2-ethoxy-1-ethynyl-4-methylbenzene | 1269479-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-ethoxy-1-ethynyl-4-methylbenzene
• 英文别名: 1-Ethoxy-2-ethynyl-4-methylbenzene；1-ethoxy-2-ethynyl-4-methylbenzene
• CAS: 1269479-58-4
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: TWPVZGUUSKGAFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙氧基乙炔 、 三氟甲烷磺酸4-甲基-2-(三甲基硅基)苯酯 在 cesium fluoride 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 12.0h， 生成 2-ethoxy-1-ethynyl-4-methylbenzene 、 1-ethoxy-2-ethynyl-4-methylbenzene
  参考文献：
  名称：

  Highly Selective Insertion of Arynes into a C(sp)−O(sp³) σ Bond

  摘要：

  Arynes react with ethoxyacetylene to afford 2-ethoxyethynylaryl derivatives through a highly chemo- and regioselective formal insertion of the aryne into the C(sp)-O(sp(3)) bond of the alkyne. Computational studies suggest that the reaction does not proceed through a mechanism initiated by the nucleophilic addition of the oxygen atom to the aryne as previously proposed but by the addition of the triple bond of the alkyne to the aryne.

  DOI：

  10.1021/ol103001k

文献信息

• Highly Selective Insertion of Arynes into a C(sp)−O(sp³) σ Bond
  作者：Krzysztof Z. Ła̧czkowski、Diego García、Diego Peña、Agustín Cobas、Dolores Pérez、Enrique Guitián

  DOI：10.1021/ol103001k

  日期：2011.3.4

  Arynes react with ethoxyacetylene to afford 2-ethoxyethynylaryl derivatives through a highly chemo- and regioselective formal insertion of the aryne into the C(sp)-O(sp(3)) bond of the alkyne. Computational studies suggest that the reaction does not proceed through a mechanism initiated by the nucleophilic addition of the oxygen atom to the aryne as previously proposed but by the addition of the triple bond of the alkyne to the aryne.