2-benzyl-6,7-dimethoxy-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline | 84500-66-3

• 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-dimethoxy-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-benzyl-6,7-dimethoxy-1-(nitromethyl)-3,4-dihydro-1H-isoquinoline
• CAS: 84500-66-3
• 化学式: C₁₉H₂₂N₂O₄
• 分子量: 342.395
• InChiKey: GNDPILCPDHSZEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyl-6,7-dimethoxy-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline 在 红铝 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 1-(aminomethyl)-2-benzyl-6,7-dimethoxy-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
• 作为产物：
  描述：

  硝基甲烷 、 2-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinolinium bromide 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到2-benzyl-6,7-dimethoxy-1-(nitromethyl)-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

文献信息

• Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp³)–H functionalization of amines
  作者：Fahima I. M. Idiris、Cécile E. Majesté、Gregory B. Craven、Christopher R. Jones

  DOI：10.1039/c8sc00181b

  日期：——

  Transition metal-free intramolecular hydride transfer onto arynes is reported for the first time. This unique transformation is utilized in redox-neutral intermolecular α-functionalization reactions of different tertiary amines, generating C(sp3)–C(sp3/sp2/sp) bonds in a single synthetic operation. Deuterium labeling studies support initial cleavage of the α-C–H bond via intramolecular 1,5-hydride

  首次报道了无过渡金属的分子内氢化物转移到芳烃上。这种独特的转化可用于不同叔胺的氧化还原中性分子间α-官能化反应，在一次合成操作中生成C（sp 3）–C（sp 3 / sp 2 / sp）键。氘标记研究支持通过分子内1，5-氢化物转移到芳烃上的α-C–H键的初始裂解，这导致一系列整合的亲核试剂的活化，并最终提供了一种新的交叉脱氢偶联反应方法，该方法利用了芳烃中间体。
• BEAUMONT, D.;WAIGH, R. D.;SUNBHANICH, METHI;NOTT, M. W., J. MED. CHEM., 1983, 26, N 4, 507-515
  作者：BEAUMONT, D.、WAIGH, R. D.、SUNBHANICH, METHI、NOTT, M. W.

  DOI：——

  日期：——