2'-fluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one | 1284129-39-0

• 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'-fluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one
• 英文别名: 3-(2-Fluorophenyl)cyclohex-2-en-1-one
• CAS: 1284129-39-0
• 化学式: C₁₂H₁₁FO
• 分子量: 190.217
• InChiKey: DKHRECZLOVECNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2'-fluoro-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 以 N-甲基吡咯烷酮 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 2'-fluoro-[1,1'-biphenyl]-3-ol
  参考文献：
  名称：

  环己烯酮的有氧氧化 Heck/脱氢反应：有效获得间位取代酚

  摘要：

  争夺（间）位：一种新型双阳离子钯（II）催化剂，采用 6,6'-二甲基-2,2'-联吡啶配体，促进环己烯酮的有氧氧化 Heck 偶联和脱氢反应。这些反应可以以一锅法顺序组合，以实现间位取代酚的直接合成（参见方案）。

  DOI：

  10.1002/anie.201209457
• 作为产物：
  描述：

  2'-fluoro-2,3,4,5-tetrahydro-1,1'-biphenyl 在 eosin 作用下， 以 乙腈 为溶剂， 反应 1.33h， 以78%的产率得到2'-fluoro-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。
• Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones
  作者：Shaikh Samser、Priyabrata Biswal、Sushanta Kumar Meher、Krishnan Venkatasubbaiah

  DOI：10.1039/d0ob02515a

  日期：——

  One-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol result in the formation of 1,5-diketone products. This simple one-pot method avoids the use of highly electrophilic vinyl ketones.

  报道了使用钯从烯丙醇和酮一锅法合成罗宾逊环化的3-芳基-环己烯酮。烯丙醇C1位置的长链脂族或芳基取代导致形成1,5-二酮产物。这种简单的一锅法避免了使用高度亲电的乙烯基酮。
• Pd-Diimine: A Highly Selective Catalyst System for the Base-Free Oxidative Heck Reaction
  作者：Aditya L. Gottumukkala、Johannes F. Teichert、Dorus Heijnen、Niek Eisink、Simon van Dijk、Catalina Ferrer、Adri van den Hoogenband、Adriaan J. Minnaard

  DOI：10.1021/jo101942f

  日期：2011.5.6

  Pd(OAc)(2)/3 is an efficient catalyst system for the base-free oxidative Heck reaction that outperforms the currently available catalysts for the more challenging substrates studied. The catalyst system is highly selective, and works at room temperature with dioxygen as the oxidant.