2,3,5,6-Tetraphenylbenzo<1,2-b:5,4-b'>difuran | 122118-04-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2,3,5,6-Tetraphenylbenzo<1,2-b:5,4-b'>difuran
• 英文别名: 2,3,5,6-tetraphenylbenzo[1,2-b:5,4-b']difuran；2,3,5,6-Tetraphenyl-benzo[1,2-b;5,4-b']difuran；m-Benzotetraphenyl-difurfuran；2,3,5,6-tetraphenylfuro[3,2-f][1]benzofuran
• CAS: 122118-04-1
• 化学式: C₃₄H₂₂O₂
• 分子量: 462.547
• InChiKey: ZQHWIGBCFJSDNI-UHFFFAOYSA-N

物化性质

• 熔点：
  222-223 °C
• 沸点：
  430.6±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,5,6-Tetraphenylbenzo<1,2-b:5,4-b'>difuran 在 铬酸 、 溶剂黄146 作用下， 生成 1,5-dibenzoyl-2,4-bis-benzoyloxy-benzene
  参考文献：
  名称：

  �ber die Kondensation von Benzoin und Resorzin

  摘要：

  DOI：

  10.1007/bf01518492
• 作为产物：
  描述：

  4,6-二苯甲酰间苯二酚 在 吡啶 、 四丁基硫酸氢铵 、 potassium carbonate 、 甲基磺酰氯 、 potassium iodide 作用下， 以 水 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 36.0h， 生成 2,3,5,6-Tetraphenylbenzo<1,2-b:5,4-b'>difuran
  参考文献：
  名称：

  Synthesis of Substituted 2,3,5,6-Tetraarylbenzo[1,2-b:4,5-b']difurans

  摘要：

  A series of substituted 2,3,5,6-tetraarylbenzo[1,2-b:5,4-b']difurans 1 was synthesized. This synthesis is based upon the photocyclization of 2,5-dibenzoylresorcinol dibenzyl ethers to the corresponding tetrahydrobenzo[1,2-b:5,4-b']difurans. Treatment of the photoproducts with methanesulfonyl chloride in pyridine afforded 1 in overall yields ranging from 30-72%. A number of these compounds have high fluorescence quantum yields (phi(f) = 0.76-0.90), and their fluorescence spectra exhibit large solvatochromic shifts. These compounds may be suitable for use as fluorescent probes.

  DOI：

  10.1021/jo00110a038

文献信息

• Two-Step, Practical, and Diversity-Oriented Synthesis of Multisubstituted Benzofurans from Phenols through Pummerer Annulation Followed by Cross-coupling
  作者：Kei Murakami、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1246/bcsj.20140241

  日期：2014.12.15

  Practical and diversity-oriented synthesis of multisubstituted benzofurans has been accomplished from simple phenols through a Pummerer annulation/cross-coupling sequence. Operationally simple and rapid reactions of phenols with ketene dithioacetal monoxides (KDMs) with the aid of trifluoroacetic anhydride provide the corresponding 2-methylsulfanylbenzo[b]furans. The scope of the reaction encompasses phenols and KDMs having a broad range of substituents. The remaining methylsulfanyl group in the annulation products is converted to various aryl groups through cross-coupling reactions that we improved specially to this end. This two-step approach to multisubstituted benzofurans is powerful enough to synthesize highly fluorescent benzofuran derivatives as well as the naturally occurring Eupomatenoid family.

  已成功实现从简单酚类化合物合成多取代苯并呋喃的实用且多样化的合成方法，采用了Pummerer环化/交叉偶联序列。酚类与酮硫酰单氧化物（KDMs）在三氟乙酸酐的帮助下发生操作简便、迅速的反应，生成相应的2-甲基硫苯并[b]呋喃。该反应的适用范围涵盖了具有广泛取代基的酚类和KDMs。环化产物中的剩余甲基硫基团通过我们特别改进的交叉偶联反应转化为各种芳基。此两步法合成多取代苯并呋喃的能力足以合成高度荧光的苯并呋喃衍生物，以及天然存在的Eupomatenoid家族。
• Condensations of benzil with phenols and aryl ethers mediated by tin(IV) chloride pentahydrate
  作者：Brian J Morrison、Oliver C Musgrave

  DOI：10.1016/s0040-4020(02)00357-5

  日期：2002.5

  The reaction of benzil with phenol at 180°C in the presence of SnCl4·5H2O produces a benzofuran, a benzofuranol, a benzodifuran, and a benzofuranone. Anhydrous tin(IV) chloride also gives a benzofuranofuranone. Other phenols and their methyl ethers yield related products. The good yields of the benzo- and naphtho-furanones make the method an attractive alternative to the benzilic acid route to such

  在SnCl 4 ·5H 2 O存在下，苯甲腈与苯酚在180°C下反应，生成苯并呋喃，苯并呋喃醇，苯并二呋喃和苯并呋喃酮。无水氯化锡（IV）也可生成苯并呋喃呋喃酮。其他酚和它们的甲基醚产生相关的产物。苯并呋喃和萘呋喃酮的高收率使该方法成为苯甲酸方法合成此类化合物的有吸引力的替代方法。
• Modular synthesis and photophysical and electrochemical properties of 2,3,5,6-tetraaryl-substituted benzo[1,2-b:5,4-b′]difurans
  作者：Hayato Tsuji、Chikahiko Mitsui、Yoshiharu Sato、Eiichi Nakamura

  DOI：10.1002/hc.20682

  日期：——

  We developed a versatile synthesis of tetraaryl-substituted benzo[1,2-b:5,4-b′]difurans (m-BDFs) via a zinc-mediated intramolecular double cyclization reaction of 4,6-bis(phenylethynyl)-1,3-benzenediol, followed by a palladium-catalyzed cross-coupling reaction. In comparison with the corresponding benzo[1,2-b:4,5-b′]difuran (p-BDF) isomers reported previously, the m-BDFs are slightly wider between

  我们通过锌介导的 4,6-双（苯基乙炔基）-1 的分子内双环化反应开发了四芳基取代的苯并 [1,2-b:5,4-b'] 二呋喃 (m-BDF) 的多功能合成,3-苯二醇，然后是钯催化的交叉偶联反应。与之前报道的相应苯并[1,2-b:4,5-b']二呋喃 (p-BDF) 异构体相比，HOMO 和 LUMO 之间的 m-BDF 稍宽，并且能级较低前者。结构异构体之间的这些性质差异可归因于共轭类型的差异。这些化合物具有高达 1 × 10−3 cm2/Vs 的高电荷载流子迁移率，这使其成为有机电子应用的有吸引力的材料。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:316–324, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.
• A new synthetic strategy for the synthesis of bioactive stilbene dimers. A direct synthesis of amurensin H
  作者：George A. Kraus、Vinayak Gupta

  DOI：10.1016/j.tetlet.2009.10.040

  日期：2009.12

  2,3-Diarylbenzofurans are efficiently generated by the cyclization of ortho-benzyloxybenzophenones using the hindered phosphazene base P-4-t-Bu. Published by Elsevier Ltd.
• Japp; Meldrum, Journal of the Chemical Society, 1899, vol. 75, p. 1042
  作者：Japp、Meldrum

  DOI：——

  日期：——