1-(6-benzyloxy-2-naphthyl)-2-nitropropene | 1148113-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(6-benzyloxy-2-naphthyl)-2-nitropropene
• CAS: 1148113-84-1
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: FVMMDGQQLSTYSR-UHFFFAOYSA-N

物化性质

• 熔点：
  151.0-153.3 °C
• 沸点：
  505.0±30.0 °C(predicted)
• 密度：
  1.219±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(6-benzyloxy-2-naphthyl)-2-nitropropene 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 以33%的产率得到(6-benzyloxy-2-naphthyl)-2-aminopropane hydrochloride
  参考文献：
  名称：

  Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

  摘要：

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.074
• 作为产物：
  描述：

  6-(benzyloxy)-2-naphthaldehyde 、 硝基乙烷 在 环己胺 、 溶剂黄146 作用下， 反应 24.0h， 以76%的产率得到1-(6-benzyloxy-2-naphthyl)-2-nitropropene
  参考文献：
  名称：

  Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

  摘要：

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.074