2-(2-adamantylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole | 918522-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(2-adamantylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole
• 英文别名: 2-[2-(1-adamantyl)propan-2-yl]-4,4-dimethyl-5H-1,3-oxazole
• CAS: 918522-44-8
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: AKTBOXHRBFFFRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-adamantylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole 在 palladium diacetate 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到2-(1,3-diiodo-2-adamantylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization

  摘要：

  A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

  DOI：

  10.1021/ol0618858
• 作为产物：
  描述：

  2-(1-Adamantyl)-2-methylpropionsaeure 在 氯化亚砜 、 三苯基膦 作用下， 生成 2-(2-adamantylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization

  摘要：

  A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

  DOI：

  10.1021/ol0618858

文献信息

• Converting <i>gem</i>-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization
  作者：Ramesh Giri、Masayuki Wasa、Steven P. Breazzano、Jin-Quan Yu

  DOI：10.1021/ol0618858

  日期：2006.12.1

  A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.