(4bS,8aS,9R)-11-(cyclobutylmethyl)-8a-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-3-carbonitrile | 1122596-57-9

• 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: (4bS,8aS,9R)-11-(cyclobutylmethyl)-8a-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-3-carbonitrile
• CAS: 1122596-57-9
• 化学式: C₂₂H₂₈N₂O
• 分子量: 336.477
• InChiKey: WAZHOIYTMMIHCD-BHIFYINESA-N

物化性质

• 沸点：
  502.3±50.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  47.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4bS,8aS,9R)-11-(cyclobutylmethyl)-8a-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-3-carbonitrile 在 氢氧化钾 、 水 作用下， 以 叔丁醇 为溶剂， 生成 (1S,9R,10S)-17-(cyclobutylmethyl)-10-hydroxy-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-triene-4-carboxamide
  参考文献：
  名称：

  Syntheses and opioid receptor binding properties of carboxamido-substituted opioids

  摘要：

  A series of 15 novel opioid derivatives were made where the prototypic phenolic-OH group of traditional opioids was replaced by a carboxamido (CONH2) group. For 2,6-methano-3-benzazocines and morphinans similar or, in a few instances, enhanced affinity for mu, delta and kappa opioid receptors was observed when the OH --> CONH2 switch was applied. For 4,5 alpha-epoxymorphinans, binding affinities for the corresponding carboxamide derivatives were much lower than the OH partner consistent with our pharmacophore hypothesis concerning carboxamide bioactive conformation. The active metabolite of tramadol and its carboxamide counterpart had comparable affinities for the three receptors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.134
• 作为产物：
  描述：

  (4bS,8aS,9R)-11-(cyclobutylmethyl)-8a-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-yl trifluoromethanesulfonate 、 氰化锌 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 (4bS,8aS,9R)-11-(cyclobutylmethyl)-8a-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-3-carbonitrile
  参考文献：
  名称：

  Syntheses and opioid receptor binding properties of carboxamido-substituted opioids

  摘要：

  A series of 15 novel opioid derivatives were made where the prototypic phenolic-OH group of traditional opioids was replaced by a carboxamido (CONH2) group. For 2,6-methano-3-benzazocines and morphinans similar or, in a few instances, enhanced affinity for mu, delta and kappa opioid receptors was observed when the OH --> CONH2 switch was applied. For 4,5 alpha-epoxymorphinans, binding affinities for the corresponding carboxamide derivatives were much lower than the OH partner consistent with our pharmacophore hypothesis concerning carboxamide bioactive conformation. The active metabolite of tramadol and its carboxamide counterpart had comparable affinities for the three receptors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.134