6-isothiocyanato-6-demethoxythebaine | 202707-79-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 6-isothiocyanato-6-demethoxythebaine
• 英文别名: (4R,7aR,12bS)-7-isothiocyanato-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
• CAS: 202707-79-7
• 化学式: C₁₉H₁₈N₂O₂S
• 分子量: 338.43
• InChiKey: QNNDNLHXBLRVSX-CCKFTAQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-isothiocyanato-6-demethoxythebaine 在 甲烷磺酸 作用下， 反应 0.33h， 以35.9%的产率得到
  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 potassium tert-butylate 、 三溴化磷 、 三苯基膦 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.5h， 生成 6-isothiocyanato-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

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).