4,5α-epoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinane | 60942-39-4

• 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: 4,5α-epoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinane
• CAS: 60942-39-4
• 化学式: C₂₄H₂₇NO₄S
• 分子量: 425.549
• InChiKey: KCKDTYMAZAVSKG-OYHFZEMUSA-N

物化性质

• 沸点：
  586.0±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4,5α-epoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 7,8-dihydro-3,6-didesoxymorphine
  参考文献：
  名称：

  Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

  摘要：

  Several 3-deoxy opioids and 3,6-dideoxydihydromorphine was synthesized to ascertain the effect of the phenolic hydroxyl group on antinociceptive potency and receptor binding affinity. Catalytic reduction of the 3-tetrazolyl ether derivatives of dihydromorphine provided the entry into the 3-deoxydihydro series. The prototype, 3-deoxymorphine, was prepared by lithium aluminum hydride reduction of 3-deoxy-N-carbethoxymorphinone, obtained via its 7-(phenylseleno) derivative. 3-Deoxydihydromorphinone and 3,6-dideoxydihydromorphine were found to be about as potent as, or more potent than, morphine in standard antiociceptive assays. Each of them, however, was less potent than the comparable 3-hydroxy analogue, and their binding affinity to the opiate receptor was substantially decreased. The epoxy ring in 3.6-dideoxydihydromorphine was found to increase the antinociceptive potency of the compound.

  DOI：

  10.1021/jm00189a007
• 作为产物：
  描述：

  4,5α-epoxy-17-methyl-3-(1-phenyl-tetrazol-5-yloxy)-morphinan-6α-ol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 72.0h， 生成 4,5α-epoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinane
  参考文献：
  名称：

  Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

  摘要：

  Several 3-deoxy opioids and 3,6-dideoxydihydromorphine was synthesized to ascertain the effect of the phenolic hydroxyl group on antinociceptive potency and receptor binding affinity. Catalytic reduction of the 3-tetrazolyl ether derivatives of dihydromorphine provided the entry into the 3-deoxydihydro series. The prototype, 3-deoxymorphine, was prepared by lithium aluminum hydride reduction of 3-deoxy-N-carbethoxymorphinone, obtained via its 7-(phenylseleno) derivative. 3-Deoxydihydromorphinone and 3,6-dideoxydihydromorphine were found to be about as potent as, or more potent than, morphine in standard antiociceptive assays. Each of them, however, was less potent than the comparable 3-hydroxy analogue, and their binding affinity to the opiate receptor was substantially decreased. The epoxy ring in 3.6-dideoxydihydromorphine was found to increase the antinociceptive potency of the compound.

  DOI：

  10.1021/jm00189a007