5-Azidopentylcyanamide | 1374238-48-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-Azidopentylcyanamide
• CAS: 1374238-48-8
• 化学式: C₆H₁₁N₅
• 分子量: 153.187
• InChiKey: JKWPNLWIHBNDSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Azidopentylcyanamide 在 盐酸羟胺 、 甲酸铵 、 potassium carbonate 、 silver nitrate 、 三乙胺 、 锌 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 phidianidine A trifluoroacetate salt
  参考文献：
  名称：

  Synthesis of Phidianidines A and B

  摘要：

  Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10(-5) M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.

  DOI：

  10.1021/jo300449n
• 作为产物：
  描述：

  溴化氰 、 1-叠氮基-5-氨基戊烷 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 5-Azidopentylcyanamide
  参考文献：
  名称：

  Synthesis of Phidianidines A and B

  摘要：

  Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10(-5) M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.

  DOI：

  10.1021/jo300449n