2-phenyl-3-(3-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene | 139174-33-7

• 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-(3-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene
• 英文别名: 8,8-dimethyl-3-(3-nitrophenyl)-2-phenyl-1-oxa-2,7-diazaspiro<4.4>nonane-6-one；(3R,5S)-8,8-dimethyl-3-(3-nitrophenyl)-2-phenyl-1-oxa-2,7-diazaspiro[4.4]nonan-6-one
• CAS: 139174-33-7
• 化学式: C₂₀H₂₁N₃O₄
• 分子量: 367.404
• InChiKey: ZFTFZCNFNQLJPT-XLIONFOSSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  2-phenyl-3-(3-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 36.0h， 以40%的产率得到8,8-dimethyl-3-(3-nitrophenyl)-2-phenyl-1-oxa-2,7-diazaspiro<4.4>nonane-6-thione
  参考文献：
  名称：

  1,3-Diploar Cycloaddition of Nitrones and Nitrile Oxides to 5,5-Dimethyl-3-methylenepyrrolidine-2-thione

  摘要：

  A simple synthesis of title compound (3) and a number of different cycloadditions are described. C-Aroyl- and C,N-diphenyl-nitrones react regio- and stereoselectively to the C=C exocyclic double bond of 3, to give only spirocycloadduct (10). On the other hand, C-phenyl-N-methylnitrone gives a mixture of diastereomeric spirocycloadducts (10) and (11). Nitrile oxides undergo 1,3-dipolar cycloaddition both to the exocyclic C=C and C=S double bonds with subsequent cycloreversion and formation of spiro-lactams (6). The appropriate spiro-thiolactams (8) were synthetized by treatment of 6 with Lawesson's reagent.

  DOI：

  10.3987/com-94-s22
• 作为产物：
  描述：

  N-(3-硝基苄基亚基)苯胺N-氧化物 、 3,3-methylene-5,5-dimethyl-2-pyrrolidinone 以 甲苯 为溶剂， 生成 2-phenyl-3-(3-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene 、 2-phenyl-3-(3-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

• 1,3-Diploar Cycloaddition of Nitrones and Nitrile Oxides to 5,5-Dimethyl-3-methylenepyrrolidine-2-thione
  作者：Lubor Fisera、Libuse Jaroskova、Iveta Matejkova、Heinz Heimgartner

  DOI：10.3987/com-94-s22

  日期：——

  A simple synthesis of title compound (3) and a number of different cycloadditions are described. C-Aroyl- and C,N-diphenyl-nitrones react regio- and stereoselectively to the C=C exocyclic double bond of 3, to give only spirocycloadduct (10). On the other hand, C-phenyl-N-methylnitrone gives a mixture of diastereomeric spirocycloadducts (10) and (11). Nitrile oxides undergo 1,3-dipolar cycloaddition both to the exocyclic C=C and C=S double bonds with subsequent cycloreversion and formation of spiro-lactams (6). The appropriate spiro-thiolactams (8) were synthetized by treatment of 6 with Lawesson's reagent.
• 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.