1,2,5-三硫杂环庚烷 5,5-二氧化物 | 145626-93-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 中文名称: 1,2,5-三硫杂环庚烷 5,5-二氧化物
• 中文别名: 1,2,5-三硫杂环庚烷5,5-二氧化物；NT-BOC-2-(5-羟基-2-甲氧基苯氧基)-乙胺
• 英文名称: Bis(2-mercaptoethyl) Sulfone Disulfide
• 英文别名: 1,2,5-trithiepane 5,5-dioxide
• CAS: 145626-93-3
• 化学式: C₄H₈O₂S₃
• 分子量: 184.304
• InChiKey: IFMXYCMBQCPKAU-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139°C
• 沸点：
  406.6±34.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dithio-D,L-threitol 、 1,2,5-三硫杂环庚烷 5,5-二氧化物 以 氘代甲醇 、 重水 为溶剂， 反应 48.0h， 生成 (4S,5S)-1,2-二噻烷-4,5-二醇 、 2,2'-磺酰基二乙硫醇
  参考文献：
  名称：

  Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials

  摘要：

  Several dithiols have been prepared that are useful for the reduction of disulfides in aqueous solution. The reduction potential of these dithiols have been determined from the measurement of the equilibrium constant of thiol/disulfide interchange with oxidized dithiothreitol using a H-1 NMR assay. The values of pK(a) of some of the dithiols were measured to estimate their rate of reduction of disulfides. Bis(2-mercaptoethyl) sulfone (2), N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine (5), and meso-2,5-dimercapto-N,N,N',N'-tetramethyladipamide (6) are especially interesting as alternatives to dithiothreitol for the reduction of disulfides.

  DOI：

  10.1021/jo00055a015
• 作为产物：
  描述：

  2,2'-磺酰基二乙硫醇 在 5,5'-二硫双(2-硝基苯甲酸) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以56%的产率得到1,2,5-三硫杂环庚烷 5,5-二氧化物
  参考文献：
  名称：

  Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials

  摘要：

  Several dithiols have been prepared that are useful for the reduction of disulfides in aqueous solution. The reduction potential of these dithiols have been determined from the measurement of the equilibrium constant of thiol/disulfide interchange with oxidized dithiothreitol using a H-1 NMR assay. The values of pK(a) of some of the dithiols were measured to estimate their rate of reduction of disulfides. Bis(2-mercaptoethyl) sulfone (2), N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine (5), and meso-2,5-dimercapto-N,N,N',N'-tetramethyladipamide (6) are especially interesting as alternatives to dithiothreitol for the reduction of disulfides.

  DOI：

  10.1021/jo00055a015

文献信息

• Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials
  作者：Guy V. Lamoureux、George M. Whitesides

  DOI：10.1021/jo00055a015

  日期：1993.1

  Several dithiols have been prepared that are useful for the reduction of disulfides in aqueous solution. The reduction potential of these dithiols have been determined from the measurement of the equilibrium constant of thiol/disulfide interchange with oxidized dithiothreitol using a H-1 NMR assay. The values of pK(a) of some of the dithiols were measured to estimate their rate of reduction of disulfides. Bis(2-mercaptoethyl) sulfone (2), N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine (5), and meso-2,5-dimercapto-N,N,N',N'-tetramethyladipamide (6) are especially interesting as alternatives to dithiothreitol for the reduction of disulfides.