3-O-叔丁基吗啡 | 34332-27-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 中文名称: 3-O-叔丁基吗啡
• 英文名称: 3-O-tert-butylmorphine
• 英文别名: (4R,4aR,7S,7aR,12bS)-3-methyl-9-[(2-methylpropan-2-yl)oxy]-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• CAS: 34332-27-9
• 化学式: C₂₁H₂₇NO₃
• 分子量: 341.45
• InChiKey: KGAFKGNBYPHAJK-JIDSPLGISA-N

物化性质

• 沸点：
  482.5±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇(6 -乙酰吗啡) 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 32.5h， 生成 3-O-叔丁基吗啡
  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

文献信息

• Mohacsi, Erno, Synthetic Communications, 1983, vol. 13, # 10, p. 827 - 832
  作者：Mohacsi, Erno

  DOI：——

  日期：——
• Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol
  作者：Erno Mohacsi、Willy Leimgruber、Herman Baruth

  DOI：10.1021/jm00352a037

  日期：1982.10

  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.