5,5-dimethyl-3-(p-nitrophenyl)-1,4,2-dioxazole | 15568-73-7

• 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: 5,5-dimethyl-3-(p-nitrophenyl)-1,4,2-dioxazole
• 英文别名: 5,5-dimethyl-3-(4-nitro-phenyl)-[1,4,2]dioxazole；2,2-Dimethyl-5-(4-nitro-phenyl)-1,3,4-dioxazol；5,5-Dimethyl-3-(4-nitrophenyl)-1,4,2-dioxazole
• CAS: 15568-73-7
• 化学式: C₁₀H₁₀N₂O₄
• 分子量: 222.2
• InChiKey: CSCHUNCLGYTCDF-UHFFFAOYSA-N

物化性质

• 熔点：
  146-149 °C
• 沸点：
  295.0±42.0 °C(Predicted)
• 密度：
  1.36±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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-3-(p-nitrophenyl)-1,4,2-dioxazole 在 Nafion-H 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 以99%的产率得到N-羟基-4-硝基苯甲酰胺
  参考文献：
  名称：

  5,5-Dimethyl-1,4,2-dioxazoles as Versatile Aprotic Hydroxamic Acid Protecting Groups

  摘要：

  5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.

  DOI：

  10.1021/jo0256890
• 作为产物：
  描述：

  N-羟基-4-硝基苯甲酰胺 、 2,2-二乙氧基丙烷 在 对甲苯磺酸 作用下， 以 乙酸乙酯 为溶剂， 生成 5,5-dimethyl-3-(p-nitrophenyl)-1,4,2-dioxazole
  参考文献：
  名称：

  The Synthesis and the Thermal Decomposition of 1, 3, 4-Dioxazole Derivatives

  摘要：

  通过苯羟肟酸与丙酮、环己酮、苯乙酮和二苯甲酮等酮的二乙基酮反应，制备出了 2，2，5-三取代的-1，3，4-二恶唑。这些二恶唑在高温（150°C 以上）下分解成苯基异氰酸酯和酮。已尝试对硝基苯中的分解反应进行动力学研究，并获得了一阶速率常数。

  DOI：

  10.1246/bcsj.40.664

文献信息

• 5,5-Dimethyl-1,4,2-dioxazoles as Versatile Aprotic Hydroxamic Acid Protecting Groups
  作者：Michel Couturier、John L. Tucker、Caroline Proulx、Ghislain Boucher、Pascal Dubé、Brian M. Andresen、Arun Ghosh

  DOI：10.1021/jo0256890

  日期：2002.7.1

  5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.
• The Synthesis and the Thermal Decomposition of 1, 3, 4-Dioxazole Derivatives
  作者：Hiroyuki Nohira、Kenji Inoue、Hirotoki Hattori、Toji Okawa、Teruaki Mukaiyama

  DOI：10.1246/bcsj.40.664

  日期：1967.3

  2, 2, 5-Tri-substituted-1, 3, 4-dioxazoles have been prepared by the reactions of benzhydroxamic acids with the diethylketals of such ketones as acetone, cyclohexanone, acetophenone and benzophenone. These dioxazoles decompose at elevated temperatures (above 150°C) into phenylisocyanates and ketones. A kinetic study of the decomposition reaction in nitrobenzene has been attempted, and the first-order rate constants have been obtained.

  通过苯羟肟酸与丙酮、环己酮、苯乙酮和二苯甲酮等酮的二乙基酮反应，制备出了 2，2，5-三取代的-1，3，4-二恶唑。这些二恶唑在高温（150°C 以上）下分解成苯基异氰酸酯和酮。已尝试对硝基苯中的分解反应进行动力学研究，并获得了一阶速率常数。