3-(phenylbuta-1,3-diyn-1-yl)pyridine | 54334-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(phenylbuta-1,3-diyn-1-yl)pyridine
• 英文别名: 3-(4-Phenylbuta-1,3-diynyl)pyridine
• CAS: 54334-99-5
• 化学式: C₁₅H₉N
• 分子量: 203.243
• InChiKey: XKFMINQSEZRBHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  361.0±24.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 (2,3-dibromo-3-phenylprop-2-enyl)-triphenylphosphanium;bromide 在 三甲基苯甲氧基胺 作用下， 以 甲醇 为溶剂， 生成 3-(phenylbuta-1,3-diyn-1-yl)pyridine
  参考文献：
  名称：

  1,4-Dehydrobromination of 1-bromo-1,2,3-butatrienes: an efficient synthesis of 1,4-disubstituted 1,3-diynes

  摘要：

  DOI：

  10.1021/jo00379a025

文献信息

• Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling
  作者：Nidhi Mishra、Sumit K. Singh、Anoop S. Singh、Anand K. Agrahari、Vinod K. Tiwari

  DOI：10.1021/acs.joc.1c02194

  日期：2021.12.17

  for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect the coupling, and no need of complete exclusion of oxygen was experienced in the presence of glycohybrid triazole ligand L3. High product yields were obtained at 130 °C for a variety of substrates including aliphatic

  已引入糖基三唑作为铜催化的 Sonogashira 反应的有效配体，以克服该反应中铜催化中横向同源偶联反应的挑战。密封管中的大气氧不影响偶联，并且在糖杂化三唑配体L3存在下不需要完全排除氧。对于包括脂肪族和芳香族末端炔烃以及不同取代的芳香族卤化物（包括 9-溴诺斯卡品）在内的各种底物，在 130 °C 下获得了高产率。相比之下，在室温下，L3-的负载非常低Cu催化体系可以在Glaser偶联中产生优异的产率，包括多种脂肪族和芳香族炔烃的同偶联和异偶联。
• Copper(I) Iodide Catalyzed Cross-Coupling Reaction of Terminal Alkynes with 1-Bromoalkynes: A Simple Synthesis of Unsymmetrical Buta-1,3-diynes
  作者：Lei Wang、Shihua Wang、Lin Yu、Pinhua Li、Lingguo Meng

  DOI：10.1055/s-0030-1259998

  日期：2011.5

  A simple synthesis of unsymmetrical buta-1,3-diynes by cross-coupling of terminal alkynes with 1-bromoalkynes in the presence of copper(I) iodide and tris(o-tolyl)phosphine was developed that gives good yields under simple and mild reaction conditions. The scope and limitations of the cross-coupling reaction were investigated. alkynes - catalysis - cross-coupling - alkadiynes

  通过在碘化铜（I）和三（邻甲苯基）膦存在下，通过末端炔与1-溴炔的交叉偶联，简单合成不对称的buta-1,3-diynes ，可在简单温和的条件下获得良好的收率反应条件。研究了交叉偶联反应的范围和局限性。 炔烃-催化-交叉偶联-炔烃
• A mild CuI-catalyzed Glaser-type homo-coupling reaction using α,α-dibromo-β-dicarbonyl compounds as oxidants
  作者：Xiaohui Fan、Na Li、Tong Shen、Xiao-Meng Cui、Hao Lv、Hong-Bo Zhu、Yong-Hong Guan

  DOI：10.1016/j.tet.2013.11.076

  日期：2014.1

  Exploration of alpha,alpha-dibromo-beta-dicarbonyl compounds as novel organic oxidants for the mild Cu(I)-catalyzed Glaser-type homo-coupling reaction has been achieved, which provides an alternatively efficient pathway for the construction of 1,3-conjugated structures. In addition, the mechanism of this reaction was investigated. (C) 2013 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes
  作者：Zheng Huang、Rui Shang、Zi-Rong Zhang、Xiao-Dan Tan、Xiao Xiao、Yao Fu

  DOI：10.1021/jo400616r

  日期：2013.5.3

  A copper-catalyzed decarboxylative coupling reaction of potassium alkynyl carboxylates with 1,1-dibromo-1-alkenes was developed for the synthesis of unsymmetrical 1,3-diyne and 1,3,5-triyne derivatives. Diverse aryl, alkenyl, alkynyl, and alkyl substituted 1,1-dibromo-1-alkenes can react smoothly with aryl and alkyl substituted propiolates to produce unsymmetrical 1,3-diynes and 1,3,5-triynes with high selectivity and good functional group compatibility.
• ZIEGLER C. B., JR.; HARRIS S. M., J. ORG. CHEM., 52,(1987) N 3, 443-446
  作者：ZIEGLER C. B., JR.、 HARRIS S. M.

  DOI：——

  日期：——