8,8-dimethyl-3-phenyl-1-oxa-2,7-diazaspiro<4.4>non-2-ene-6-one | 139059-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8,8-dimethyl-3-phenyl-1-oxa-2,7-diazaspiro<4.4>non-2-ene-6-one
• 英文别名: 3-phenyl-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4.4>non-2-ene；8,8-Dimethyl-3-phenyl-1-oxa-2,7-diazaspiro[4.4]non-2-en-6-one
• CAS: 139059-89-5
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: PFBFFBAAZBAVTM-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8,8-dimethyl-3-phenyl-1-oxa-2,7-diazaspiro<4.4>non-2-ene-6-one 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以40%的产率得到8,8-dimethyl-3-phenyl-1-oxa-2,7-diazaspiro<4.4>non-2-ene-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：

  3,3-methylene-5,5-dimethyl-2-pyrrolidinone 、 benzohydroximoyl chloride 在 三乙胺 作用下， 以 乙醚 为溶剂， 以77%的产率得到8,8-dimethyl-3-phenyl-1-oxa-2,7-diazaspiro<4.4>non-2-ene-6-one
  参考文献：
  名称：

  Regioselectivity in the 1,3-dipolar cycloaddition of nitrile oxides to 3,3-methylene-5,5-dimethyl-2-pyrrolidinone

  摘要：

  Nitrile oxides add regioselectively to the carbon-carbon double bond of 3,3-methylene-5,5-dimethyl-2-pyrrolidinone (1), giving exclusively spiro-isoxazolines: 3-aryl-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro[4,4]non-2-enes 3 a-1. The regiochemistry of the 1,3-dipolar cycloaddition to 1 seems to be controlled by the steric effect of the methyl groups at the ring junction and by frontier orbital interactions.

  DOI：

  10.1007/bf00815920

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.
• Regioselectivity in the 1,3-dipolar cycloaddition of nitrile oxides to 3,3-methylene-5,5-dimethyl-2-pyrrolidinone
  作者：Peter Oravec、L. Fišera、Peter Ertl、Daniel Végh

  DOI：10.1007/bf00815920

  日期：1991.10

  Nitrile oxides add regioselectively to the carbon-carbon double bond of 3,3-methylene-5,5-dimethyl-2-pyrrolidinone (1), giving exclusively spiro-isoxazolines: 3-aryl-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro[4,4]non-2-enes 3 a-1. The regiochemistry of the 1,3-dipolar cycloaddition to 1 seems to be controlled by the steric effect of the methyl groups at the ring junction and by frontier orbital interactions.