17-cyclopropylmethyl-3-methoxy-8β-methyl-6-methylene-morphinane | 78686-35-8

• 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-3-methoxy-8β-methyl-6-methylene-morphinane
• 英文别名: (1R,9R,10R,11S)-17-(cyclopropylmethyl)-4-methoxy-11-methyl-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
• CAS: 78686-35-8
• 化学式: C₂₃H₃₁NO
• 分子量: 337.505
• InChiKey: IUBIDMAHZPMISI-AZIXLERZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  17-Cyclopropylmethyl-3-Methoxy-8β-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80%的产率得到17-cyclopropylmethyl-3-methoxy-8β-methyl-6-methylene-morphinane
  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

• 17-Cyclobutylmethyl-3-hydroxy-.beta.-methyl-6-methylene morphinane, and
  申请人：Miles Laboratories, Inc.

  公开号：US04259329A1

  公开（公告）日：1981-03-31

  Disclosed are 6-methylene-morphinan compounds corresponding to the formula: ##STR1## wherein R.sub.1 and R.sub.3 are H or methyl and R.sub.2 is cyclopropylmethyl or cyclobutylmethyl. These compounds are useful as mixed analgesics/narcotic antagonists.

  本发明涉及一种6-亚甲基吗啡的化合物，其对应的化学式为：##STR1## 其中R.sub.1和R.sub.3为氢或甲基，R.sub.2为环丙甲基或环丁甲基。这些化合物可用作混合镇痛剂/麻醉拮抗剂。
• 17-Cycloalkylmethyl-6-methylene-morphinane-derivatives
  申请人：MILES LABORATORIES, INC.

  公开号：EP0027925A1

  公开（公告）日：1981-05-06

  Disclosed are 6-methylene, morphinan compounds corresponding to the formula: wherein R1 und R3 are H or methyl and R2 is cyclopropylmethyl or cyclobutylmethyl. These compounds are useful as mixed analgesics/narcotic antagonists.

  所公开的 6-亚甲基吗啡烷化合物符合以下式子： 其中 R1 和 R3 为 H 或甲基，R2 为环丙基甲基或环丁基甲基。这些化合物可用作混合镇痛剂/麻醉拮抗剂。
• US4259329A
  申请人：——

  公开号：US4259329A

  公开（公告）日：1981-03-31
• 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.