N-methyl-2-(p-hydroxy-benzyl)piperidine | 139158-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-methyl-2-(p-hydroxy-benzyl)piperidine
• 英文别名: 4-(1-Methyl-[2]piperidylmethyl)-phenol；4-[(1-Methyl-2-piperidinyl)methyl]phenol；4-[(1-methylpiperidin-2-yl)methyl]phenol
• CAS: 139158-21-7
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: IQEZXSLXROTHQF-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C(Solv: benzene (71-43-2))
• 沸点：
  324.0±15.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-methyl-2-cyano-2-(p-methoxy-benzyl)-piperidine 在 三溴化硼 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 1.17h， 生成 N-methyl-2-(p-hydroxy-benzyl)piperidine
  参考文献：
  名称：

  Structure-activity studies of morphine fragments. II. Synthesis, opiate receptor binding, analgetic activity and conformational studies of 2-R-2(hydroxybenzyl)piperidines

  摘要：

  In this study, a series of 2-benzyl piperidines, that can be regarded as flexible fragments of fused ring opioids, have been synthesized and their pharmacological and conformational profiles determined. These combined studies reveal that, despite the weak activity of the only analog previously reported, modifications of it can lead to compounds with significant opioid receptor affinity and analgetic activity. Conformational studies of these compounds indicate that they can bind to these receptors in either an phenyl-axial and phenyl-equatorial conformer. Features such as the position of the phenolic OH group, the nature of the other 2-substituent and of the N-substituent appear to modulate receptor recognition and activation. However, the 2-benzyl piperidines do not appear to bind or act at the opioid receptors in the same conformation or orientation as their more rigid fused ring counterparts, the benzomorphans. In general, a change from p-OH to m-OH benzyl analogs reduces efficacy and its is possible that the m-OH analogs could be promising analgesics with low physical dependence liability.

  DOI：

  10.1016/0223-5234(91)90002-5

文献信息

• PIPERIDINE DERIVATIVES. PART II. 2-PHENYL- AND 2-PHENYLALKYL-PIPERIDINES¹
  作者：JOHN LEE、ALBERT ZIERING、STEPHEN D. HEINEMAN、LEO BERGER

  DOI：10.1021/jo01170a021

  日期：1947.11
• Structure-activity studies of morphine fragments. II. Synthesis, opiate receptor binding, analgetic activity and conformational studies of 2-R-2(hydroxybenzyl)piperidines
  作者：GH Loew、JA Lawson、L Toll、W Polgar、ET Uyeno

  DOI：10.1016/0223-5234(91)90002-5

  日期：1991.11

  In this study, a series of 2-benzyl piperidines, that can be regarded as flexible fragments of fused ring opioids, have been synthesized and their pharmacological and conformational profiles determined. These combined studies reveal that, despite the weak activity of the only analog previously reported, modifications of it can lead to compounds with significant opioid receptor affinity and analgetic activity. Conformational studies of these compounds indicate that they can bind to these receptors in either an phenyl-axial and phenyl-equatorial conformer. Features such as the position of the phenolic OH group, the nature of the other 2-substituent and of the N-substituent appear to modulate receptor recognition and activation. However, the 2-benzyl piperidines do not appear to bind or act at the opioid receptors in the same conformation or orientation as their more rigid fused ring counterparts, the benzomorphans. In general, a change from p-OH to m-OH benzyl analogs reduces efficacy and its is possible that the m-OH analogs could be promising analgesics with low physical dependence liability.