tert-butyl (2S)-2-[2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethyl]pyrrolidine-1-carboxylate | 142319-40-2

• 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 (2S)-2-[2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethyl]pyrrolidine-1-carboxylate
• CAS: 142319-40-2
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: PVNVMYAFHHYOAV-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethyl]pyrrolidine-1-carboxylate 270.0 ℃ 、399.97 Pa 条件下， 以83%的产率得到(6S,8aR)-octahydro-6-aminoindolizine
  参考文献：
  名称：

  A novel thermolytic annulation of an oxazolidinone: an enantiospecific synthesis of (-)-slaframine

  摘要：

  Optically pure beta-aminopiperidines can be prepared in high yields through a thermolytic annulation sequence involving ring opening of an oxazolidinone.

  DOI：

  10.1021/jo00042a002
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 palladium on activated charcoal 正丁基锂 、 氢气 、 二异丁基氢化铝 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 tert-butyl (2S)-2-[2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  A novel thermolytic annulation of an oxazolidinone: an enantiospecific synthesis of (-)-slaframine

  摘要：

  Optically pure beta-aminopiperidines can be prepared in high yields through a thermolytic annulation sequence involving ring opening of an oxazolidinone.

  DOI：

  10.1021/jo00042a002

文献信息

• A novel thermolytic annulation of an oxazolidinone: an enantiospecific synthesis of (-)-slaframine
  作者：Mukund P. Sibi、James W. Christensen、Biqin Li、Paul A. Renhowe

  DOI：10.1021/jo00042a002

  日期：1992.7

  Optically pure beta-aminopiperidines can be prepared in high yields through a thermolytic annulation sequence involving ring opening of an oxazolidinone.
• Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹
  作者：Mukund P. Sibi、James W. Christensen

  DOI：10.1021/jo9908546

  日期：1999.8.1

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.