2-methyl-5-phenyl-2-azabicyclo[3.3.1]nonane | 744220-55-1

• 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: 2-methyl-5-phenyl-2-azabicyclo[3.3.1]nonane
• 英文别名: 2-methyl-5-phenyl-2-aza-bicyclo[3.3.1]nonane；2-Methyl-5-phenyl-2-aza-bicyclo[3.3.1]nonan
• CAS: 744220-55-1
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: OTGKRUAWZDLVFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenyl-2-azabicyclo[3.3.1]nonane 在 palladium on activated charcoal 盐酸 、 copper(l) iodide 、 1,10-菲罗啉 、 氢气 、 硝酸 、 caesium carbonate 、 溶剂黄146 、 potassium iodide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 47.5h， 生成 5-(4-methoxyphenyl)-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
• 作为产物：
  描述：

  1-甲基-4-苯基-1,2,3,6-四氢吡啶 在 正丁基锂 、 甲酸 、 磷酸 、 氢气 作用下， 反应 68.0h， 生成 2-methyl-5-phenyl-2-azabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Application of metalated enamines to alkaloid synthesis. An expedient approach to the synthesis of morphine-based analgesics

  摘要：

  DOI：

  10.1021/ja00538a065

文献信息

• STRUCTURES RELATED TO MORPHINE. II. AN ISOMER OF N-METHYLMORPHINAN
  作者：EVERETTE L. MAY、JAMES G. MURPHY

  DOI：10.1021/jo01369a021

  日期：1954.4
• A critical structural determinant of opioid receptor interaction with phenolic 5-phenylmorphans
  作者：In Jong Kim、Christina M Dersch、Richard B Rothman、Arthur E Jacobson、Kenner C Rice

  DOI：10.1016/j.bmc.2004.05.038

  日期：2004.8

  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.
• Application of metalated enamines to alkaloid synthesis. An expedient approach to the synthesis of morphine-based analgesics
  作者：D. A. Evans、C. H. Mitch、R. C. Thomas、D. M. Zimmerman、R. L. Robey

  DOI：10.1021/ja00538a065

  日期：1980.8