2,5-bis(3-chlorophenyl)furan | 1222-59-9

• 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(3-chlorophenyl)furan
• CAS: 1222-59-9
• 化学式: C₁₆H₁₀Cl₂O
• 分子量: 289.161
• InChiKey: JPXZHTXDGIPCRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-(3-chlorophenyl)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67%的产率得到2,5-bis(3-chlorophenyl)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

• 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。
• Mono- and Biscouplings Using Triarylbismuths for the Atom-Efficient Arylations of Functionalized Furans under Palladium Catalysis
  作者：Maddali Rao、Dheeraj Awasthi、Jalindar Talode

  DOI：10.1055/s-0032-1316567

  日期：2012.8

  Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one

  钯催化的功能化溴呋喃与三芳基铋的交叉偶联反应已被描述用于功能化芳基呋喃系统的原子经济合成。使用三芳基铋与各种 2-溴呋喃和 2,5-二溴呋喃的偶联反应顺利进行，在短反应时间（1 小时）内以高产率得到相应的 2-芳基呋喃和 2,5-二芳基呋喃。