O(2)-((5-nitro-2-(tetrahydropyran-2-yloxy)phenyl)methyl)-1-( N,N-diethylamino)diazen-1-ium-1,2-diolate | 1070883-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O(2)-((5-nitro-2-(tetrahydropyran-2-yloxy)phenyl)methyl)-1-( N,N-diethylamino)diazen-1-ium-1,2-diolate
• CAS: 1070883-64-5
• 化学式: C₁₆H₂₄N₄O₆
• 分子量: 368.39
• InChiKey: GBALYLKBEMUQLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112.5
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  O(2)-((5-nitro-2-(tetrahydropyran-2-yloxy)phenyl)methyl)-1-( N,N-diethylamino)diazen-1-ium-1,2-diolate 在 盐酸 作用下， 以 乙醚 为溶剂， 以90%的产率得到O(2)-(2-hydroxy-5-nitrobenzyl)-1-( N,N-diethylamino)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  2-Hydroxy-5-nitrobenzyl as a Diazeniumdiolate Protecting Group: Application in NO-Releasing Polymers with Enhanced Biocompatibility

  摘要：

  The 2-hydroxy-5-nitrobenzyl group is shown to be an effective protecting group for diazenlumdiolates. O-2-(2-Hydroxy-5-nitrobenzyl)-substituted diazeniumdiolates display enhanced thermal stability, but efficiently release nitric oxide (NO) in pH 7.4 aqueous solutions. A lipophilic analogue incorporated into hydrophobic polymers shows NO surface flux rates comparable to that of the natural endothelium. Importantly, these polymer formulations also show significantly enhanced biocompatibility in vivo with use of a porcine implant model.

  DOI：

  10.1021/ol801883f
• 作为产物：
  描述：

  2-(2-bromomethyl-4-nitrophenoxy)tetrahydropyran 、 sodium N,N-(diethylamino)diazen-1-ium-1,2-diolate 在 15-冠醚-5 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以70%的产率得到O(2)-((5-nitro-2-(tetrahydropyran-2-yloxy)phenyl)methyl)-1-( N,N-diethylamino)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  2-Hydroxy-5-nitrobenzyl as a Diazeniumdiolate Protecting Group: Application in NO-Releasing Polymers with Enhanced Biocompatibility

  摘要：

  The 2-hydroxy-5-nitrobenzyl group is shown to be an effective protecting group for diazenlumdiolates. O-2-(2-Hydroxy-5-nitrobenzyl)-substituted diazeniumdiolates display enhanced thermal stability, but efficiently release nitric oxide (NO) in pH 7.4 aqueous solutions. A lipophilic analogue incorporated into hydrophobic polymers shows NO surface flux rates comparable to that of the natural endothelium. Importantly, these polymer formulations also show significantly enhanced biocompatibility in vivo with use of a porcine implant model.

  DOI：

  10.1021/ol801883f