1-((1R,5R,6R)-6-Benzylamino-9-oxa-2-aza-bicyclo[3.3.1]non-2-yl)-2-(3,4-dichloro-phenyl)-ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((1R,5R,6R)-6-Benzylamino-9-oxa-2-aza-bicyclo[3.3.1]non-2-yl)-2-(3,4-dichloro-phenyl)-ethanone
• 英文别名: 1-[(1R,5R,6R)-6-(benzylamino)-9-oxa-2-azabicyclo[3.3.1]nonan-2-yl]-2-(3,4-dichlorophenyl)ethanone
• 化学式: C₂₂H₂₄Cl₂N₂O₂
• 分子量: 419.351
• InChiKey: OOUKGGSDJSBPOW-KCZVDYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3,4-Dichloro-phenyl)-1-((1R,5R,6R)-6-{[1-phenyl-meth-(E)-ylidene]-amino}-9-oxa-2-aza-bicyclo[3.3.1]non-2-yl)-ethanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以40.7 mg的产率得到1-((1R,5R,6R)-6-Benzylamino-9-oxa-2-aza-bicyclo[3.3.1]non-2-yl)-2-(3,4-dichloro-phenyl)-ethanone
  参考文献：
  名称：

  Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues

  摘要：

  Starting with methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu -receptors than for kappa -receptors. The most mu -active compound 18b (K-i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu -receptors.

  DOI：

  10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b

文献信息

• Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues
  作者：Georg Höfner、Benedikt Streicher、Bernhard Wünsch

  DOI：10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b

  日期：2001.9

  Starting with methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu -receptors than for kappa -receptors. The most mu -active compound 18b (K-i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu -receptors.