(E)-1-(4-bromobut-2-enyl)-5-bromo-6-azauracil | 872722-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: (E)-1-(4-bromobut-2-enyl)-5-bromo-6-azauracil
• 英文别名: 6-bromo-2-[(E)-4-bromobut-2-enyl]-1,2,4-triazine-3,5-dione
• CAS: 872722-48-0
• 化学式: C₇H₇Br₂N₃O₂
• 分子量: 324.959
• InChiKey: PNIDXIJDDRAAQT-OWOJBTEDSA-N

物化性质

• 熔点：
  128-130 °C
• 密度：
  2.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-bromobut-2-enyl)-5-bromo-6-azauracil 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 diethyl (E)-4-(5-bromo-3-propargyl-6-azauracil-1-yl)but-2-enephosphonate
  参考文献：
  名称：

  一些不饱和6-氮嘧啶无环核苷的合成及生物活性

  摘要：

  A useful route is described for obtaining Z and E unsaturated alkylating agents 3 and 4. Coupling 6-azauracits 5 and 6 with unsaturated alkylating agent followed by the deprolection with H' resin gave acyclonucleosides 11-14 in good overall yields. Unsaturated acyclonucleosides phosphonates 19 and 20 were prepared using potassium carbonate as base and 4-bromobut-2-enyl diethyl phosphonate 16 as the alkylating agent. The introduction of a propargyl group at the N-3 position of acyclonucleasides 7, 8, 17, 18, 19, and 20 was achieved using potassium carbonate in DMF.

  DOI：

  10.1081/ncn-200055695
• 作为产物：
  描述：

  5-溴-6-氮尿嘧啶 、 1,4-二溴-2-丁烯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以50%的产率得到(E)-1-(4-bromobut-2-enyl)-5-bromo-6-azauracil
  参考文献：
  名称：

  一些不饱和6-氮嘧啶无环核苷的合成及生物活性

  摘要：

  A useful route is described for obtaining Z and E unsaturated alkylating agents 3 and 4. Coupling 6-azauracits 5 and 6 with unsaturated alkylating agent followed by the deprolection with H' resin gave acyclonucleosides 11-14 in good overall yields. Unsaturated acyclonucleosides phosphonates 19 and 20 were prepared using potassium carbonate as base and 4-bromobut-2-enyl diethyl phosphonate 16 as the alkylating agent. The introduction of a propargyl group at the N-3 position of acyclonucleasides 7, 8, 17, 18, 19, and 20 was achieved using potassium carbonate in DMF.

  DOI：

  10.1081/ncn-200055695

文献信息

• Synthesis and Biological Activity of Some Unsaturated 6-Azauracil Acyclonucleosides
  作者：Youssef Kabbaj、Hassan Bihi Lazrek、Jean Louis Barascut、Jean Louis Imbach

  DOI：10.1081/ncn-200055695

  日期：2005.3.1

  A useful route is described for obtaining Z and E unsaturated alkylating agents 3 and 4. Coupling 6-azauracits 5 and 6 with unsaturated alkylating agent followed by the deprolection with H' resin gave acyclonucleosides 11-14 in good overall yields. Unsaturated acyclonucleosides phosphonates 19 and 20 were prepared using potassium carbonate as base and 4-bromobut-2-enyl diethyl phosphonate 16 as the alkylating agent. The introduction of a propargyl group at the N-3 position of acyclonucleasides 7, 8, 17, 18, 19, and 20 was achieved using potassium carbonate in DMF.