1-[dimethyl(2-hydroxylethyl)silyl]pyrene | 1146028-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-[dimethyl(2-hydroxylethyl)silyl]pyrene
• 英文别名: 1-[(2-hydroxyethyl)dimethylsilyl]pyrene；2-[Dimethyl(pyren-1-yl)silyl]ethanol；2-[dimethyl(pyren-1-yl)silyl]ethanol
• CAS: 1146028-91-2
• 化学式: C₂₀H₂₀OSi
• 分子量: 304.464
• InChiKey: JZRCXNHHBOVNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[dimethyl(2-hydroxylethyl)silyl]pyrene 在 hydrazine monohydrate 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  在小凹槽中具有两个连续甲硅烷基化芘部分的修饰寡 DNA 在与完全互补的 DNA 链结合时显示出准分子荧光信号

  摘要：

  合成了在 C-2' 位置具有带有甲硅烷基化芘的连续修饰核苷酸残基的寡聚 DNA。荧光 oligoDNA 显示出显着的准分子荧光信号。

  DOI：

  10.1246/cl.2010.1254
• 作为产物：
  描述：

  1-溴芘 在 正丁基锂 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 为溶剂， 生成 1-[dimethyl(2-hydroxylethyl)silyl]pyrene
  参考文献：
  名称：

  在小凹槽中具有两个连续甲硅烷基化芘部分的修饰寡 DNA 在与完全互补的 DNA 链结合时显示出准分子荧光信号

  摘要：

  合成了在 C-2' 位置具有带有甲硅烷基化芘的连续修饰核苷酸残基的寡聚 DNA。荧光 oligoDNA 显示出显着的准分子荧光信号。

  DOI：

  10.1246/cl.2010.1254

文献信息

• Synthesis and Properties of Novel Fluorescently Labeled Oligonucleotides Possessing Silylated Pyrene at the 5′-Terminus
  作者：Tomohisa Moriguchi、Daisuke Moki、Tohru Sekiguchi、Takahiko Kato、Kazuo Shinozuka

  DOI：10.1246/cl.140800

  日期：2015.1.5

  Previously, we reported a novel fluorescence dye, a silylated pyrene derivative, as a DNA labeling agent. In this study, new silylated pyrene derivatives with different linker lengths and different substituents on the silicon atom have been prepared and introduced into oligonucleotides. In particular, when the diphenylsilylpyrene derivative was introduced as a fluorescence dye, the fluorescence intensity of the duplex was enhanced about 20 times compared to the signal in the absence of the target DNA.

  之前，我们报道了一种新型荧光染料，硅化芘衍生物，作为DNA标记剂。在本研究中，我们合成了不同链长和不同硅原子取代基的新硅化芘衍生物，并将其引入到寡核苷酸中。特别是，当将二苯硅基芘衍生物作为荧光染料引入时，双链的荧光强度与缺乏靶DNA时的信号相比增强了约20倍。
• Development of the excimer probe responsible for DNA target bearing the silylated pyrenes at base moiety
  作者：Tomohisa Moriguchi、Mayumi Ichimura、Mitsuhisa Kato、Kenya Suzuki、Yuki Takahashi、Kazuo Shinozuka

  DOI：10.1016/j.bmcl.2014.08.018

  日期：2014.9

  For the development of the excimer probe responsible for DNA target, the deoxyuridine phosphoramidite derivative bearing the silylated pyrene attached at the C-5 position was prepared and incorporated into oligonucleotides. The modified oligonucleotides showed the excimer emission in the absence of the target DNA, on the other hands, the excimer emission was quenched in the presence of the target DNA. For the utilization of the fluorescence behavior, the novel molecular beacon probe containing the silylated pyrene-modified nucleoside at the stem region was designed and the fluorescence property of the probe found to show the responsibility for DNA target. (C) 2014 Elsevier Ltd. All rights reserved.
• Modified OligoDNA Having Two Consecutive Silylated-pyrene Moieties in Minor Groove Exhibiting an Excimer Fluorescent Signal upon Binding to Fully Complementary DNA Strand
  作者：Mika Mogi、Md. Gias Uddin、Mayumi Ichimura、Tomohisa Moriguchi、Kazuo Shinozuka

  DOI：10.1246/cl.2010.1254

  日期：2010.12.5

  OligoDNA possessing consecutive modified nucleotide residues bearing silylated pyrene at C-2′ position was synthesized. The fluorescent oligoDNA exhibited marked excimer fluorescent signal upon bin...

  合成了在 C-2' 位置具有带有甲硅烷基化芘的连续修饰核苷酸残基的寡聚 DNA。荧光 oligoDNA 显示出显着的准分子荧光信号。