3-(_tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone | 144152-46-5

• 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: 3-(_tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone
• 英文别名: [(4R,4aS,7aR,12bS)-9-[tert-butyl(dimethyl)silyl]oxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate
• CAS: 144152-46-5
• 化学式: C₂₅H₃₅NO₅Si
• 分子量: 457.642
• InChiKey: SCDXDIDZMKQFOH-CKZJNZIISA-N

物化性质

• 沸点：
  517.4±50.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(_tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone 在 盐酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 59.0h， 生成 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-(butyldimethylsilyl)morphine 在 palladium on activated charcoal manganese(IV) oxide 、 氢气 、 silica gel 作用下， 以 乙醇 、 氯仿 为溶剂， 25.0~40.0 ℃ 、101.33 kPa 条件下， 反应 6.83h， 生成 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

文献信息

• An improved synthesis of noroxymorphone
  作者：Aleyamma Ninan、Malcolm Sainsbury

  DOI：10.1016/s0040-4020(01)80016-8

  日期：1992.1

  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%.