2-butyrylisonicotinonitrile | 132854-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-butyrylisonicotinonitrile
• 英文别名: 2-Butanoylpyridine-4-carbonitrile
• CAS: 132854-99-0
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: PUEYBGALNKUNEN-UHFFFAOYSA-N

物化性质

• 沸点：
  292.6±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氰基吡啶 、 2-戊酮酸 在 NH₄S₂O₈ 、 silver nitrate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以94%的产率得到2-butyrylisonicotinonitrile
  参考文献：
  名称：

  Homolytic acylation of protonated pyridines and pyrazines with .alpha.-keto acids: the problem of monoacylation

  摘要：

  The silver-catalyzed decarboxylation of alpha-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives. Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring. Although the introduction of an acyl group strongly activates the heterocyclic ring toward further substitution, monoacylation can be achieved by taking advantage of the difference in basicity and lipophilicity between the starting base and the monoacylation products in a two-phase system.

  DOI：

  10.1021/jo00008a050

文献信息

• Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C–H Functionalization
  作者：Duy N. Mai、Ryan D. Baxter

  DOI：10.1021/acs.orglett.6b01754

  日期：2016.8.5

  of heteroarenes using unprotected amino acids as stable alkyl radical precursors is reported. This one-pot procedure is performed open to air under aqueous conditions and is effective for several natural and unnatural amino acids. Heterocycles of varying structure are suitably functionalized, and reactivity trends reflect the nucleophilic character of the radical species generated.

  据报道，使用未保护的氨基酸作为稳定的烷基自由基前体，可以有效，通用地进行杂芳烃的CH烷基化反应。这种一锅法在水性条件下露天进行，对几种天然和非天然氨基酸均有效。适当地官能化可变结构的杂环，并且反应性趋势反映了所产生的自由基物种的亲核特性。
• FONTANA, FRANCESCA;MINISCI, FRANCESCO;BARBOSA, MARIA CLAUDIA NOGUEIRA;VIS+, J. ORG. CHEM., 56,(1991) N, C. 2866-2869
  作者：FONTANA, FRANCESCA、MINISCI, FRANCESCO、BARBOSA, MARIA CLAUDIA NOGUEIRA、VIS+

  DOI：——

  日期：——