(Z)-N-isopropyl-4-methylbenzylideneamine N-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)-N-isopropyl-4-methylbenzylideneamine N-oxide
• 英文别名: 1-(4-methylphenyl)-N-propan-2-ylmethanimine oxide
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: INQLPBFMPSCMEE-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  对甲基苯甲醛 、 N-异丙基羟胺 以 乙醇 为溶剂， 反应 5.0h， 生成 (Z)-N-isopropyl-4-methylbenzylideneamine 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

• 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.