3-((1R,2S)-2-Dimethylamino-cyclopropyl)-phenol | 110826-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-((1R,2S)-2-Dimethylamino-cyclopropyl)-phenol
• 英文别名: 3-[(1R,2S)-2-(dimethylamino)cyclopropyl]phenol
• CAS: 110826-13-6
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: LYTWDOIYZATBOZ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [(1S,2R)-2-(3-Methoxy-phenyl)-cyclopropyl]-dimethyl-amine; hydrochloride 在 氢溴酸 作用下， 反应 2.5h， 以52%的产率得到3-((1R,2S)-2-Dimethylamino-cyclopropyl)-phenol
  参考文献：
  名称：

  N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists

  摘要：

  N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.

  DOI：

  10.1021/jm00396a014