O2-(2-acetylthioethyl) 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate | 259686-44-7

• 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: O2-(2-acetylthioethyl) 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate
• 英文别名: 2-acetylsulfanylethoxyimino-oxido-pyrrolidin-1-ylazanium
• CAS: 259686-44-7
• 化学式: C₈H₁₅N₃O₃S
• 分子量: 233.291
• InChiKey: WNUMMCSRSMJXFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  67.97
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  O2-(2-acetylthioethyl) 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate 在 双氧水 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 生成 O2-(2-oxysulfonylethyl sodium salt) 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  O²-(N-Hydroxy(methoxy)-2-ethanesulfonamido) Protected Diazen-1-ium-1,2-diolates: Nitric Oxide Release via a Base-Induced β-Elimination Cleavage

  摘要：

  O-2-(Ethanesulfohydroxamic acid) and O-2-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O-2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O-2-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a beta-elimination cleavage reaction.

  DOI：

  10.1021/ol200053z
• 作为产物：
  描述：

  2-乙酰硫代乙基碘 、 sodium 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate 在 15-冠醚-5 、 碳酸氢钠 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.08h， 以20%的产率得到O2-(2-acetylthioethyl) 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  O²-(N-Hydroxy(methoxy)-2-ethanesulfonamido) Protected Diazen-1-ium-1,2-diolates: Nitric Oxide Release via a Base-Induced β-Elimination Cleavage

  摘要：

  O-2-(Ethanesulfohydroxamic acid) and O-2-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O-2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O-2-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a beta-elimination cleavage reaction.

  DOI：

  10.1021/ol200053z