17-Cyclopropylmethyl-7α,8β-dimethyl-3-hydroxy-morphinan-6-one | 75702-31-7

• 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-7α,8β-dimethyl-3-hydroxy-morphinan-6-one
• 英文别名: (1S,9R,10R,11R,12S)-17-(cyclopropylmethyl)-4-hydroxy-11,12-dimethyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
• CAS: 75702-31-7
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: OPCNDODYLHTBLM-UMBRSOPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7α,8β-Dimethyl-3-methoxymorphinan-6-one Hydrochloride 在 氢溴酸 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.33h， 生成 17-Cyclopropylmethyl-7α,8β-dimethyl-3-hydroxy-morphinan-6-one
  参考文献：
  名称：

  Analgesic narcotic antagonists. 4. 7-Methyl-N-(cycloalkylmethyl)-3-hydroxy morphinan-6-one and -isomorphinan-6-one

  摘要：

  3,6-Dimethoxy-7 beta, 17-dimethyl-4-hydroxy-5,6,8,14-tetradehydromorphinan (2) was converted to the 4-deoxy compound 4 and hydrolyzed to a mixture of the B/C-cis (C series) and B/C-trans (T series) isomers of 7,8-didehydromorphinan-6-one, 5. Hydrogenation of the separated isomers gave 7-methyl-6-oxo derivatives 6a. 7,8-Dimethyl-(6b) or 7-methyl-8-ethylmorphinan-6-one (6c) was prepared by reaction of 5 with lithium organocuprates. The analgesic N-methyl compounds 6 were converted to 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 10--13. Some of these compounds had mixed profiles of narcotic agonist-antagonist effects. Studies with drug-dependent monkeys indicated that several of these compounds with an analgesic-antagonist ratio of less than 0.4 substitute for morphine.

  DOI：

  10.1021/jm00186a025

文献信息

• 7-Methyl and 7-methyl-8-lower alkyl B/C cis or trans morphinan-6-one compounds, process for their preparation and pharmaceutical preparations containing them
  申请人：MILES LABORATORIES, INC.

  公开号：EP0019254B1

  公开（公告）日：1982-09-01
• US4230712A
  申请人：——

  公开号：US4230712A

  公开（公告）日：1980-10-28
• Analgesic narcotic antagonists. 4. 7-Methyl-N-(cycloalkylmethyl)-3-hydroxy morphinan-6-one and -isomorphinan-6-one
  作者：David L. Leland、Michael P. Kotick

  DOI：10.1021/jm00186a025

  日期：1980.12

  3,6-Dimethoxy-7 beta, 17-dimethyl-4-hydroxy-5,6,8,14-tetradehydromorphinan (2) was converted to the 4-deoxy compound 4 and hydrolyzed to a mixture of the B/C-cis (C series) and B/C-trans (T series) isomers of 7,8-didehydromorphinan-6-one, 5. Hydrogenation of the separated isomers gave 7-methyl-6-oxo derivatives 6a. 7,8-Dimethyl-(6b) or 7-methyl-8-ethylmorphinan-6-one (6c) was prepared by reaction of 5 with lithium organocuprates. The analgesic N-methyl compounds 6 were converted to 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 10--13. Some of these compounds had mixed profiles of narcotic agonist-antagonist effects. Studies with drug-dependent monkeys indicated that several of these compounds with an analgesic-antagonist ratio of less than 0.4 substitute for morphine.