3-ethynyl-4-(methoxymethoxy)-5-propylbenzonitrile | 1449697-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethynyl-4-(methoxymethoxy)-5-propylbenzonitrile
• CAS: 1449697-03-3
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: ZJQGNSCJKIRQQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-iodo-4-(methoxymethoxy)-5-propylbenzonitrile 、 3-ethynyl-4-(methoxymethoxy)-5-propylbenzonitrile 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三乙胺 作用下， 反应 19.0h， 以93%的产率得到5,5′-(ethyne-1,2-diyl)bis[4-(methoxymethoxy)-3-propylbenzonitrile]
  参考文献：
  名称：

  Exploring the Potential of Diarylacetylenediols as Hydrogen Bonding Catalysts

  摘要：

  In the course of a search for new classes of hydrogen bonding catalysts, we have examined diarylacetylenediols as potential catalysts for the Diels-Alder reaction. General and efficient methods have been developed for the preparation of these diols. Their structures were systematically modified, and increased activity was observed for those possessing an electron-withdrawing group on the aryl groups. The electron-deficient diarylacetylenediol catalysts, while more active, undergo spontaneous cyclization to the corresponding benzo[b]furans. A mechanism is postulated to explain this facile transformation. Computational studies performed on 2-ethynylphenol help to explain the effect of the alkyne on the conformation and hydrogen bond donating ability of the adjacent OH group. Finally, the crystal structure of one of the diols is reported, and it displays an intricate network of intermolecular hydrogen bonds.

  DOI：

  10.1021/jo400926n
• 作为产物：
  描述：

  4-(methoxymethoxy)-3-propyl-5-[(trimethylsilyl)ethynyl]benzonitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以100%的产率得到3-ethynyl-4-(methoxymethoxy)-5-propylbenzonitrile
  参考文献：
  名称：

  Exploring the Potential of Diarylacetylenediols as Hydrogen Bonding Catalysts

  摘要：

  In the course of a search for new classes of hydrogen bonding catalysts, we have examined diarylacetylenediols as potential catalysts for the Diels-Alder reaction. General and efficient methods have been developed for the preparation of these diols. Their structures were systematically modified, and increased activity was observed for those possessing an electron-withdrawing group on the aryl groups. The electron-deficient diarylacetylenediol catalysts, while more active, undergo spontaneous cyclization to the corresponding benzo[b]furans. A mechanism is postulated to explain this facile transformation. Computational studies performed on 2-ethynylphenol help to explain the effect of the alkyne on the conformation and hydrogen bond donating ability of the adjacent OH group. Finally, the crystal structure of one of the diols is reported, and it displays an intricate network of intermolecular hydrogen bonds.

  DOI：

  10.1021/jo400926n