3,6-dimethoxy-7β,17-dimethyl-4-hydroxy-5,6,8,14-tetradehydro-morphinane | 74466-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3,6-dimethoxy-7β,17-dimethyl-4-hydroxy-5,6,8,14-tetradehydro-morphinane
• 英文别名: 3,6-dimethoxy-7β,17-dimethyl-4-hydroxy-5,6,8,14-tetrahydromorphinan；3,6-Dimethoxy-7beta,17-dimethyl-4-hydroxy-5,6,8,14-tetradehydromorphinane；(1S,9R,12R)-4,13-dimethoxy-12,17-dimethyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaen-3-ol
• CAS: 74466-73-2
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: OIGNAFFLFPTCOX-URFZZILJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dimethoxy-7β,17-dimethyl-4-hydroxy-5,6,8,14-tetradehydro-morphinane 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 90.0~100.0 ℃ 、344.73 kPa 条件下， 反应 1.17h， 生成 7α,17-Dimethyl-4-hydroxy-3-methoxy-B/C-cis-morphinan-6-one
  参考文献：
  名称：

  Analgesic narcotic antagonists. 3. Preparation of 7.beta.-methyldihydrothebaine-.vphi.

  摘要：

  DOI：

  10.1021/jo01308a016
• 作为产物：
  描述：

  thebaine 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醚 、 苯 为溶剂， 以74%的产率得到3,6-dimethoxy-7β,17-dimethyl-4-hydroxy-5,6,8,14-tetradehydro-morphinane
  参考文献：
  名称：

  Analgesic narcotic antagonists. 3. Preparation of 7.beta.-methyldihydrothebaine-.vphi.

  摘要：

  DOI：

  10.1021/jo01308a016

文献信息

• Method for the introduction of a methyl group into the 7 position of the
  申请人：Miles Laboratories, Inc.

  公开号：US04242514A1

  公开（公告）日：1980-12-30

  Disclosed is a novel method for the introduction of a 7-methyl group into the morphinan nucleus to thereby provide precursors for the preparation of therapeutically useful 7-methyl-4,5.alpha.-epoxy morphinan and morphinan-6-one compounds. The method involves reacting thebaine, dihydrothebaine or the enol acetate of dihydrocodeinone with lithium dimethyl cuprate to form the corresponding 7-methyl-4,5.alpha.-epoxy cleaved product.

  本发明揭示了一种新颖的方法，用于将7-甲基基团引入吗啡烷骨架中，从而提供用于制备治疗有用的7-甲基-4,5α-环氧吗啡烷和吗啡烷-6-酮化合物的前体。该方法涉及将吗啡碱、二氢吗啡碱或二氢可待因酮的烯醇醋酸酯与锂二甲基铜酸盐反应，形成相应的7-甲基-4,5α-环氧断裂产物。
• 7-Methyl-8.beta.-lower alkyl or 7-methyl-8-lower alkyl B/C cis or trans
  申请人：Miles Laboratories, Inc.

  公开号：US04230712A1

  公开（公告）日：1980-10-28

  Disclosed are 7-methyl, 8.beta.-lower alkyl and 7 methyl-8-lower alkyl substituted B/C Cis or Trans morphinan-6-one compounds characterized by the structural formula: ##STR1## Specific compounds, included within the scope of the foregoing general formula wherein R.sub.1 is H or methyl, R.sub.2 is cyclopropylmethyl or cyclobutylmethyl, R.sub.3 is H, methyl, ethyl or n-propyl and R.sub.4 is H or methyl are useful as mixed analgesics/narcotic antagonists.

  公开的是7-甲基，8.beta.-低烷基和7-甲基-8-低烷基取代的B/C顺反异构体吗啡酮化合物，其结构式为：##STR1## 特定的化合物包括在上述一般式范围内，其中R.sub.1为H或甲基，R.sub.2为环丙基甲基或环丁基甲基，R.sub.3为H，甲基，乙基或正丙基，R.sub.4为H或甲基，可用作混合镇痛剂/鸦片拮抗剂。
• 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：EP0019254A1

  公开（公告）日：1980-11-26

  Disclosed are 7-methyl and 7-methyl-8- lower alkyl substituted B/C Cis or Trans morphinan-6-one compounds characterized by the structural formula: Specific compounds, included within the scope of the foregoing general formula wherein R1 is H or methyl, R2 is cyclopropylmethyl or cyclobutylmethyl and R3 is H, methyl or ethyl are useful as mixed analgesics/narcotic antagonists.

  本发明公开了 7-甲基和 7-甲基-8-低级烷基取代的 B/C 顺式或反式吗啡烷-6-酮化合物，其特征在于结构式如下： 包括在前述通式范围内的特定化合物，其中 R1 是 H 或甲基，R2 是环丙基甲基或环丁基甲基，R3 是 H、甲基或乙基，可用作混合镇痛剂/麻醉拮抗剂。
• 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.
• 7- and 7,8-substituted 4,5-alpha-epoxymorphinan-6-ones and therapeutically active compositions containing them
  申请人：MILES LABORATORIES, INC.

  公开号：EP0023576B1

  公开（公告）日：1982-06-23