5-(4-iodophenyl)-2-methyl-2-azabicyclo[3.3.1]nonane | 744220-58-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5-(4-iodophenyl)-2-methyl-2-azabicyclo[3.3.1]nonane
• CAS: 744220-58-4
• 化学式: C₁₅H₂₀IN
• 分子量: 341.235
• InChiKey: JQOSVZAUMJRKNN-UHFFFAOYSA-N

物化性质

• 沸点：
  360.1±42.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(4-iodophenyl)-2-methyl-2-azabicyclo[3.3.1]nonane 在 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 1,10-菲罗啉 、 potassium carbonate 、 caesium carbonate 、 氯甲酸-2,2,2-三氯乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 54.0h， 生成 5-(4-methoxyphenyl)-2-(2-phenyl)ethyl-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
• 作为产物：
  描述：

  在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 、 potassium iodide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 5-(4-iodophenyl)-2-methyl-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