6β,7-diphenylmorphine | 175657-04-2

• 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: 6β,7-diphenylmorphine
• 英文别名: (4R,4aR,7S,7aR,12bS)-3-methyl-6,7-diphenyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• CAS: 175657-04-2
• 化学式: C₂₉H₂₇NO₃
• 分子量: 437.538
• InChiKey: DKQQDROIIVNQSQ-PYZXZWNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6β,7-diphenylmorphine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 8β-bromo-6,7-didehydro-4,5α-epoxy-6,7-diphenyl-17-methylmorphinan-3-ol
  参考文献：
  名称：

  Boron Tribromide-Catalyzed Rearrangement of 7,7-Diphenylhydromorphone to 6,7-Diphenylmorphine:  A Novel Conversion of Ketones to Allylic Alcohols

  摘要：

  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.

  DOI：

  10.1021/jo951526i
• 作为产物：
  描述：

  7,7-Diphenylhydrocodone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 6β,7-diphenylmorphine
  参考文献：
  名称：

  Boron Tribromide-Catalyzed Rearrangement of 7,7-Diphenylhydromorphone to 6,7-Diphenylmorphine:  A Novel Conversion of Ketones to Allylic Alcohols

  摘要：

  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.

  DOI：

  10.1021/jo951526i

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.