17-(cyclopropylmethyl)-7-(1-hydroxy-1-methylethyl)isomorphinan-3,6-diol | 82373-10-2

• 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: 17-(cyclopropylmethyl)-7-(1-hydroxy-1-methylethyl)isomorphinan-3,6-diol
• CAS: 82373-10-2
• 化学式: C₂₃H₃₃NO₃
• 分子量: 371.52
• InChiKey: KFBQRZHPKRMWKO-OLYSJDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  63.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  甲基锂 、 以 四氢呋喃 为溶剂， 生成 17-(cyclopropylmethyl)-7-(1-hydroxy-1-methylethyl)isomorphinan-3,6-diol
  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