1-<4-Hydroxy-anilino>-buten-(1)-on-(3) | 5622-21-9

• 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: 1-<4-Hydroxy-anilino>-buten-(1)-on-(3)
• CAS: 5622-21-9
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: CUTATWSUSADQJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  对氨基苯酚 、 3-丁炔-2-酮 以 水 为溶剂， 生成 1-<4-Hydroxy-anilino>-buten-(1)-on-(3)
  参考文献：
  名称：

  Remarkable catalytic effect of H+ in Michael-type additions of anilines to 3-butyn-2-one

  摘要：

  Second-order rate constants (k(N)) for the Michael-type reaction of 3-butyn-2-one (1) with a series of anilines in H2O have been determined spectrophotometrically. The k(N) values are dependent on the free aniline fraction (F-N). The plot of log k(N) vs pK(a) of the conjugate acid of the anilines is linear for the reactions run at F-N=1.00. However, the Bronsted-type plot for the reactions performed at F-N=0.50 is nonlinear, suggesting a change in the reaction mechanism as the basicity of anilines changes. The analysis of the kinetic results has revealed that the reaction of anilines proceeds through the protonated form of the substrate 1 as well as the unprotonated. The protonated form of 1 is of the order of 10(9) times more reactive than the unprotonated form toward anilines. The contribution of the reaction with the protonated species to the k(N) is suggested to be responsible for the nonlinear Bronsted-type plot obtained for the reactions run at F-N=0.50. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00981-4

文献信息

• Über die Kondensation von Isatinsäuren mit Acylacetaldehyd-diacetalen bzw. Acylacetaldehyd-enoläthern
  作者：K. Hohenlohe-Oehringen、A. Rhomberg、H. Bretschneider

  DOI：10.1007/bf00905498

  日期：1966.1