2-phenyl-3-(4-methylphenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene | 139174-35-9

• 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: 2-phenyl-3-(4-methylphenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene
• 英文别名: 2-phenyl-3-(4-methylphenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro[4,4]-non-2-ene；(3R,5S)-8,8-dimethyl-3-(4-methylphenyl)-2-phenyl-1-oxa-2,7-diazaspiro[4.4]nonan-6-one
• CAS: 139174-35-9；139174-44-0
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: WNRGWQTUWWJEHX-NQIIRXRSSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-N-(4-methylbenzylidene)aniline oxide 、 3,3-methylene-5,5-dimethyl-2-pyrrolidinone 以 甲苯 为溶剂， 生成 1-Oxa-2,7-diazaspiro[4.4]nonan-6-one,8,8-dimethyl-3-(4-methylphenyl)-2-phenyl-, trans- 、 2-phenyl-3-(4-methylphenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene
  参考文献：
  名称：

  Regio- and stereoselectivity in the 1,3-dipolar cycloaddition of C,N-diarylnitrones to 3,3-methylene-5,5-dimethyl-2-pyrrolidinone

  摘要：

  Regio- and stereoselectivity of the nitrone cycloaddition with 3,3-methylene-5,5-dimethyl-2-pyrrolidinone ((1) is discussed. Nitrones react regioselectively with 1 to give a mixture of diastereoisomeric spiro-cycloadducts 3 and 4, in which 3 always dominates. Both 3 and 4 result from the approach which binds the carbon of the nitrone with the exocyclic carbon of 1 and the oxygen to the spiro carbon. The structure and steric configuration of the adducts have been assigned on the basis of H-1- and C-13-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the reactants were performed, the regio- and stereochemistry of the cycloaddition seems to be controlled by steric effects.

  DOI：

  10.1007/bf00823428