2-{Methyl-[(R)-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)methyl]-amino}-ethanol | 123883-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-{Methyl-[(R)-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)methyl]-amino}-ethanol
• 英文别名: 2-[methyl-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]amino]ethanol
• CAS: 123883-19-2
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: YMBBBFBKAJRYNL-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-{Methyl-[(R)-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)methyl]-amino}-ethanol 在 三氯化铝 、 五氯化磷 、 氯 、 三氯化铁 作用下， 以 乙腈 为溶剂， 反应 9.25h， 生成 (R)-5-chloro-2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth<1,8-cd>azepine
  参考文献：
  名称：

  1,9-Alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines with affinity for the .alpha.2-adrenoceptor and the 5-HT1A receptor

  摘要：

  A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and alpha 2-adrenoceptor affinity by using radioligand receptor binding techniques. Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone. The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azapines (4c, 4m, 4n), which had pKi values of 7.9-8.1. The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c). These compounds had a relatively low affinity for the alpha 2-adrenoceptor (pKi of 7 or less). On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indeno[1,7-cd]azepine (3b) had high affinity for both the alpha 2-adrenoceptor (pKi = 8.1) and 5-HT1A receptor (pKi = 7.6). These results indicate that the two receptors may share common recognition sites.

  DOI：

  10.1021/jm00164a026
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 、 R-四氢萘甲酸 生成 2-{Methyl-[(R)-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)methyl]-amino}-ethanol
  参考文献：
  名称：

  1,9-Alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines with affinity for the .alpha.2-adrenoceptor and the 5-HT1A receptor

  摘要：

  A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and alpha 2-adrenoceptor affinity by using radioligand receptor binding techniques. Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone. The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azapines (4c, 4m, 4n), which had pKi values of 7.9-8.1. The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c). These compounds had a relatively low affinity for the alpha 2-adrenoceptor (pKi of 7 or less). On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indeno[1,7-cd]azepine (3b) had high affinity for both the alpha 2-adrenoceptor (pKi = 8.1) and 5-HT1A receptor (pKi = 7.6). These results indicate that the two receptors may share common recognition sites.

  DOI：

  10.1021/jm00164a026