3-((4aS,10aS)-10a-Methyl-1,3,4,5,10,10a-hexahydro-2H-benzo[g]isoquinolin-4a-yl)-phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-((4aS,10aS)-10a-Methyl-1,3,4,5,10,10a-hexahydro-2H-benzo[g]isoquinolin-4a-yl)-phenol
• 英文别名: 3-[(4aS,10aS)-10a-methyl-1,2,3,4,5,10-hexahydrobenzo[g]isoquinolin-4a-yl]phenol
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: PKCBXVCRCOSVSD-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((4aS,10aS)-10a-Methyl-1,3,4,5,10,10a-hexahydro-2H-benzo[g]isoquinolin-4a-yl)-phenol 在 TEA 、 硼烷 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 生成 3-((4aS,10aS)-10a-Methyl-2-phenethyl-1,3,4,5,10,10a-hexahydro-2H-benzo[g]isoquinolin-4a-yl)-phenol
  参考文献：
  名称：

  N-substituted octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines are opioid receptor pure antagonists

  摘要：

  N-Methyl- and N-phenylethyl-(+/-)-1,2,3,4,4a,5,10,10a-octahydro-4a-(3-hydroxyphenyl)-10a-methyl- benzo[g]isoquinolines (4 and 5, respectively) were found to be pure opioid antagonists. These compounds were shown to share many of the characteristics identified with the N-methyl- and N-phenylethyl trans-3,4-dimethyl-4(3-hydroxyphenyl)piperidine (1 and 2, respectively) including N-substituent mediated potency and a lack of N-substituent mediated antagonism. These data suggest that compounds 4 and 5 and the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines (1 and 2) may interact with opioid receptors similarly. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00576-9
• 作为产物：
  描述：

  邻二氯苄 在 sodium tetrahydroborate 、 氢溴酸 、 仲丁基锂 、 溶剂黄146 、 sodium iodide 作用下， 以 甲苯 为溶剂， 生成 3-((4aS,10aS)-10a-Methyl-1,3,4,5,10,10a-hexahydro-2H-benzo[g]isoquinolin-4a-yl)-phenol
  参考文献：
  名称：

  N-substituted octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines are opioid receptor pure antagonists

  摘要：

  N-Methyl- and N-phenylethyl-(+/-)-1,2,3,4,4a,5,10,10a-octahydro-4a-(3-hydroxyphenyl)-10a-methyl- benzo[g]isoquinolines (4 and 5, respectively) were found to be pure opioid antagonists. These compounds were shown to share many of the characteristics identified with the N-methyl- and N-phenylethyl trans-3,4-dimethyl-4(3-hydroxyphenyl)piperidine (1 and 2, respectively) including N-substituent mediated potency and a lack of N-substituent mediated antagonism. These data suggest that compounds 4 and 5 and the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines (1 and 2) may interact with opioid receptors similarly. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00576-9

文献信息

• Substituted piperidine compounds and methods of their use
  申请人：Dolle Ellwood Roland

  公开号：US20050203123A1

  公开（公告）日：2005-09-15

  Certain 4-aryl-piperidine compounds, including N-substituted 9β-substituted-5-(3-substituted-phenyl)morphans and N-substituted octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines, pharmaceutical compositions, and methods of their use, inter alia, as opioid antagonists are disclosed.

  某些4-芳基哌啶化合物，包括N-取代的9β-取代-5-(3-取代-苯基)吗啡烷和N-取代的八氢-4a-(3-羟基苯基)-10a-甲基-苯并[g]异喹啉，以及包含它们的药物组合物和用途，例如作为阿片类药物拮抗剂，被披露。
• US7767814B2
  申请人：——

  公开号：US7767814B2

  公开（公告）日：2010-08-03
• N-substituted octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines are opioid receptor pure antagonists
  作者：James B. Thomas、S.Wayne Mascarella、Jason P. Burgess、Heng Xu、Karen B. McCullough、Richard B. Rothman、Judith L. Flippen-Anderson、Clifford F. George、Buddy E. Cantrell、Dennis M. Zimmerman、F.Ivy Carroll

  DOI：10.1016/s0960-894x(98)00576-9

  日期：1998.11

  N-Methyl- and N-phenylethyl-(+/-)-1,2,3,4,4a,5,10,10a-octahydro-4a-(3-hydroxyphenyl)-10a-methyl- benzo[g]isoquinolines (4 and 5, respectively) were found to be pure opioid antagonists. These compounds were shown to share many of the characteristics identified with the N-methyl- and N-phenylethyl trans-3,4-dimethyl-4(3-hydroxyphenyl)piperidine (1 and 2, respectively) including N-substituent mediated potency and a lack of N-substituent mediated antagonism. These data suggest that compounds 4 and 5 and the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines (1 and 2) may interact with opioid receptors similarly. (C) 1998 Elsevier Science Ltd. All rights reserved.