2'-O-(1-amino-6-naphthyl)uridine | 1198420-64-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-O-(1-amino-6-naphthyl)uridine
• 英文别名: 1-[(2R,3R,4R,5R)-3-(5-aminonaphthalen-2-yl)oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1198420-64-2
• 化学式: C₁₉H₁₉N₃O₆
• 分子量: 385.376
• InChiKey: PFYZYSYNLGTSOR-VDHUWJSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2'-脱水尿苷 、 5-氨基-2-萘酚 以62%的产率得到2'-O-(1-amino-6-naphthyl)uridine
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 2′-O-Aryluridine Derivatives

  摘要：

  A new method for the synthesis of 2'-O-aryluridines was developed via the microwave-mediated reaction of 2,2'-anhydrouridine with aromatic alcohols. Aminophenol and aminonaphthol derivatives underwent selective 2'-O-arylation with 2,2'-anhydrouridine to produce 2'-O-(aminoaryl)uridine derivatives. These reactions proved to proceed without the need for any bases or solvents, but better results were obtained by use of N,N-dimethylacetamide (DMA) as the solvent in some cases.

  DOI：

  10.1021/ol902142w

文献信息

• Microwave-Assisted Synthesis of 2′-<i>O</i>-Aryluridine Derivatives
  作者：Yusuke Oeda、Yoshihiro Iijima、Haruhiko Taguchi、Akihiro Ohkubo、Khoji Seio、Mitsuo Sekine

  DOI：10.1021/ol902142w

  日期：2009.12.17

  A new method for the synthesis of 2'-O-aryluridines was developed via the microwave-mediated reaction of 2,2'-anhydrouridine with aromatic alcohols. Aminophenol and aminonaphthol derivatives underwent selective 2'-O-arylation with 2,2'-anhydrouridine to produce 2'-O-(aminoaryl)uridine derivatives. These reactions proved to proceed without the need for any bases or solvents, but better results were obtained by use of N,N-dimethylacetamide (DMA) as the solvent in some cases.