5,5-dimethyl-3-(2-phenylethyl)-1,4,2-dioxazole | 443682-81-3

• 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-(2-phenylethyl)-1,4,2-dioxazole
• CAS: 443682-81-3
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: SXQABIZRDUQFRD-UHFFFAOYSA-N

物化性质

• 沸点：
  264.9±33.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-3-(2-phenylethyl)-1,4,2-dioxazole 在 Nafion-H 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 3-苯丙酸乙酯
  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-3-苯基丙酰胺 、 2,2-二乙氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以73%的产率得到5,5-dimethyl-3-(2-phenylethyl)-1,4,2-dioxazole
  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

文献信息

• Synthesis of five-membered cyclic nitrones based on the Lewis acid-catalysed [3+2]-annulation reaction of donor–acceptor cyclopropanes with 1,4,2-dioxazoles
  作者：Zhe-Hao Wang、Huan-Huan Zhang、Peng-Fei Xu、Yong-Chun Luo

  DOI：10.1039/c8cc04656e

  日期：——

  A novel synthesis of five-membered cyclic nitrones has been developed based on the Lewis acid-catalysed [3+2]-annulation reaction of D–A cyclopropanes with 1,4,2-dioxazoles. Broad substrate scope and generally good yield make this reaction useful in the preparation of nitrones. When a suitable 1,4,2-dioxazole was used, nitrone and tetrahydrofuran could be prepared in one pot with high atom economy

  基于路易斯酸催化D–A环丙烷与1,4,2-二恶唑的[3 + 2]环化反应，开发了五元环硝酮的新型合成方法。广泛的底物范围和通常良好的产率使该反应可用于制备硝酮。当使用合适的1,4,2-二恶唑时，可以在一个具有高原子经济性的锅中制备硝酮和四氢呋喃。
• 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.