5-(4-chlorophenyl)-2,3-diphenylfuran | 60355-38-6

• 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: 5-(4-chlorophenyl)-2,3-diphenylfuran
• 英文别名: 5-(4-chloro-phenyl)-2,3-diphenyl-furan
• CAS: 60355-38-6
• 化学式: C₂₂H₁₅ClO
• 分子量: 330.813
• InChiKey: GNXSILSSRHDRAW-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  427.9±33.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(4-chloro-phenyl)-1,2-diphenyl-but-2-ene-1,4-dione 在 四碘化二磷 作用下， 以 氯仿 为溶剂， 反应 0.33h， 以70%的产率得到5-(4-chlorophenyl)-2,3-diphenylfuran
  参考文献：
  名称：

  Demirdji, S. H.; Haddadin, M. J.; Issidorides, C. H., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 495 - 496

  摘要：

  DOI：

文献信息

• X-ray Absorption and Electron Paramagnetic Resonance Guided Discovery of the Cu-Catalyzed Synthesis of Multiaryl-Substituted Furans from Aryl Styrene and Ketones Using DMSO as the Oxidant
  作者：Yong Wu、Zhiyuan Huang、Yi Luo、Dong Liu、Yi Deng、Hong Yi、Jyh-Fu Lee、Chih-Wen Pao、Jeng-Lung Chen、Aiwen Lei

  DOI：10.1021/acs.orglett.7b00865

  日期：2017.5.5

  serving not only as a solvent but also as an oxidant to promote the oxidation of Cu(I) to Cu(II) has been demonstrated. X-ray absorption and electron paramagnetic resonance evidence revealed a single-electron redox process where DMSO could oxidize Cu(I) to Cu(II). The novel discovery guided the rational design of copper-catalyzed oxidative cyclization of aryl ketones with styrenes to furans, providing a new

  已经证明了DMSO的第一个例子，其不仅用作溶剂而且用作促进Cu（I）氧化成Cu（II）的氧化剂。X射线吸收和电子顺磁共振证据表明，单电子氧化还原过程中DMSO可以将Cu（I）氧化为Cu（II）。这项新发现指导了铜催化芳基酮与苯乙烯的氧化环化反应成呋喃的合理设计，为从廉价且容易获得的起始原料合成多芳基取代的呋喃提供了一种新方法。
• 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。
• Radical Based Strategy toward the Synthesis of 2,3-Dihydrofurans from Aryl Ketones and Aromatic Olefins
  作者：Togati Naveen、Rajesh Kancherla、Debabrata Maiti

  DOI：10.1021/ol502688r

  日期：2014.10.17

  with a wide range of aromatic olefins has been developed. This strategy allowed convenient access to 2,3-dihydrofuran derivatives. The versatility of the protocol is shown by synthesizing α-methyl dihydrofurans, which serve as an intermediate for the synthesis of vitamin B1. In addition, the applicability of the protocol in conjugated systems is demonstrated. A radical pathway was presumed and supported

  已经开发了铜介导的芳族酮与多种芳族烯烃的环化。该策略允许方便地获得2，3-二氢呋喃衍生物。该协议的多功能性通过合成α-甲基二氢呋喃显示出来，α-甲基二氢呋喃用作维生素B1的合成中间体。此外，还证明了该协议在共轭系统中的适用性。假定并支持自由基途径用于芳基酮与烯烃的环化。
• Base-catalysed [3 + 2] cycloaddition of propargylamines and aldehydes to substituted furans
  作者：Jinhai Shen、Jing Zhao、Bing Hu、Yangxin Chen、Longqiao Wu、Qihua You、Li Zhao

  DOI：10.1039/c7gc03618c

  日期：——

  A base-catalysed [3 + 2] cycloaddition reaction of propargylamines and aldehydes for the regiospecific synthesis of substituted furans under metal-free conditions is developed. Propargylamines are used as allenyl anion equivalents and applied in [3 + 2] cycloaddition reactions with aldehydes. Various substituted furans are provided up to 91% yield for 28 examples.

  开发了在无金属条件下炔丙基胺和醛的碱催化[3 + 2]环加成反应，用于取代呋喃的区域特异性合成。炔丙基胺用作烯基阴离子的等价物，并用于与醛的[3 + 2]环加成反应中。对于28个实例，提供了高达91％产率的各种取代呋喃。