ethenyl (4R,4aS,7S,7aR,12bS)-4a,7-diacetyloxy-9-methoxy-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate | 144264-78-8

• 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: ethenyl (4R,4aS,7S,7aR,12bS)-4a,7-diacetyloxy-9-methoxy-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate
• CAS: 144264-78-8
• 化学式: C₂₄H₂₅NO₈
• 分子量: 455.464
• InChiKey: DNMCNXSFLQGDHH-WSEOTULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethenyl (4R,4aS,7S,7aR,12bS)-4a,7-diacetyloxy-9-methoxy-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate 在 盐酸 、 ammonium hydroxide 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (4R,4aS,7S,7aR,12bS)-9-methoxy-3-prop-2-enyl-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol
  参考文献：
  名称：

  Synthesis of N-Demethyl-N-Substituted-14-Hydroxycodeine and Morphine Derivatives⁺

  摘要：

  A fews representatives (1b-d) of a novel group of structurally related morphine-antagonist compounds have been prepared in stereochemically homogeneous form. The employed procedures involve O-demethylation either of the corresponding codeine derivatives 2b-d, or those of the N-alkylated analogues 2b,c, synthesized from N-demethylthebaine (7a) by means of N-alkylation and subsequent transformations of 7b,d, - compounds selected from the resulting functionalized thebaines 7b-e.

  DOI：

  10.1080/00397919208021649
• 作为产物：
  描述：

  氯甲酸乙烯酯 、 14-hydroxycodeine diacatate 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以72%的产率得到ethenyl (4R,4aS,7S,7aR,12bS)-4a,7-diacetyloxy-9-methoxy-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of N-Demethyl-N-Substituted-14-Hydroxycodeine and Morphine Derivatives⁺

  摘要：

  A fews representatives (1b-d) of a novel group of structurally related morphine-antagonist compounds have been prepared in stereochemically homogeneous form. The employed procedures involve O-demethylation either of the corresponding codeine derivatives 2b-d, or those of the N-alkylated analogues 2b,c, synthesized from N-demethylthebaine (7a) by means of N-alkylation and subsequent transformations of 7b,d, - compounds selected from the resulting functionalized thebaines 7b-e.

  DOI：

  10.1080/00397919208021649