佐尔啡诺 | 77287-89-9

• 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: 佐尔啡诺
• 中文别名: 少法醇
• 英文名称: N-(cyclobutylmethyl)-8β-methyl-6-methylenemorphinan-3-ol
• 英文别名: xorphanol；17-cyclobutylmethyl-3-hydroxy-8β-methyl-6-methylene morphinane；(1R,9R,10R,11S)-17-(cyclobutylmethyl)-11-methyl-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
• CAS: 77287-89-9
• 化学式: C₂₃H₃₁NO
• 分子量: 337.505
• InChiKey: AZJPPZHRNFQRRE-AZIXLERZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  17-Cyclobutylmethyl-3-hydroxy-8beta-methylmorphinan-6-one 、 亚甲基三苯基膦烷 以 二甲基亚砜 为溶剂， 反应 1.0h， 以82%的产率得到佐尔啡诺
  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

文献信息

• US4334071A
  申请人：——

  公开号：US4334071A

  公开（公告）日：1982-06-08
• US7927613B2
  申请人：——

  公开号：US7927613B2

  公开（公告）日：2011-04-19
• Analgesic narcotic antagonists. 9. 6-Methylene-8.beta.-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans
  作者：Joseph O. Polazzi、Michael P. Kotick、John F. Howes、Ann R. Bousquet

  DOI：10.1021/jm00144a029

  日期：1981.12

  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.