5-(4-fluorophenyl)-3-methyl-2-phenylfuran | 1443441-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(4-fluorophenyl)-3-methyl-2-phenylfuran
• CAS: 1443441-68-6
• 化学式: C₁₇H₁₃FO
• 分子量: 252.288
• InChiKey: XMXRRGWFERXUKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-氟苯基)-2-硝基乙烯 、 苯丙酮 在 叔丁基过氧化氢 、 copper(I) bromide dimethylsulfide complex 作用下， 以 癸烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到5-(4-fluorophenyl)-3-methyl-2-phenylfuran
  参考文献：
  名称：

  Regioselective Synthesis of Multisubstituted Furans via Copper-Mediated Coupling between Ketones and β-Nitrostyrenes

  摘要：

  A copper-mediated intermolecular annulation of alkyl ketones and beta-nitrostyrenes has been developed for the regioselective synthesis of multisubstituted furan derivatives in good yields. This protocol is applicable to both cyclic and acyclic ketones.

  DOI：

  10.1021/acs.joc.5b00704

文献信息

• Domino Radical Addition/Oxidation Sequence with Photocatalysis: One-Pot Synthesis of Polysubstituted Furans from α-Chloro-Alkyl Ketones and Styrenes
  作者：Shuang Wang、Wen-Liang Jia、Lin Wang、Qiang Liu、Li-Zhu Wu

  DOI：10.1002/chem.201602053

  日期：2016.9.19

  A new domino reaction has been developed that allows the combination of styrenes and α‐alkyl ketone radicals to afford a wide array of polysubstituted furans in good to excellent yields under mild and simple reaction conditions. The key to success of this novel protocol is the use of photocatalyst fac‐Ir(ppy)3 and oxidant K2S2O8. Mechanistic studies by a radical scavenger and photoluminescence quenching

  已开发出一种新的多米诺反应，该反应允许苯乙烯和α-烷基酮自由基的组合在温和简单的反应条件下以良好或优异的收率提供各种各样的多取代呋喃。该新协议成功的关键是使用光催化剂fac ‐Ir（ppy）3和氧化剂K 2 S 2 O 8。通过自由基清除剂和光致发光猝灭的机理研究表明，自由基加成/氧化途径是可行的。
• A co-operative effect of visible light photo-catalysis and CoFe₂O₄ nanoparticles for green synthesis of furans in water
  作者：Fooleswar Verma、Puneet K. Singh、Smita R. Bhardiya、Manorama Singh、Ankita Rai、Vijai K. Rai

  DOI：10.1039/c6nj04091h

  日期：——

  A novel approach to poly-functionalized furan synthesis is disclosed via oxidative decarboxylative [3+2] cycloaddition using co-operative catalysis by visible light and CoFe2O4 nanoparticles under ambient reaction conditions with water as a solvent. Although the reported method is efficient without catalyst in the presence of visible light (70% yield in 4 h at rt), the use of catalyst not only increases

  在环境反应条件下，以水为溶剂，通过可见光和CoFe 2 O 4纳米粒子的协同催化，通过氧化脱羧[3 + 2]环加成反应，公开了一种多官能化呋喃合成的新方法。尽管所报道的方法在可见光存在下不使用催化剂也是有效的（在室温4小时内产率为70％），但使用催化剂不仅可以提高产率（91％），而且可以加快转化率（在室温2小时） 。
• Copper-catalyzed regioselective synthesis of furan via tandem cycloaddition of ketone with an unsaturated carboxylic acid under air
  作者：Monoranjan Ghosh、Subhajit Mishra、Kamarul Monir、Alakananda Hajra

  DOI：10.1039/c4ob01320d

  日期：——

  A catalytic decarboxylative annulation has been developed for the regioselective synthesis of trisubstituted furans by the cycloaddition of ketones with α,β-unsaturated carboxylic acids under ambient air. A library of furan derivatives were obtained in good yields from the readily available substrates in the combination of a catalytic amount of Cu-salt and a stoichiometric amount of water. Water plays

  已经开发了一种催化脱羧环化反应，用于通过在环境空气中将酮与α，β-不饱和羧酸环加成而进行区域选择性合成三取代呋喃。在催化量的铜盐和化学计量的水的组合下，从容易获得的底物中以高收率获得了呋喃衍生物库。在此催化转化中，水起着至关重要的作用。
• Synthesis of Polysubstituted Furans via Copper-Mediated Annulation of Alkyl Ketones with α,β-Unsaturated Carboxylic Acids
  作者：Yuzhu Yang、Jinzhong Yao、Yuhong Zhang

  DOI：10.1021/ol400912v

  日期：2013.7.5

  A novel copper-mediated annulation of alkyl ketones with alpha,beta-unsaturated carboxylic acids has been accomplished. This reaction provides a facile and regio-defined method for the synthesis of 2,3,5-trisubstituted furans from simple chemical reagents.