tert-butyl (R)-2-oxo-5-vinylpyrrolidine-1-carboxylate | 1215309-48-0

• 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: tert-butyl (R)-2-oxo-5-vinylpyrrolidine-1-carboxylate
• 英文别名: (5R)-N-(tert-butyloxycarbonyl)-5-vinylpyrrolidin-2-one；tert-butyl (2R)-2-ethenyl-5-oxopyrrolidine-1-carboxylate
• CAS: 1215309-48-0
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: PXRBKNSGFKJKIA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2-oxo-5-vinylpyrrolidine-1-carboxylate 在 三氟乙酸 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(5R)-5-vinyl-2-pyrrolidinone
  参考文献：
  名称：

  Enantioselective synthesis of condensed and transannular ring skeletons containing pyrrolidine moiety

  摘要：

  A new approach toward condensed and transannular ring structures Containing pyrrolidine unit has been developed, based on diastereoselective nucleophilic addition of lithium of alpha-diazoacetoacetate to chiral N-sulfillyl imine and ring-closing metathesis (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.12.013
• 作为产物：
  描述：

  3-allyl 1-tert-butyl (R)-2-oxo-5-vinylpyrrolidine-1,3-dicarboxylate 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到tert-butyl (R)-2-oxo-5-vinylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of condensed and transannular ring skeletons containing pyrrolidine moiety

  摘要：

  A new approach toward condensed and transannular ring structures Containing pyrrolidine unit has been developed, based on diastereoselective nucleophilic addition of lithium of alpha-diazoacetoacetate to chiral N-sulfillyl imine and ring-closing metathesis (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.12.013

文献信息

• Total Synthesis of (–)-Sessilifoliamide C and (–)-8-<i>epi</i>-Stemoamide
  作者：Adam T. Hoye、Peter Wipf

  DOI：10.1021/ol200743u

  日期：2011.5.20

  A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifollamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.
• [EN] SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES<br/>[FR] SYNTHÈSE ET APPLICATION DE POLYVINYLEPYRROLIDINONES SUBSTITUÉES CHIRALES
  申请人：UNIV KANSAS STATE

  公开号：WO2017172763A1

  公开（公告）日：2017-10-05

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.