5t-methyl-2r-phenyl-oxazolidin-4-one | 42463-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5t-methyl-2r-phenyl-oxazolidin-4-one
• 英文别名: (+/-)-5t-methyl-2r-phenyl-oxazolidin-4-one；(+/-)-5t-Methyl-2r-phenyl-oxazolidin-4-on；(2R,5R)-5-methyl-2-phenyl-1,3-oxazolidin-4-one
• CAS: 42463-59-2；65298-06-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: VONZYNDINIIEFA-GMSGAONNSA-N

物化性质

• 熔点：
  131-134 °C
• 沸点：
  386.7±42.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (3R)-3-phenyl-2-tosyl-1,2-oxaziridine 在 samarium diiodide 、 (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 18.25h， 生成 5t-methyl-2r-phenyl-oxazolidin-4-one
  参考文献：
  名称：

  Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

  摘要：

  An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and alpha-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2016.10.012

文献信息

• Pilgram,K.; Pollard,G.E., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 1029 - 1033
  作者：Pilgram,K.、Pollard,G.E.

  DOI：——

  日期：——
• 218. Mechanism and extension of the Fischer oxazole synthesis
  作者：J. W. Cornforth、R. H. Cornforth

  DOI：10.1039/jr9490001028

  日期：——
• Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines
  作者：Ryan W.F. Kerr、Mark D. Greenhalgh、Alexandra M.Z. Slawin、Polly L. Arnold、Andrew D. Smith

  DOI：10.1016/j.tetasy.2016.10.012

  日期：2017.1

  An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and alpha-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations. (C) 2016 Published by Elsevier Ltd.