(-)-3-tert-butoxy-N-methylmorphinan

• 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-tert-butoxy-N-methylmorphinan
• 英文别名: 17-Methyl-4-[(2-methylpropan-2-yl)oxy]-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
• 化学式: C₂₁H₃₁NO
• 分子量: 313.483
• InChiKey: HWTLPRHSBYNYIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Dextrorphan 、 N,N-二甲基甲酰胺二叔丁基缩醛 反应 12.0h， 以59%的产率得到(-)-3-tert-butoxy-N-methylmorphinan
  参考文献：
  名称：

  Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol

  摘要：

  3-O-tert-Butylmorphine (5) was prepared from 6-O-acetylmorphine (3) via alkylation with N,N-dimethylformamide di-tert-butyl acetal, followed by hydrolytic removal of the 3-(dimethylamino)-2-propenoate group. The same process was used to prepare the tert-butyl ether of levorphanol (6), (-)-3-tert-butoxy-N-methylmorphinan (8). Both 5 and 8 exhibited in vitro affinity for the opiate receptor comparable to codeine and had analgesic properties in the writhing test. Only 5 exhibited activity in the tail-flick procedure and neither compound showed significant antitussive activity.

  DOI：

  10.1021/jm00352a037