3-phenyl-5,5-dimethyl-5,6-dihydro[1,4]oxazin-2-one | 53153-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: 3-phenyl-5,5-dimethyl-5,6-dihydro[1,4]oxazin-2-one
• 英文别名: 5,6-dihydro-5,5-dimethyl-3-phenyl-1,4-oxazin-2-one；5,5-dimethyl-3-phenyl-5,6-dihydro-[1,4]oxazin-2-one；5,5-Dimethyl-3-phenyl-5,6-dihydro-1,4-oxazinon-(2)；5,5-Dimethyl-3-phenyl-5,6-dihydro-2H-1,4-oxazin-2-on；3,3-dimethyl-5-phenyl-2H-1,4-oxazin-6-one
• CAS: 53153-47-2
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: GWZQESTUGPCLKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-5,5-dimethyl-5,6-dihydro[1,4]oxazin-2-one 在 3,5,5-三甲基-3-(3,5,5-三甲基-2-氧代-吗啉-3-基)吗啉-2-酮 作用下， 以 甲醇 为溶剂， 生成 5,5-dimethyl-3-phenylmorpholin-2-one
  参考文献：
  名称：

  Electron-transfer chemistry of the merostabilized 3,5,5-trimethyl-2-morpholinon-3-yl radical

  摘要：

  DOI：

  10.1021/ja00394a020
• 作为产物：
  描述：

  2-benzoyl-4,4-dimethyl-2-oxazoline 在 silica gel 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到3-phenyl-5,5-dimethyl-5,6-dihydro[1,4]oxazin-2-one
  参考文献：
  名称：

  Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation

  摘要：

  The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) or by chloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability to act either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles in form of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.08.040

文献信息

• Biekert,E.; Sonnenbichler,J., Chemische Berichte, 1961, vol. 94, p. 2785 - 2791
  作者：Biekert,E.、Sonnenbichler,J.

  DOI：——

  日期：——
• Photochemical reactivity of imino lactones. Photoreduction and photoelimination
  作者：Tad H. Koch、John A. Olesen、James DeNiro

  DOI：10.1021/jo00889a003

  日期：1975.1
• Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation
  作者：Leonardo Degennaro、Vito Capriati、Claudia Carlucci、Saverio Florio、Renzo Luisi、Irene Nuzzo、Corrado Cuocci

  DOI：10.1016/j.tet.2009.08.040

  日期：2009.10

  The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) or by chloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability to act either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles in form of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reserved
• Electron-transfer chemistry of the merostabilized 3,5,5-trimethyl-2-morpholinon-3-yl radical
  作者：John M. Burns、Donald L. Wharry、Tad H. Koch

  DOI：10.1021/ja00394a020

  日期：1981.2