4-(4-(N,N-dimethylamino)phenyl)-but-3-yn-1-ol | 61899-20-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-(N,N-dimethylamino)phenyl)-but-3-yn-1-ol
• 英文别名: 4-(4-dimethylaminophenyl)-but-3-yn-1-ol；4-p-Dimethylaminophenyl-3-butin-1-ol；4-[4-(Dimethylamino)phenyl]but-3-YN-1-OL
• CAS: 61899-20-5
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: IHOWLJXQRLIENZ-UHFFFAOYSA-N

物化性质

• 沸点：
  338.4±27.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  羰基二氰化物 、 4-(4-(N,N-dimethylamino)phenyl)-but-3-yn-1-ol 以 乙醚 为溶剂， 反应 12.0h， 以86%的产率得到4-[4-(Dimethylamino)phenyl]but-3-ynyl cyanoformate
  参考文献：
  名称：

  Palladium-Catalyzed C−CN Activation for Intramolecular Cyanoesterification of Alkynes

  摘要：

  Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

  DOI：

  10.1021/ol200274h

文献信息

• Quantitative Evaluation of the Stability of <i>gem</i>-Diaurated Species in Reactions with Nucleophiles
  作者：Alexander Zhdanko、Martin E. Maier

  DOI：10.1021/om400083f

  日期：2013.3.25

  The reactivity of diaurated species toward nucleophiles was investigated. The reaction yields vinyl gold species and is described as simple S(N)2 ligand exchange at gold. Using suitably strong nucleophiles, equilibrium constants were determined to measure the stability of various diaurated species. On the basis of these equilibrium constants the influence of ligand and the nature of vinyl cores on the stability were analyzed. These results have direct implication for gold catalysis: it was demonstrated that vinyl gold intermediates bind the catalytic LAu+ species generally stronger than an alkyne (the substrate) by a factor of 10(6)-10(9). This demonstrates that the formation of diaurated species from vinyl gold intermediates is thermodynamically favored in a catalytic reaction.