N-tert-butyl-N-[2-(5-methylpyridyl)]hydroxylamine | 1439378-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-tert-butyl-N-[2-(5-methylpyridyl)]hydroxylamine
• 英文别名: N-tert-butyl-N-2-(5-methylpyridyl)hydroxylamine；N-tert-butyl-N-(5-methylpyridin-2-yl)hydroxylamine
• CAS: 1439378-74-1
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: UKVATOKFTATMEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-N-[2-(5-methylpyridyl)]hydroxylamine 在 air 作用下， 生成
  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-溴-5-甲基吡啶 、 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 6.0h， 以62%的产率得到N-tert-butyl-N-[2-(5-methylpyridyl)]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。
• Synthesis and characterization of aluminum nitroxide complexes
  作者：Thomas M. Herb、Andrew M. Poitras、Kenneth G. Richardson、Bren E. Cole、Justin A. Bogart、Patrick J. Carroll、Eric J. Schelter、Christopher R. Graves

  DOI：10.1016/j.poly.2015.12.005

  日期：2016.8

  trimethylaluminum yielded the aluminum complex (pyNO−)AlMe2·AlMe3 (3), which was also characterized by 1H and 13C NMR spectroscopies and single-molecule X-ray diffraction. The electronic structure of the (μ-pyNO−)Al(CH3)2}2 and (μ-CH3pyNO−)Al(CH3)2}2 complexes were interrogated using UV–Vis electronic absorption spectroscopy and electrochemistry. The cyclic voltammograms of the complexes show two separate oxidation

  摘要我们报道了吡啶基氮氧化物（RpyNO-）配体的铝配合物的合成。通过吡啶基羟胺之间的1：1反应制备了二聚配合物（μ-pyNO-）Al（CH3）2} 2（1）和（μ-CH3pyNO-）Al（CH3）2} 2（2）。配体前体RpyNOH和三甲基铝。两种化合物均通过1 H和13 C NMR光谱表征。X射线结构分析表明1和2是同构的，其二聚体结构是由Al2O2核形成的。pyNOH与两当量的三甲基铝反应生成铝络合物（pyNO-）AlMe2·AlMe3（3），其特征还在于1H和13C NMR光谱学以及单分子X射线衍射。（μ-pyNO-）Al（CH3）2} 2和（μ-CH3pyNO-）Al（CH3）2} 2配合物的电子结构使用紫外可见电子吸收光谱法和电化学方法进行了研究。配合物的循环伏安图显示了两个独立的氧化过程，其电位均取决于RpyNO-配体的取代方式。
• 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.