3-(phenylbuta-1,3-diyn-1-yl)aniline | 82690-38-8

• 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: 3-(phenylbuta-1,3-diyn-1-yl)aniline
• 英文别名: 3-(4-Phenylbuta-1,3-diyn-1-yl)aniline；3-(4-phenylbuta-1,3-diynyl)aniline
• CAS: 82690-38-8
• 化学式: C₁₆H₁₁N
• 分子量: 217.27
• InChiKey: ZXCJPZATEVLOQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氨基苯乙炔 、 苯乙炔 在 copper(l) iodide 、 sodium tetrachloropalladate(II) 、 氧气 、 三乙胺 、 3-(二苯基膦)丙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以57%的产率得到3-(phenylbuta-1,3-diyn-1-yl)aniline
  参考文献：
  名称：

  Pd / Cu催化末端炔烃的交叉偶联在室温下合成不对称的1,3-二炔

  摘要：

  通过在氧存在下使用3-（二苯基膦基）丙酸作为配体，通过两个不同的末端炔烃的PdCl / CuI催化的氧化偶合，开发了一种不对称的1,3-二炔的简便实用的合成路线。该系统不仅适用于芳族炔烃，还适用于杂芳族和脂族炔烃，它们在室温下以中等至良好的收率转化成相应的不对称1,3-二炔。此外，不对称的1,3-二炔也以克为单位获得。机理研究表明，氧气在催化循环中起关键作用。

  DOI：

  10.1002/cjoc.201600197

文献信息

• Synthesis of Unsymmetrical 1,3-Diynes via Pd/Cu-Catalyzed Cross-Coupling of Terminal Alkynes at Room Temperature
  作者：Yashuai Liu、Ping Liu、Ningning Gu、Jianwei Xie、Yan Liu、Bin Dai

  DOI：10.1002/cjoc.201600197

  日期：2016.9

  A facile and practical synthetic route of unsymmetrical 1,3‐diynes via the PdCl/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3‐(diphenylphosphino)propanoic acid as a ligand in the presence of oxygen. This system is suitable for not only aromatic alkynes but also heteroaromatic and aliphatic alkynes which were transformed into the corresponding unsymmetrical

  通过在氧存在下使用3-（二苯基膦基）丙酸作为配体，通过两个不同的末端炔烃的PdCl / CuI催化的氧化偶合，开发了一种不对称的1,3-二炔的简便实用的合成路线。该系统不仅适用于芳族炔烃，还适用于杂芳族和脂族炔烃，它们在室温下以中等至良好的收率转化成相应的不对称1,3-二炔。此外，不对称的1,3-二炔也以克为单位获得。机理研究表明，氧气在催化循环中起关键作用。
• Recyclable Cu/C₃N₄ composite catalysed homo- and cross-coupling of terminal alkynes under mild conditions
  作者：Hang Xu、Keying Wu、Jing Tian、Li Zhu、Xiaoquan Yao

  DOI：10.1039/c7gc03120c

  日期：——

  for the homo- & cross-coupling of terminal alkynes. Excellent functional group tolerance and good yields were observed with oxygen as an oxidant in an isopropanol solution (or as additive) under ambient conditions. Furthermore, the composite catalyst shows good recyclability and can be recovered simply and reused several times without significant loss in its catalytic activities.

  制备了Cu / C 3 N 4复合材料，并将其用作高效和环保的末端炔烃均相和交叉偶联催化剂。在环境条件下，使用氧气作为异丙醇溶液（或作为添加剂）的氧化剂，观察到出色的官能团耐受性和良好的产率。此外，该复合催化剂显示出良好的可循环性，并且可以简单地回收并重复使用几次而不会显着降低其催化活性。
• MOF‐Supported Copper Complex‐Catalyzed Synthesis of Unsymmetrical 1,3‐Diynes Without External Additives
  作者：Deng‐Yue Zheng、Rongxian Bai、Minghao Li、Yanlong Gu

  DOI：10.1002/cctc.202200235

  日期：2022.7.7

  AbstractCu complexes supported on metal‐organic frameworks (MOFs) with N1,N1,N2,N2‐tetramethylethylenediamine (TMEDA) were prepared via post‐synthetic modification, and proved to be highly efficient for Glaser heterocoupling reactions. Compared with some referential catalysts, which were prepared by using a series of copper salts and Cu0 nanoparticles as the copper sources, the newly designed MIL‐101‐NH‐TMEDA⋅CuClx exhibited highest catalytic activity and selectivity in the model Glaser heterocoupling reaction. Much lower activity was observed with the homogeneous counterpart, TMEDA⋅CuCl4. Intriguingly, the Glaser heterocoupling reactions over MIL‐101‐NH‐TMEDA⋅CuClx catalyst can be conducted without adding external ligands, base, or acid, which are always necessary in the previously reported systems. The dense catalytic active sites in the MOF channels and the adsorption properties of the MOF were conjectured to be partially responsible for the observed high catalytic activity, which may allow the formation of a unique internal environment in the three‐dimensional porous framework that significantly boosted progress of the reactions. The X‐ray photoelectron spectroscopy (XPS) results showed also that the catalytically active copper species changed from CuII to CuI after catalytic use.