2,5-bis(o-tolyl)furan

• 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(o-tolyl)furan
• 英文别名: 2,5-Bis(2-methylphenyl)furan；2,5-bis(2-methylphenyl)furan
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: HDEUVEAMTUEELS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-(2-methylphenyl)prop-2-ynoic acid 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74%的产率得到2,5-bis(o-tolyl)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

• Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence
  作者：Fabian Klukas、Alexander Grunwald、Franziska Menschel、Thomas J J Müller

  DOI：10.3762/bjoc.10.60

  日期：——

  5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira-Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active molecules all representatives are particularly interesting due to their bright blue luminescence with remarkably

  2,5-二（杂）芳基呋喃在伪五组分反应中很容易通过 Sonogashira-Glaser 偶联序列获得，然后以连续的一锅方式进行超碱介导的 (KOH/DMSO) 环化。除了天然产物和生物活性分子的直接合成之外，所有代表都特别有趣，因为它们具有非常高的量子产率的明亮蓝色发光。标题化合物的电子结构还通过 DFT 计算进行了研究。
• 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。
• Nickel catalysis synthesis of 2,5-disubstituted furans from aryl (alkyl) iodide
  作者：Zhongqiang Sun

  DOI：10.1080/10426507.2023.2249576

  日期：2024.1.2

  A new methodology using various aryl(alkyl)iodides and CaC2 as coupling partners has been developed for the successful preparation of 2,5-disubstituted furans in good to excellent yields. The broad...

  开发了一种使用各种芳基（烷基）碘化物和 CaC2 作为偶联配偶体的新方法，成功制备了 2,5-二取代呋喃，收率良好。广泛的...
• Copper-catalyzed direct synthesis of furans and thiophenes via decarboxylative coupling of alkynyl carboxylic acids with H2O or Na2S
  作者：Francis Mariaraj Irudayanathan、Gabriel Charles Edwin Raja、Sunwoo Lee

  DOI：10.1016/j.tet.2015.05.017

  日期：2015.7

  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.