2,2'-oxydiethanesulfenyl dichloride | 1360548-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2'-oxydiethanesulfenyl dichloride
• 英文别名: 2-(2-Chlorosulfanylethoxy)ethyl thiohypochlorite；2-(2-chlorosulfanylethoxy)ethyl thiohypochlorite
• CAS: 1360548-28-2
• 化学式: C₄H₈Cl₂OS₂
• 分子量: 207.145
• InChiKey: GNQGBSBVNPIXME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-乙基甲基胺 、 2,2'-oxydiethanesulfenyl dichloride 以 二氯甲烷 为溶剂， 以60%的产率得到N-[2-[2-[ethyl(methyl)amino]sulfanylethoxy]ethylsulfanyl]-N-methylethanamine
  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
• 作为产物：
  描述：

  2-巯基乙醚 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 2,2'-oxydiethanesulfenyl dichloride
  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

• Biodegradable Polymers with Sulfenamide Bonds for Drug Delivery Applications
  申请人：Bowden Ned B.

  公开号：US20140099506A1

  公开（公告）日：2014-04-10

  The present invention provides polysulfenamides and methods of making same.

  本发明提供了聚硫胺酰胺及其制备方法。
• US9345776B2
  申请人：——

  公开号：US9345776B2

  公开（公告）日：2016-05-24
• [EN] NEW BIODEGRADABLE POLYMERS WITH SULFENAMIDE BONDS FOR DRUG DELIVERY APPLICATIONS<br/>[FR] NOUVEAUX POLYMÈRES BIODÉGRADABLES AYANT DES LIAISONS SULFÉNAMIDE POUR DES APPLICATIONS D'ADMINISTRATION DE MÉDICAMENTS
  申请人：UNIV IOWA RES FOUND

  公开号：WO2012115806A1

  公开（公告）日：2012-08-30

  The present invention provides polysulfenamides and methods of making same.
• 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.