(1R,9R,10R)-17-(cyclobutylmethyl)-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol | 79413-34-6

• 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: (1R,9R,10R)-17-(cyclobutylmethyl)-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
• CAS: 79413-34-6
• 化学式: C₂₂H₂₉NO
• 分子量: 323.478
• InChiKey: XEZKLCMKMVVJHI-NNWRFLSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,9R,10R)-17-(cyclobutylmethyl)-4-hydroxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one 、 亚甲基三苯基膦烷 以 二甲基亚砜 为溶剂， 反应 1.0h， 以87%的产率得到(1R,9R,10R)-17-(cyclobutylmethyl)-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
  参考文献：
  名称：

  Analgesic narcotic antagonists. 9. 6-Methylene-8.beta.-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans

  摘要：

  Series of N-(cyclopropylmethyl) (P series) or N-(cyclobutylmethyl) (B series) 3-methoxy (1) or 3-hydroxy (2) morphinan-6-ones with hydrogen (a), methyl (b), or ethyl (c) groups in the 8 beta position were converted to the 6-methylene compounds 3 or 4 by reaction with Ph3P = CH2. One member of this new series, N-(cyclobutylmethyl)-8 beta-methyl-6-methylenemorphinan-3-ol (4Bb), had potent mixed agonist-narcotic antagonist properties and, in contrast to the previously studied 6-oxo compound 2Bb, did not substitute for morphine in dependent rats or monkeys.

  DOI：

  10.1021/jm00144a029