2,2'-dimethyl-2,2'-disulfanediyl-bis-propionaldehyde dioxime | 10533-62-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2'-dimethyl-2,2'-disulfanediyl-bis-propionaldehyde dioxime
• CAS: 10533-62-7
• 化学式: C₈H₁₆N₂O₂S₂
• 分子量: 236.359
• InChiKey: HNOOHYBUKVOCHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  131.5-132 °C
• 沸点：
  369.2±27.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2'-dimethyl-2,2'-disulfanediyl-bis-propionaldehyde dioxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2-巯基-2-甲基-1-丙胺
  参考文献：
  名称：

  New Thionitrites: Synthesis, Stability, and Nitric Oxide Generation

  摘要：

  In order to study the influence of substitutions at the alpha and beta carbon atoms on the stability of the S-NO bond, water-soluble thionitrites RSNO have been synthesized by nitrosation of cysteamine and mercaptoethanol derivatives and characterized. H-1 and C-13 NMR spectroscopies have proven to be excellent probes for the nitrosation of thiols. In water, at physiological pH, the compounds decomposed into nitric oxide NO and the corresponding disulfides. The rate at which NO was released was very sensitive to modifications at the alpha and beta carbon atoms. Tertiary thionitrites were more stable than primary thionitrites. The beta-substituents decreased the rates of decomposition in the following order: OH > NHCOCH3 > NH3+. S-Nitrosocysteamine derivatives were greatly stabilized at low pH. The compounds described here might be convenient and useful as vehicles for spontaneous generation of nitric oxide in biological systems, at rates that can be finely tuned and controlled over a wide range.

  DOI：

  10.1021/jo00102a028
• 作为产物：
  描述：

  2-氯-2-甲基丙醛肟 在 sodium hydrogensulfide 作用下， 以 乙醇 为溶剂， 生成 2,2'-dimethyl-2,2'-disulfanediyl-bis-propionaldehyde dioxime
  参考文献：
  名称：

  Ogloblin,K.A.; Samartsev,M.A., Journal of general chemistry of the USSR, 1960, vol. 30, p. 820 - 833

  摘要：

  DOI：

文献信息

• Ogloblin,K.A.; Samartsev,M.A., Journal of general chemistry of the USSR, 1960, vol. 30, p. 820 - 833
  作者：Ogloblin,K.A.、Samartsev,M.A.

  DOI：——

  日期：——
• New Thionitrites: Synthesis, Stability, and Nitric Oxide Generation
  作者：Beatrice Roy、A. du Moulinet d'Hardemare、Marc Fontecave

  DOI：10.1021/jo00102a028

  日期：1994.11

  In order to study the influence of substitutions at the alpha and beta carbon atoms on the stability of the S-NO bond, water-soluble thionitrites RSNO have been synthesized by nitrosation of cysteamine and mercaptoethanol derivatives and characterized. H-1 and C-13 NMR spectroscopies have proven to be excellent probes for the nitrosation of thiols. In water, at physiological pH, the compounds decomposed into nitric oxide NO and the corresponding disulfides. The rate at which NO was released was very sensitive to modifications at the alpha and beta carbon atoms. Tertiary thionitrites were more stable than primary thionitrites. The beta-substituents decreased the rates of decomposition in the following order: OH > NHCOCH3 > NH3+. S-Nitrosocysteamine derivatives were greatly stabilized at low pH. The compounds described here might be convenient and useful as vehicles for spontaneous generation of nitric oxide in biological systems, at rates that can be finely tuned and controlled over a wide range.