1-ethynyl-2-((4-methoxyphenyl)ethynyl)-4-methylbenzene | 1415461-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-ethynyl-2-((4-methoxyphenyl)ethynyl)-4-methylbenzene
• 英文别名: 1-Ethynyl-2-[2-(4-methoxyphenyl)ethynyl]-4-methylbenzene；1-ethynyl-2-[2-(4-methoxyphenyl)ethynyl]-4-methylbenzene
• CAS: 1415461-95-8
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: UXTPAHRZOFGAEF-UHFFFAOYSA-N

物化性质

• 沸点：
  395.6±42.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-ethynyl-2-((4-methoxyphenyl)ethynyl)-4-methylbenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦氯金 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 邻二甲苯 为溶剂， 反应 9.66h， 生成 6-(4-methoxyphenyl)-3-methylnaphtho[1,2-b]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：

  2-[2-[2-(4-Methoxyphenyl)ethynyl]-4-methylphenyl]ethynyl-trimethylsilane 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 以94%的产率得到1-ethynyl-2-((4-methoxyphenyl)ethynyl)-4-methylbenzene
  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

• Nucleophilic Selenocyclization Reaction of Benzodiynes Promoted by Sodium Selenide: Synthesis of Isoselenochromenes
  作者：Adriano Maroneze、Fabíola Caldeira、Davi F. Back、Cristina Wayne Nogueira、Gilson Zeni

  DOI：10.1002/asia.202400225

  日期：——

  We describe here the synthesis of isoselenochromenes via a nucleophilic selenocyclization reaction of benzodiynes with sodium selenide. The central parameters that affect this cyclization reaction were studied, and the best reaction conditions were applied to different substrates to determine the scope of the method. The results indicated that isoselenochromenes were obtained in higher yields when

  我们在这里描述了通过苯并二炔与硒化钠的亲核硒环化反应合成异硒色烯。研究了影响该环化反应的中心参数，并将最佳反应条件应用于不同的底物，以确定该方法的范围。结果表明，当在室温、氮气气氛下向元素硒（2当量）的二甲基甲酰胺（2 mL）溶液中添加NaBH 4 （3当量）进行反应时，以更高的产率获得异硒色烯。 1小时后，在室温下添加苯二炔(0.25mmol)的EtOH(3mL)溶液。将反应在75℃下搅拌直至起始材料耗尽。最佳条件适用于具有富电子、贫电子芳环以及直接与炔烃键合的烷基的苯二炔。将相同的反应条件扩展到异硫色烯衍生物，但未能制备出异四色烯。使用文献中可用的经典方法，异硒色烯很容易转化为三类新的有机硒化合物。我们还进行了几次对照实验来提出反应机制。
• 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.