5'-O-(4,4'-dimethoxytrityl)-5-[4-(9-anthracenyl)buta-1,3-diynyl]-2'-deoxyuridine | 936743-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-5-[4-(9-anthracenyl)buta-1,3-diynyl]-2'-deoxyuridine
• CAS: 936743-52-1
• 化学式: C₄₈H₃₈N₂O₇
• 分子量: 754.839
• InChiKey: QCJRFMOWFQWLPO-DZRFKLJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  57.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  112.01
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-5-[4-(9-anthracenyl)buta-1,3-diynyl]-2'-deoxyuridine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到5'-O-(4,4'-dimethoxytrityl)-5-[4-(9-anthracenyl)buta-1,3-diynyl]-2'-deoxyuridine-3'-O-(2-cyanoethyl-N,N-diisopropyl) phosphoramidite
  参考文献：
  名称：

  Naphthalenyl- and anthracenyl-ethynyl dT analogues as base discriminating fluorescent nucleosides and intramolecular energy transfer donors in oligonucleotide probes

  摘要：

  Fluorescent thymidine analogues functionalised in the 5-position with the moieties naphthalenylethynyl (NeT), anthracenylethynyl (AeT) and anthracenylbuta-1,3-diynyl (AeeT) have been incorporated into oligonucleotides. The modified oligonucleotides undergo significant emission enhancement when hybridised to fully complementary strands and a decrease in fluorescence emission when the modified thymine is paired with guanine. Thus these analogues are potentially useful as base discriminating fluorescent nucleosides (BDFs). When a fluorescein dT monomer is incorporated into the same oligonucleotide strand as the modified base, energy transfer enhances the fluorescein emission, particularly upon duplex formation. These dual-labelled probes may be useful for genetic analysis to detect point mutations and SNPs and could provide multiplexing capability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.090
• 作为产物：
  描述：

  9-溴蒽 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 氢氧化钾 、 copper(l) iodide 、 四丁基氟化铵 、 正丁胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.42h， 生成 5'-O-(4,4'-dimethoxytrityl)-5-[4-(9-anthracenyl)buta-1,3-diynyl]-2'-deoxyuridine
  参考文献：
  名称：

  Naphthalenyl- and anthracenyl-ethynyl dT analogues as base discriminating fluorescent nucleosides and intramolecular energy transfer donors in oligonucleotide probes

  摘要：

  Fluorescent thymidine analogues functionalised in the 5-position with the moieties naphthalenylethynyl (NeT), anthracenylethynyl (AeT) and anthracenylbuta-1,3-diynyl (AeeT) have been incorporated into oligonucleotides. The modified oligonucleotides undergo significant emission enhancement when hybridised to fully complementary strands and a decrease in fluorescence emission when the modified thymine is paired with guanine. Thus these analogues are potentially useful as base discriminating fluorescent nucleosides (BDFs). When a fluorescein dT monomer is incorporated into the same oligonucleotide strand as the modified base, energy transfer enhances the fluorescein emission, particularly upon duplex formation. These dual-labelled probes may be useful for genetic analysis to detect point mutations and SNPs and could provide multiplexing capability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.090