(Z)-N-isopropyl-4-methoxybenzylideneamine N-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-N-isopropyl-4-methoxybenzylideneamine N-oxide
• 英文别名: 1-(4-methoxyphenyl)-N-propan-2-ylmethanimine oxide
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: LMTAICBQXKYRKM-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-N-isopropyl-4-methoxybenzylideneamine N-oxide 在 mercury(II) oxide 作用下， 以 氘代氯仿 为溶剂， 生成 (Z)-N-isopropyl-4-methoxybenzylideneamine N-oxide
  参考文献：
  名称：

  Regiochemistry and mechanism of oxidation ofN-benzyl-N-alkylhydroxylamines to nitrones

  摘要：

  The oxidation of various N-(o-, m-, p-substituted benzyl)-N-alkylhydroxylamines and their dideuteriobenzyl (PhCD2) counterparts was carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. An overwhelming preference for the formation of conjugated nitrones is observed in the oxidation of N-benzyl-N-isopropylhydroxylamines. Considerable intra- and intermolecular kinetic isotope effects and negative rho values in the Hammet plots point towards a mechanistic pathway that involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction. The conformation of unstable (E)-nitrones, which readily isomerize to the more stable (Z)-nitrones, is deduced from H-1 NMR data. The E = Z isomerization was found to be a bimolecular process. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200008)13:8<443::aid-poc253>3.0.co;2-9

文献信息

• One-Pot Synthesis of Functionalized Nitrones from Nitro Compounds
  作者：Valérie Gautheron-Chapoulaud、Shashi U. Pandya、Pascale Cividino、Géraldine Masson、Sandrine Py、Yannick Vallée

  DOI：10.1055/s-2001-16042

  日期：——

  The zinc-mediated reduction of nitroalkanes and nitroarenes in the presence of aldehydes is an efficient method to synthesize a wide range of nitrones. This method is mild enough to accommodate a variety of functional groups. It is particularly useful when the intermediate hydroxylamines are unstable and/or water-soluble. We used it to prepare several aromatic, aliphatic and highly functionalized sugar-derived nitrones.

  在醛的存在下，锌介导的硝基烷烃和硝基芳烃的还原是一种高效合成多种硝酮的方法。该方法足够温和，能适应各种官能团。当中间体羟胺不稳定和/或水溶性时，这种方法尤为有用。我们利用它制备了多种芳香族、脂肪族和高功能化的糖衍生物硝酮。
• Access to Nitrones from Amines via Electrocatalysis at Room Temperature
  作者：Gaurav Shukla、Dhananjay Yadav、Saurabh Singh、Maya Shankar Singh

  DOI：10.1002/adsc.202200188

  日期：2022.6.21

  synthesis of nitrones from bench stable amines has been developed under constant current electrolysis at room temperature, rendering metal and external oxidant-free protocol in an alkaline medium. The electrocatalysis steps of reported strategy involve anodic oxidation of benzyl amines followed by cathodic reduction of nitro-functional group in an undivided cell affording functional nitrones. The robustness

  在室温下恒流电解下开发了一种用于从台式稳定的胺合成硝酮的自启动电氧化方案，在碱性介质中呈现无金属和外部氧化剂的方案。报道的策略的电催化步骤涉及苄胺的阳极氧化，然后在提供功能性硝酮的未分裂电池中对硝基官能团进行阴极还原。耐受底物范围、无氧化剂条件和操作友好的程序反映了电催化的稳健性。此外，循环伏安法和控制实验研究也支持碱性介质中的电化学过程。
• 10.1021/acs.joc.4c00512
  作者：Xing, Jian、Tang, Hong-Yu、Chen, Jing-Lin、Huang, Zheng、Liang, Jun-Jie、Quan, Yao-Sheng、Mao, Jian-Gang

  DOI：10.1021/acs.joc.4c00512

  日期：——

  methodology for the synthesis of nitrones via palladium-catalyzed redox cross-coupling of nitro compounds and alcohols is established. The protocol is a mild, convenient, ligand-free, and scalable synthesis method that can be compatible with various nitro compounds and alcohols. Nitrone is a significant multifunctional platform synthon which can be synthesized directly and efficiently via this tactic from

  建立了一种通过硝基化合物和醇的钯催化氧化还原交叉偶联合成硝酮的新方法。该方案是一种温和、方便、无配体、可扩展的合成方法，可以与各种硝基化合物和醇兼容。硝酮是一种重要的多功能平台合成子，可以通过这种策略从市售且廉价的原材料直接有效地合成。
• Regiochemistry and mechanism of oxidation ofN-benzyl-N-alkylhydroxylamines to nitrones
  作者：Azfar Hassan、Mohammed I. M. Wazeer、Mohammed T. Saeed、Mohammad N. Siddiqui、Sk. Asrof Ali

  DOI：10.1002/1099-1395(200008)13:8<443::aid-poc253>3.0.co;2-9

  日期：2000.8

  The oxidation of various N-(o-, m-, p-substituted benzyl)-N-alkylhydroxylamines and their dideuteriobenzyl (PhCD2) counterparts was carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. An overwhelming preference for the formation of conjugated nitrones is observed in the oxidation of N-benzyl-N-isopropylhydroxylamines. Considerable intra- and intermolecular kinetic isotope effects and negative rho values in the Hammet plots point towards a mechanistic pathway that involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction. The conformation of unstable (E)-nitrones, which readily isomerize to the more stable (Z)-nitrones, is deduced from H-1 NMR data. The E = Z isomerization was found to be a bimolecular process. Copyright (C) 2000 John Wiley & Sons, Ltd.