1,2-dihydro-6-isopropyl-2,2,4-trimethylquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2-dihydro-6-isopropyl-2,2,4-trimethylquinoline
• 英文别名: 6-Isopropyl-2,2,4-trimethyl-1H-quinoline；2,2,4-trimethyl-6-propan-2-yl-1H-quinoline
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: YQUFLVWOPAIRRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 、 4-异丙基苯胺 在 碘 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以38%的产率得到1,2-dihydro-6-isopropyl-2,2,4-trimethylquinoline
  参考文献：
  名称：

  On the Mechanism of the Skraup−Doebner−Von Miller Quinoline Synthesis

  摘要：

  The mechanism of the formation of substituted quinolines from anilines and alpha,beta-unsaturated ketones has been studied by the use of C-13-labeled ketones in cross-over experiments. In the reaction of doubly labeled C-13(2,4) mesityl oxide, a 100% scrambling of the label in the quinoline product was observed, whereas only a small (5-10%) amount of the starting mesityl oxide showed scrambling of the label. Similarly, the reaction of triply labeled pulegone clearly shows that the label in the product is 100% scrambled, whereas the label in the starting pulegone is retained. On the basis of these studies, a mechanistic pathway for the Skraup quinoline synthesis is proposed that involves a fragmentation-recombination mechanism. The aniline component condenses with the alpha,beta-unsaturated ketone initially in a conjugate fashion, followed by a fragmentation to the corresponding imine and the ketone itself. These fragments recombine to form the quinoline product.

  DOI：

  10.1021/jo052410h

文献信息

• Novel facile synthesis of 2,2,4 substituted 1,2-dihydroquinolines via a modified Skraup reaction
  作者：Maria-Elena Theoclitou、Leslie A. Robinson

  DOI：10.1016/s0040-4039(02)00614-7

  日期：2002.5

  A variety of 2,2,4 substituted 1,2-dihydroquinolines were synthesized from substituted anilines or aminoheterocycles and the corresponding ketones in good yield via the use of lanthanide catalysts and microwave technology. This method can be readily applied to the general synthesis of combinatorial libraries of dihydroquinolines.

  通过使用镧系元素催化剂和微波技术，由取代的苯胺或氨基杂环以及相应的酮以高收率合成了各种2,2,4个取代的1,2-二氢喹啉。该方法可以容易地应用于二氢喹啉组合库的一般合成。