1-phenethyl-4-piperidine | 117523-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 1-phenethyl-4-piperidine
• 英文别名: 1-phenethyl-4-[N-(2,1,3-benzothiadiazol-4-yl)amino]piperidine；N-[1-(2-phenylethyl)piperidin-4-yl]-2,1,3-benzothiadiazol-4-amine
• CAS: 117523-90-7
• 化学式: C₁₉H₂₂N₄S
• 分子量: 338.476
• InChiKey: MKTBXZXWWASMLY-UHFFFAOYSA-N

物化性质

• 熔点：
  85-88 °C
• 沸点：
  497.0±40.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  41.05
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 1-phenethyl-4-piperidine 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以60%的产率得到N-(2,1,3-benzothiadiazol-4-yl)-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide
  参考文献：
  名称：

  New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties

  摘要：

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.

  DOI：

  10.1021/jm00123a028
• 作为产物：
  描述：

  N-(2,1,3-benzothiadiazol-4-yl)-1-(2-phenylethyl)piperidin-4-imine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-phenethyl-4-piperidine
  参考文献：
  名称：

  New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties

  摘要：

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.

  DOI：

  10.1021/jm00123a028

文献信息

• BAGLEY, JEROME R.;SPENCER, H. KENNETH
  作者：BAGLEY, JEROME R.、SPENCER, H. KENNETH

  DOI：——

  日期：——
• BAGLEY, JEROME R.;WYNN, RICHARD L.;RUDO, FRIEDA G.;DOORLEY, BRIAN M.;SPEN+, J. MED. CHEM., 32,(1989) N, C. 663-671
  作者：BAGLEY, JEROME R.、WYNN, RICHARD L.、RUDO, FRIEDA G.、DOORLEY, BRIAN M.、SPEN+

  DOI：——

  日期：——