N-(tert-butyloxycarbonyl)-2-phenethyl-5-carbethoxy-1,2,3,6-tetrahydropyridine | 134420-85-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: N-(tert-butyloxycarbonyl)-2-phenethyl-5-carbethoxy-1,2,3,6-tetrahydropyridine
• 英文别名: 1-O-tert-butyl 5-O-ethyl 2-(2-phenylethyl)-3,6-dihydro-2H-pyridine-1,5-dicarboxylate
• CAS: 134420-85-2
• 化学式: C₂₁H₂₉NO₄
• 分子量: 359.466
• InChiKey: NEXQKRQIBWOYDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-2-phenethyl-5-carbethoxy-1,2,3,6-tetrahydropyridine 在 盐酸 作用下， 反应 3.0h， 以63%的产率得到6-phenethylguvacine hydrochloride
  参考文献：
  名称：

  GABA-uptake inhibitors: construction of a general pharmacophore model and successful prediction of a new representative

  摘要：

  A model for the pharmacophore of GABA-uptake inhibitors was established using published structure-activity data and molecular modeling. The model accounted for the activities of different classes of GABA-uptake inhibitors. Analogues of guvacine substituted at position 6 were synthesized in order to confirm the model. 6-(3,3-Diphenylpropyl)guvacine (30f), which fit well with the pharmacophore, had an in vitro IC50 of 0.1-mu-M. This value is as good as those of the best GABA-uptake inhibitors known today.

  DOI：

  10.1021/jm00112a032
• 作为产物：
  描述：

  ethyl N-(tert-butyloxycarbonyl)-N-(2-carbethoxyethyl)-3-amino-5-phenylvalerate 在 镍 1,5-二氮杂双环[4.3.0]壬-5-烯 、 氢气 、 sodium 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 25.0~80.0 ℃ 、6.08 MPa 条件下， 反应 27.0h， 生成 N-(tert-butyloxycarbonyl)-2-phenethyl-5-carbethoxy-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  GABA-uptake inhibitors: construction of a general pharmacophore model and successful prediction of a new representative

  摘要：

  A model for the pharmacophore of GABA-uptake inhibitors was established using published structure-activity data and molecular modeling. The model accounted for the activities of different classes of GABA-uptake inhibitors. Analogues of guvacine substituted at position 6 were synthesized in order to confirm the model. 6-(3,3-Diphenylpropyl)guvacine (30f), which fit well with the pharmacophore, had an in vitro IC50 of 0.1-mu-M. This value is as good as those of the best GABA-uptake inhibitors known today.

  DOI：

  10.1021/jm00112a032