2,2'-磺酰基二乙硫醇 | 145626-87-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 中文名称: 2,2'-磺酰基二乙硫醇
• 中文别名: 4-((4-氨基苯基)磺酰基)-1-(叔丁基氧羰基)哌嗪
• 英文名称: Bis(2-mercaptoethyl) Sulfone
• 英文别名: Bis(2-mercaptoethyl)sulfone；2-(2-sulfanylethylsulfonyl)ethanethiol
• CAS: 145626-87-5
• 化学式: C₄H₁₀O₂S₃
• mdl: MFCD00467637
• 分子量: 186.32
• InChiKey: YWXCBLUCVBSYNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58°C
• 沸点：
  375.6±27.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  二(2-乙酰基巯基乙基)砜 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以90%的产率得到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
• 作为试剂：
  描述：

  达西司坦 在 碳酸氢钠 、 magnesium methanolate 、 2,2'-磺酰基二乙硫醇 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 124.0h， 生成 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside
  参考文献：
  名称：

  First Total Synthesis of Mycothiol and Mycothiol Disulfide

  摘要：

  The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-alpha,beta-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.

  DOI：

  10.1021/ol0362008

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.