tert-butyl 4-bromo-7-oxo-6-azabicyclo[3.2.1]oct-2-ene-6-carboxylate | 891862-20-7

• 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 4-bromo-7-oxo-6-azabicyclo[3.2.1]oct-2-ene-6-carboxylate
• 英文别名: tert-butyl (1R,4S,5S)-4-bromo-7-oxo-6-azabicyclo[3.2.1]oct-2-ene-6-carboxylate
• CAS: 891862-20-7
• 化学式: C₁₂H₁₆BrNO₃
• 分子量: 302.168
• InChiKey: WVMFDUNXBOHDLW-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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 4-bromo-7-oxo-6-azabicyclo[3.2.1]oct-2-ene-6-carboxylate 、 乙醇 在 caesium carbonate 作用下， 反应 2.0h， 以100%的产率得到(S)-ethyl 5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-dienecarboxylate
  参考文献：
  名称：

  A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid

  摘要：

  A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; (4) good overall yield (ca. 30%, still not completely optimized); and (5) scalability.

  DOI：

  10.1021/ja0616433
• 作为产物：
  描述：

  tert-butyl 7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以95%的产率得到tert-butyl 4-bromo-7-oxo-6-azabicyclo[3.2.1]oct-2-ene-6-carboxylate
  参考文献：
  名称：

  A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid

  摘要：

  A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; (4) good overall yield (ca. 30%, still not completely optimized); and (5) scalability.

  DOI：

  10.1021/ja0616433

文献信息

• INTERMEDIATE COMPOUNDS OF TAMIFLU, METHODS OF PREPARATION AND USES THEREOF
  申请人：Ma Dawei

  公开号：US20140221662A1

  公开（公告）日：2014-08-07

  Chiral amino compounds, methods of preparation and uses thereof. Tamiflu can be obtained from the said compounds. Multi-substituted chiral tetrahydropyrrolyl amine which can be used as intermediate compounds of medicament can also be produced by the said compounds.

  手性氨基化合物，其制备方法及用途。 好病毒药物达菌素可以从这些化合物中获得。 这些化合物还可以制备用作药物中间体的多取代手性四氢吡咯基胺。
• US9040738B2
  申请人：——

  公开号：US9040738B2

  公开（公告）日：2015-05-26
• A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid
  作者：Yeung、Sungwoo Hong、E. J. Corey

  DOI：10.1021/ja0616433

  日期：2006.5.1

  A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; (4) good overall yield (ca. 30%, still not completely optimized); and (5) scalability.