2,5-bis(4-ethylphenyl)furan | 1376960-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,5-bis(4-ethylphenyl)furan
• 英文别名: 2,5-bis(p-ethylphenyl)furan
• CAS: 1376960-11-0
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: NDOBJGGCBRIBIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-(4-乙基苯基)丙炔酸 在 copper(l) iodide 、 1,10-菲罗啉 、 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以88%的产率得到2,5-bis(4-ethylphenyl)furan
  参考文献：
  名称：

  Copper-catalyzed direct synthesis of furans and thiophenes via decarboxylative coupling of alkynyl carboxylic acids with H2O or Na2S

  摘要：

  2,5-Diaryl-substituted furans were synthesized from the copper-catalyzed decarboxylative coupling of aryl-substituted aryl propiolic acids in the presence of H2O. The homocoupling of alkynyl carboxylic acids provided 1,4-diaryldiynes, which then reacted with H2O to give the desired furans through cyclization. Addition of the copper catalyst was critical, and the addition of a ligand increased the yield of products in both the homocoupling and cyclization reactions. In addition, thiophenes could be obtained when the reaction was conducted in the presence of Na2S. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.017

文献信息

• A general approach to arylated furans, pyrroles, and thiophenes
  作者：Qingwei Zheng、Ruimao Hua、Jianhua Jiang、Lei Zhang

  DOI：10.1016/j.tet.2014.09.025

  日期：2014.11

  A general and practical synthetic method for aryl-substituted five-membered heterocycles has been developed. In the presence of KOH (30%), 1,4-diaryl-1,3-butadiynes undergo the cyclocondensation reaction with water, primary amines, and Na2S·9H2O in DMSO at 80 °C to afford 2,5-diarylfurans, 1,2,5-trisubstituted pyrroles, and 2,5-diarylthiophenes in good to high yields. Further studies have disclosed

  已经开发了用于芳基取代的五元杂环的通用且实用的合成方法。在KOH（30％）存在下，1,4-二芳基-1,3-丁二炔与水，伯胺和Na 2 S·9H 2 O在DMSO中于80°C进行环缩合反应，得到2,5 -二芳基呋喃，1,2,5-三取代的吡咯和2,5-二芳基噻吩的产率高至高。进一步的研究表明，芳烃取代的五元杂环还可以通过一锅，两步策略由DMSO中的末端炔烃首先由CuCl催化，然后通过添加KOH促进1的环缩合而合成。原位生成3-丁二炔。
• Copper(I)-Catalyzed Synthesis of 2,5-Disubstituted Furans and Thiophenes from Haloalkynes or 1,3-Diynes
  作者：Huanfeng Jiang、Wei Zeng、Yibiao Li、Wanqing Wu、Liangbing Huang、Wei Fu

  DOI：10.1021/jo300692d

  日期：2012.6.1

  A regioselective synthesis of 2,5-disubstituted furans using copper(I) catalyst from haloalkynes in a one-pot procedure has been reported. This chemistry proceeds through the hydration reaction of 1,3-diynes, which can be readily prepared from the coupling reaction of haloalkynes in the presence of CuI. The procedure also can be used for the facile synthesis of 2,5-disubstituted thiophenes.

  已经报道了使用一锅法从卤代炔烃中使用铜（I）催化剂进行区域选择性合成2,5-二取代的呋喃。该化学过程是通过1,3-二炔的水合反应进行的，这很容易从卤代炔在CuI存在下的偶联反应中制备。该方法还可用于2，5-二取代噻吩的简便合成。
• Gold-catalyzed formation of C–O and C–C bonds: An efficient domino reaction synthesis of functionalized furans
  作者：Pengfeng Guo

  DOI：10.1016/j.catcom.2015.04.030

  日期：2015.8

  An efficient gold-catalyzed domino reaction for the synthesis of furan derivatives from haloalkynes has been described. This transformation has provided a new route for the formation of C-O and C-C bonds that prepare functionalized furans. (C) 2015 Elsevier B.V. All rights reserved.