Propylcyanoformimidat | 30867-65-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: Propylcyanoformimidat
• 英文别名: Propyl cyanomethanimidate
• CAS: 30867-65-3
• 化学式: C₅H₈N₂O
• 分子量: 112.131
• InChiKey: LGIZVQHLFBYMEG-UHFFFAOYSA-N

物化性质

• 沸点：
  54.5 °C(Press: 20 Torr)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Propylcyanoformimidat 在 sulfur monochloride 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 3-(4-Propoxy-[1,2,5]thiadiazol-3-yloxy)-1-aza-bicyclo[2.2.2]octane
  参考文献：
  名称：

  1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists

  摘要：

  The acetyl group of the muscarinic agonist aceclidine 4 was replaced by various 1,2,5-thiadiazoles to provide a new series of potent m(1) muscarinic agonists 17 and 18. Optimal mi muscarinic agonist potency was achieved when the 1,2,g-thiadiazole substituent was either a butyloxy, 17d, or butylthio, 18d, group. Although 1,2,5-oxadiazole 37 and pyrazine 39 are iso-pi-electronic with 1,2,5-thiadiazole 17d, both analogues were substantially less active than 17d. Compounds with high muscarinic affinity and/or m(1) muscarinic agonist efficacy were also obtained when the 3-oxyquinuclidine moiety of 17d or 18c was replaced by ethanolamines, hydroxypyrrolidines, hydroxyazetidine, hydroxyisotropanes, or hydroxyazanorbornanes. The structure-activity data support the participation of the oxygen or sulfur atom in the substituent on the 1,2,5-thiadiazole in the activation of the m(1) receptor. Several of these new 1,2,5-thiadiazoles have m(1) agonist efficacy, potency, and selectivity comparable to those of xanomeline 2 in the muscarinic tests investigated.

  DOI：

  10.1021/jm970125n
• 作为产物：
  描述：

  丙醇 、 氰 在 三乙胺 作用下， 反应 1.0h， 生成 Propylcyanoformimidat
  参考文献：
  名称：

  1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists

  摘要：

  The acetyl group of the muscarinic agonist aceclidine 4 was replaced by various 1,2,5-thiadiazoles to provide a new series of potent m(1) muscarinic agonists 17 and 18. Optimal mi muscarinic agonist potency was achieved when the 1,2,g-thiadiazole substituent was either a butyloxy, 17d, or butylthio, 18d, group. Although 1,2,5-oxadiazole 37 and pyrazine 39 are iso-pi-electronic with 1,2,5-thiadiazole 17d, both analogues were substantially less active than 17d. Compounds with high muscarinic affinity and/or m(1) muscarinic agonist efficacy were also obtained when the 3-oxyquinuclidine moiety of 17d or 18c was replaced by ethanolamines, hydroxypyrrolidines, hydroxyazetidine, hydroxyisotropanes, or hydroxyazanorbornanes. The structure-activity data support the participation of the oxygen or sulfur atom in the substituent on the 1,2,5-thiadiazole in the activation of the m(1) receptor. Several of these new 1,2,5-thiadiazoles have m(1) agonist efficacy, potency, and selectivity comparable to those of xanomeline 2 in the muscarinic tests investigated.

  DOI：

  10.1021/jm970125n