4-(3-氯-4-甲氧基苯基)-1,2,3,4-四氢异喹啉 | 110014-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 4-(3-氯-4-甲氧基苯基)-1,2,3,4-四氢异喹啉
• 英文名称: 4-(3-chloro-4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 110014-07-8
• 化学式: C₁₆H₁₆ClNO
• 分子量: 273.762
• InChiKey: VFZJLXWOSWJVOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(3-chloro-4-methoxyphenyl)-2-aminoethanol hydrochloride 在 sodium tetrahydroborate 、 三氯化铝 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 4-(3-氯-4-甲氧基苯基)-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Evaluation of isomeric 4-(chlorohydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines as dopamine D-1 antagonists

  摘要：

  The isomeric 4-(3-chloro-4-hydroxyphenyl)- and 4-(4-chloro-3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines, the N-methyl derivative of the 4-(4-chloro-3-hydroxyphenyl) isomer, and 4-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline were synthesized and evaluated for dopamine D-1 antagonist activity. The 4-(3-chloro-4-hydroxyphenyl) and the 4-(3-hydroxyphenyl) isomer possessed similar potencies as D-1 antagonists. Introduction of the N-methyl group enhanced potency about twofold. The "pharmacophore" for selective dopamine D-1 antagonist activity appears to be a tertiary 2-(3-hydroxyphenyl)-2-phenethylamine.

  DOI：

  10.1021/jm00393a033

文献信息

• Evaluation of isomeric 4-(chlorohydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines as dopamine D-1 antagonists
  作者：Robert M. Riggs、David E. Nichols、Mark M. Foreman、Lewis L. Truex

  DOI：10.1021/jm00393a033

  日期：1987.10

  The isomeric 4-(3-chloro-4-hydroxyphenyl)- and 4-(4-chloro-3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines, the N-methyl derivative of the 4-(4-chloro-3-hydroxyphenyl) isomer, and 4-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline were synthesized and evaluated for dopamine D-1 antagonist activity. The 4-(3-chloro-4-hydroxyphenyl) and the 4-(3-hydroxyphenyl) isomer possessed similar potencies as D-1 antagonists. Introduction of the N-methyl group enhanced potency about twofold. The "pharmacophore" for selective dopamine D-1 antagonist activity appears to be a tertiary 2-(3-hydroxyphenyl)-2-phenethylamine.