4-t-butylperoxy-2,4,6-trimethyl-2,5-cyclohexadien-1-one | 136612-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 4-t-butylperoxy-2,4,6-trimethyl-2,5-cyclohexadien-1-one
• 英文别名: 4-(tert-butylperoxy)-2,4,6-trimethylcyclohexa-2,5-dienone；4-tert-Butylperoxy-2,4,6-trimethyl-cyclohexa-2,5-dienon；4-Tert-butylperoxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one
• CAS: 136612-99-2
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: XMFBCTJHNAORMI-UHFFFAOYSA-N

物化性质

• 沸点：
  284.6±40.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叔丁基过氧化氢 、 2,4,6-三甲酚 在 phenyltrimethylammonium tribromide 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以62%的产率得到4-t-butylperoxy-2,4,6-trimethyl-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  “三重奏杰克”-强大的一锅金属无酚苯胺氧化，叠氮化和过氧化反应†

  摘要：

  本文中，我们公开了一种通过苯酚的胺化和叠氮化氧化脱芳香化反应生成含氮季碳中心的高效方法。相同的方案也已成功用于实现酚的氧化过氧化。最简单的无金属反应条件表明了对“三重奏”的轻松突破-氧化胺化，叠氮化和过氧化。在一个罐中已合成了多种多样的多官能化杂环。

  DOI：

  10.1039/c7nj00169j

文献信息

• The Oxidation of<i>p</i>-Substituted Phenols Using a<i>t</i>-Butyl Hydroperoxide–Heteropolyacid System
  作者：Masao Shimizu、Hideo Orita、Takashi Hayakawa、Yoshihito Watanabe、Katsuomi Takehira

  DOI：10.1246/bcsj.64.2583

  日期：1991.8

  The oxidation of p-substituted phenols with t-BuOOH in the presence of heteropolyacids was carried out. 4-t-Butylperoxy-2,5-cyclohexadien-1-ones were obtained in good yields by the oxidation of 2,4,6-trialkylsubstituted phenols in this oxidation system.

  在中文里，这句话可以翻译为：在杂多酸的存在下，使用叔丁基过氧化氢对对位取代的苯酚进行了氧化反应。在这种氧化体系中，通过氧化2,4,6-三烷基取代的苯酚，得到了产率良好的4-叔丁基过氧-2,5-环己二烯-1-酮。
• 638. Alkylperoxy-radicals. Part I. Reactions with 2: 4: 6-trialkylphenols
  作者：A. F. Bickel、E. C. Kooyman

  DOI：10.1039/jr9530003211

  日期：——
• Cobalt Schiff Base Complex-Catalyzed Oxidation of Anilines with <i>tert</i>-Butyl Hydroperoxide
  作者：Stefan Förster、Anton Rieker、Kazushige Maruyama、Kunihiko Murata、Akira Nishinaga

  DOI：10.1021/jo952198p

  日期：1996.1.1

  Cobalt Schiff base complexes [Co(SB)] catalyze the oxidation of anilines (1) with tert-butyl hydroperoxide to give nitrobenzenes 2 and 4-(tert-butylperoxy)-2,5-cyclohexadien-1-imine derivatives 3 in yield distributions depending on the substitution mode of the substrate. 4-Alkyl- and 4-aryl-2,6-di-tert-butylanilines gave mixtures of 2 and 3, where the higher the bulkiness of the 4-substituent, the higher the yield of 2. With 2,4,6-trimethylaniline, the ratio of oxidations of the nitrogen and C-4 atoms was almost the same; but a hydrolyzed product 5 of the imine was obtained. 2,4,6-Triphenylaniline gave only 2. Nitrobenzene derivatives were also obtained from 2,6-dialkylanilines and 4-substituted anilines. The catalytic activity of Co(SB) depended on the nature of the SB ligand: the formal potential E degrees and steric factors seem to affect the reaction rate. Kinetic studies showed that the key step may involve hydrogen abstraction from the aniline, presumably by t-BuO(.) generated from homolytic decomposition of initially formed Co-III(SB)(OO-t-Bu). A precursor of 2 was found to be the nitrosobenzene derivative.
• Co(salen) catalyzed oxidation of 2,4,6-trisubstituted anilines with tert-butylhydroperoxide
  作者：Akira Nishinaga、Stefan Fo¨rster、Emerich Eichhorn、Bernd Speiser、Anton Rieker

  DOI：10.1016/s0040-4039(00)60100-4

  日期：1992.7

  Co(salen) catalyzed oxidation of 2,4,6-trisubstituted (preferentially 2,6-di-tert-butylated) anilines with tert-butylhydroperoxide gives 4-tert-butylperoxy-2,5-cyclohexadien-1-imine and nitrobenzene derivatives. The relative ratio of the products depends on the nature of the substituents in the substrate.
• “A Jack of Trio”-robust one-pot metal free oxidative amination, azidation and peroxidation of phenols
  作者：Debayan Sarkar、Manoj Kumar Ghosh、Nilendri Rout、Puspendu Kuila

  DOI：10.1039/c7nj00169j

  日期：——

  containing quaternary carbon centres via aminative and azidative oxidative dearomatization of phenols. The same protocol has also been successfully employed to achieve oxidative peroxidation of phenols. The simplest metal free reaction conditions delineate an easy breakthrough to the “Trio”- oxidative amination, azidation and peroxidation. An array of diverse polyfunctionalised heterocycles has been synthesized

  本文中，我们公开了一种通过苯酚的胺化和叠氮化氧化脱芳香化反应生成含氮季碳中心的高效方法。相同的方案也已成功用于实现酚的氧化过氧化。最简单的无金属反应条件表明了对“三重奏”的轻松突破-氧化胺化，叠氮化和过氧化。在一个罐中已合成了多种多样的多官能化杂环。