14-acetylnoroxymorphone hydrochloride | 144333-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 14-acetylnoroxymorphone hydrochloride
• CAS: 144333-31-3
• 化学式: C₁₈H₁₉NO₅*ClH
• 分子量: 365.814
• InChiKey: QIJOUMKMCLPWCV-RKXJKUSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  14-acetylnoroxymorphone hydrochloride 在 硫酸 作用下， 反应 5.0h， 以88%的产率得到14-羟基二氢降吗啡酮盐酸盐
  参考文献：
  名称：

  An improved synthesis of noroxymorphone

  摘要：

  A brief synthesis of noroxymorphone is described which involves the oxidation of 3-O-(t)butyldimethylsilylmorphine by manganese dioxide. The initial product is the corresponding morphinone which is further oxidised to the 14-hydroxymorphinone. After hydrogenation the 7,8-dihydro-14-hydroxymorphinone is acetylated and N-demethylation of the 14-O-acetylated product is achieved using vinyl chloroformate as the reagent. The overall yield from morphine is 40-45%.

  DOI：

  10.1016/s0040-4020(01)80016-8
• 作为产物：
  描述：

  3-(_tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone 在 盐酸 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 73.0h， 生成 14-acetylnoroxymorphone hydrochloride
  参考文献：
  名称：

  An improved synthesis of noroxymorphone

  摘要：

  A brief synthesis of noroxymorphone is described which involves the oxidation of 3-O-(t)butyldimethylsilylmorphine by manganese dioxide. The initial product is the corresponding morphinone which is further oxidised to the 14-hydroxymorphinone. After hydrogenation the 7,8-dihydro-14-hydroxymorphinone is acetylated and N-demethylation of the 14-O-acetylated product is achieved using vinyl chloroformate as the reagent. The overall yield from morphine is 40-45%.

  DOI：

  10.1016/s0040-4020(01)80016-8