(S)-4-(pyren-1-yloxy)butane-1,2-diol | 1241385-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (S)-4-(pyren-1-yloxy)butane-1,2-diol
• 英文别名: (2S)-4-pyren-1-yloxybutane-1,2-diol
• CAS: 1241385-35-2
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: NBKKADLSYYIAGN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(pyren-1-yloxy)butane-1,2-diol 在 N,N'-diisopropylammonium tetrazolide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-1-(bis(4-methoxyphenyl)phenylmethoxy-4-(pyren-1-yloxy))butan-2-yl 2-cyanoethyl diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis of a new intercalating nucleic acid analogue with pyrenol insertions and the thermal stability of the resulting oligonucleotides towards DNA over RNA

  摘要：

  A new intercalating nucleic acid monomer Y was obtained via alkylation of pyren-1-ol with (S)-(+)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol under Mitsunobu conditions followed by hydrolysis with 80% aqueous acetic acid to give a diol which was tritylated with 4,4'-dimethoxytrityl chloride followed by treatment with 2-cyanoethyltetraisopropylphosphordiamidite in the presence of N,N'-diisopropylammonium tetrazolide. In this way the monomer Y was obtained as its dimethoxytrityl-protected phosphoramidite building block for standard DNA synthesis. The corresponding oligonucleotides from Y have nearly identical hybridization properties with those of intercalating nucleic acid (INA) where neighboring oxygen and carbon atoms are interchanged in the linker. The synthesis of monomer Y avoids the use of allergic intermediates which are a problem in the synthesis of INA.

  DOI：

  10.1007/s00706-010-0320-6
• 作为产物：
  描述：

  1-羟基芘 在 水 、 溶剂黄146 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.42h， 生成 (S)-4-(pyren-1-yloxy)butane-1,2-diol
  参考文献：
  名称：

  Synthesis of a new intercalating nucleic acid analogue with pyrenol insertions and the thermal stability of the resulting oligonucleotides towards DNA over RNA

  摘要：

  A new intercalating nucleic acid monomer Y was obtained via alkylation of pyren-1-ol with (S)-(+)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol under Mitsunobu conditions followed by hydrolysis with 80% aqueous acetic acid to give a diol which was tritylated with 4,4'-dimethoxytrityl chloride followed by treatment with 2-cyanoethyltetraisopropylphosphordiamidite in the presence of N,N'-diisopropylammonium tetrazolide. In this way the monomer Y was obtained as its dimethoxytrityl-protected phosphoramidite building block for standard DNA synthesis. The corresponding oligonucleotides from Y have nearly identical hybridization properties with those of intercalating nucleic acid (INA) where neighboring oxygen and carbon atoms are interchanged in the linker. The synthesis of monomer Y avoids the use of allergic intermediates which are a problem in the synthesis of INA.

  DOI：

  10.1007/s00706-010-0320-6