7-carbethoxy-3-hydroxy-17-methylisomorphinan-6-one | 89423-97-2

• 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: 7-carbethoxy-3-hydroxy-17-methylisomorphinan-6-one
• 英文别名: 7-carboethoxy-3-methoxy-17-methyl-14α-morphinan-6-one；ethyl (1S,9R,10S)-4-methoxy-17-methyl-13-oxo-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-12-carboxylate
• CAS: 89423-97-2
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: WUGZFHIGKDHJFG-TZLGMAPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-carbethoxy-3-hydroxy-17-methylisomorphinan-6-one 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以89%的产率得到7-carboethoxy-3-hydroxy-17-methyl-14α-morphinan-6-one
  参考文献：
  名称：

  Novel opiates and antagonists. 5. 7-Carbethoxy-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones

  摘要：

  A direct conversion of deoxydihydrothebaine-phi (1) to 3-methoxymorphinan-6-one (3Ca) and its trans isomer 3Ta was achieved in excellent yield by the catalytic reduction of 1 in AcOH containing CF3COOH. Treatment of 3Ca or 3Ta with NaH and diethyl carbonate formed the corresponding 7-carbethoxy derivatives 4a which, on O-demethylation, furnished the 3-hydroxy compounds 4b. The analgesic N-methyl compounds 3 were converted to the 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 6--8. Two of these compounds, one in the cis (7Ca) and the other in the trans (7Ta) series, showed mixed agonist/antagonist activity in the pentazocine range.

  DOI：

  10.1021/jm00350a020
• 作为产物：
  描述：

  (1R,9R)-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaene 在 palladium on activated charcoal 氢气 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 7-carbethoxy-3-hydroxy-17-methylisomorphinan-6-one
  参考文献：
  名称：

  Novel opiates and antagonists. 5. 7-Carbethoxy-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones

  摘要：

  A direct conversion of deoxydihydrothebaine-phi (1) to 3-methoxymorphinan-6-one (3Ca) and its trans isomer 3Ta was achieved in excellent yield by the catalytic reduction of 1 in AcOH containing CF3COOH. Treatment of 3Ca or 3Ta with NaH and diethyl carbonate formed the corresponding 7-carbethoxy derivatives 4a which, on O-demethylation, furnished the 3-hydroxy compounds 4b. The analgesic N-methyl compounds 3 were converted to the 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 6--8. Two of these compounds, one in the cis (7Ca) and the other in the trans (7Ta) series, showed mixed agonist/antagonist activity in the pentazocine range.

  DOI：

  10.1021/jm00350a020

文献信息

• US4423221A
  申请人：——

  公开号：US4423221A

  公开（公告）日：1983-12-27
• Novel opiates and antagonists. 5. 7-Carbethoxy-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones
  作者：Patricia Herlihy、Haldean C. Dalzell、John F. Howes、Raj K. Razdan

  DOI：10.1021/jm00350a020

  日期：1982.8

  A direct conversion of deoxydihydrothebaine-phi (1) to 3-methoxymorphinan-6-one (3Ca) and its trans isomer 3Ta was achieved in excellent yield by the catalytic reduction of 1 in AcOH containing CF3COOH. Treatment of 3Ca or 3Ta with NaH and diethyl carbonate formed the corresponding 7-carbethoxy derivatives 4a which, on O-demethylation, furnished the 3-hydroxy compounds 4b. The analgesic N-methyl compounds 3 were converted to the 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 6--8. Two of these compounds, one in the cis (7Ca) and the other in the trans (7Ta) series, showed mixed agonist/antagonist activity in the pentazocine range.