[(1S,2R)-2-(3,4-Dimethoxy-phenyl)-cyclopropyl]-dipropyl-amine | 110826-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [(1S,2R)-2-(3,4-Dimethoxy-phenyl)-cyclopropyl]-dipropyl-amine
• 英文别名: (1S,2R)-2-(3,4-dimethoxyphenyl)-N,N-dipropylcyclopropan-1-amine
• CAS: 110826-25-0
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: BQPGPFFTYQCSSG-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉酸酸 在 palladium diacetate 盐酸 、 sodium hydroxide 、 二苯基膦叠氮化物 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 133.0h， 生成 [(1S,2R)-2-(3,4-Dimethoxy-phenyl)-cyclopropyl]-dipropyl-amine
  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