6-ethynyl-2-acetonaphthone | 1429057-57-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-ethynyl-2-acetonaphthone
• 英文别名: 1-(6-Ethynylnaphthalen-2-yl)ethanone
• CAS: 1429057-57-7
• 化学式: C₁₄H₁₀O
• 分子量: 194.233
• InChiKey: KCFPVJZZHCKYPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-ethynyl-2-acetonaphthone 、 5-碘-2'-脱氧结核菌素 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以89%的产率得到
  参考文献：
  名称：

  Synthesis of solvatofluorochromic 7-arylethynylated 7-deaza-2′-deoxyadenosine derivatives: application to the design of environmentally sensitive fluorescent probes forming stable DNA duplexes

  摘要：

  We synthesized environmentally sensitive fluorescent (ESF) 7-deaza-2'-deoxyadenosine derivatives including ethynylanthracene substituted (atz)A (1) and ethynylnaphthalene substituted (nz)A (2a), (cnz)A (2b), (anz)A (2c), and (dnz)A (2d), and investigated their photophysical properties. Among them, only push-pull type cyano- and acetyl-substituted naphthylethynylated 7-deaza-2'-deoxyadenosine, (cnz)A (2b) and (anz)A (2c), exhibited remarkable solvatofluorochromic properties (Delta lambda = 71 and 63 nm, respectively). We incorporated non-solvatofluorochromic (atz)A (1) and solvatofluorochromic (cnz)A (2b) into oligodeoxynucleotides and found that (cnz)A (2b) forms a stable base pair with both thymine and cytosine, being accompanied by a change of fluorescence intensity. Such ESF nucleosides can be used for studying structures and functions of nucleic acids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.063

文献信息

• 2-Ethynylnaphthalene-modified 8-aza-3,7-dideaza-2′-deoxyadenosine derivative discriminates thymine in target DNA via changes in the fluorescence wavelength
  作者：Shoutoku Koboku、Masaki Yanagi、Ayaka Funato、Azusa Suzuki、Yoshio Saito

  DOI：10.1016/j.tetlet.2020.151841

  日期：2020.5

  2a37zA (1c), switched emission modes between the ICT and the locally excited states by changing their molecular geometry. With their electron-withdrawing substituents, 2c37zA (1b) and 2a37zA (1c) had a wide range of fluorescence wavelength that was due to the combination of these two emission modes (Δλ = 142 and 96 nm, respectively). In the ODN duplexes, 2c37zA (1b) formed a stable base pair with thymine

  开发了新型的环境敏感型荧光嘌呤核苷2n37z A（1a），2c37z A（1b）和2a37z A（1c）。其中，与先前报道的1n37z A（2）（约50-120 nm）相比，含有吸电子取代基的2c37z A（1b）和2a37z A（1c）表现出高度的溶剂化性，并发出更长的波长。 。新开发的2-乙炔基萘衍生物2n37z A（1a），2c37z A（1b）和2a37z A（1c）通过改变它们的分子几何结构在ICT和局部激发态之间切换发射模式。有了它们的吸电子取代基，2c37z A（1b）和2a37z A（1c）具有很宽的荧光波长范围，这是由于这两种发射模式的组合（分别为Δλ= 142和96 nm）。在ODN双工中，2c37z A（1b）与胸腺嘧啶形成稳定的碱基对，并能够通过各自的荧光波长偏移来区分。因此，2c37z A（1b）可用于检测靶核酸序列中的单碱基改变。