2,2-dimethyl-5-methoxy-5-phenyl-1,3,4-Δ³-oxadiazoline | 92573-96-1

• 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: 2,2-dimethyl-5-methoxy-5-phenyl-1,3,4-Δ³-oxadiazoline
• 英文别名: 2-methoxy-5,5-dimethyl-2-phenyl-Δ³-1,3,4-oxadiazoline；2,2-dimethyl-5-methoxy-5-phenyl-Δ³-1,3,4-oxadiazoline；2-Methoxy-5,5-dimethyl-2-phenyl-[1,3,4]oxadiazole；2-methoxy-5,5-dimethyl-2-phenyl-1,3,4-oxadiazole
• CAS: 92573-96-1
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: JVIRWDBFQMINBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-methoxy-5-phenyl-1,3,4-Δ³-oxadiazoline 以 苯 为溶剂， 反应 5.0h， 以90%的产率得到2-methoxy-3,3-dimethyl-2-phenyl-oxirane
  参考文献：
  名称：

  Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to .DELTA.3-1,3,4-oxadiazolines and 1,3,4-oxadiazoles

  摘要：

  The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-DELTA(3)-1,3,4-oxadiazolines 3. The thermal stability of a given oxadiazoline and what products were formed by its thermal decomposition was found to depend on the natures of the substituents at C-2. Thus, 2-methoxy-2-phenyloxadiazolines preferentially yielded oxiranes 5, whereas 2-alkyl-2-methoxyoxadiazolines preferentially gave enol ethers 6. 2,2-Dimethoxyoxadiazolines decomposed to the parent ketones and many unidentified products. The electrolytic oxidation of aldehyde N-acylhydrazones 2 gave 2,5-disubstituted 1,3,4-oxadiazoles 4. The oxidative cyclization of the N-benzoylhydrazones of aliphatic aldehydes gave especially high yields of the corresponding heterocycles.

  DOI：

  10.1021/jo00031a014
• 作为产物：
  描述：

  甲醇 、 N-(丙-2-亚基氨基)苯甲酰胺 在 sodium acetate 作用下， 以70%的产率得到2,2-dimethyl-5-methoxy-5-phenyl-1,3,4-Δ³-oxadiazoline
  参考文献：
  名称：

  Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to .DELTA.3-1,3,4-oxadiazolines and 1,3,4-oxadiazoles

  摘要：

  The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-DELTA(3)-1,3,4-oxadiazolines 3. The thermal stability of a given oxadiazoline and what products were formed by its thermal decomposition was found to depend on the natures of the substituents at C-2. Thus, 2-methoxy-2-phenyloxadiazolines preferentially yielded oxiranes 5, whereas 2-alkyl-2-methoxyoxadiazolines preferentially gave enol ethers 6. 2,2-Dimethoxyoxadiazolines decomposed to the parent ketones and many unidentified products. The electrolytic oxidation of aldehyde N-acylhydrazones 2 gave 2,5-disubstituted 1,3,4-oxadiazoles 4. The oxidative cyclization of the N-benzoylhydrazones of aliphatic aldehydes gave especially high yields of the corresponding heterocycles.

  DOI：

  10.1021/jo00031a014

文献信息

• Bekhazi, Michel; Smith, Peter J.; Warkentin, John, Canadian Journal of Chemistry, 1984, vol. 62, p. 1646 - 1652
  作者：Bekhazi, Michel、Smith, Peter J.、Warkentin, John

  DOI：——

  日期：——
• Photolysis of 2-alkoxy-.DELTA.3-1,3,4-oxadiazolines. A new route to diazoalkanes
  作者：Michael W. Majchrzak、Michel Bekhazi、Irene Tse-Sheepy、John Warkentin

  DOI：10.1021/jo00269a019

  日期：1989.4
• Yang Rui-Yang, Dai Li-Xin, J. Org. Chem., 58 (1993) N 12, S 3381-3383
  作者：Yang Rui-Yang, Dai Li-Xin

  DOI：——

  日期：——
• BEKHAZI, M.;SMITH, P. J.;WARKENTIN, J., CAN. J. CHEM., 1984, 62, N 8, 1646-1652
  作者：BEKHAZI, M.、SMITH, P. J.、WARKENTIN, J.

  DOI：——

  日期：——
• Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to .DELTA.3-1,3,4-oxadiazolines and 1,3,4-oxadiazoles
  作者：Toshiro Chiba、Mitsuhiro Okimoto

  DOI：10.1021/jo00031a014

  日期：1992.2

  The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-DELTA(3)-1,3,4-oxadiazolines 3. The thermal stability of a given oxadiazoline and what products were formed by its thermal decomposition was found to depend on the natures of the substituents at C-2. Thus, 2-methoxy-2-phenyloxadiazolines preferentially yielded oxiranes 5, whereas 2-alkyl-2-methoxyoxadiazolines preferentially gave enol ethers 6. 2,2-Dimethoxyoxadiazolines decomposed to the parent ketones and many unidentified products. The electrolytic oxidation of aldehyde N-acylhydrazones 2 gave 2,5-disubstituted 1,3,4-oxadiazoles 4. The oxidative cyclization of the N-benzoylhydrazones of aliphatic aldehydes gave especially high yields of the corresponding heterocycles.