1-[2-(2-naphthyloxy)ethyl]uracil | 1424798-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[2-(2-naphthyloxy)ethyl]uracil
• 英文别名: 1-(2-Naphthalen-2-yloxyethyl)pyrimidine-2,4-dione
• CAS: 1424798-82-2
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: NSENJYOAKFNIFA-UHFFFAOYSA-N

物化性质

• 熔点：
  211-213 °C
• 密度：
  1.283±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-(2-naphthyloxy)ethyl]uracil 、 氯化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以80%的产率得到3-Benzyl-1-[2-(2-naphthyloxy)ethyl]pyrimidine-2,4-dione
  参考文献：
  名称：

  N1,N3-disubstituted uracils as nonnucleoside inhibitors of HIV-1 reverse transcriptase

  摘要：

  A series of phenyloxyethyl and cinnamyl derivatives of substituted uracils were synthesized and found to exhibit potent activity against HIV-RT and HIV replication in cell culture. In general, the cinnamyl derivatives proved superior to the phenyloxyethyl derivatives, however 1-[2-(4-methylphenoxy)ethyl]3-(3,5-dimethylbenzyl)uracil (19) exhibited the highest activity (EC50 = 0.27 mu M) thus confirming that the 3-benzyluracil fragment in the NNRTI structure can be regarded as a functional analogue of the benzophenone pharmacophore typically found in NNRTIs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.027
• 作为产物：
  描述：

  1-[2-(2-naphthyloxy)ethyl]-3-benzoyluracil 在 ammonium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 生成 1-[2-(2-naphthyloxy)ethyl]uracil
  参考文献：
  名称：

  Selective N1-Alkylation of 1,3-Dibenzoyluracils: One-Pot Way to N1-Monosubstituted Uracil Derivatives

  摘要：

  A new method for synthesis of N(-)(1)monosubstituted uracils and 5- and 6-methyluracil derivatives was developed. It consists in the selective N-1-deprotection of N-1,N-3-dibenzoyluracils in anhydrous dimethylformamide in the presence of potassium carbonate at room temperature and subsequent N-1-alkylation by allyl, benzyl or phenacyl type halides or by primary alcohols toluenesulfonates conducted one pot without isolation of the intermediates. Final N-3-debenzoylation by aqueous-alcoholic solution of ammonia affords the corresponding N-1-monosubstituted uracil derivatives with overall yields of 52-84%.

  DOI：

  10.3987/com-17-13696