2-methyl-4-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline | 345228-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-methyl-4-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 4-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline；4-(3,4-dimethoxyphenyl)-2-methyl-3,4-dihydro-1H-isoquinoline
• CAS: 345228-39-9
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: WRUWYJKVTFOSMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 在 氢溴酸 作用下， 反应 4.0h， 以37%的产率得到2-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide
  参考文献：
  名称：

  Dopamine agonist properties of N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines

  摘要：

  A series of homologous N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines was synthesized and examined for a dopamine-like ability to dilate the renal artery. The N-methyl derivative was equipotent to the 3',4'-dihydroxy derivative of the antidepressant agent nomifensine, indicating that the 8-amino group of the latter is not essential for dopamine-like activity. The N-ethyl homologue was reduced in potency when compared to the N-methyl, and the N-n-propyl, surprisingly, was essentially devoid of activity. This was unexpected in view of the fact that in all series of dopamine-like agents reported to date, N-alkylation, when one of the alkyls was an n-propyl group, either allowed retention or enhancement of potency.

  DOI：

  10.1021/jm00140a021
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酮 在 sodium tetrahydroborate 、 三氯化铝 、 溴 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 4.0h， 生成 2-methyl-4-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Dopamine agonist properties of N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines

  摘要：

  A series of homologous N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines was synthesized and examined for a dopamine-like ability to dilate the renal artery. The N-methyl derivative was equipotent to the 3',4'-dihydroxy derivative of the antidepressant agent nomifensine, indicating that the 8-amino group of the latter is not essential for dopamine-like activity. The N-ethyl homologue was reduced in potency when compared to the N-methyl, and the N-n-propyl, surprisingly, was essentially devoid of activity. This was unexpected in view of the fact that in all series of dopamine-like agents reported to date, N-alkylation, when one of the alkyls was an n-propyl group, either allowed retention or enhancement of potency.

  DOI：

  10.1021/jm00140a021

文献信息

• Nucleophilic Addition of β-Amino Carbanions to Arynes: One-Pot Synthesis of 4-Aryl-<i>N</i>-methyl-1,2,3,4-tetrahydroisoquinolines
  作者：Kamal Nain Singh、Paramjit Singh、Pushpinder Singh、Yadwinder Singh Deol

  DOI：10.1021/ol300360r

  日期：2012.5.4

  A novel approach for the direct C-4 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines by nucleophilic addition of beta-aminocarbanions to benzynes is described which provides a one-pot procedure for synthesis of the title compounds.
• JACOB, J. N.;NICHOLS, D. E.;KOHLI, J. D.;GLOCK, D., J. MED. CHEM., 1981, 24, N 8, 1013-1015
  作者：JACOB, J. N.、NICHOLS, D. E.、KOHLI, J. D.、GLOCK, D.

  DOI：——

  日期：——
• Dopamine agonist properties of N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines
  作者：James N. Jacob、David E. Nichols、Jai D. Kohli、Dana Glock

  DOI：10.1021/jm00140a021

  日期：1981.8

  A series of homologous N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines was synthesized and examined for a dopamine-like ability to dilate the renal artery. The N-methyl derivative was equipotent to the 3',4'-dihydroxy derivative of the antidepressant agent nomifensine, indicating that the 8-amino group of the latter is not essential for dopamine-like activity. The N-ethyl homologue was reduced in potency when compared to the N-methyl, and the N-n-propyl, surprisingly, was essentially devoid of activity. This was unexpected in view of the fact that in all series of dopamine-like agents reported to date, N-alkylation, when one of the alkyls was an n-propyl group, either allowed retention or enhancement of potency.