| 79798-04-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• CAS: 79798-04-2
• 化学式: C₂₅H₃₉NO₉P₂
• 分子量: 559.533
• InChiKey: VITGBTASCOFYBE-ASDQOZNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  101.99
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 3-deoxy-7,8-dihydromorphine
  参考文献：
  名称：

  (-)-4-Hydroxymorphinanones: their synthesis and analgesic activity

  摘要：

  A facile procedure is described for the conversion of morphine, via the diphosphate ester derivative 1 followed by catalytic reduction and treatment with Li/NH3, to 3-deoxy-7,8-dihydromorphine (3). Oxidation with benzophenone tert-butoxide converted 3 to the ketone 4, which on treatment with Zn/NH4Cl formed (-)-4-hydroxymorphinan-6-one 5. Reaction of 5 with diazomethane formed the methyl ether 6. The N-cyclopropylmethyl analogues of 4 and 5 were also prepared, i.e., 8c and 9 from 4. The antinociceptive activity of these compounds was tested. Compounds 5, 6, 8c, and 9 showed potent antiwrithing activity and, based on these data, a structure-activity relationship in morphinans is discussed.

  DOI：

  10.1021/jm00144a013
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  (-)-4-Hydroxymorphinanones: their synthesis and analgesic activity

  摘要：

  A facile procedure is described for the conversion of morphine, via the diphosphate ester derivative 1 followed by catalytic reduction and treatment with Li/NH3, to 3-deoxy-7,8-dihydromorphine (3). Oxidation with benzophenone tert-butoxide converted 3 to the ketone 4, which on treatment with Zn/NH4Cl formed (-)-4-hydroxymorphinan-6-one 5. Reaction of 5 with diazomethane formed the methyl ether 6. The N-cyclopropylmethyl analogues of 4 and 5 were also prepared, i.e., 8c and 9 from 4. The antinociceptive activity of these compounds was tested. Compounds 5, 6, 8c, and 9 showed potent antiwrithing activity and, based on these data, a structure-activity relationship in morphinans is discussed.

  DOI：

  10.1021/jm00144a013