2-phenyl-3-(4-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene | 139174-34-8

• 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-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene
• 英文别名: 2-phenyl-3-(4-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro[4,4]-non-2-ene；(3R,5S)-8,8-dimethyl-3-(4-nitrophenyl)-2-phenyl-1-oxa-2,7-diazaspiro[4.4]nonan-6-one
• CAS: 139174-34-8
• 化学式: C₂₀H₂₁N₃O₄
• 分子量: 367.404
• InChiKey: JKTKMCVKOVCHGY-XLIONFOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-nitrobenzylidene)aniline N-oxide 、 3,3-methylene-5,5-dimethyl-2-pyrrolidinone 以 甲苯 为溶剂， 以87%的产率得到2-phenyl-3-(4-nitrophenyl)-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

文献信息

• Regio- and stereoselectivity in the 1,3-dipolar cycloaddition of C,N-diarylnitrones to 3,3-methylene-5,5-dimethyl-2-pyrrolidinone
  作者：Peter Oravec、Ľubor Fišera、Igor Goljer、Peter Ertl

  DOI：10.1007/bf00823428

  日期：1991.11

  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.