N,N'-[Bis(3-hydroxypropyl)]-2,6-naphthalenedicarboxamide | 225663-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-[Bis(3-hydroxypropyl)]-2,6-naphthalenedicarboxamide
• 英文别名: 2-N,6-N-bis(3-hydroxypropyl)naphthalene-2,6-dicarboxamide
• CAS: 225663-91-2
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: RLQUZWGUQVSPQY-UHFFFAOYSA-N

物化性质

• 沸点：
  737.0±50.0 °C(predicted)
• 密度：
  1.245±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-[Bis(3-hydroxypropyl)]-2,6-naphthalenedicarboxamide 在 吡啶 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 N-[3-[O-(2-Cyanoethyl-N,N-diisopropylamino)phosphoramidite]propyl]-N'-[3-O-(dimethoxytrityl)propyl]-2,6-naphthalenedicarboxamide
  参考文献：
  名称：

  Naphthalenedicarboxamides as Fluorescent Probes of Inter- and Intramolecular Electron Transfer in Single Strand, Hairpin, and Duplex DNA

  摘要：

  The 2,6-naphthalenedicarboxamide chromophore has been investigated as a fluorescent probe for DNA hairpin and duplex formation and DNA electron transfer. The high fluorescence quantum yield and long singlet lifetime of this chromophore make it an attractive candidate for these studies. The kinetics of intermolecular quenching of a naphthalenedicarboxamide by nucleosides is dependent upon the nucleoside oxidation potential and solvent. Bis(oligonucleotide) conjugates containing naphthalene linkers have been prepared by means of conventional phosphoramidite chemistry. The base-sequence dependence of the naphthalene fluorescence intensity and decay times in both single-strand and hairpin conjugates indicates that singlet naphthalene is quenched by neighboring dA more efficiently than by dT, in accord with an electron-transfer quenching mechanism. These data are analyzed by means of a three-state model which includes a nonemissive "dark" state. Duplexes formed between complementary naphthalene-linked oligonucleotides display naphthalene excimer emission. The base-sequence dependence of the excimer emission quantum yields indicates that the excimer is not quenched by neighboring dA but that distance-dependent electron-transfer quenching by dG may occur. Quenching serves to protect the naphthalene chromophore from photobleaching in both single strand and duplex structures.

  DOI：

  10.1021/jp9845423
• 作为产物：
  描述：

  2,6-萘二甲酰二氯 、 3-氨基-1-丙醇 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以88%的产率得到N,N'-[Bis(3-hydroxypropyl)]-2,6-naphthalenedicarboxamide
  参考文献：
  名称：

  Naphthalenedicarboxamides as Fluorescent Probes of Inter- and Intramolecular Electron Transfer in Single Strand, Hairpin, and Duplex DNA

  摘要：

  The 2,6-naphthalenedicarboxamide chromophore has been investigated as a fluorescent probe for DNA hairpin and duplex formation and DNA electron transfer. The high fluorescence quantum yield and long singlet lifetime of this chromophore make it an attractive candidate for these studies. The kinetics of intermolecular quenching of a naphthalenedicarboxamide by nucleosides is dependent upon the nucleoside oxidation potential and solvent. Bis(oligonucleotide) conjugates containing naphthalene linkers have been prepared by means of conventional phosphoramidite chemistry. The base-sequence dependence of the naphthalene fluorescence intensity and decay times in both single-strand and hairpin conjugates indicates that singlet naphthalene is quenched by neighboring dA more efficiently than by dT, in accord with an electron-transfer quenching mechanism. These data are analyzed by means of a three-state model which includes a nonemissive "dark" state. Duplexes formed between complementary naphthalene-linked oligonucleotides display naphthalene excimer emission. The base-sequence dependence of the excimer emission quantum yields indicates that the excimer is not quenched by neighboring dA but that distance-dependent electron-transfer quenching by dG may occur. Quenching serves to protect the naphthalene chromophore from photobleaching in both single strand and duplex structures.

  DOI：

  10.1021/jp9845423