3-(_tbutyldimethylsilyl)-14-hydroxymorphinone | 144152-45-4

• 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: 3-(_tbutyldimethylsilyl)-14-hydroxymorphinone
• 英文别名: (4R,4aS,7aR,12bS)-9-[tert-butyl(dimethyl)silyl]oxy-4a-hydroxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 144152-45-4
• 化学式: C₂₃H₃₁NO₄Si
• 分子量: 413.589
• InChiKey: YCVVZUNLQWQXMA-XEDHWARRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(_tbutyldimethylsilyl)-14-hydroxymorphinone 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 62.5h， 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 manganese(IV) oxide 、 silica gel 作用下， 以 氯仿 为溶剂， 反应 3.33h， 生成 3-(_tbutyldimethylsilyl)-14-hydroxymorphinone
  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%.