3-(4-methoxyphenyl)-5,5-dimethyl-1,4,2-dioxazole | 443682-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-5,5-dimethyl-1,4,2-dioxazole
• CAS: 443682-79-9
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: NBPDLSBWESUMQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  254.9±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-5,5-dimethyl-1,4,2-dioxazole 在 Nafion-H 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 茴香酸乙酯
  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：

  对甲氧基苯甲酰氯 在 D(+)-10-樟脑磺酸 、 盐酸羟胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 3-(4-methoxyphenyl)-5,5-dimethyl-1,4,2-dioxazole
  参考文献：
  名称：

  二恶唑，金催化中的一种新型轻度硝基转移试剂：高效合成功能化恶唑

  摘要：

  已经开发了金催化的酰胺与1,4,2-二恶唑的区域选择性[3 + 2]环加成反应，这为在温和的反应条件下高官能化的恶唑提供了一种新颖的方法。发现1,4,2-二恶唑起作用...

  DOI：

  10.1039/c6cc02776h

文献信息

• Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: highly efficient synthesis of functionalized oxazoles
  作者：Ming Chen、Ning Sun、Haoyi Chen、Yuanhong Liu

  DOI：10.1039/c6cc02776h

  日期：——

  A gold-catalyzed regioselective [3+2] cycloaddition of ynamides with 1,4,2-dioxazoles has been developed, which offers a novel approach to highly functionalized oxazoles under mild reaction conditions. 1,4,2-Dioxazole was found to act...

  已经开发了金催化的酰胺与1,4,2-二恶唑的区域选择性[3 + 2]环加成反应，这为在温和的反应条件下高官能化的恶唑提供了一种新颖的方法。发现1,4,2-二恶唑起作用...
• 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.
• Tf₂NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles
  作者：Yingying Zhao、Yancheng Hu、Chunxiang Wang、Xincheng Li、Boshun Wan

  DOI：10.1021/acs.joc.7b00076

  日期：2017.4.7

  An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol

  开发了前所未有的Tf 2 NH催化的酰胺与二恶唑的正式[3 + 2]环加成反应，以构建各种多取代的4-氨基恶唑。该方法具有恶唑基序的无金属催化双分子组装，低成本催化剂，异常温和的反应条件，非常短的反应时间，广泛的底物范围和高效率。这种无金属的方案可以在面向药物的合成中找到应用。