5-(4-fluorophenyl)-2,3-diphenylfuran | 811813-14-6

• 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-fluorophenyl)-2,3-diphenylfuran
• CAS: 811813-14-6
• 化学式: C₂₂H₁₅FO
• 分子量: 314.359
• InChiKey: FRFQUSILSRYKET-UHFFFAOYSA-N

物化性质

• 沸点：
  403.5±33.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  2

反应信息

• 作为产物：
  描述：

  在 甲醇 作用下， 以 1,2-二氯乙烷 为溶剂， 以54.2 mg的产率得到5-(4-fluorophenyl)-2,3-diphenylfuran
  参考文献：
  名称：

  Successively Recycle Waste as Catalyst: A One-Pot Wittig/1,4-Reduction/Paal–Knorr Sequence for Modular Synthesis of Substituted Furans

  摘要：

  A one-pot tandem Wittig/conjugate reduction/PaalKnorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.

  DOI：

  10.1021/acs.orglett.5b00442

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。
• Brønsted Acid-Catalyzed Cycloisomerization of But-2-yne-1,4-diols with or without 1,3-Dicarbonyl Compounds to Tri- and Tetrasubstituted Furans
  作者：Srinivasa Reddy Mothe、Sherman Jun Liang Lauw、Prasath Kothandaraman、Philip Wai Hong Chan

  DOI：10.1021/jo301093f

  日期：2012.8.17

  efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH·H2O-mediated tandem alkylation/cycloisomerization of the propargylic

  描述了一种布朗斯台德酸催化的方法，该方法通过有或没有1,3-二羰基化合物的丁-2-炔基-1,4-二醇的环异构化反应有效地制备三和四取代的呋喃。通过稍微改变反应条件，利用醇类底物的正交反应模式，观察到产物选择性的差异。在室温下，p -TsOH·H 2炔丙基-1,4-二醇与β二羰基化合物的O-介导的串联烷基化/烷基环异构发现选择性发生，以提供四取代的呋喃产物。另一方面，发现将反应温度升高至80℃会导致优先的p -TsOH·H 2。O催化不饱和醇的脱水重排，并形成2,3,5-三取代的呋喃加合物。
• 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。
• Successively Recycle Waste as Catalyst: A One-Pot Wittig/1,4-Reduction/Paal–Knorr Sequence for Modular Synthesis of Substituted Furans
  作者：Long Chen、Yi Du、Xing-Ping Zeng、Tao-Da Shi、Feng Zhou、Jian Zhou

  DOI：10.1021/acs.orglett.5b00442

  日期：2015.3.20

  A one-pot tandem Wittig/conjugate reduction/PaalKnorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.