1-[6-(2,5-Dioxopyrrolidin-1-yl)sulfanylhexylsulfanyl]pyrrolidine-2,5-dione | 35718-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-[6-(2,5-Dioxopyrrolidin-1-yl)sulfanylhexylsulfanyl]pyrrolidine-2,5-dione
• 英文别名: 1-[6-(2,5-dioxopyrrolidin-1-yl)sulfanylhexylsulfanyl]pyrrolidine-2,5-dione
• CAS: 35718-32-2
• 化学式: C₁₄H₂₀N₂O₄S₂
• 分子量: 344.456
• InChiKey: ZKLBDQZQSOFQCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-氯代丁二酰亚胺 、 1,6-己二硫醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到1-[6-(2,5-Dioxopyrrolidin-1-yl)sulfanylhexylsulfanyl]pyrrolidine-2,5-dione
  参考文献：
  名称：

  New Class of Biodegradable Polymers Formed from Reactions of an Inorganic Functional Group

  摘要：

  Although numerous small molecules have been synthesized with sulfenamide bonds (R2N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH2)(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C6D6 for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D2O. Polysulfenamides were fabricated into micrometer-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.

  DOI：

  10.1021/ma300190b

文献信息

• New Class of Biodegradable Polymers Formed from Reactions of an Inorganic Functional Group
  作者：Jun Yoo、Denison J. Kuruvilla、Sheetal R. D’Mello、Aliasger K. Salem、Ned B. Bowden

  DOI：10.1021/ma300190b

  日期：2012.3.13

  Although numerous small molecules have been synthesized with sulfenamide bonds (R2N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH2)(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C6D6 for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D2O. Polysulfenamides were fabricated into micrometer-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.