4,5α-epoxy-6-oxo-morphinane-17-carboxylic acid ethyl ester | 69663-75-8

• 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: 4,5α-epoxy-6-oxo-morphinane-17-carboxylic acid ethyl ester
• CAS: 69663-75-8
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: MHPKAAXIBORGPC-JBYDNAENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5α-epoxy-6-oxo-morphinane-17-carboxylic acid ethyl ester 在 盐酸 、 sodium periodate 作用下， 以 乙酸乙酯 、 叔丁醇 为溶剂， 反应 2.0h， 生成 4,5α-epoxy-6-oxo-morphin-7-ene-17-carboxylic acid ethyl ester
  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 二苯甲酮 、 potassium tert-butylate 、 氢气 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 0.83h， 生成 4,5α-epoxy-6-oxo-morphinane-17-carboxylic acid ethyl ester
  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