Morphinan-6-ol, 7,8-didehydro-3,4-dimethoxy-17-methyl-, (6a)- | 25744-30-3

• 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: Morphinan-6-ol, 7,8-didehydro-3,4-dimethoxy-17-methyl-, (6a)-
• 英文别名: 7,8-didehydro-3,4-dimethoxy-17-methylmorphinan-6α-ol
• CAS: 25744-30-3；112462-83-6
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: SVWZQRXSUUZQHY-TXRSIGLOSA-N

物化性质

• 沸点：
  469.7±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Morphinan-6-ol, 7,8-didehydro-3,4-dimethoxy-17-methyl-, (6a)- 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以31%的产率得到6α-acetoxy-7,8-didehydro-3,4-dimethoxy-17-methylmorphinan
  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 sodium tetrahydroborate 、 cerium(III) chloride 、 ammonium chloride 、 sodium methylate 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 丙酮 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