3-Mercapto-4,5-dihydroxy-toluol | 71594-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-Mercapto-4,5-dihydroxy-toluol
• 英文别名: 5-Methyl-3-sulfanylbenzene-1,2-diol；5-methyl-3-sulfanylbenzene-1,2-diol
• CAS: 71594-50-8
• 化学式: C₇H₈O₂S
• 分子量: 156.205
• InChiKey: OUXFETMBJQSBHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-methylbenzo-1,2-quinone 生成 3-Mercapto-4,5-dihydroxy-toluol
  参考文献：
  名称：

  Synthesis, redox characteristics, and in vitro norepinephrine uptake inhibiting properties of 2-(2-mercapto-4,5-dihydroxyphenyl)ethylamine (6-mercaptodopamine)

  摘要：

  In an attempt to further characterize the structural features of 6-hydroxydopamine analogues that are associated with in vivo neuronal degeneration, the synthesis of 6-mercaptodopamine was undertaken. Although reaction conditions leading to the 1,4 addition of thiols to the model quinone 4-methyl-o-benzoquinone were achieved, attempts to obtain 6-thiolated dopamine analogues by this route failed. The synthesis of 6-mercaptodopamine was achieved by the regioselective thiocyanation of O,O-dimethyldopamine, followed by bis-O-demethylation and reductive cleavage of the S-cyano group. Unlike 6-hydroxydopamine, 6-mercaptodopamine was resistant to autoxidation at pH 7.4. Cyclic voltammometric analysis, however, indicated that electrochemically generated oxidation species of 6-mercaptodopamine are unstable and undergo spontaneous reaction, presumably intramolecular cyclization. In vivo tests revealed that 6-mercaptodopamine inhibits the uptake of tritium-labeled norepinephrine by isolated rat heart atria, although to a much lesser extent than 6-hydroxydopamine.

  DOI：

  10.1021/jm00197a008

文献信息

• Synthesis, redox characteristics, and in vitro norepinephrine uptake inhibiting properties of 2-(2-mercapto-4,5-dihydroxyphenyl)ethylamine (6-mercaptodopamine)
  作者：Charles G. Chavdarian、Neal Castagnoli

  DOI：10.1021/jm00197a008

  日期：1979.11

  In an attempt to further characterize the structural features of 6-hydroxydopamine analogues that are associated with in vivo neuronal degeneration, the synthesis of 6-mercaptodopamine was undertaken. Although reaction conditions leading to the 1,4 addition of thiols to the model quinone 4-methyl-o-benzoquinone were achieved, attempts to obtain 6-thiolated dopamine analogues by this route failed. The synthesis of 6-mercaptodopamine was achieved by the regioselective thiocyanation of O,O-dimethyldopamine, followed by bis-O-demethylation and reductive cleavage of the S-cyano group. Unlike 6-hydroxydopamine, 6-mercaptodopamine was resistant to autoxidation at pH 7.4. Cyclic voltammometric analysis, however, indicated that electrochemically generated oxidation species of 6-mercaptodopamine are unstable and undergo spontaneous reaction, presumably intramolecular cyclization. In vivo tests revealed that 6-mercaptodopamine inhibits the uptake of tritium-labeled norepinephrine by isolated rat heart atria, although to a much lesser extent than 6-hydroxydopamine.