5-(dihexylaminomethyl)uracil | 149437-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(dihexylaminomethyl)uracil
• 英文别名: 5-[(dihexylamino)methyl]-1H-pyrimidine-2,4-dione
• CAS: 149437-43-4
• 化学式: C₁₇H₃₁N₃O₂
• 分子量: 309.452
• InChiKey: AQQLASODBMVJMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(dihexylaminomethyl)uracil 在 amino sulphate 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 34.0h， 生成 1-(2,3-dideoxy-3-fluoro-α-D-erythro-pentafuranosyl)-5-(dihexylaminomethyl)-uracil
  参考文献：
  名称：

  Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents

  摘要：

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.

  DOI：

  10.1007/bf00808509
• 作为产物：
  描述：

  聚合甲醛 、 二已胺 、 尿嘧啶 以 乙二醇二甲醚 为溶剂， 反应 14.0h， 以66%的产率得到5-(dihexylaminomethyl)uracil
  参考文献：
  名称：

  Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents

  摘要：

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.

  DOI：

  10.1007/bf00808509

文献信息

• Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents
  作者：Mohammed S. Motawia、Per T. Jørgensen、Anni Larnkjær、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/bf00808509

  日期：1993.1

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.