[2-13C]-mesityl oxide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-13C]-mesityl oxide
• 英文别名: 4-methyl(213C)pent-3-en-2-one
• 化学式: C₆H₁₀O
• 分子量: 99.1338
• InChiKey: SHOJXDKTYKFBRD-PTQBSOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [2-13C]-mesityl oxide 、 4-异丙基苯胺 在 碘 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 [4-13C]-1,2-dihydro-6-isopropyl-2,2,4-trimethylquinoline 、 [2-13C]-1,2-dihydro-6-isopropyl-2,2,4-trimethylquinoline 、 [2,4-13C2]-1,2-dihydro-6-isopropyl-2,2,4-trimethylquinoline 、 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
• 作为产物：
  描述：

  氯代叔丁烷 、 乙酰氯-1-13C 在 三氯化铝 作用下， 反应 3.0h， 生成 [2-13C]-mesityl oxide
  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