7α-phenylhydromorphone

• 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: 7α-phenylhydromorphone
• 英文别名: (4R,4aR,6R,7aR,12bS)-9-hydroxy-3-methyl-6-phenyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: DWROUHBHTAABDG-UAIRLVHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二氢可待因酮 在 三溴化硼 、 lithium hexamethyldisilazane 作用下， 反应 2.5h， 生成 7α-phenylhydromorphone
  参考文献：
  名称：

  Synthesis of 7-Arylmorphinans. Probing the “Address” Requirements for Selectivity at Opioid δ Receptors

  摘要：

  Through arylation of 6-keto opiates with diaryliodonium iodide, a series of 7-aryl opiates (38) have been prepared in an effort to investigate the effect of conformational mobility of the delta "address" moiety on opioid agonist and antagonist potencies. Evaluation of the ligands in the mouse vas deferens and guinea pig ileum preparations revealed that they were less potent and less selective than the conformationally constrained ligands, naltrindole (1, NTI) and 7-(spiroindanyl)oxymorphone (2, SIOM), at delta opioid receptors. It is concluded that the coplanarity of the address moiety with the C ring of the morphinan structure enhances delta antagonist potency and selectivity.

  DOI：

  10.1021/jm9802214

文献信息

• Boron Tribromide-Catalyzed Rearrangement of 7,7-Diphenylhydromorphone to 6,7-Diphenylmorphine:  A Novel Conversion of Ketones to Allylic Alcohols
  作者：Peng Gao、Philip S. Portoghese

  DOI：10.1021/jo951526i

  日期：1996.1.1

  A novel boron tribromide-catalyzed rearrangement of ketones to allylic alcohols was discovered in the 7-phenylmorphinan-6-one system. The reaction involved the stereospecific migration of an axial 7 beta-phenyl (or a hydrogen) to the C-6 carbonyl carbon, followed by the elimination of the H-8 proton leading to the generation of allylic alcohols. A possible mechanistic pathway for this rearrangement is discussed.
• Synthesis of 7-Arylmorphinans. Probing the “Address” Requirements for Selectivity at Opioid δ Receptors
  作者：Peng Gao、Dennis L. Larson、Philip S. Portoghese

  DOI：10.1021/jm9802214

  日期：1998.7.1

  Through arylation of 6-keto opiates with diaryliodonium iodide, a series of 7-aryl opiates (38) have been prepared in an effort to investigate the effect of conformational mobility of the delta "address" moiety on opioid agonist and antagonist potencies. Evaluation of the ligands in the mouse vas deferens and guinea pig ileum preparations revealed that they were less potent and less selective than the conformationally constrained ligands, naltrindole (1, NTI) and 7-(spiroindanyl)oxymorphone (2, SIOM), at delta opioid receptors. It is concluded that the coplanarity of the address moiety with the C ring of the morphinan structure enhances delta antagonist potency and selectivity.