tert-butyl [(1R,2S,6S)-7-acetyl-4-cyano-7-azabicyclo[4.1.0]hept-4-en-2-yl]carbamate | 927395-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: tert-butyl [(1R,2S,6S)-7-acetyl-4-cyano-7-azabicyclo[4.1.0]hept-4-en-2-yl]carbamate
• 英文别名: tert-butyl N-[(1R,2S,6S)-7-acetyl-4-cyano-7-azabicyclo[4.1.0]hept-4-en-2-yl]carbamate
• CAS: 927395-72-0
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: IXVYVIHVPRXNOQ-RMQNUCIVSA-N

物化性质

• 沸点：
  484.9±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 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：
  82.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl [(1R,2S,6S)-7-acetyl-4-cyano-7-azabicyclo[4.1.0]hept-4-en-2-yl]carbamate 、 3-戊醇 在 5A molecular sieve 、 三氟化硼乙醚 作用下， 反应 1.0h， 以56%的产率得到tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-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：

  tert-butyl (1R,5S,6S)-6-acetylamino-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate 在 锂丁酯 、 caesium carbonate 、 戴斯-马丁氧化剂 、 三苯基膦 、 偶氮二甲酸二乙酯 、 对硝基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 正丁醇 为溶剂， 反应 25.42h， 生成 tert-butyl [(1R,2S,6S)-7-acetyl-4-cyano-7-azabicyclo[4.1.0]hept-4-en-2-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

文献信息

• Second Generation Catalytic Asymmetric Synthesis of Tamiflu:  Allylic Substitution Route
  作者：Tsuyoshi Mita、Nobuhisa Fukuda、Francesc X. Roca、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ol062663c

  日期：2007.1.1

  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.