3-(4-phenylbuta-1,3-diynyl)thiophene | 105836-25-7

• 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-(4-phenylbuta-1,3-diynyl)thiophene
• CAS: 105836-25-7
• 化学式: C₁₄H₈S
• 分子量: 208.284
• InChiKey: NLRUZQLBLYAXBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 、 copper(II) ferrite 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.0h， 生成 3-(4-phenylbuta-1,3-diynyl)thiophene
  参考文献：
  名称：

  Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes

  摘要：

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

  DOI：

  10.1021/jo5011069

文献信息

• A co-operative Ni–Cu system for C_sp–C_sp and C_sp–C_sp2 cross-coupling providing a direct access to unsymmetrical 1,3-diynes and en-ynes
  作者：Nirmalya Mukherjee、Debasish Kundu、Brindaban C. Ranu

  DOI：10.1039/c4cc07413k

  日期：——

  An efficient cross coupling of alkynes with alkynyl and alkenyl halides catalysed by a Ni–Cu system without any ligand leading to the synthesis of a series of functionalised 1,3-di-ynes and en-ynes has been achieved.

  一种高效的Ni-Cu体系催化的炔烃与炔基卤化物和烯基卤化物的交叉偶联反应，在没有任何配体的情况下，成功合成了一系列官能化的1,3-二炔和烯-炔化合物。
• 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。
• Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes
  作者：J. Schörgenhumer、M. Waser

  DOI：10.1039/c8ob02375a

  日期：——

  A variety of unsymmetrical 1,3-diynes can easily be accessed in good yields under catalyst- and transition metal-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.

  通过使末端炔烃与高价碘基亲电炔烃转移试剂反应，可以轻松地在无催化剂和无过渡金属的条件下以高收率轻松获得各种不对称的1,3-二炔。
• Copper porphyrin-catalyzed aerobic oxidative coupling of terminal alkynes with high TON
  作者：Wen-Bing Sheng、Tie-Qiao Chen、Ming-Zhong Zhang、Mi Tian、Guo-Fang Jiang、Can-Cheng Guo

  DOI：10.1016/j.tetlet.2016.02.075

  日期：2016.4

  Copper porphyrin-catalyzed Glaser–Hay-type couplings of terminal alkynes generating 1,3-diynes are described. This reaction features high TON (up to 950) and is complete in an hour, providing a facile, clean, and efficient protocol to access various 1,3-diynes including those with functional groups under mild reaction conditions. This transformation would take place via a radical process.

  描述了铜卟啉催化的生成1,3-二炔的末端炔烃的Glaser-Hay型偶联。该反应具有高TON（高达950）的特性，并且在一小时内即可完成，提供了一种温和，干净，高效的操作方案，可在温和的反应条件下接触各种1,3-二炔，包括带有官能团的1,3-二炔。这种转变将通过一个根本性的过程进行。
• One‐pot synthesis of unsymmetrical 1,3‐butadiyne derivatives
  作者：Zhicai Zhao

  DOI：10.1002/bkcs.12762

  日期：2023.10

  An efficient co-operative Ni/Cu system for Cadiot–Chodkiewicz coupling utilizes CaC2 as the alkyne source. The advantage of this cross-coupling reaction lies in the low cost of using cheap and readily available raw materials and the simplicity of operation. A series of functionalized diaryl, aryl-alkyl, and aryl-heteroaryl 1,3-diynes are obtained in moderate to high yields.

  Cadiot-Chodkiewicz 耦合的高效协同 Ni/Cu 系统利用 CaC 2作为炔烃源。这种交叉偶联反应的优点在于使用廉价易得的原材料成本低且操作简单。以中等到高产率获得了一系列官能化二芳基、芳基-烷基和芳基-杂芳基1,3-二炔。