10-Keto-oxycodone | 96445-11-3

• 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: 10-Keto-oxycodone
• 英文别名: 10-ketooxycodone；(4S,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-1,2,4,5,6,7a-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,13-dione
• CAS: 96445-11-3
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: GVANAKCNZBHGPN-VSZNYVQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10-Keto-oxycodone 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 43.0h， 以37%的产率得到(5alpha)-4,5-环氧-3,14-二羟基-17-甲基-吗喃-6,10-二酮
  参考文献：
  名称：

  10-Ketonaltrexone and 10-ketooxymorphone

  摘要：

  Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.

  DOI：

  10.1021/jm00145a024
• 作为产物：
  描述：

  10α-hydroxyoxycodone 在 CrO₃-DMP 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以7 mg的产率得到10-Keto-oxycodone
  参考文献：
  名称：

  10-Ketonaltrexone and 10-ketooxymorphone

  摘要：

  Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.

  DOI：

  10.1021/jm00145a024

文献信息

• Preparation of 10-Keto Morphinans by Benzylic Oxidation
  申请人：Sun Hang

  公开号：US20110071296A1

  公开（公告）日：2011-03-24

  The present invention provides processes for the preparation of 10-keto and/or 10-hydroxy morphinans. In particular, the invention provides to processes for preparing a 10-keto morphinan by chromium-catalyzed benzylic oxidation of a morphinan with a periodic acid.

  本发明提供了制备10-酮基和/或10-羟基吗啡酮类化合物的方法。具体而言，该发明提供了一种通过铬催化苯基氧化吗啡酮类化合物以制备10-酮基吗啡酮的方法。
• US8314237B2
  申请人：——

  公开号：US8314237B2

  公开（公告）日：2012-11-20