(E)-1-(4-bromophenyl)-4-phenyl-but-1-en-3-yne | 1201221-02-4

• 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: (E)-1-(4-bromophenyl)-4-phenyl-but-1-en-3-yne
• 英文别名: 1-bromo-4-[(E)-4-phenylbut-1-en-3-ynyl]benzene
• CAS: 1201221-02-4
• 化学式: C₁₆H₁₁Br
• 分子量: 283.167
• InChiKey: KHDXULBNGQVCPW-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-溴肉桂醛 在 四(三苯基膦)钯 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (E)-1-(4-bromophenyl)-4-phenyl-but-1-en-3-yne
  参考文献：
  名称：

  De novo synthesis of functionalized 1,3-enynes and extended conjugated molecular systems

  摘要：

  钯催化的1,3-二烯基二溴化物与三芳基双锑的偶联被证明可用于合成多种1,3-炔烃。

  DOI：

  10.1039/c5ra01544h

文献信息

• Palladium-Free Synthesis of Conjugated Enynes by Direct Olefination of Terminal Alkynes Using Vinyl Bromides
  作者：Yunyun Liu、Jianguo Yang、Weiliang Bao

  DOI：10.1002/ejoc.200900954

  日期：2009.11

  A series of conjugated enynes were successfully synthesized by the direct copper-catalyzed coupling reaction of vinyl bromides and alkynes. The reaction proceeds smoothly in DMF at 110 °C to give the corresponding products in good to excellent yields. The protocol is tolerant to a broad range of functional groups on the substrates. Moreover, the products were furnished as specific E isomers, as the

  通过乙烯基溴和炔烃的直接铜催化偶联反应，成功合成了一系列共轭烯炔。该反应在 DMF 中在 110 °C 下顺利进行，以良好到极好的收率得到相应的产物。该协议可以容忍基板上的各种功能组。此外，产品以特定的 E 异构体形式提供，因为乙烯基溴的立体化学得以保留。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Copper-catalyzed Umpolung Sonogashira-type Coupling of Arene Boronic Acids under Visible Light
  作者：Jingwei Ma、Qian Wang、Yang Sun、Eva Zhu、Xiaobao Li、Haibo Tan、Guangying Chen、Chao Zheng

  DOI：10.1039/d3cc00682d

  日期：——

  catalyst catalyzed efficient cross-coupling of aryl and alkenyl boronic acids with alkynyl-1,2-benziodoxol-3(1H)-ones to afford diaryl alkynes and enynes under mild visible light irradiation conditions using a catalytic amount of base or even in the absence of base. The reaction applies copper as the catalyst and tolerates a variety of functional moieties including aryl bromide and iodide.

  我们在此报道了铜催化剂催化芳基和烯基硼酸与炔基-1,2-苯并氧醇-3(1 H )-酮的有效交叉偶联，在温和的可见光照射条件下使用催化量提供二芳基炔烃和烯炔基地或什至在没有基地的情况下。该反应使用铜作为催化剂，并耐受多种功能基团，包括芳基溴化物和碘化物。
• Highly regio- and stereoselective synthesis of 1,3-enynes from unactivated ethylenes via palladium-catalyzed cross-coupling
  作者：Yanmei Wen、Azhong Wang、Huanfeng Jiang、Shifa Zhu、Liangbin Huang

  DOI：10.1016/j.tetlet.2011.07.092

  日期：2011.11

  An efficient procedure for regio- and stereoselective synthesis of a series of conjugated enynes by a simple Pd-catalyzed cross-coupling reaction of unactivated ethylenes and ethynyl bromide has been developed. The reaction proceeds smoothly in DMF to give the corresponding products in good to excellent yields. The protocol can tolerate a broad range of functional groups on the substrates. (C) 2011 Elsevier Ltd. All rights reserved.
• De novo synthesis of functionalized 1,3-enynes and extended conjugated molecular systems
  作者：Maddali L. N. Rao、Priyabrata Dasgupta、Venneti N. Murty

  DOI：10.1039/c5ra01544h

  日期：——

  Pd-catalyzed coupling of 1,3-dienyldibromides with triarylbismuths was demonstrated for the synthesis of a diverse range of 1,3-enynes.

  钯催化的1,3-二烯基二溴化物与三芳基双锑的偶联被证明可用于合成多种1,3-炔烃。