7β-bromo-6β-azidodeoxyneopine | 202707-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7β-bromo-6β-azidodeoxyneopine
• 英文别名: (4R,6R,7S,7aR,12bS)-7-azido-6-bromo-9-methoxy-3-methyl-2,4,6,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
• CAS: 202707-80-0
• 化学式: C₁₈H₁₉BrN₄O₂
• 分子量: 403.278
• InChiKey: OYJPNSRBJKFFBH-PFCVXKDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7β-bromo-6β-azidodeoxyneopine 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以75.7%的产率得到6-azido-6-demethoxythebaine
  参考文献：
  名称：

  Syntheses and transformations of novel nitrogen and sulfur containing morphinanedienes

  摘要：

  The synthesis of 6-azido-6-demethoxythebaine (10) has been performed starting from thebaine (1). Compound 10 undergoes a cycloaddition reaction with the azadienophile PTAD to form bridgehead azide 14. The acid catalyzed rearrangement of isothiocyanato diene 11 obtained from azido diene 10 and thiocyanato dienes 8 and 9 leads to sulfur containing derivatives of apocodeine (17-20).

  DOI：

  10.1007/bf00807259
• 作为产物：
  描述：

  6β-azido-14β-hydroxydeoxycodeine 在 三溴化磷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以77.8%的产率得到7β-bromo-6β-azidodeoxyneopine
  参考文献：
  名称：

  Syntheses and transformations of novel nitrogen and sulfur containing morphinanedienes

  摘要：

  The synthesis of 6-azido-6-demethoxythebaine (10) has been performed starting from thebaine (1). Compound 10 undergoes a cycloaddition reaction with the azadienophile PTAD to form bridgehead azide 14. The acid catalyzed rearrangement of isothiocyanato diene 11 obtained from azido diene 10 and thiocyanato dienes 8 and 9 leads to sulfur containing derivatives of apocodeine (17-20).

  DOI：

  10.1007/bf00807259

文献信息

• Syntheses and transformations of novel nitrogen and sulfur containing morphinanedienes
  作者：C. Csutor�s、S. Ber�nyi、B. Czak�、S. Makleit

  DOI：10.1007/bf00807259

  日期：1997.12

  The synthesis of 6-azido-6-demethoxythebaine (10) has been performed starting from thebaine (1). Compound 10 undergoes a cycloaddition reaction with the azadienophile PTAD to form bridgehead azide 14. The acid catalyzed rearrangement of isothiocyanato diene 11 obtained from azido diene 10 and thiocyanato dienes 8 and 9 leads to sulfur containing derivatives of apocodeine (17-20).