trans-1,3-dimethyl-4-propionyl-4-(3-pyridyl)piperidine | 141446-60-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-1,3-dimethyl-4-propionyl-4-(3-pyridyl)piperidine
• 英文别名: 1-[(3R,4R)-1,3-dimethyl-4-pyridin-3-ylpiperidin-4-yl]propan-1-one
• CAS: 141446-60-8；141446-61-9
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: UQFOSZJQFQAFCF-SWLSCSKDSA-N

物化性质

• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-hydroxyethyl)-N-(2-hydroxypropyl)methylamine 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 十六烷基三丁基溴化铵 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 48.0h， 生成 trans-1,3-dimethyl-4-propionyl-4-(3-pyridyl)piperidine
  参考文献：
  名称：

  Synthesis and analgesic activity of 3-methyl derivatives of 4-(pyridyl) isosteres of ketobemidone

  摘要：

  A series of cis- and trans-1,3-dimethyl-4-propionyl-4-(pyridyl)piperidines 7 were prepared. Analgesic testing, using the rat 4% NaCl writhing assay, indicated that cis- and trans-7 were generally more potent than the corresponding 3-unsubstituted analogues 2. The point of attachment of the pyridyl ring to the C-4 position was a determinant of activity for the cis-diastereomers 7 where the relative potency order was 2-pyridyl (7a) greater-than-or-equal-to 4-pyridyl (7e) > 3-pyridyl (7c). Compounds 7 possessing cis-(3-Me/pyridyl) substituents were generally more active than the corresponding trans-(3-Me/pyridyl) diastereomer. The most potent compound, cis-1,3-dimethyl-4-propionyl-4-(2-pyridyl)piperidine 7a, inhibited writhing by 82% for a 2 mg/kg sc dose relative to the reference drug meperidine (ED50 = 0.6 mg/kg sc).

  DOI：

  10.1016/0223-5234(92)90065-9

文献信息

• Synthesis and analgesic activity of 3-methyl derivatives of 4-(pyridyl) isosteres of ketobemidone
  作者：JK Buolamwini、EE Knaus

  DOI：10.1016/0223-5234(92)90065-9

  日期：1992.1

  A series of cis- and trans-1,3-dimethyl-4-propionyl-4-(pyridyl)piperidines 7 were prepared. Analgesic testing, using the rat 4% NaCl writhing assay, indicated that cis- and trans-7 were generally more potent than the corresponding 3-unsubstituted analogues 2. The point of attachment of the pyridyl ring to the C-4 position was a determinant of activity for the cis-diastereomers 7 where the relative potency order was 2-pyridyl (7a) greater-than-or-equal-to 4-pyridyl (7e) > 3-pyridyl (7c). Compounds 7 possessing cis-(3-Me/pyridyl) substituents were generally more active than the corresponding trans-(3-Me/pyridyl) diastereomer. The most potent compound, cis-1,3-dimethyl-4-propionyl-4-(2-pyridyl)piperidine 7a, inhibited writhing by 82% for a 2 mg/kg sc dose relative to the reference drug meperidine (ED50 = 0.6 mg/kg sc).