(Z)‑1‑(4‑chlorophenyl)‑N‑isopropylmethanimine oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)‑1‑(4‑chlorophenyl)‑N‑isopropylmethanimine oxide
• 英文别名: (Z)-N-isopropyl-4-chlorobenzylideneamine N-oxide；(z)-1-(4-chlorophenyl)-N-isopropylmethanimine oxide；1-(4-chlorophenyl)-N-propan-2-ylmethanimine oxide
• 化学式: C₁₀H₁₂ClNO
• 分子量: 197.664
• InChiKey: PIAZMAPCYYZRRO-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 N-异丙基羟胺 以 乙醇 为溶剂， 反应 5.0h， 生成 (Z)‑1‑(4‑chlorophenyl)‑N‑isopropylmethanimine 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

• Aliphatic nitro compounds chemistry: oximes–nitrones tunable production through directed tandem synthesis
  作者：Foad Kazemi、Moosa Ramdar、Jamal Davarpanah

  DOI：10.1007/s00706-018-2326-4

  日期：2019.2

  AbstractReduction of aliphatic nitro compounds in the presence of aldehydes and dialdehydes for tunable directed synthesis of oximes, nitrones, nitrone–oximes, and dinitrones was reported. The slow and nonselective reduction of aliphatic nitro compounds was directed by condensation of in situ prepared alkylhydroxylamines with aromatic aldehydes. Mononitrones and dinitrones were synthesized at reflux

  摘要据报导，在醛和二醛存在下还原脂肪族硝基化合物可调谐合成肟，硝酮，硝酮肟和二硝基酮。脂肪族硝基化合物的缓慢且非选择性的还原是通过原位制备的烷基羟胺与芳族醛的缩合来实现的。在四氢呋喃中，使用SnCl 2 ·2H 2 O和Na 2 CO 3分别在回流和55°C条件下合成单硝酮和二硝酮。研究发现，当使用二醛作为醛源时，催化量的羧酸（如3-苯基丙酸）的存在相对于硝酮肟和二肟而言，可以提高二硝酮的收率。 图形概要
• 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。
• 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.