N-vinyloxycarbonyl-3-(^tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone | 144152-44-3

• 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: N-vinyloxycarbonyl-3-(^tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone
• 英文别名: ethenyl (4R,4aS,7aR,12bS)-4a-acetyloxy-9-[tert-butyl(dimethyl)silyl]oxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate
• CAS: 144152-44-3
• 化学式: C₂₇H₃₅NO₇Si
• 分子量: 513.663
• InChiKey: HJRQJMBHHIFVNG-VNBBPEHGSA-N

物化性质

• 沸点：
  580.7±50.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-vinyloxycarbonyl-3-(^tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到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
• 作为产物：
  描述：

  3-(_tbutyldimethylsilyl)-14-hydroxymorphinone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 75.5h， 生成 N-vinyloxycarbonyl-3-(^tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone
  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