3-((2-ethynylphenyl)ethynyl)thiophene | 1415461-90-3

• 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-((2-ethynylphenyl)ethynyl)thiophene
• 英文别名: 3-[2-(2-Ethynylphenyl)ethynyl]thiophene；3-[2-(2-ethynylphenyl)ethynyl]thiophene
• CAS: 1415461-90-3
• 化学式: C₁₄H₈S
• 分子量: 208.284
• InChiKey: QUJFRUUYYHJUBK-UHFFFAOYSA-N

物化性质

• 沸点：
  351.7±22.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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

• 作为反应物：
  描述：

  2-碘苯酚 、 3-((2-ethynylphenyl)ethynyl)thiophene 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 邻二甲苯 为溶剂， 反应 8.0h， 以57%的产率得到2-(2-(thiophen-3-ylethynyl)phenyl)benzofuran
  参考文献：
  名称：

  Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes

  摘要：

  The Sonogashira/5-endo-dig/6-endo-dig cascade fuses a polycyclic aromatic backbone to the electron-rich furan subunit. The transformation proceeds in modest yields as a one-pot reaction. Efficiency of the full cascade is increased by removal of base prior to the addition of gold catalyst. Under these conditions, conversion to the full cascade products is achieved in nearly quantitative yields without purification of the intermediate products. Extension of the cascade toward triynes opens access to benzofuran-fused chrysene derivatives.

  DOI：

  10.1021/ol302922t
• 作为产物：
  描述：

  3-((2-bromophenyl)ethynyl)thiophene 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三叔丁基膦 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 16.0h， 生成 3-((2-ethynylphenyl)ethynyl)thiophene
  参考文献：
  名称：

  Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes

  摘要：

  The Sonogashira/5-endo-dig/6-endo-dig cascade fuses a polycyclic aromatic backbone to the electron-rich furan subunit. The transformation proceeds in modest yields as a one-pot reaction. Efficiency of the full cascade is increased by removal of base prior to the addition of gold catalyst. Under these conditions, conversion to the full cascade products is achieved in nearly quantitative yields without purification of the intermediate products. Extension of the cascade toward triynes opens access to benzofuran-fused chrysene derivatives.

  DOI：

  10.1021/ol302922t

文献信息

• Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes
  作者：Philip M. Byers、Julian I. Rashid、Rana K. Mohamed、Igor V. Alabugin

  DOI：10.1021/ol302922t

  日期：2012.12.7

  The Sonogashira/5-endo-dig/6-endo-dig cascade fuses a polycyclic aromatic backbone to the electron-rich furan subunit. The transformation proceeds in modest yields as a one-pot reaction. Efficiency of the full cascade is increased by removal of base prior to the addition of gold catalyst. Under these conditions, conversion to the full cascade products is achieved in nearly quantitative yields without purification of the intermediate products. Extension of the cascade toward triynes opens access to benzofuran-fused chrysene derivatives.
• Synthesis of Naphthalenyl Triflates via the Cationic Annulation of Benzodiynes with Triflic Acid
  作者：Chenxin Ge、Guohua Wang、Panpan Wu、Chao Chen

  DOI：10.1021/acs.orglett.9b01590

  日期：2019.7.5

  A highly efficient and regioselective annulation of benzodiynes promoted by triflic acid has been developed. This protocol provides a step and atom-economic access to a series of naphthalenyl triflates. Furthermore, direct synthetic applications of this reaction are also elaborated through cross-coupling reactions to generate synthetically useful multisubstituted naphthalenes.