5,5-Dimethyl-2-((E)-styryl)-4,5-dihydro-oxazole | 124210-99-7

• 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-2-((E)-styryl)-4,5-dihydro-oxazole
• 英文别名: 5,5-Dimethyl-2-(2-phenylethenyl)-4,5-dihydro-1,3-oxazole；5,5-dimethyl-2-(2-phenylethenyl)-4H-1,3-oxazole
• CAS: 124210-99-7
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: SHNSQSMILYVDRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-cinnamoyl-2,2-dimethylaziridine 在 硫酸 作用下， 反应 2.0h， 生成 5,5-Dimethyl-2-((E)-styryl)-4,5-dihydro-oxazole
  参考文献：
  名称：

  Isomerisation Catalysee Par le Gel de Silice et L'argile Activee de N-Acyl-2,2-Dimethylaziridines: Approche Mecanistique

  摘要：

  Silica gel and activated clay, behaving as Lewis acids, reacted with N-acyl-2,2-dimethylaziridines 1 to lead to pentacoordinated aziridinium silicate ions. The regiospecific ring opening on the CMe2 carbon side of the intermediate I involves, after removal of the catalyst, the zwitterion II. The zwitterion II undergoes either a transfer of proton leading to the N-methallylamide 2 or intramolecular cyclization reaction leading to the oxazoline 3. The unstable oxazoline 3 on catalyst is hydrated in turn into amidoalcohol 4 via the oxazolinium silicate III.

  DOI：

  10.1080/10426500903023079

文献信息

• Archier-Jay, Danielle; Besbes, Neji; Laurent, Andre, Bulletin de la Societe Chimique de France, 1989, # 44, p. 537 - 543
  作者：Archier-Jay, Danielle、Besbes, Neji、Laurent, Andre、Laurent, Eliane、Lesniak, Stanislaw、Tardivel, Robert

  DOI：——

  日期：——
• Reductive ring opening of N-acylaziridines : Different outcomes of chemical and electrochemical reactions
  作者：D. Archier-Jay、N. Besbes、A. Laurent、E. Laurent、H. Stamm、R. Tardivel

  DOI：10.1016/s0040-4039(00)99669-2

  日期：1989.1
• Isomerisation Catalysee Par le Gel de Silice et L'argile Activee de <i>N</i>-Acyl-2,2-Dimethylaziridines: Approche Mecanistique
  作者：Néji Besbes、Houyem Jellali、Patrick Pale、Mohamed Lotfi Efrit、Ezzeddine Srasra

  DOI：10.1080/10426500903023079

  日期：2010.3.24

  Silica gel and activated clay, behaving as Lewis acids, reacted with N-acyl-2,2-dimethylaziridines 1 to lead to pentacoordinated aziridinium silicate ions. The regiospecific ring opening on the CMe2 carbon side of the intermediate I involves, after removal of the catalyst, the zwitterion II. The zwitterion II undergoes either a transfer of proton leading to the N-methallylamide 2 or intramolecular cyclization reaction leading to the oxazoline 3. The unstable oxazoline 3 on catalyst is hydrated in turn into amidoalcohol 4 via the oxazolinium silicate III.