(E)-4-(4-bromophenyl)-N-methyl-4-(3-pyridyl)-3-buten-1-ylamine | 112969-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-(4-bromophenyl)-N-methyl-4-(3-pyridyl)-3-buten-1-ylamine
• 英文别名: (E)-4-(4-bromophenyl)-N-methyl-4-pyridin-3-ylbut-3-en-1-amine
• CAS: 112969-69-4
• 化学式: C₁₆H₁₇BrN₂
• 分子量: 317.228
• InChiKey: VQVDJYDOAZXKDF-FZSIALSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-bromo-1-(4-bromophenyl)-1-(3-pyridyl)-1-butene 在 氨 、 甲胺 作用下， 以 四氢呋喃 为溶剂， 以385 mg的产率得到(Z)-4-(4-bromophenyl)-N-methyl-4-(3-pyridyl)-3-buten-1-ylamine
  参考文献：
  名称：

  Homoallylic amines related to zimeldine. Comparative study on neuronal serotonin and norepinephrine reuptake based on conformational analysis

  摘要：

  A number of tertiary and secondary homoallylic amines, i.e. (Z)- and (E)-4-(4-bromophenyl)-4-(3-pyridyl)-3-buten-1-ylamines, were synthesized in diastereomerically pure forms. The compounds were evaluated as neuronal norepinephrine (NE) and serotonin (5-HT) uptake inhibitors under in vitro and ex vivo conditions and compared with the tricyclics amitriptyline and nortriptyline having homoallylic side chains and with the corresponding diastereomers in the zimeldine series having allylic side chains. The Z isomers of the new homoallylic derivatives (3Z, 4Z) were specific 5-HT uptake inhibitors in analogy with the corresponding allylic derivatives zimeldine (1Z) and norzimeldine (2Z). Likewise, the selectivity profile of the homoallylic (3E, 4E) and the allylic (1E, 2E) derivatives was comparable. In general, the homoallylic compounds were less potent inhibitors than their allylic counterparts. The similarities and discrepancies were evaluated in terms of conformational preferences determined by CAMSEQ molecular mechanics calculations. Homonorzimeldine (4Z) can accommodate energetically favored, but less populated, conformations having amino nitrogen atom to aromatic ring center distances comparable to those in norzimeldine. These facts correlate to retained 5-HT selectivity but diminished potency of 4Z compared to 2Z.

  DOI：

  10.1021/jm00400a005

文献信息

• Homoallylic amines related to zimeldine. Comparative study on neuronal serotonin and norepinephrine reuptake based on conformational analysis
  作者：Thomas Hoegberg、Svante B. Ross、Peter Stroem、Gary L. Grunewald、Mary W. Creese、Jeffrey D. Bunce

  DOI：10.1021/jm00400a005

  日期：1988.5

  A number of tertiary and secondary homoallylic amines, i.e. (Z)- and (E)-4-(4-bromophenyl)-4-(3-pyridyl)-3-buten-1-ylamines, were synthesized in diastereomerically pure forms. The compounds were evaluated as neuronal norepinephrine (NE) and serotonin (5-HT) uptake inhibitors under in vitro and ex vivo conditions and compared with the tricyclics amitriptyline and nortriptyline having homoallylic side chains and with the corresponding diastereomers in the zimeldine series having allylic side chains. The Z isomers of the new homoallylic derivatives (3Z, 4Z) were specific 5-HT uptake inhibitors in analogy with the corresponding allylic derivatives zimeldine (1Z) and norzimeldine (2Z). Likewise, the selectivity profile of the homoallylic (3E, 4E) and the allylic (1E, 2E) derivatives was comparable. In general, the homoallylic compounds were less potent inhibitors than their allylic counterparts. The similarities and discrepancies were evaluated in terms of conformational preferences determined by CAMSEQ molecular mechanics calculations. Homonorzimeldine (4Z) can accommodate energetically favored, but less populated, conformations having amino nitrogen atom to aromatic ring center distances comparable to those in norzimeldine. These facts correlate to retained 5-HT selectivity but diminished potency of 4Z compared to 2Z.