2-hydroxy-3-phenoxy-3-benzenepropanenitrile | 133534-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxy-3-phenoxy-3-benzenepropanenitrile
• 英文别名: 2-Hydroxy-3-phenoxy-3-phenylpropanenitrile
• CAS: 133534-42-6；133534-78-8
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: GWDLFXIMGLKMLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-phenoxy-3-benzenepropanenitrile 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 8.0h， 生成 3-(1-hydroxy-2-phenoxy-2-phenyl)ethyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Research of potential antidepressant drugs with α2-adrenoreceptor antagonist and NA-uptake inhibiting properties: synthesis of 2-(1-hydroxy-2-phenoxy-2-phenyl)ethyl-4,5-dihydro-1H-imidazole derivatives

  摘要：

  A series of 2-(1-hydroxy-2-phenoxy-2-phenyl)ethyl-4,5-dihydro-1H-imidazole derivatives has been synthesized with the aim of finding potential antidepressant drugs endowed with both NA-uptake and alpha-2-antagonist properties. The structure of the new compounds was designed by mixing the common elements present in reboxetine and alpha-aryloxy-benzyl derivatives of ethanolamine, both having NA-uptake inhibitory properties in vitro, and in idazoxan, a potent and selective alpha-2-adrenoreceptor antagonist. The new hybrids allow a good fitting of the common features without the strong steric interactions occurring when the structure of reboxetine is superimposed on that of idazoxan. However, the new derivatives did not display significant interaction with the NA-uptake system and the alpha-2-adrenoreceptors and proved inactive in the antireserpine test taken as a model of potential antidepressant activity. The possible relationship between the structural changes made in the parent molecules and the complete loss of activity on both systems is discussed.

  DOI：

  10.1016/0223-5234(90)90195-9
• 作为产物：
  描述：

  ethyl 2-phenoxy-2-phenylacetate 在 potassium cyanide 、 sodium metabisulfite 、 氢氧化钾 、 氯化亚砜 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 甲醇 、 二乙二醇二甲醚 为溶剂， 反应 59.5h， 生成 2-hydroxy-3-phenoxy-3-benzenepropanenitrile
  参考文献：
  名称：

  Melloni; Carniel; Della Torre, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 235 - 242

  摘要：

  DOI：

文献信息

• DOSTERT, P.;MELLONI, P.;DELLA, TORRE A.;VARASI, M.;MERLINI, L.;BONSIGNORI+, EUR. J. MED. CHEM., 25,(1990) N, C. 757-763
  作者：DOSTERT, P.、MELLONI, P.、DELLA, TORRE A.、VARASI, M.、MERLINI, L.、BONSIGNORI+

  DOI：——

  日期：——
• Melloni; Carniel; Della Torre, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 235 - 242
  作者：Melloni、Carniel、Della Torre、et al.

  DOI：——

  日期：——
• Research of potential antidepressant drugs with α2-adrenoreceptor antagonist and NA-uptake inhibiting properties: synthesis of 2-(1-hydroxy-2-phenoxy-2-phenyl)ethyl-4,5-dihydro-1H-imidazole derivatives
  作者：P Dostert、P Melloni、A Della Torre、M Varasi、L Merlini、A Bonsignori、S Ricciardi

  DOI：10.1016/0223-5234(90)90195-9

  日期：1990.11

  A series of 2-(1-hydroxy-2-phenoxy-2-phenyl)ethyl-4,5-dihydro-1H-imidazole derivatives has been synthesized with the aim of finding potential antidepressant drugs endowed with both NA-uptake and alpha-2-antagonist properties. The structure of the new compounds was designed by mixing the common elements present in reboxetine and alpha-aryloxy-benzyl derivatives of ethanolamine, both having NA-uptake inhibitory properties in vitro, and in idazoxan, a potent and selective alpha-2-adrenoreceptor antagonist. The new hybrids allow a good fitting of the common features without the strong steric interactions occurring when the structure of reboxetine is superimposed on that of idazoxan. However, the new derivatives did not display significant interaction with the NA-uptake system and the alpha-2-adrenoreceptors and proved inactive in the antireserpine test taken as a model of potential antidepressant activity. The possible relationship between the structural changes made in the parent molecules and the complete loss of activity on both systems is discussed.