1-ethyl-4-(phenylbuta-1,3-diyn-1-yl)benzene | 1402831-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-ethyl-4-(phenylbuta-1,3-diyn-1-yl)benzene
• 英文别名: 1-Ethyl-4-(4-phenylbuta-1,3-diynyl)benzene；1-ethyl-4-(4-phenylbuta-1,3-diynyl)benzene
• CAS: 1402831-16-6
• 化学式: C₁₈H₁₄
• 分子量: 230.309
• InChiKey: ZAAHXVGFVHHWJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-乙基苯乙炔 、 苯乙炔 在 三乙胺 作用下， 以 水 、 异丙醇 为溶剂， 以58 %的产率得到1-ethyl-4-(phenylbuta-1,3-diyn-1-yl)benzene
  参考文献：
  名称：

  一种可回收的Cu@C2N纳米催化剂应用于炔烃的转化：可通过pH值切换获得酮和1,3-二炔

  摘要：

  开发合成工艺简单、高效、不含贵金属的多相催化剂在合成化学中具有重要价值。迄今为止，很少考虑多相催化剂在不同酸性和碱性条件下的性能。在此，我们展示了一种多功能Cu@C 2 N催化剂，用于炔烃的pH可切换水合和Glaser-Hay反应，最大产率分别达到92%和95%。高效的转化源于强大的金属-载体协同效应，因为C 2 N载体吸附反应底物，而Cu金属很好地活化反应底物，协同促进炔烃的转化。此外，Cu@C 2 N催化剂表现出良好的底物兼容性和可回收性，可以简单地回收并重复使用五次，而不会显着损失其催化活性。此外，Cu@C 2 N催化剂具有丰富的酸性和碱性位点，C 2 N可以很好地稳定Cu的价态和分散形式。这项工作证明了C 2 N基催化剂在催化领域的成功应用。有机合成领域，并为设计低成本、适应性广、环境友好的催化系统指出了方向。

  DOI：

  10.1039/d3gc04314b

文献信息

• Copper (II) catalyzed homocoupling and heterocoupling of terminal alkynes
  作者：Maria Katrina Holganza、Leslie Trigoura、Suzanne Elfarra、Yoona Seo、Jeremy Oiler、Yalan Xing

  DOI：10.1016/j.tetlet.2019.03.057

  日期：2019.4

  Cu(OTf)2 catalyzed homo– and heterocoupling of aromatic and aliphatic terminal alkynes has been developed. Symmetric and unsymmetric 1,3-diynes have been synthesized in good yields under an aerobic condition in the presence of an organic base DBU. This reaction features mild conditions, a wide substrate scope, and excellent functional group compatibility.

  已经开发出Cu（OTf）2催化的芳香族和脂肪族末端炔烃的均相和杂偶合。在有机碱DBU的存在下，好氧条件下合成了对称和不对称的1,3-二炔。该反应具有温和的条件，广泛的底物范围和出色的官能团相容性。
• Highly efficient synthesis of unsymmetrical 1,3-diynes from organoalane reagents and alkynyl bromides mediated by a nickel catalyst
  作者：Song Mo、Xue-Bei Shao、Gang Zhang、Qing-Han Li

  DOI：10.1039/c7ra02758c

  日期：——

  Highly efficient and simple cross-coupling reactions of alkynylbromides with organoalane reagents for the synthesis of unsymmetrical 1,3-diynes derivatives using Ni(OAc)2 (2–5 mol%)/(o-furyl)3P (4–10 mol%) as a catalyst are reported. Excellent yields (up to 94%) were obtained for a wide range of substrates at rt or 60 °C for 2–3 h in Et2O or toluene.

  炔基溴化物与有机烷烃试剂的高效简单交叉偶联反应，用于使用Ni（OAc）2（2–5 mol％）/（o-呋喃基）3 P（4–10 mol ）合成不对称的1,3-二炔衍生物报道了作为催化剂的％。在Et 2 O或甲苯中，在rt或60°C下进行2–3 h的各种底物，均可获得优异的收率（高达94％）。
• Copper(I) Hydroxyapatite Catalyzed Sonogashira Reaction of Alkynes with Styrenyl Bromides. Reaction of <i>cis</i>-Styrenyl Bromides Forming Unsymmetric Diynes
  作者：Debasree Saha、Tanmay Chatterjee、Manabendra Mukherjee、Brindaban C. Ranu

  DOI：10.1021/jo3015819

  日期：2012.10.19

  terminal alkynes and styrenyl bromides has been achieved under the catalysis of hydroxyapatite-supported copper(I). The trans-styrenyl bromides produce the usual trans-enyne products, whereas the cis-styrenyl bromides lead to unsymmetric 1,3-diynes by the cross coupling of terminal alkyne and the alkyne generated from the cis-styrenyl bromide. A series of trans-enynes and unsymmetric 1,3-diynes have been synthesized

  在羟基磷灰石负载的铜（I）的催化下，实现了末端炔烃和苯乙烯基溴化物的有效Sonogashira偶联。所述反式-styrenyl溴化物产生通常的反式-enyne产品，而顺式-styrenyl溴化物导致由末端炔的交叉耦合，并从所产生的炔不对称1,3-二炔顺-styrenyl溴化物。通过该方案已经合成了一系列反式-烯炔和不对称的1，3-二炔。
• Enaminone ligand-assisted homo- and cross-coupling of terminal alkynes under mild conditions
  作者：Yunyun Liu、Chunping Wang、Xiaobo Wang、Jie-Ping Wan

  DOI：10.1016/j.tetlet.2013.05.063

  日期：2013.7

  Copper-catalyzed oxidative coupling reactions of terminal alkynes have been performed at room temperature by using enaminone as effective ligand. Both symmetrical and unsymmetrical 1,3-diynes bearing various functional groups have been synthesized in moderate to excellent yields via homo- and cross-coupling reactions. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.