N,N'-dithio(bis(ethylmethylamine)) | 1355394-62-5

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: N,N'-dithio(bis(ethylmethylamine))
• 英文别名: di(ethylmethylamine)disulfide
• CAS: 1355394-62-5
• 化学式: C₆H₁₆N₂S₂
• 分子量: 180.338
• InChiKey: SUCUGAQVRMHNAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-dithio(bis(ethylmethylamine)) 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.62h， 生成 S-chloro-N-ethyl-N-methylthiohydroxylamine
  参考文献：
  名称：

  Synthesis of the First Poly(diaminosulfide)s and an Investigation of Their Applications as Drug Delivery Vehicles

  摘要：

  This paper reports the first examples of poly(diaminosulfide)s that were synthesized by the reaction of a sulfur transfer reagent and several secondary diamines. The diaminosulfide group has the general structure of R2N-S-NR2, and although it has been used in the synthesis of small molecules, it has never been utilized in the synthesis of macromolecules until this report. A series of poly(diaminosulfide)s were synthesized at elevated temperatures, and the molecular weights of the polymers were as high as 12 400 g mol(-1) with conversions for the polymerization reaction up to 99%. The rate constants for the transamination reactions that lead to the polymers were measured in several solvents to provide an understanding of the reaction conditions necessary to polymerize the monomers. The degradation of diaminosulfides was studied in D2O, C6D6, CD3OD, CDCl3, and DMSO-d(6)/D2O to demonstrate that they were very stable in organic solvents but degraded within hours under aqueous conditions. These results clearly demonstrated that diaminosulfides are very stable in organic solvents under ambient conditions. Poly(diaminosulfide)s have sufficient stabilities to be useful for many applications. The ability of these polymers to function as drug delivery vehicles was studied by the fabrication of nanoparticles of a water-insoluble poly(diaminosulfide) with a dye. The microparticles were readily absorbed into human embryonic 293 cells and possessed no measurable toxicity toward these same cells.

  DOI：

  10.1021/ma2023167
• 作为产物：
  描述：

  二氯化二硫 、 N-乙基甲基胺 以 Petroleum ether 为溶剂， 反应 1.08h， 以78%的产率得到N,N'-dithio(bis(ethylmethylamine))
  参考文献：
  名称：

  Synthesis of the First Poly(diaminosulfide)s and an Investigation of Their Applications as Drug Delivery Vehicles

  摘要：

  This paper reports the first examples of poly(diaminosulfide)s that were synthesized by the reaction of a sulfur transfer reagent and several secondary diamines. The diaminosulfide group has the general structure of R2N-S-NR2, and although it has been used in the synthesis of small molecules, it has never been utilized in the synthesis of macromolecules until this report. A series of poly(diaminosulfide)s were synthesized at elevated temperatures, and the molecular weights of the polymers were as high as 12 400 g mol(-1) with conversions for the polymerization reaction up to 99%. The rate constants for the transamination reactions that lead to the polymers were measured in several solvents to provide an understanding of the reaction conditions necessary to polymerize the monomers. The degradation of diaminosulfides was studied in D2O, C6D6, CD3OD, CDCl3, and DMSO-d(6)/D2O to demonstrate that they were very stable in organic solvents but degraded within hours under aqueous conditions. These results clearly demonstrated that diaminosulfides are very stable in organic solvents under ambient conditions. Poly(diaminosulfide)s have sufficient stabilities to be useful for many applications. The ability of these polymers to function as drug delivery vehicles was studied by the fabrication of nanoparticles of a water-insoluble poly(diaminosulfide) with a dye. The microparticles were readily absorbed into human embryonic 293 cells and possessed no measurable toxicity toward these same cells.

  DOI：

  10.1021/ma2023167