(4R,4aR,7aR,12bS)-6-acetyl-3-(cyclopropylmethyl)-9-methoxy-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one | 82331-88-2

• 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: (4R,4aR,7aR,12bS)-6-acetyl-3-(cyclopropylmethyl)-9-methoxy-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 82331-88-2
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: OHTVSMGBAJOEFI-POJQQAQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,4aR,7aR,12bS)-6-acetyl-3-(cyclopropylmethyl)-9-methoxy-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以84%的产率得到(4R,4aR,7aR,12bS)-6-acetyl-3-(cyclopropylmethyl)-9-hydroxy-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
  参考文献：
  名称：

  Novel opiates and antagonists. 4. 7-Alkanoylhydromorphone

  摘要：

  A series of 7-alkanoyl-substituted hydromorphone derivatives were prepared by acylation of the morpholine enamines. The most potent compound (6i) of the series was found to have agonist activity of the same order of magnitude as that of buprenorphine. The N-cyclopropylmethyl-substituted series was found to exhibit structure-activity relationships for analgesia and narcotic antagonism similar to those of the endo-ethanotetrahydrooripavines.

  DOI：

  10.1021/jm00350a019
• 作为产物：
  描述：

  17-(cyclopropylmethyl)-4,5α-epoxy-3-methoxy-6-oxo-morphinan 在 对甲苯磺酸 、 三乙胺 作用下， 以 三氯乙烯 、 苯 为溶剂， 反应 80.0h， 生成 (4R,4aR,7aR,12bS)-6-acetyl-3-(cyclopropylmethyl)-9-methoxy-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
  参考文献：
  名称：

  Novel opiates and antagonists. 4. 7-Alkanoylhydromorphone

  摘要：

  A series of 7-alkanoyl-substituted hydromorphone derivatives were prepared by acylation of the morpholine enamines. The most potent compound (6i) of the series was found to have agonist activity of the same order of magnitude as that of buprenorphine. The N-cyclopropylmethyl-substituted series was found to exhibit structure-activity relationships for analgesia and narcotic antagonism similar to those of the endo-ethanotetrahydrooripavines.

  DOI：

  10.1021/jm00350a019