tert-butyl (1R,5S,6S)-6-acetylamino-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate | 927395-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: tert-butyl (1R,5S,6S)-6-acetylamino-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate
• 英文别名: tert-butyl (1R,5S,6S)-6-acetamido-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate
• CAS: 927395-67-3
• 化学式: C₁₄H₂₀N₂O₅
• 分子量: 296.323
• InChiKey: ZOWZNSZZKSRTBA-DCAQKATOSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,5S,6S)-6-acetylamino-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate 在 caesium carbonate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 16.0h， 生成 tert-butyl [(1S,2S)-2-acetylamino-5-oxocyclohex-3-en-1-yl]carbamate
  参考文献：
  名称：

  Second Generation Catalytic Asymmetric Synthesis of Tamiflu:  Allylic Substitution Route

  摘要：

  Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the CC double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route.

  DOI：

  10.1021/ol062663c
• 作为产物：
  描述：

  (4S,5S)-4-azido-5-(tert-butoxycarbonylamino)cyclohexene 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 碘 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 39.0h， 生成 tert-butyl (1R,5S,6S)-6-acetylamino-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate
  参考文献：
  名称：

  Second Generation Catalytic Asymmetric Synthesis of Tamiflu:  Allylic Substitution Route

  摘要：

  Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the CC double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route.

  DOI：

  10.1021/ol062663c