1-(4-methoxyphenyl)-4-(o-toluenyl)buta-1,3-diyne | 1217554-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)-4-(o-toluenyl)buta-1,3-diyne
• CAS: 1217554-47-6
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: VPAJWYFDNAWNKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  3-(4-甲氧基苯基)丙酸 、 2-乙炔基甲苯 在 copper(l) iodide 、 1,10-菲罗啉 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以49%的产率得到1-(4-methoxyphenyl)-4-(o-toluenyl)buta-1,3-diyne
  参考文献：
  名称：

  铜催化的丙酸与末端炔烃的脱羧交叉偶联

  摘要：

  开发了铜催化的丙酸与末端炔烃的脱羧交叉偶联反应，导致在温和条件下产生不对称的1,3-共轭二炔。该方法提供了用于sp-sp键形成的新颖的脱羧交叉偶联。与有机卤化物相比，这种方法仅产生二氧化碳作为副产物。

  DOI：

  10.1016/j.tetlet.2009.12.138

文献信息

• Cu-Based ternary deep eutectic solvents for homo- and cross-coupling reactions of terminal alkynes
  作者：Weixu Lu、Xiaoqiang Yu、Ming Bao

  DOI：10.1039/d3gc01166f

  日期：——

  In this paper, a set of copper-based ternary deep eutectic solvents (Cu-DESs) is synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occur under exogenous-ligand-free, base-free, and additive-free conditions and provide satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times and the only by-product

  本文合成了一套铜基三元低共熔溶剂（Cu-DES），并将其应用于末端炔烃的格拉泽型均聚和交叉偶联。这些反应在无外源配体、无碱和无添加剂的条件下发生，并在温和条件下提供令人满意的优异产率（高达 99%）。Cu-DES可以回收8次，唯一的副产物是水，完全符合绿色化学原理。
• The Inorganic Ligand‐Supported Copper Catalyst Catalyzing Alkyne Coupling Reactions
  作者：Mengjie Deng、Ya Xie、Junting Zhou、Da Shi、Sheng Han、Linke Wu、Han Yu

  DOI：10.1002/ejoc.202301238

  日期：2024.6.3

  Glaser‐coupled synthesized 1,3‐diyne can participate in the generation of conjugated polymers and is now widely used in organic and polymer synthesis. Currently, the catalysts in coupling are mostly based on the complexation of noble metals with complex organic ligands, which inevitably increases the research cost and storage difficulty. However, polymetallic oxides (POMs), with acidic and redox properties, can be used as excellent inorganic ligands with low cost and easy storage. In this work, we have synthesized copper catalysts 1, (NH4)4[CuMo6O18(OH)6] with polymetallic oxides as inorganic ligands in a facile way and applied them in the coupling of alkynes to obtain (non)symmetrical conjugated 1,3‐diynes in high yields without bases, finally proposing a reasonable reaction path. In addition, the catalyst showed good tolerance to a variety of different groups, further demonstrating its excellent catalytic activity. It is worth mentioning that the catalyst maintained its good structure and activity after six cycles, demonstrating its promising potential for industrial applications. Thus, this paper provides a new strategy for the preparation of (un)symmetrical diynes using polymetallic oxides of Cu as catalysts, and also demonstrates the potential of multi‐acid catalysts for organocatalytic applications.