O2-vinyl-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate | 1438393-93-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O2-vinyl-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate
• 英文别名: (2-carboxypyrrolidin-1-yl)-ethenoxyimino-oxidoazanium
• CAS: 1438393-93-1
• 化学式: C₇H₁₁N₃O₄
• 分子量: 201.182
• InChiKey: GWWLLMQXASWEMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 O2-vinyl-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 以71%的产率得到O2-vinyl [2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate methyl ester
  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-vinyl 1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以50%的产率得到O2-vinyl-[2-(carboxylato)pyrrolidin-1-yl]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