thebainone

• 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: thebainone
• 英文别名: (1S,9R)-3-hydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: SLJDAVMWFVYEFI-HJFZTSBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thebainone 在 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium methylate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.33h， 生成 Morphinan-6-ol, 7,8-didehydro-3,4-dimethoxy-17-methyl-, (6a)-
  参考文献：
  名称：

  Synthesis of 7,8-Didehydro-3,4-Dimethoxy-17-Methylmorphinan-6-one and the Regioselective Reduction of the Keto Function (Chemistry of Opium Alkaloids, Part XXIV)

  摘要：

  Abstract7,8‐Didehydro‐3,4‐dimethoxy‐17‐methylmorphinan‐6‐one (2) was prepared by reductive opening of the epoxy bridge of codeinone, followed by methylation with Rodionow's reagent. Reduction of the title compound with sodium tetrahydroborate in the presence of cerium(III) chloride afforded a mixture of 7,8‐didehydro‐3,4‐dimethoxy‐17‐methylmorphinan‐6α‐ol (3) and ‐6β‐ol (4) in a ratio of 4:1 from which the 6α‐epimer was crystallized and converted into the acetate (7).

  DOI：

  10.1002/bscb.19870960408
• 作为产物：
  描述：

  codeinone 在 ammonium chloride 、 锌 作用下， 以 丙酮 为溶剂， 生成 thebainone
  参考文献：
  名称：

  Synthesis of 7,8-Didehydro-3,4-Dimethoxy-17-Methylmorphinan-6-one and the Regioselective Reduction of the Keto Function (Chemistry of Opium Alkaloids, Part XXIV)

  摘要：

  Abstract7,8‐Didehydro‐3,4‐dimethoxy‐17‐methylmorphinan‐6‐one (2) was prepared by reductive opening of the epoxy bridge of codeinone, followed by methylation with Rodionow's reagent. Reduction of the title compound with sodium tetrahydroborate in the presence of cerium(III) chloride afforded a mixture of 7,8‐didehydro‐3,4‐dimethoxy‐17‐methylmorphinan‐6α‐ol (3) and ‐6β‐ol (4) in a ratio of 4:1 from which the 6α‐epimer was crystallized and converted into the acetate (7).

  DOI：

  10.1002/bscb.19870960408

文献信息

• US7767428B2
  申请人：——

  公开号：US7767428B2

  公开（公告）日：2010-08-03
• Synthesis of 7,8-Didehydro-3,4-Dimethoxy-17-Methylmorphinan-6-one and the Regioselective Reduction of the Keto Function (Chemistry of Opium Alkaloids, Part XXIV)
  作者：R. A. van Gurp、T. S. Lie、C. Mense、L. Maat

  DOI：10.1002/bscb.19870960408

  日期：——

  Abstract7,8‐Didehydro‐3,4‐dimethoxy‐17‐methylmorphinan‐6‐one (2) was prepared by reductive opening of the epoxy bridge of codeinone, followed by methylation with Rodionow's reagent. Reduction of the title compound with sodium tetrahydroborate in the presence of cerium(III) chloride afforded a mixture of 7,8‐didehydro‐3,4‐dimethoxy‐17‐methylmorphinan‐6α‐ol (3) and ‐6β‐ol (4) in a ratio of 4:1 from which the 6α‐epimer was crystallized and converted into the acetate (7).