N-丙基-去甲氢羟吗啡酮 | 119822-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: N-丙基-去甲氢羟吗啡酮
• 英文名称: 19,20-dihydronaloxone
• 英文别名: N-Propyl-14-OH-dihydromorphinan-6-one；(4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-propyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 119822-06-9
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: GJGXERIYLTUUMY-GRGSLBFTSA-N

物化性质

• 沸点：
  532.6±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-丙基-去甲氢羟吗啡酮 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 1'-benzyl-6,7-dedihydro-3,14-dihydroxy-4,5α-epoxy-17-propyl-4'-phenylpyrrolo[2',3':6,7]morphinan
  参考文献：
  名称：

  4‘-Arylpyrrolomorphinans:  Effect of a Pyrrolo-N-benzyl Substituent in Enhancing δ-Opioid Antagonist Activity

  摘要：

  A new method for the preparation of N-benzylpyrrolomorphinans has been developed. Thus Michael reaction of the benzylimines of oxycodones and oxymorphones with nitrostyrenes gave a series of 4'-aryl-N-benzylpyrrolomorphinans. These were selective delta antagonists of much higher in vitro potency (with 5a having K-e delta = <1 nM) than their binding affinities predicted. In mice in vivo assays 5a showed good delta antagonist activity in the antiwrithing analgesic assay and also inhibited delta agonist-induced convulsant activity.

  DOI：

  10.1021/jm010841w

文献信息

• [EN] PROCESS FOR THE PREPARATION OF MORPHINANE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DE MORPHINANE
  申请人：SANECA PHARMACEUTICALS A S

  公开号：WO2019009820A1

  公开（公告）日：2019-01-10

  The invention describes the process of catalytic O-demethylation of 3-methoxy-morphinane compounds using boron tribromide. Addition of catalysts reduces the reaction time, improves reacting the substrate to give the product in very good purity and yield. The said approach can be used, for example, for the preparation of oxymorphone, naltrexone, naloxone and nalbuphine from their respective O-methyl derivatives.

  本发明描述了使用三溴化硼催化剂进行3-甲氧基吗啡烷类化合物的催化O-去甲基化过程。添加催化剂可缩短反应时间，提高底物的反应性，从而以非常高的纯度和收率给出产物。该方法可用于制备羟吗啡酮、纳曲酮、纳洛酮和纳布啡等化合物，这些化合物是从它们各自的O-甲基衍生物制备而来的。
• PROCESS FOR THE PREPARATION OF MORPHINANE COMPOUNDS
  申请人：Saneca Pharmaceuticals a.s.

  公开号：EP3649131A1

  公开（公告）日：2020-05-13
• 4‘-Arylpyrrolomorphinans:  Effect of a Pyrrolo-<i>N</i>-benzyl Substituent in Enhancing δ-Opioid Antagonist Activity
  作者：Sanjay K. Srivastava、Stephen M. Husbands、Mario D. Aceto、Carl N. Miller、John R. Traynor、John W. Lewis

  DOI：10.1021/jm010841w

  日期：2002.1.1

  A new method for the preparation of N-benzylpyrrolomorphinans has been developed. Thus Michael reaction of the benzylimines of oxycodones and oxymorphones with nitrostyrenes gave a series of 4'-aryl-N-benzylpyrrolomorphinans. These were selective delta antagonists of much higher in vitro potency (with 5a having K-e delta = <1 nM) than their binding affinities predicted. In mice in vivo assays 5a showed good delta antagonist activity in the antiwrithing analgesic assay and also inhibited delta agonist-induced convulsant activity.