1-benzyl-5-hydroxy-5-vinylpyrrolidin-2-one | 353796-55-1

• 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: 1-benzyl-5-hydroxy-5-vinylpyrrolidin-2-one
• 英文别名: 1-Benzyl-5-ethenyl-5-hydroxypyrrolidin-2-one
• CAS: 353796-55-1
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: VFEXLXGAFPWOCO-UHFFFAOYSA-N

物化性质

• 沸点：
  403.3±45.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-hydroxy-5-vinylpyrrolidin-2-one 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 23.0h， 生成 diethyl 2-[(2E)-2-(1-benzyl-5-oxopyrrol-2-ylidene)ethyl]propanedioate
  参考文献：
  名称：

  SYNTHESIS OF EXOCYCLIC ENAMIDES VIA STEREOCONTROLLED ALLYLIC ISOMERIZATION AND 1,3-TRANSPOSITION

  摘要：

  In the presence of pyridinium para-toluenesulfonate (PPTS) an allylic alcohol moiety exocyclic to a lactam ring undergoes allylic isomerisation, or if the solvent is nucleophilic, 1,3-transposition can occur. All the rearrangements occurred with stereocontrol.

  DOI：

  10.1081/scc-100104405
• 作为产物：
  描述：

  1-苄基吡咯烷-2,5-二酮 、 vinylmagnesium bromide 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到1-benzyl-5-hydroxy-5-vinylpyrrolidin-2-one
  参考文献：
  名称：

  Sequential 1,4- and 1,2-Addition Reactions to α,β-Unsaturated N-Acyliminium Ions: A New Strategy for the Synthesis of Spiro and Bridged Heterocycles

  摘要：

  Novel bicyclic and tetracyclic spirocycles and tricyclic bridged heterocyclic systems can be readily prepared from sequential 1,4- and 1,2-addition reactions of latent bis-nucleophiles to alpha,beta-unsaturated N-acyliminium ions.

  DOI：

  10.1021/ol4029513

文献信息

• Stereocontrolled Formation of Epoxy Peroxide FunctionalityAppended to a Lactam Ring
  作者：Charles M. Marson、Afzal Khan、Rod A. Porter

  DOI：10.1021/jo001313f

  日期：2001.7.1

  The action of tert-butyl hydroperoxide and tin(IV) chloride upon allylic alcohols containing a lactam ring leads mainly to epoxy alkyl peroxides with high diastereoselection. Both the stereochemistry and the products formed are in marked contrast to the reactions of the analogous carbocyclic allylic alcohols with tert-butyl hydroperoxide-VO(acac)2.

  叔丁基氢过氧化物和氯化锡（IV）对含有内酰胺环的烯丙基醇的作用主要导致具有高非对映选择性的环氧烷基过氧化物。立体化学和形成的产物均与类似的碳环烯丙基醇与叔丁基氢过氧化物-VO（acac）2的反应形成鲜明对比。
• Synthesis of spirocyclic heterocycles from α,β-unsaturated <i>N</i>-acyliminium ions
  作者：Thanphat Thaima、Arife Yazici、Chiramet Auranwiwat、Anthony C. Willis、Uta Wille、Thunwadee Limtharakul、Stephen. G. Pyne

  DOI：10.1039/d0ob02075c

  日期：——

  The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational

  由4（S）-O-取代的羟基-5-羟基-5-乙烯基-N-烷基吡咯烷酮-2-酮原位产生的α，β-不饱和N-酰基亚胺离子与烯丙基硅烷和吲哚的反应导致形成螺环杂环的报道。六个单晶X射线结构和广泛的2D NMR实验证实了这些产品的结构和立体化学。此外，计算研究还提供了机械学见解和对这些反应的立体化学结果的理解。
• SYNTHESIS OF EXOCYCLIC ENAMIDES VIA STEREOCONTROLLED ALLYLIC ISOMERIZATION AND 1,3-TRANSPOSITION
  作者：Afzal Khan、Charles M. Marson、Rod A. Porter

  DOI：10.1081/scc-100104405

  日期：2001.1

  In the presence of pyridinium para-toluenesulfonate (PPTS) an allylic alcohol moiety exocyclic to a lactam ring undergoes allylic isomerisation, or if the solvent is nucleophilic, 1,3-transposition can occur. All the rearrangements occurred with stereocontrol.
• Sequential 1,4- and 1,2-Addition Reactions to α,β-Unsaturated <i>N</i>-Acyliminium Ions: A New Strategy for the Synthesis of Spiro and Bridged Heterocycles
  作者：Arife Yazici、Stephen G. Pyne

  DOI：10.1021/ol4029513

  日期：2013.11.15

  Novel bicyclic and tetracyclic spirocycles and tricyclic bridged heterocyclic systems can be readily prepared from sequential 1,4- and 1,2-addition reactions of latent bis-nucleophiles to alpha,beta-unsaturated N-acyliminium ions.