dihydrocodeinone oxime | 5965-16-2

• 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: dihydrocodeinone oxime
• 英文别名: 4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one oxime；4,5α-Epoxy-3-methoxy-17-methyl-morphinan-6-on-oxim
• CAS: 5965-16-2
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: ZABTXUQRTPTNSR-DCONWNQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  54.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dihydrocodeinone oxime 在 sodium tetrahydroborate 、 氯化亚砜 、 硫酸 、 水 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 ethyl 3-(3-methoxy-8-methyl-7,8,9,10-tetrahydro-1H,6H-7,10a-methanobenzofuro[3,4-de]azocin-11-yl)propanoate
  参考文献：
  名称：

  Preparation and analgesic activity of (-)-11.alpha.-substituted 1,2,3,4,5,6-hexahydro-6.alpha.,7-(methyleneoxy)-2,6-methano-3-benzazocines

  摘要：

  Dihydrocodeinone oxime (1) under Beckmann rearrangement conditions gave a product (2) that facilitated the preparation of (-)-11 alpha-substituted 1,2,3,4,5,6-hexahydro-6 alpha,7-(methyleneoxy)-2,6-methano-3-benzazocines, a hitherto little-examined series of morphine partial structures. Compounds 7a and 12 gave good levels of agonist antinociceptive activity. Masking of the 8-oxygen function, as in 6 and 8, dramatically reduced mouse hot-plate activity, as did its loss (9).

  DOI：

  10.1021/jm00160a022
• 作为产物：
  描述：

  二氢可待因酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 2.0h， 以98.6%的产率得到dihydrocodeinone oxime
  参考文献：
  名称：

  Preparation and analgesic activity of (-)-11.alpha.-substituted 1,2,3,4,5,6-hexahydro-6.alpha.,7-(methyleneoxy)-2,6-methano-3-benzazocines

  摘要：

  Dihydrocodeinone oxime (1) under Beckmann rearrangement conditions gave a product (2) that facilitated the preparation of (-)-11 alpha-substituted 1,2,3,4,5,6-hexahydro-6 alpha,7-(methyleneoxy)-2,6-methano-3-benzazocines, a hitherto little-examined series of morphine partial structures. Compounds 7a and 12 gave good levels of agonist antinociceptive activity. Masking of the 8-oxygen function, as in 6 and 8, dramatically reduced mouse hot-plate activity, as did its loss (9).

  DOI：

  10.1021/jm00160a022