1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-cyanophenyl)-1H-1,2,3-triazole | 1416718-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-cyanophenyl)-1H-1,2,3-triazole
• CAS: 1416718-00-7
• 化学式: C₃₀H₂₆N₄O₅
• 分子量: 522.56
• InChiKey: TXZRHUMLIRGDFJ-UPRLRBBYSA-N

物化性质

• 熔点：
  175-180 °C
• 沸点：
  729.5±70.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  116.33
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-cyanophenyl)-1H-1,2,3-triazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90.8%的产率得到1-(2′-deoxy-β-D-ribofuranosyl)-4-(4-cyanophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair

  摘要：

  We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible pi-pi stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.

  DOI：

  10.1021/jo302033f
• 作为产物：
  描述：

  甲基-2-脱氧-D-核糖 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-cyanophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair

  摘要：

  We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible pi-pi stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.

  DOI：

  10.1021/jo302033f