tert-butyl 7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate | 891862-19-4

• 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 7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate
• 英文别名: tert-butyl (1S,5S)-7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate
• CAS: 891862-19-4
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: BVNTYOMNCKWQHK-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 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 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
• 作为产物：
  描述：

  (S)-cyclohex-3-ene-1-carboxamide 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 22.0h， 生成 tert-butyl 7-oxo-6-azabicyclo[3.2.1]oct-3-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

• PROCESS FOR THE PREPARATION OF OSELTAMIVIR AND METHYL 3-EPI-SHIKIMATE
  申请人：Council of Scientific & Industrial Research

  公开号：US20140243537A1

  公开（公告）日：2014-08-28

  The present invention discloses high yielding enantioselective process for synthesis of Oseltamivir from readily available starting material, cis-1,4-butene diol. The process features incorporation of chirality using sharpless asymmetric epoxidation (AE) and diastereoselective Barbier allylation and construction of cyclohexene carboxylic acid ester core through a ring closing metathesis (RCM) reaction. Further also disclosed herein is synthesis of (−)-methyl 3-epi-shikimate.

  本发明揭示了一种高产高对映选择性的奥司他韦合成工艺，从易得的起始物质顺式-1,4-丁二醇出发。该工艺采用Sharpless不对称环氧化（AE）和立体选择性的Barbier烯丙基化，通过环内酯交换反应（RCM）构建环己烯羧酸酯核心以引入手性。此外，还揭示了(−)-甲基3-epi-香椿糖酸的合成。
• 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。
• An efficient process for the bromolactamization of unsaturated acids
  作者：Ying-Yeung Yeung、E.J. Corey

  DOI：10.1016/j.tetlet.2007.08.113

  日期：2007.10

  Bromolactamization of the N-Boc derivatives of unsaturated amides using N-bromosuccinimide and lithium t-butoxide in tetrahydrofuran occurs smoothly to give excellent yields of bromo N-Boc α-lactams, which are valuable as synthetic intermediates.

  使用N-溴琥珀酰亚胺和叔丁醇锂在四氢呋喃中对不饱和酰胺的N- Boc衍生物进行溴内酰胺化反应可顺利进行，从而获得优异的溴N -Bocα-内酰胺收率，这是有价值的合成中间体。
• US9040738B2
  申请人：——

  公开号：US9040738B2

  公开（公告）日：2015-05-26
• US9150498B2
  申请人：——

  公开号：US9150498B2

  公开（公告）日：2015-10-06