2-(2-氨基乙基)-5-甲氧基苯-1,4-二醇 | 38411-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-(2-氨基乙基)-5-甲氧基苯-1,4-二醇
• 英文名称: 2.5-Dihydroxy-4-methoxy-1-aminoaethyl-benzol
• 英文别名: 2.5-Dihydroxy-4-methoxyphenethylamin；2-(2-amino-ethyl)-5-methoxy-hydroquinone；2-(2-Amino-aethyl)-5-methoxy-hydrochinon；2-(2-Aminoethyl)-5-methoxybenzene-1,4-diol
• CAS: 38411-82-4
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: QJPNZUPVNUCQJP-UHFFFAOYSA-N

物化性质

• 沸点：
  390.9±37.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-氨基乙基)-5-甲氧基苯-1,4-二醇 在 氢溴酸 作用下， 生成 5-(2-氨基乙基)苯-1,2,4-三醇盐酸盐
  参考文献：
  名称：

  Non-enzymatic Conversions of Dopamine to Norepinephrine and Trihydroxyphenethylamines¹

  摘要：

  DOI：

  10.1021/ja01532a028
• 作为产物：
  描述：

  异香兰素 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium dihydrogenphosphate 、 potassium nitrososulfonate 、 ammonium acetate 、 氢气 、 盐酸甲胺 、 sodium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 2-(2-氨基乙基)-5-甲氧基苯-1,4-二醇
  参考文献：
  名称：

  A New Synthesis of 6-Hydroxydopamine

  摘要：

  描述了一种高效合成6-羟基多巴胺的方法。关键步骤涉及将N-保护的3-羟基-4-甲氧基苯乙胺氧化为相应的p-醌，方法是使用弗雷米盐。

  DOI：

  10.1139/v72-488

文献信息

• Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine
  作者：Alice C. Cheng、Neal Castagnoli

  DOI：10.1021/jm00370a014

  日期：1984.4

  In an attempt to evaluate the possible relationship between the neurotoxicity of 6-hydroxydopamine and the redox properties and electrophilic reactivity of the 6-hydroxydopamine-p-hydroquinone/p-quinone system, we have synthesized a series of 6-hydroxydopamine analogues in which the C4-hydroxy group is replaced with various electron-donating and electron-withdrawing substituents. With the aid of cyclic voltammetry, the formal oxidation potentials (E degrees ') for the p-hydroquinone/p-quinone redox couples and the rates of cyclization of the p-quinones to the corresponding p-iminoquinones were determined. As expected, electron-rich p-hydroquinones were easily oxidized to the p-quinones, which underwent cyclization slowly, whereas the oxidation of electron-poor p-hydroquinones required higher voltages and yielded p-quinones, which cyclized readily at pH 7.4. The neurotoxic potential of these compounds showed that in vivo destruction of noradrenergic terminals, as measured by inhibition of norepinephrine uptake by rat heart slices, occurred only with those analogues bearing electron-donating substituents. Potent neurotoxic properties were associated only with the 4-amino and 4-hydroxy derivatives, both of which form p-quinones, which do not cyclize readily at pH 7.4. These results support the thesis that the p-quinone derived from 6-hydroxydopamine may be an important species in the mediation of the neurodestruction caused by 6-hydrodopamine.
• Chemical and Enzymatic Routes to Methoxydopamines
  作者：John Daly、Leopold Horner、Bernhard Witkop

  DOI：10.1021/ja01484a022

  日期：1961.12
• Non-enzymatic Conversions of Dopamine to Norepinephrine and Trihydroxyphenethylamines¹
  作者：Siro Senoh、Bernhard Witkop

  DOI：10.1021/ja01532a028

  日期：1959.12
• A New Synthesis of 6-Hydroxydopamine
  作者：Pius A. Wehrli、F. Pigott、V. Chu

  DOI：10.1139/v72-488

  日期：1972.9.15

  An efficient synthesis of 6-hydroxydopamine is described. The key step involves oxidation of an N-protected 3-hydroxy-4-methoxyphenethylamine to the corresponding p-quinone by means of Fremy's salt.

  描述了一种高效合成6-羟基多巴胺的方法。关键步骤涉及将N-保护的3-羟基-4-甲氧基苯乙胺氧化为相应的p-醌，方法是使用弗雷米盐。