N-tert-butyl-N-[2-(3-methoxypyridyl)]hydroxylamine | 1439378-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-tert-butyl-N-[2-(3-methoxypyridyl)]hydroxylamine
• 英文别名: N-tert-butyl-N-(3-methoxypyridin-2-yl)hydroxylamine
• CAS: 1439378-72-9
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: OIOSGEUSOKFABU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-N-[2-(3-methoxypyridyl)]hydroxylamine 在 air 作用下， 生成 C₁₀H₁₅N₂O₂
  参考文献：
  名称：

  Fine-Tuning the Oxidative Ability of Persistent Radicals: Electrochemical and Computational Studies of Substituted 2-Pyridylhydroxylamines

  摘要：

  N-tert-Butyl-N-2-pyridylhydroxylamines were synthesized from 2-halopyridines and 2-methyl-2-nitrosopropane using magnesium halogen exchange. The use of Turbo Grignard generated the metallo-2-pyridyl intermediate more reliably than alkyllithium reagents. The hydroxylamines were characterized using NMR, electrochemistry, and density functional theory. Substitution of the pyridyl ring in the 3-, 4-, and 5-positions was used to vary the potential of the nitroxyl/oxoammonium redox couple by 0.95 V. DFT computations of the electrochemical properties agree with experiment and provide a toolset for the predictive design of pyridyl nitroxides.

  DOI：

  10.1021/jo400944r
• 作为产物：
  描述：

  2-碘-3-甲氧基吡啶 、 2-methyl-2-nitrosopropane dimer 在 isopropyl magnesium chloride - lithium chloride complex 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以69%的产率得到N-tert-butyl-N-[2-(3-methoxypyridyl)]hydroxylamine
  参考文献：
  名称：

  Fine-Tuning the Oxidative Ability of Persistent Radicals: Electrochemical and Computational Studies of Substituted 2-Pyridylhydroxylamines

  摘要：

  N-tert-Butyl-N-2-pyridylhydroxylamines were synthesized from 2-halopyridines and 2-methyl-2-nitrosopropane using magnesium halogen exchange. The use of Turbo Grignard generated the metallo-2-pyridyl intermediate more reliably than alkyllithium reagents. The hydroxylamines were characterized using NMR, electrochemistry, and density functional theory. Substitution of the pyridyl ring in the 3-, 4-, and 5-positions was used to vary the potential of the nitroxyl/oxoammonium redox couple by 0.95 V. DFT computations of the electrochemical properties agree with experiment and provide a toolset for the predictive design of pyridyl nitroxides.

  DOI：

  10.1021/jo400944r

文献信息

• A Ligand Field Series for the 4f-Block from Experimental and DFT Computed Ce(IV/III) Electrochemical Potentials
  作者：Justin A. Bogart、Andrew J. Lewis、Michael A. Boreen、Heui Beom Lee、Scott A. Medling、Patrick J. Carroll、Corwin H. Booth、Eric J. Schelter

  DOI：10.1021/ic503000z

  日期：2015.3.16

  Understanding of the sensitivity of the reduction potential of cerium(IV) cations to ligand field strength has yet to benefit from systematic variation of the ligand environment. Detailed analyses for a series of seven cerium(IV) tetrakis(pyridyl-nitroxide) compounds and their cerium(III) analogues in varying ligand field strengths are presented. Electrochemical, spectroscopic, and computational results

  铈（IV）阳离子的还原电势对配体场强的敏感性的了解尚未受益于配体环境的系统变化。详细分析了一系列七种铈（IV）四（吡啶基-硝基氧）化合物及其铈（III）类似物在不同配体场强下的分布。电化学，光谱和计算结果表明，电子性质与配体取代基密切相关。结合已报道的八配位化合物的电化学数据，DFT计算揭示了与配体场强相关的大量铈（IV / III）氧化还原电势，建立了用于调节铈氧化还原热力学和配体场强的半经验预测模型。各种科学领域的应用都利用了铈的基本氧化还原热力学。这样的应用将从评估铈化合物的氧化还原循环的实验和理论相结合的方法中受益。
• Fine-Tuning the Oxidative Ability of Persistent Radicals: Electrochemical and Computational Studies of Substituted 2-Pyridylhydroxylamines
  作者：Justin A. Bogart、Heui Beom Lee、Michael A. Boreen、Minsik Jun、Eric J. Schelter

  DOI：10.1021/jo400944r

  日期：2013.6.21

  N-tert-Butyl-N-2-pyridylhydroxylamines were synthesized from 2-halopyridines and 2-methyl-2-nitrosopropane using magnesium halogen exchange. The use of Turbo Grignard generated the metallo-2-pyridyl intermediate more reliably than alkyllithium reagents. The hydroxylamines were characterized using NMR, electrochemistry, and density functional theory. Substitution of the pyridyl ring in the 3-, 4-, and 5-positions was used to vary the potential of the nitroxyl/oxoammonium redox couple by 0.95 V. DFT computations of the electrochemical properties agree with experiment and provide a toolset for the predictive design of pyridyl nitroxides.