N-(tert-butyloxycarbonyl)-2-propyl-5-carbethoxy-4-piperidone | 134420-80-7

• 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-propyl-5-carbethoxy-4-piperidone
• 英文别名: 1-O-tert-butyl 3-O-ethyl 4-oxo-6-propylpiperidine-1,3-dicarboxylate
• CAS: 134420-80-7
• 化学式: C₁₆H₂₇NO₅
• 分子量: 313.394
• InChiKey: NWDVDRNYTNLGKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-2-propyl-5-carbethoxy-4-piperidone 在 镍 氢气 作用下， 以 乙醇 为溶剂， 80.0 ℃ 、6.08 MPa 条件下， 生成 4-Hydroxy-6-propyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester
  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-aminocaproate 在 sodium 作用下， 以 乙醇 、 苯 为溶剂， 反应 24.0h， 以85%的产率得到N-(tert-butyloxycarbonyl)-2-propyl-5-carbethoxy-4-piperidone
  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