N,N-bis(4-tert-butylphenyl)hydroxylamine | 34548-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: N,N-bis(4-tert-butylphenyl)hydroxylamine
• 英文别名: N,N-Bis(4-(tert-butyl)phenyl)hydroxylamine
• CAS: 34548-99-7
• 化学式: C₂₀H₂₇NO
• 分子量: 297.44
• InChiKey: SIVPUOJYWIUVPF-UHFFFAOYSA-N

物化性质

• 沸点：
  416.9±38.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-bis(4-tert-butylphenyl)hydroxylamine 在 C(CH₃)(CH₃)CH(CH₃)N(CH₃)C(CH₃)(C₆H₁₃)N-O* 作用下， 以 正己烷 为溶剂， 生成 bis(4-tert-butylphenyl)aminoxyl radical
  参考文献：
  名称：

  位阻羟胺-硝酰基体系中氢原子的交换反应

  摘要：

  测定了喹啉、咪唑啉、吡咯烷和哌啶系列的空间位阻硝酰基自由基-羟胺以及二芳基羟胺体系中氢原子的直接和反向交换反应的速率常数。建立了水胺还原能力的量表。低同位素效应值是羟胺-硝酰基自由基体系中氢交换反应的典型特征。

  DOI：

  10.1007/bf02495549
• 作为产物：
  描述：

  bis(4-tert-butylphenyl)aminoxyl radical 在 C(CH₃)(CH₃)CH(CH₃)N(CH₃)C(CH₃)(C₆H₁₃)N-OH 作用下， 以 正己烷 为溶剂， 生成 N,N-bis(4-tert-butylphenyl)hydroxylamine
  参考文献：
  名称：

  位阻羟胺-硝酰基体系中氢原子的交换反应

  摘要：

  测定了喹啉、咪唑啉、吡咯烷和哌啶系列的空间位阻硝酰基自由基-羟胺以及二芳基羟胺体系中氢原子的直接和反向交换反应的速率常数。建立了水胺还原能力的量表。低同位素效应值是羟胺-硝酰基自由基体系中氢交换反应的典型特征。

  DOI：

  10.1007/bf02495549
• 作为试剂：
  描述：

  4-氧-2,2,6,6-四甲基哌啶-1-氧自由基 在 N,N-bis(4-tert-butylphenyl)hydroxylamine 作用下， 以 正己烷 为溶剂， 生成 1-羟基-2,2,6,6-四甲基哌啶-4-酮
  参考文献：
  名称：

  位阻羟胺-硝酰基体系中氢原子的交换反应

  摘要：

  测定了喹啉、咪唑啉、吡咯烷和哌啶系列的空间位阻硝酰基自由基-羟胺以及二芳基羟胺体系中氢原子的直接和反向交换反应的速率常数。建立了水胺还原能力的量表。低同位素效应值是羟胺-硝酰基自由基体系中氢交换反应的典型特征。

  DOI：

  10.1007/bf02495549

文献信息

• Reductive bromination of N, N-bis(4-tert-butylphenyl)hydroxylamine
  作者：V. A. Golubev、Yu. D. Kim

  DOI：10.1007/s11172-019-2556-6

  日期：2019.6

  Unlike most arenes, N, N-bis(4-tert-butylphenyl)hydroxylamine reacts with Br2via the reductive bromination mechanism. Here, two hydrogens in ortho positions of benzene rings are substituted by Br2 and provide two-electron reduction of hydroxylamine to amine.

  与大多数芳烃不同，N, N-双（4-叔丁基苯基）羟胺通过还原溴化机制与 Br2 反应。这里，苯环邻位的两个氢被 Br2 取代，并提供羟胺到胺的双电子还原。
• Effect of the chemical structure of nitroxyl radicals on their reactivity in the reaction with hydrazobenzene and tetranitromethane
  作者：A. D. Malievskii、S. V. Koroteev、L. B. Volodarskii、A. B. Shapiro

  DOI：10.1007/bf00958847

  日期：1990.11

  The reaction rate constants of reduction of stable radicals of different classes by hydrazobenzene in hexane at approximately 20-degrees-C, in the range of 0.4-5.10(3) M-1.sec-1, were determined; a single scale of the oxidative properties of stable nitroxyl radicals was constructed. The rate constants of oxidation of a series of nitroxyl radicals by tetranitromethane in aqueous medium at approximately 20-degrees-C, in the range of 0.06-10 M-1.sec-1, were determined. It was shown that the oxidative properties of the nitroxyl group decrease slightly with an increase in its reducing properties for nitroxyl radicals of the piperidine and imidazoline series in reactions with ascorbic acid and tetranitromethane in aqueous medium, respectively.
• Preparative syntheses of bis(4-tert-butylphenyl)aminoxyl
  作者：V. A. Golubev、V. D. Sen’

  DOI：10.1134/s1070428013040106

  日期：2013.4

  Bis(4-tert-butylphenyl)aminoxyl was obtained in 80 and 95% yield by oxidation of the corresponding amine and hydroxylamine with H2O2/WO (4) (2-) in methanol at 65A degrees C. The oxidation of bis(4-tert-butylphenyl)hydroxylamine to bis(4-tert-butylphenyl)aminoxyl was catalyzed by Cu+ and Ag+ ions which also catalyzed disproportionation of the former to bis(4-tert-butylphenyl)amine and bis(4-tert-butylphenyl)aminoxyl. Mechanisms of the catalytic oxidation of the amine and hydroxylamine and disproportionation of the latter were proposed.
• Acid-catalyzed disproportionation of N,N-bis(4-tert-butylphenyl)hydroxylamine. Synthesis and structure of 10-[5-tert-butyl-2-(4-tert-butylphenylamino)phenyl]-3,7-di-tert-butylphenoxazine
  作者：V. A. Golubev、V. V. Tkachev、V. D. Sen’

  DOI：10.1134/s1070428014050108

  日期：2014.5

  New method of synthesis was developed for N,N-bis(4-tert-butylphenyl)hydroxylamine by reduction of the corresponding aminoxyl with hydrazine hydrate. At the treatment with strong acids this hydroxylamine derivative is converted in bis(4-tert-butylphenyl)amine and 10-[5-tert-butyl-2-(4-tert-butylphenylamino) phenyl]-3,7-di-tert-butylphenoxazine. The structure of the latter was established by X-ray diffraction analysis. The mechanism was suggested of the acid-catalyzed disproportionation of N,N-bis(4-tert-butylphenyl) hydroxylamine.
• US4434307A
  申请人：——

  公开号：US4434307A

  公开（公告）日：1984-02-28