2-benzyl-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline | 84500-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-benzyl-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-benzyl-6,7-bis(phenylmethoxy)-3,4-dihydro-1H-isoquinoline
• CAS: 84500-88-9
• 化学式: C₃₀H₂₉NO₂
• 分子量: 435.566
• InChiKey: LJYQOCYFWOGHJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-benzyl-6,7-bis(benzyloxy)-3,4-dihydroisoquinolinium bromide 在 aluminium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 生成 2-benzyl-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines and their actions at adrenoceptors in vivo and in vitro

  摘要：

  An improved synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines has been developed by using aluminum hydride reduction of 1-cyano-1,2,3,4-tetrahydroisoquinolines. Three 1-(aminomethyl)-6,7-dihydroxytetrahydroisoquinolines were tested for actions at beta adrenoceptors in order to examine a proposed similarity between this series and the related phenylethanolamines. The aminomethyl, (isopropylamino)methyl, and (tert-butylamino)methyl derivatives all showed weak partial agonist activity at beta adrenoceptors and the first also showed weak alpha adrenoceptor agonist activity in vivo. Their low potency implies that the catechol group of THIQ sympathomimetics, such as trimetoquinol, binds differently from that of the natural catecholamines. The protonation behavior of representative aminomethyl-THIQ's was investigated by pKa measurement and 1H and 13C NMR, and the compounds were shown to be substantially monoprotonated, on the exocyclic nitrogen, at physiological pH.

  DOI：

  10.1021/jm00358a010