N³-p-tolyluridine

• 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: N³-p-tolyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(4-methylphenyl)pyrimidine-2,4-dione
• 化学式: C₁₆H₁₈N₂O₆
• 分子量: 334.329
• InChiKey: USVSJXAAUHLDMD-NMFUWQPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲苯硼酸 、 尿嘧啶核苷 在 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以45%的产率得到N³-p-tolyluridine
  参考文献：
  名称：

  Regioselective arylation of 2′-deoxyribonucleosides on amido or imino sites by copper(II)-mediated direct coupling with arylboronic acids

  摘要：

  N-1-Aryl derivatives of 2'-deoxyguanosine (dG) were synthesized by copper(II)-mediated coupling of dG with arylboronic acids. Analogous aryl derivatives of 2'-deoxyinosine (dIn), 2'-deoxyuridine (dU), thymidine (T), 2'-deoxyadenosine (dA), and 2'-deoxycytidine (dC) were also conveniently synthesized by this method. Arylation took place preferentially on the amido functions in dG and dIn and the imino functions in dU or T. Remarkably, the nucleosides themselves served as internal ligands as well as reactants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.072

文献信息

• Regioselective arylation of 2′-deoxyribonucleosides on amido or imino sites by copper(II)-mediated direct coupling with arylboronic acids
  作者：Qing Dai、Chongzhao Ran、Ronald G. Harvey

  DOI：10.1016/j.tet.2005.11.072

  日期：2006.2

  N-1-Aryl derivatives of 2'-deoxyguanosine (dG) were synthesized by copper(II)-mediated coupling of dG with arylboronic acids. Analogous aryl derivatives of 2'-deoxyinosine (dIn), 2'-deoxyuridine (dU), thymidine (T), 2'-deoxyadenosine (dA), and 2'-deoxycytidine (dC) were also conveniently synthesized by this method. Arylation took place preferentially on the amido functions in dG and dIn and the imino functions in dU or T. Remarkably, the nucleosides themselves served as internal ligands as well as reactants. (c) 2005 Elsevier Ltd. All rights reserved.