O2-vinyl 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate | 1181668-17-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: O2-vinyl 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate
• CAS: 1181668-17-6
• 化学式: C₅H₁₁N₃O₃
• 分子量: 161.161
• InChiKey: ULKMYMGIQBKTNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.13
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  O2-vinyl 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以57%的产率得到O2-vinyl 1-[N-(carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide prodrug

  摘要：

  An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide (NO) prodrug, in an overall yield of 26% in four steps from prolinol is reported: the previously published yield of this transformation was 1%. Using this revised strategy, the sarcosine analogue (14) of V-PROLI/NO was prepared. Finally, the methyl ester of V-PROLI/NO (15) was found to be an esterase-activated prodrug form of V-PROLI/NO. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.05.089
• 作为产物：
  描述：

  O2-(2-bromoethyl) 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate 在 2,8,9-三甲基-2,5,8,9-四氮杂-1-磷双环(3,3,3)十一烷 作用下， 以 乙腈 为溶剂， 以55%的产率得到O2-vinyl 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide prodrug

  摘要：

  An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide (NO) prodrug, in an overall yield of 26% in four steps from prolinol is reported: the previously published yield of this transformation was 1%. Using this revised strategy, the sarcosine analogue (14) of V-PROLI/NO was prepared. Finally, the methyl ester of V-PROLI/NO (15) was found to be an esterase-activated prodrug form of V-PROLI/NO. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.05.089