method was applied to various functionalized arenes and cyclic enones and allowed the synthesis of β‐aryl cyclic enones in modest to high yields.

  研究了由Pd（OAc）2和3-硝基吡啶组成的简单催化剂体系，用于通过CH活化将简单的芳烃与环状烯酮，特别是具有挑战性的未取代环状烯酮进行好氧氧化Heck偶联。这种新方法被应用于各种功能化的芳烃和环状烯酮，并允许以中等至高收率合成β-芳基环状烯酮。
• Copper-catalyzed oxidative aromatization of 2-cyclohexen-1-ones to phenols in the presence of catalytic hydrogen bromide under molecular oxygen
  作者：Kotaro Kikushima、Yuta Nishina

  DOI：10.1039/c3ra43071e

  日期：——

  Catalytic oxidative aromatization has been achieved using 2-cyclohexen-1-ones to obtain phenol derivatives in the presence of a catalytic amount of copper salt and aqueous HBr under molecular oxygen. The amount of HBr was successfully reduced to a catalytic quantity, and the other additive such as a ligand and an oxidant as well as inert conditions were unnecessary. Various mono-, di-, and trisubstituted

  在分子氧下，在催化量的铜盐和HBr水溶液存在下，使用2-环己烯-1-酮实现了催化氧化芳构化，从而获得了苯酚衍生物。HBr的量已成功减少到催化量，并且不需要其他添加剂（例如配体和氧化剂）以及惰性条件。可以在廉价和简单的条件下合成在所需位置具有取代基的各种单，二和三取代的苯酚。还证明了氧化芳构化/溴化顺序可得到具有过量HBr的溴酚。
• Visible Light Promoted Allylic C–H Oxidation
  作者：Vishal Srivastava、Pravin K. Singh、Praveen P. Singh

  DOI：10.5562/cca3126

  日期：——

  A mild and efficient one-pot visible light-induced method has been developed for the allylic oxidation. The oxidation of allylic systems has played a prominent role in this context as possibly the most widely applied C-H functionalization, owing to the utility of enones. The allylic C-H oxidation is relatively simple and predictable, even on a preparative scale, because active species generated at the allylic position are stabilized by the double bond.