oxycodindole

• 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: oxycodindole
• 英文别名: (4bS,8aS,14bR)-1-methoxy-7-methyl-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazole-8a-ol；Oxycodone indole；(1S,2S,13R,21R)-16-methoxy-22-methyl-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaen-2-ol
• 化学式: C₂₄H₂₄N₂O₃
• 分子量: 388.466
• InChiKey: HPRLAWOHFRYBFS-IBURTVSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  oxycodindole 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以69%的产率得到(4bS,8R,8aS,14bR)-5,6,7,8,14,14b-六氢-7-甲基-4,8-甲桥苯并呋喃并(2,3-a)吡啶并(4,3-b)咔唑-1,8a(9H)-二醇
  参考文献：
  名称：

  L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives¹

  摘要：

  L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N-decarbomethoxylation and O-demethylation in one pot, or only render N-decarbomethoxylation in high yield without accompanying O-demethylation.

  DOI：

  10.1021/jo9801972
• 作为产物：
  描述：

  羟可待酮 、 苯肼 在 盐酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到oxycodindole
  参考文献：
  名称：

  JP2019509321A5

  摘要：

  公开号：

  JP2019509321A5

文献信息

• L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives¹
  作者：Andrew Coop、James W. Janetka、John W. Lewis、Kenner C. Rice

  DOI：10.1021/jo9801972

  日期：1998.6.1

  L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N-decarbomethoxylation and O-demethylation in one pot, or only render N-decarbomethoxylation in high yield without accompanying O-demethylation.
• JP2019509321A5
  申请人：——

  公开号：JP2019509321A5

  公开（公告）日：2019-04-04