Dodecyl pyridin-3-yl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dodecyl pyridin-3-yl ketone
• 英文别名: 1-(3-Pyridyl)tridecan-1-one；1-pyridin-3-yltridecan-1-one
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: QYMLMZBABHFZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dodecyl pyridin-3-yl ketone 在 盐酸羟胺 、 sodium carbonate 、 copper dichloride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 十三醛
  参考文献：
  名称：

  Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane

  摘要：

  AbstractThe goal of the research was to study the reactivity of the hydrophobic 2‐ and 3‐pyridineketoximes under exposure to UV‐VIS light. The photodegradation was conducted in both toluene and heptane for 10 h under atmosphere of argon. Ten‐hour irradiation experiments demonstrated that the pyridineketoximes underwent the facile E‐Z photoisomerization, photo‐Beckmann rearrangement, and to a lesser extent, the photosubstitution to the pyridine ring. From LC‐MS and NMR analysis of the irradiated solutions, it was found that the photosubstitution proceeded to give the corresponding 6‐substituted 2‐ or 3‐pyridylketoxime via the replacement of the ring hydrogen by the benzyl or heptyl group. The photo‐Beckmann rearrangement led to the formation of the corresponding amides, but also other products formed in the photo‐decomposition reaction.

  DOI：

  10.1111/php.12453
• 作为产物：
  描述：

  3-氰基吡啶 、 magnesium,dodecane,bromide 以 乙醚 为溶剂， 生成 Dodecyl pyridin-3-yl ketone
  参考文献：
  名称：

  Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane

  摘要：

  AbstractThe goal of the research was to study the reactivity of the hydrophobic 2‐ and 3‐pyridineketoximes under exposure to UV‐VIS light. The photodegradation was conducted in both toluene and heptane for 10 h under atmosphere of argon. Ten‐hour irradiation experiments demonstrated that the pyridineketoximes underwent the facile E‐Z photoisomerization, photo‐Beckmann rearrangement, and to a lesser extent, the photosubstitution to the pyridine ring. From LC‐MS and NMR analysis of the irradiated solutions, it was found that the photosubstitution proceeded to give the corresponding 6‐substituted 2‐ or 3‐pyridylketoxime via the replacement of the ring hydrogen by the benzyl or heptyl group. The photo‐Beckmann rearrangement led to the formation of the corresponding amides, but also other products formed in the photo‐decomposition reaction.

  DOI：

  10.1111/php.12453

文献信息

• Quaternary Pyridinium Ketoximes - New Efficient Micellar Hydrolytic Catalysts
  作者：Radek Cibulka、František Hampl、Hana Kotoučová、Jiří Mazáč、František Liška

  DOI：10.1135/cccc20000227

  日期：——

  A series of quaternized alkyl pyridyl ketoximes was synthesized and tested as micellar hydrolytic catalysts. 2- And 4-[1-(hydroxyimino)tridecyl]-1-methylpyridinium bromides were surprisingly efficient, most probably due to the location of their nucleophilic hydroxyimino group below the micellar surface. Absorbance of the reaction mixture vs time plots exhibited remarkable positive deviation from the first-order kinetics when hydrolysis of 4-nitrophenyl phosphates was catalyzed by 1-dodecyl-3-[1-(hydroxyimino)ethyl]- or 3-[1-(hydroxyimino)tridecyl]-1-methylpyridinium bromide.

  一系列季铵化烷基吡啶酮肟化合物被合成并作为胶束水解催化剂进行测试。2-和4-[1-(羟基亚胺)十三烷基]-1-甲基吡啶溴化物表现出出乎意料的高效，很可能是因为它们的亲核羟基亚胺基团位于胶束表面以下。当1-十二烷基-3-[1-(羟基亚胺)乙基]-或3-[1-(羟基亚胺)十三烷基]-1-甲基吡啶溴化物催化4-硝基苯磷酸酯水解时，反应混合物的吸光度与时间的关系图表现出与一阶动力学明显不同的正偏离。
• Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane
  作者：Karolina Wieszczycka、Joanna Zembrzuska

  DOI：10.1111/php.12453

  日期：2015.7

  AbstractThe goal of the research was to study the reactivity of the hydrophobic 2‐ and 3‐pyridineketoximes under exposure to UV‐VIS light. The photodegradation was conducted in both toluene and heptane for 10 h under atmosphere of argon. Ten‐hour irradiation experiments demonstrated that the pyridineketoximes underwent the facile E‐Z photoisomerization, photo‐Beckmann rearrangement, and to a lesser extent, the photosubstitution to the pyridine ring. From LC‐MS and NMR analysis of the irradiated solutions, it was found that the photosubstitution proceeded to give the corresponding 6‐substituted 2‐ or 3‐pyridylketoxime via the replacement of the ring hydrogen by the benzyl or heptyl group. The photo‐Beckmann rearrangement led to the formation of the corresponding amides, but also other products formed in the photo‐decomposition reaction.