4-((1S,9S,13R)-9,12,13-Trimethyl-8-oxa-12-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-1-ylmethyl)-phenol | 143951-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-((1S,9S,13R)-9,12,13-Trimethyl-8-oxa-12-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-1-ylmethyl)-phenol
• CAS: 143951-13-7
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: OJPMTLUCPSFZMK-JHVJFLLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-Methoxyphenylmagnesium bromide 在 氢溴酸 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 4-((1S,9S,13R)-9,12,13-Trimethyl-8-oxa-12-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-1-ylmethyl)-phenol
  参考文献：
  名称：

  Synthesis of C-2 substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines: binding studies on opioid receptors

  摘要：

  The racemic C-2 substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines 8a-k were prepared in three steps from the readily available 2-cyano-1,2,5,6-tetrahydropyridines 4a-c. This involved alkylation of the anion of 4a-c with the appropriate alkyl halide, displacement of thc cyano group in 5 or 6 by reaction with a Grignard reagent and cyclization under Grewe conditions (HBr, reflux). The equilibrium binding affinities of compounds 8a-k for the mu, delta and kappa-opioid receptor types were determined. Compounds 8c, 8e, 8j and 8k bearing a phenyl or olefinic substituent at C-2 display high kappa-receptor binding affinities demonstrating that the presence of a substituent at this position is important for kappa-receptor binding. The insensitivity of the binding of compounds 8j and 8k to sodium ions and guanine nucleotides at both mu and kappa-sites suggests that these 2-substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines could behave as partial agonists or antagonists. The binding of the molecule 8e to mu and kappa sites was inhibited in the presence of these allosteric effectors, whereas N-methyl-2-phenyl-1,2,3,4,5.6-hexahydro-2,6-methano-3-benzazocine 8c appears to display the same kappa-agonist/mu-antagonist pharmacological profile as bremazocine 2.

  DOI：

  10.1016/0223-5234(92)90150-y