2-pivaloylaminopyridine N-oxide | 171520-81-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-pivaloylaminopyridine N-oxide
• 英文别名: 2-pivalamidopyridine 1-oxide；2-pivalamidopyridine-1-oxide
• CAS: 171520-81-3
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: OGQMZNMEUKKRIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  460.5±18.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.04
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-pivaloylaminopyridine N-oxide 在 碘 、 lithium diisopropyl amide 作用下， 生成 2-iodo-6-pivaloylaminopyridine N-oxide
  参考文献：
  名称：

  Mongin, Olivier; Rocca, Patrick; Thomas-dit-Dumont, Laurence, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2503 - 2508

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基吡啶 、 三甲基乙酸 在 氯化亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 13.0h， 以80%的产率得到2-pivaloylaminopyridine N-oxide
  参考文献：
  名称：

  Pd（II）催化的吡啶N-氧化物直接活化未活化C sp 3 -H键的芳基化

  摘要：

  已开发出一种新型的Pd（II）催化的吡啶N-氧化物直接催化芳族碘化物与脂族酰胺中未活化的C sp 3 -H键的远程芳基化。该方案允许在烷基羧酸酰胺的β-或γ- Csp 3原子上安装各种芳基。通过HR-MS和1 H NMR方法已经确定了该转化的关键的双环中间体。

  DOI：

  10.1021/acs.joc.5b00489

文献信息

• Rapid and Selective in situ Reduction of Pyridine-N-oxides with Tetra­hydroxydiboron
  作者：Allyn Londregan、David Piotrowski、Jun Xiao

  DOI：10.1055/s-0033-1340010

  日期：——

  Pyridine-N-oxides are often used as reactive precursors in the syntheses of substituted pyridines. Isolation and subsequent reduction of the associated pyridine-N-oxide intermediates can be challenging. We have discovered that tetrahydroxydiboron functions as a mild, versatile, and remarkably selective reducing agent for pyridine-N-oxides and may be used in an in situ fashion, thus obviating the isolation of N-oxide-containing intermediates
• Copper- or Nickel-Enabled Oxidative Cross-Coupling of Unreactive C(sp³)–H Bonds with Azole C(sp²)–H Bonds: Rapid Access to β-Azolyl Propanoic Acid Derivatives
  作者：Guangying Tan、Luoqiang Zhang、Xingrong Liao、Yang Shi、Yimin Wu、Yudong Yang、Jingsong You

  DOI：10.1021/acs.orglett.7b02265

  日期：2017.9.15

  beta-Azolyl propanoic acid derivatives are frequently found in biologically active molecules and pharmaceuticals. Here, we report the oxidative heteroarylation of unactivated C(sp(3))-H bonds with azole C(sp(2))-H bonds via copper or nickel catalysis with the aid of removable bidentate auxiliary, which provides a rapid pathway to beta-azolyl propanoic acid derivatives. A variety of azoles such as oxazole, benzoxazole, thiazole, benzothiazoles, benzimidazole, purine, and even [1,2,4]triazolo[1,5-a]pyrimidine could be engaged
• Palladium-Catalyzed Selective β-Arylation of Aliphatic Amides Using a Removable <i>N</i>,<i>O</i>-Bidentate Auxiliary
  作者：Shou-Kun Zhang、Xin-Yan Yang、Xue-Mei Zhao、Peng-Xiang Li、Jun-Long Niu、Mao-Ping Song

  DOI：10.1021/acs.organomet.5b00581

  日期：2015.9.14

  A new method for palladium-catalyzed beta-arylation of aliphatic and cycloaliphatic amides without conventional silver salts utilizing 2-aminopyridine-1-oxide moiety (PyO) as an N,O-bidentate group has been developed. Reactions proceeded smoothly in DMSO solvent in the presence of K2HPO4 center dot 3H(2)O, providing the beta-arylated aliphatic amide products in a moderate-to-good yield. An important cyclopalladium intermediate, successfully obtained with a modest yield, could be converted to the monoarylation product and be used as catalyst in arylation reaction. Moreover, the PyO directing group was easily removed under base condition to I generate aliphatic acids.