1-benzyl-5-(2-methoxyphenyl)-2-azabicyclo[3.3.1]nonane | 744220-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-5-(2-methoxyphenyl)-2-azabicyclo[3.3.1]nonane
• 英文别名: 2-Benzyl-5-(2-methoxyphenyl)-2-azabicyclo[3.3.1]nonane
• CAS: 744220-49-3
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: QYXPBEINCDXQIU-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: hexane (110-54-3))
• 沸点：
  442.6±45.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-(2-methoxyphenyl)-2-azabicyclo[3.3.1]nonane 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢溴酸 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 2-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol
  参考文献：
  名称：

  A critical structural determinant of opioid receptor interaction with phenolic 5-phenylmorphans

  摘要：

  The opioid receptor binding affinities of N-methyl- and N-phenethyl-5-phenylmorphans with a meta-hydroxy substituent [3-(2-methyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (1a), and 3-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (1b)] were compared with the affinities of four new ligands bearing an ortho- or para-hydroxyl substituent (2-(2-metliyl-2-azabicyclo[3.3.1]non-5-yl)phenol (2a) and 2-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (2b), 4-(2-methyl-2-azabicyclo[3.3.1]non-5-yl)-phenol(3a), and 4-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (3b)) that were synthesized from 2-bromoanisole or the known 2-methyl-5phenyl-2-azabicyclo[3.3.1]nonane (13), respectively. The data indicated that either the electronic state of the phenolic ring is critical for the ligand's interaction with an opioid receptor, or that there must be a specific distance and angle for a hydrogen bond between the phenolic moiety and an amino acid in the binding domain that cannot be altered. (C) 2004 Elsevier Ltd. All riahts reserved.

  DOI：

  10.1016/j.bmc.2004.05.038
• 作为产物：
  描述：

  2-溴苯甲醚 在 sodium tetrahydroborate 、 正丁基锂 、 甲酸 、 磷酸 、 仲丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 环己烷 、 甲苯 为溶剂， 反应 112.5h， 生成 1-benzyl-5-(2-methoxyphenyl)-2-azabicyclo[3.3.1]nonane
  参考文献：
  名称：

  A critical structural determinant of opioid receptor interaction with phenolic 5-phenylmorphans

  摘要：

  The opioid receptor binding affinities of N-methyl- and N-phenethyl-5-phenylmorphans with a meta-hydroxy substituent [3-(2-methyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (1a), and 3-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (1b)] were compared with the affinities of four new ligands bearing an ortho- or para-hydroxyl substituent (2-(2-metliyl-2-azabicyclo[3.3.1]non-5-yl)phenol (2a) and 2-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (2b), 4-(2-methyl-2-azabicyclo[3.3.1]non-5-yl)-phenol(3a), and 4-(2-phenethyl-2-azabicyclo[3.3.1]non-5-yl)-phenol (3b)) that were synthesized from 2-bromoanisole or the known 2-methyl-5phenyl-2-azabicyclo[3.3.1]nonane (13), respectively. The data indicated that either the electronic state of the phenolic ring is critical for the ligand's interaction with an opioid receptor, or that there must be a specific distance and angle for a hydrogen bond between the phenolic moiety and an amino acid in the binding domain that cannot be altered. (C) 2004 Elsevier Ltd. All riahts reserved.

  DOI：

  10.1016/j.bmc.2004.05.038