6-mercaptodopamine | 72515-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-mercaptodopamine
• 英文别名: 1,2-Benzenediol, 4-(2-aminoethyl)-5-mercapto-；4-(2-aminoethyl)-5-sulfanylbenzene-1,2-diol
• CAS: 72515-46-9
• 化学式: C₈H₁₁NO₂S
• 分子量: 185.247
• InChiKey: BXYIJNMKWHWMAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  以99%的产率得到
  参考文献：
  名称：

  Mascagna D., dIschia M., Costantini C., Prota G., Synth. Commun, 24 (1994) N 1, S 35- 42

  摘要：

  DOI：

文献信息

• A Convenient Access to Dihydroxybenzenethiols<i>via</i>Reduction of<i>Iso</i>-Thiouronium Salts with Sodium Borohydride
  作者：D. Mascagna、M. d'Ischia、C. Costantini、G. Prota

  DOI：10.1080/00397919408012622

  日期：1994.1

  Abstract An improved procedure for the preparation of unstable dihydroxybenzenethiols in high yields is reported, involving mild reduction of the corresponding iso-thiouronium salts with sodium borohydride.

  摘要 报道了一种以高产率制备不稳定二羟基苯硫醇的改进方法，包括用硼氢化钠温和还原相应的异硫脲盐。
• 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.
• Mascagna D., dIschia M., Costantini C., Prota G., Synth. Commun, 24 (1994) N 1, S 35- 42
  作者：Mascagna D., dIschia M., Costantini C., Prota G.

  DOI：——

  日期：——