8β-ethyldihydrocodeinone | 71968-12-2

• 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: 8β-ethyldihydrocodeinone
• 英文别名: 4,5α-Epoxy-8β-ethyl-3-methoxy-17-methylmorphinan-6-one；4,5alpha-Epoxy-8beta-ethyl-3-methoxy-17-methylmorphinan-6one；(4R,4aR,5S,7aR,12bS)-5-ethyl-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 71968-12-2
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: XIJFDJRRWBECQH-CVXZJHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8β-ethyldihydrocodeinone 在 盐酸 、 碳酸氢钠 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 考诺封
  参考文献：
  名称：

  Rm values and structure-activity relationship of benzodiazepines

  摘要：

  Quantitative structure-activity relationships (QSAR) have been formulated for the activities of a series of benzodiazepines in rats. The lipophilic character of molecules was expressed by means of the chromatographic Rm values which were very well correlated with experimental or calculated log P values. The ideal lipophilic character for activity of benzodiazepines in the exploratory behavior test is not far from that of compounds acting in the central nervous system as unspecific depressant agents. The results of both the conflict and exploratory behavior studies might support the hypothesis of different sites of action for the antianxiety and sedative effects of benzodiazepines.

  DOI：

  10.1021/jm00176a016
• 作为产物：
  描述：

  蒂巴因 在 copper(l) iodide 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 8β-ethyldihydrocodeinone
  参考文献：
  名称：

  Rm values and structure-activity relationship of benzodiazepines

  摘要：

  Quantitative structure-activity relationships (QSAR) have been formulated for the activities of a series of benzodiazepines in rats. The lipophilic character of molecules was expressed by means of the chromatographic Rm values which were very well correlated with experimental or calculated log P values. The ideal lipophilic character for activity of benzodiazepines in the exploratory behavior test is not far from that of compounds acting in the central nervous system as unspecific depressant agents. The results of both the conflict and exploratory behavior studies might support the hypothesis of different sites of action for the antianxiety and sedative effects of benzodiazepines.

  DOI：

  10.1021/jm00176a016

文献信息

• 7,8 and 7-8 Substituted 4,5.alpha.-epoxymorphinan-6-one compounds, and
  申请人：Miles Laboratories, Inc.

  公开号：US04272541A1

  公开（公告）日：1981-06-09

  Disclosed are 7,8 and 7-8 substituted 4,5.alpha.-epoxymorphinan-6-one compounds characterized by the structural formula: ##STR1## In the foregoing formula R.sub.1 may be H or methyl, R.sub.2 is cyclopropylmethyl, cyclobutylmethyl, allyl or tetrahydrofurfuryl, R.sub.3 is H, .beta.-methyl, .beta.-ethyl or .alpha.-ethyl and R.sub.4 is H or .alpha.-methyl. Particular compounds corresponding to the foregoing description are useful as mixed analgesics/narcotic antagonists whereas others have been found to be pure narcotic antagonists.

  所披露的是以结构式为特征的7,8和7-8取代的4,5.alpha.-环氧吗啡-6-酮化合物：##STR1## 在上述式中，R.sub.1可以是H或甲基，R.sub.2是环丙基甲基，环丁基甲基，烯丙基或四氢呋喃甲基，R.sub.3是H，β-甲基，β-乙基或α-乙基，R.sub.4是H或α-甲基。与上述描述相对应的特定化合物可用作混合镇痛剂/麻醉拮抗剂，而其他一些已被发现是纯麻醉拮抗剂。
• Analgesic narcotic antagonists. 5. 7,7-Dimethyldihydrocodeinones and 7,7-dimethyldihydromorphinones
  作者：David L. Leland、Michael P. Kotick

  DOI：10.1021/jm00138a015

  日期：1981.6

  7-dimethyl-6-ones 7 were as active as dihydrocodeinone in agonist assays. One compound of this series, N-(cyclopropylmethyl)-7,7-dimethyldihydronorcodeinone (11a), was a potent mixed agonist-narcotic antagonist.

  在含水二恶烷中用甲醛-Ca（OH）2处理二氢可待因酮（1a）或8β-甲基（1b）或8β-乙基（1c）类似物得到相应的7,7-双（羟甲基）-6β- ols 2a-c。2的二甲苯磺酰化，然后还原LiEt3BH，得到7,7-二甲基-6β-醇（6a）或7α-甲基-6β，7β-氧杂环丁烷化合物（5b，c）。使用LiAlH4-AlCl3将化合物5b和5c裂解为6b或6c。通过氧化-还原序列证实了6a的C 6-醇基的构型，该氧化-还原序列给出了7，7-二甲基-5α-醇8a。氧化6得到C6-酮7a-c，将其转化为N-（环烷基甲基）衍生物11和12及其相应的3-羟基化合物14和15。3-甲氧基-7,7-二甲基-6-酮在激动剂测定中，7种具有与二氢可待因酮同样的活性。这个系列的一种化合物
• US4272541A
  申请人：——

  公开号：US4272541A

  公开（公告）日：1981-06-09
• Rm values and structure-activity relationship of benzodiazepines
  作者：G. L. Biagi、A. M. Barbaro、M. C. Guerra、M. Babbini、M. Gaiardi、M. Bartoletti、P. A. Borea

  DOI：10.1021/jm00176a016

  日期：1980.2

  Quantitative structure-activity relationships (QSAR) have been formulated for the activities of a series of benzodiazepines in rats. The lipophilic character of molecules was expressed by means of the chromatographic Rm values which were very well correlated with experimental or calculated log P values. The ideal lipophilic character for activity of benzodiazepines in the exploratory behavior test is not far from that of compounds acting in the central nervous system as unspecific depressant agents. The results of both the conflict and exploratory behavior studies might support the hypothesis of different sites of action for the antianxiety and sedative effects of benzodiazepines.