2-苯基-2-乙氧基-4-(2-羟乙基)吗啉 | 101776-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 2-苯基-2-乙氧基-4-(2-羟乙基)吗啉
• 英文名称: 2-phenyl-2-ethoxy-4-(2-hydroxyethyl)morpholine
• 英文别名: 2-(2-ethoxy-2-phenyl-morpholino)-ethanol；2-(2-Aethoxy-2-phenyl-morpholino)-aethanol；2-(2-ethoxy-2-phenylmorpholin-4-yl)ethanol
• CAS: 101776-96-9
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: BSFIJKIZPXTHHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-苯基-2-乙氧基-4-(2-羟乙基)吗啉 在 三溴甲烷 、 三(二甲胺基)膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-phenyl-2-ethoxy-4-(2-bromoethyl)morpholine
  参考文献：
  名称：

  Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15

  摘要：

  Work on the synthesis and investigation into the biological activity of a 2-bromoethylamine (mustard) analogue of hemicholinium-3 (HC-3) and hemicholinium-15 (HC-15) is reported. Hemicholinium-3 bromo mustard (HC3-BrM, 5) and hemicholinium-15 bromo mustard (HC15-BrM, 11) cyclize in aqueous solution to a biethylenimine derivative (6) and a monoethylenimine derivative (12) that are structurally almost identical with HC-3 (1) and HC-15 (8), respectively. As with HC-3 or HC-15, these mustards strongly inhibited sodium-dependent, high-affinity choline uptake (SDHACU) activity in vitro. This inhibitory activity was found to result solely from the interaction of the cyclized ethylenimine form of the mustards with the uptake system. When compared on an equivalent concentration basis, HC3-BrM effected substantially greater inhibition of SDHACU than HC-3 and is, thus, at present the most potent known synthetic inhibitor of this uptake system. Synaptosomes incubated with a low concentration of precyclized HC3-BrM (25 nM) and then treated to remove all free and reversibly bound drug exhibited a maintained reduction (approximately 32%) in the Vmax of SDHACU activity. This behavior is in marked contrast to the findings with HC-3, the inhibition of which was totally removed by simple washing. It is suggested that the biethylenimine form of HC3-BrM undergoes a covalent, and thus possibly irreversible, bond formation with group(s) functionally involved with the SDHACU system.

  DOI：

  10.1021/jm00355a021
• 作为产物：
  描述：

  乙醇 、 二乙醇胺 、 2-溴苯乙酮 反应 3.0h， 生成 2-苯基-2-乙氧基-4-(2-羟乙基)吗啉
  参考文献：
  名称：

  Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15

  摘要：

  Work on the synthesis and investigation into the biological activity of a 2-bromoethylamine (mustard) analogue of hemicholinium-3 (HC-3) and hemicholinium-15 (HC-15) is reported. Hemicholinium-3 bromo mustard (HC3-BrM, 5) and hemicholinium-15 bromo mustard (HC15-BrM, 11) cyclize in aqueous solution to a biethylenimine derivative (6) and a monoethylenimine derivative (12) that are structurally almost identical with HC-3 (1) and HC-15 (8), respectively. As with HC-3 or HC-15, these mustards strongly inhibited sodium-dependent, high-affinity choline uptake (SDHACU) activity in vitro. This inhibitory activity was found to result solely from the interaction of the cyclized ethylenimine form of the mustards with the uptake system. When compared on an equivalent concentration basis, HC3-BrM effected substantially greater inhibition of SDHACU than HC-3 and is, thus, at present the most potent known synthetic inhibitor of this uptake system. Synaptosomes incubated with a low concentration of precyclized HC3-BrM (25 nM) and then treated to remove all free and reversibly bound drug exhibited a maintained reduction (approximately 32%) in the Vmax of SDHACU activity. This behavior is in marked contrast to the findings with HC-3, the inhibition of which was totally removed by simple washing. It is suggested that the biethylenimine form of HC3-BrM undergoes a covalent, and thus possibly irreversible, bond formation with group(s) functionally involved with the SDHACU system.

  DOI：

  10.1021/jm00355a021