2-苯基-3-(对甲氧基苯基)苯并呋喃 | 25433-77-6

• 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
• 中文名称: 2-苯基-3-(对甲氧基苯基)苯并呋喃
• 英文名称: 2-phenyl-3-(p-methoxyphenyl)benzofuran
• 英文别名: 3-(4-methoxyphenyl)-2-phenylbenzofuran；3-(4-Methoxyphenyl)-2-phenyl-1-benzofuran
• CAS: 25433-77-6
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: SUGGHVBAOGPICW-UHFFFAOYSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  429.3±40.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苯基-3-(对甲氧基苯基)苯并呋喃 以 四氢呋喃 为溶剂， 反应 216.0h， 生成 6-Methoxy-13-oxa-indeno[1,2-l]phenanthrene
  参考文献：
  名称：

  Photochemistry of vinyl halides. Formation of benzofurans by photolysis of .beta.-(o-methoxyphenyl)vinyl bromides

  摘要：

  DOI：

  10.1021/jo00339a012
• 作为产物：
  描述：

  1-(methoxymethoxy)-2-(phenylethynyl)benzene 在 盐酸 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 三苯基膦氯金 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 2-苯基-3-(对甲氧基苯基)苯并呋喃
  参考文献：
  名称：

  双光氧化还原/金催化芳基重氮盐对邻炔基苯酚的芳香环化：苯并呋喃的灵活合成

  摘要：

  描述了一种通过双重光氧化还原/金催化的芳基重氮盐对邻炔基苯酚进行芳基环化的新方法。反应在室温下在没有碱和/或添加剂的情况下平稳进行，并为苯并呋喃衍生物提供了一种有效的方法。转换的范围很广，并讨论了局限性。提议该反应通过光还原还原产生的乙烯基金（III）中间体进行，该中间体经过还原消除以提供杂环偶联加合物。

  DOI：

  10.1021/acs.joc.6b01060

文献信息

• Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions
  作者：Nataliya A. Markina、Yu Chen、Richard C. Larock

  DOI：10.1016/j.tet.2013.02.003

  日期：2013.4

  efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent

  利用Sonogashira反应条件，已经开发出一种有效的一锅法，由市售的2-碘苯酚，末端乙炔和芳基碘化物合成2,3-二取代的苯并[b]呋喃。在将2-碘苯酚与末端炔烃进行最初的Sonogashira偶联后，涉及芳基碘化物的环化反应可提供2,3-二取代的苯并[b]呋喃，收率非常好。微波辐射的使用缩短了反应时间并使副产物最小化。该方法对于构建高度取代的苯并[b]呋喃及其类似物的库特别有用。
• A one-pot domino C–H, C–C activation in coumarins: a fast track to 2,3-diaryl benzo[<i>b</i>]furans
  作者：Mehdi Khoobi、Fatemeh Molaverdi、Farnaz Jafarpour、Masoumeh Abbasnia、Maciej Kubicki、Abbas Shafiee

  DOI：10.1039/c5cc01427a

  日期：——

  An approach to synthesize 2,3-diaryl benzo[b]furans using coumarins and aryl bromides is developed.

  使用香豆素和芳基溴化物合成2,3-二芳基苯并呋喃的方法已经开发。
• Gold‐Catalyzed 1,2‐Dicarbofunctionalization of Alkynes with Organohalides**
  作者：Shashank P. Sancheti、Yukta Singh、Manoj V. Mane、Nitin T. Patil

  DOI：10.1002/anie.202310493

  日期：2023.10.16

  The first report of 1,2-dicarbofunctionalization of alkynes using organohalides as coupling partners in the field of gold catalysis has been presented. Mechanistic investigations, including NMR, tandem mass spectrometry and DFT studies, reveal that an oxidative addition/carbophilic activation pathway is preferred over the migratory insertion/cis-trans isomerization pathway.

  首次报道了金催化领域中使用有机卤化物作为偶联伙伴的炔烃 1,2-二碳官能化反应。包括 NMR、串联质谱和 DFT 研究在内的机理研究表明，氧化加成/亲碳活化途径优于迁移插入/顺反异构化途径。
• Synthesis of Conformationally Restricted 2,3-Diarylbenzo[<i>b</i>]furan by the Pd-Catalyzed Annulation of <i>o</i>-Alkynylphenols:  Exploring a Combinatorial Approach
  作者：Youhong Hu、Kenneth J. Nawoschik、Yun Liao、Jian Ma、Reza Fathi、Zhen Yang

  DOI：10.1021/jo0303160

  日期：2004.4.1

  The palladium/bpy-catalyzed annulation of o-alkynylphenol with various aryl halides to generate diversified 2,3-diarylbenzo[b]furan is herein described. This method provides an efficient synthetic pathway for the combinatorial synthesis of conformationally restricted 2,3-diarylbenzo[b]furan for drug discovery.
• Competition of Mechanisms in the Photochemical Cleavage of the C−X Bond of Aryl-Substituted Vinyl Halides
  作者：Carlo Galli、Patrizia Gentili、Alessandra Guarnieri、Shinjiro Kobayashi、Zvi Rappoport

  DOI：10.1021/jo981164p

  日期：1998.12.1

  The photolysis of aryl halides causes homolysis of the carbon-halogen bond and formation of aryl radicals. In contrast, photolysis of vinyl halides can induce both heterolysis of the C-X bond, thereby generating vinyl cations, and homolysis, giving vinyl radicals. Examples of this competition among pathways is reported here for three vinylic precursors, namely, 1,2,2-triphenylbromoethene (1), 1-phenyl-2,2-bis(o-methoxyphenyl)-1-bromoethene (11), and beta-bromostyrene (19). Incursion of the photoinduced S(RN)1 process, through the intermediacy of the vinyl radical, is verified in the presence of reducing nucleophiles, such as the enolate ions of ketones, and in part with (EtO)(2)PO-. Conversely, incursion of the heterolytic path, and intermediacy of the vinyl cation, occurs in the presence of weak electron-donor anions, such as NO2-, N-3(-), and Cl-. The vinyl cation produced from 19, which is less stable than those derived from 1 and 11, gives phenylacetylene via an E1-type elimination. An estimate is provided for the intramolecular rate of interception of the vinyl cation derived from 11 by the ortho-methoxy groups of the beta-o-anisyl substituents. Finally, evidence against a photoinduced electron transfer from RO- ions to vinyl halide 1 is presented.