3-(4-penten-1-yl)-2-pyrrolidinone | 155193-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(4-penten-1-yl)-2-pyrrolidinone
• 英文别名: 3-(Pent-4-enyl)-2-pyrrolidinone；3-pent-4-enylpyrrolidinone；3-Pent-4-enylpyrrolidin-2-one
• CAS: 155193-58-1
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: QLMCCSBVHVXTCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-penten-1-yl)-2-pyrrolidinone 在 劳森试剂 作用下， 以 乙二醇二甲醚 为溶剂， 反应 4.0h， 以82%的产率得到3-pent-4-enylpyrrolidinone-2-thione
  参考文献：
  名称：

  Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones

  摘要：

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.

  DOI：

  10.3987/com-93-s32
• 作为产物：
  描述：

  5-碘-1-戊烯 在 正丁基锂 、 氨 、 lithium 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 0.33h， 生成 3-(4-penten-1-yl)-2-pyrrolidinone
  参考文献：
  名称：

  Studies on the Intramolecular Cycloaddition Reaction of Mesoionics Derived from the Rhodium(II)-Catalyzed Cyclization of Diazoimides

  摘要：

  A series of alkenyl-substituted imides were prepared by treating the appropriate amide with 2,2,6-trimethyl-4H-1,3-dioxen-4-one in xylene at 140-degrees-C to give the N-acetoacylated imides. Exposure of these imides to standard diazo transfer conditions gave the desired diazoimides. The carbenoid intermediate derived by treatment of the diazoimide with rhodium(II) acetate undergoes ready cyclization onto the neighboring amide carbonyl oxygen atom to generate an isomunchnone intermediate. Subsequent 1,3-dipolar cycloaddition across the pendant olefin affords the cycloadduct in high yield. The stereochemical assignment of several of the cycloadducts was deduced by X-ray crystallography. The stereochemical outcome of the reaction is the consequence of an endo cycloaddition of the neighboring pi-bond across the transient isomunchnone dipole. Molecular mechanics calculations were used to model energy differences between the endo and exo diastereomers. The calculations reveal that the endo diastereomers are significantly (8-12 kcal/mol) lower in energy than the corresponding exo isomers thereby providing a rationale for the preferred endo cycloaddition. Ring opening of the cycloadducts occurred readily producing a transient N-acyliminium ion which either lost a proton to give an enamide or was reduced by Et3SiH to afford a bicyclic piperidine ring.

  DOI：

  10.1021/jo00085a035

文献信息

• Olefinic-Amide and Olefinic-Lactam Cyclizations
  作者：Jie Zhou、Jon D. Rainier

  DOI：10.1021/ol901448n

  日期：2009.8.20

  Olefinic-amide and olefinic-lactam cyclization reactions that result in the generation of cyclic enamides are described.
• Padwa Albert, Zhang Zhijia J., Heterocycles, 37 (1994) N 1, S 441-459
  作者：Padwa Albert, Zhang Zhijia J.

  DOI：——

  日期：——
• Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones
  作者：Albert Padwa、Zhijia J. Zhang

  DOI：10.3987/com-93-s32

  日期：——

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.
• Studies on the Intramolecular Cycloaddition Reaction of Mesoionics Derived from the Rhodium(II)-Catalyzed Cyclization of Diazoimides
  作者：Albert Padwa、Donald L. Hertzog、William R. Nadler、Martin H. Osterhout、Alan T. Price

  DOI：10.1021/jo00085a035

  日期：1994.3

  A series of alkenyl-substituted imides were prepared by treating the appropriate amide with 2,2,6-trimethyl-4H-1,3-dioxen-4-one in xylene at 140-degrees-C to give the N-acetoacylated imides. Exposure of these imides to standard diazo transfer conditions gave the desired diazoimides. The carbenoid intermediate derived by treatment of the diazoimide with rhodium(II) acetate undergoes ready cyclization onto the neighboring amide carbonyl oxygen atom to generate an isomunchnone intermediate. Subsequent 1,3-dipolar cycloaddition across the pendant olefin affords the cycloadduct in high yield. The stereochemical assignment of several of the cycloadducts was deduced by X-ray crystallography. The stereochemical outcome of the reaction is the consequence of an endo cycloaddition of the neighboring pi-bond across the transient isomunchnone dipole. Molecular mechanics calculations were used to model energy differences between the endo and exo diastereomers. The calculations reveal that the endo diastereomers are significantly (8-12 kcal/mol) lower in energy than the corresponding exo isomers thereby providing a rationale for the preferred endo cycloaddition. Ring opening of the cycloadducts occurred readily producing a transient N-acyliminium ion which either lost a proton to give an enamide or was reduced by Et3SiH to afford a bicyclic piperidine ring.