5-ethynylbenzo[c][1,2,5]oxadiazole | 1246965-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5-ethynylbenzo[c][1,2,5]oxadiazole
• 英文别名: 5-Ethynyl-2,1,3-benzoxadiazole；5-ethynyl-2,1,3-benzoxadiazole
• CAS: 1246965-55-8
• 化学式: C₈H₄N₂O
• 分子量: 144.133
• InChiKey: DWLBSYNZTUNOLI-UHFFFAOYSA-N

物化性质

• 熔点：
  66.0-66.5 °C
• 沸点：
  240.2±32.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethynylbenzo[c][1,2,5]oxadiazole 、 5-碘-2'-脱氧胞苷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  苯并呋喃烷作为DNA电化学检测的新氧化还原标记：迈向DNA碱基的多电位氧化还原编码。

  摘要：

  苯并呋喃烷已直接或通过乙炔连接子连接到核苷和dNTPs上，作为一种新的氧化还原标记，可用于核苷酸序列的电化学分析。已经开发了通过聚合酶将苯并呋喃烷修饰的dNTP进行引物延伸掺入的方法，用于构建标记的寡核苷酸探针。结合硝基苯基和氨基苯基标记，我们已经成功开发了DNA碱基的三电位编码，并探索了相关的电化学电位。苯并呋喃烷和硝基苯基可还原标记的组合已被证明对核苷酸序列的比例分析是极好的，并且适用于生物分析应用。

  DOI：

  10.1002/chem.201301868
• 作为产物：
  描述：

  5-((trimethylsilyl)ethynyl)benzo[c][1,2,5]oxadiazole 在 四丁基氟化铵 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以72%的产率得到5-ethynylbenzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  Identification of fluorogenic and quenched benzoxadiazole reactive chromophores

  摘要：

  The Sharpless-Meldal reaction was employed to generate triazole-substituted, alkynyl, azido and tri-azolyl-benzoxadiazole as well as nitro-benzoxadiazole fluorophores Linkage of the triazole to the benzoxadiazole ring at C4 gave chromophores which were fluorogenic, while attachment through NI resulted in quenching The 4-azalo-7-nitrobenzoxadiazole underwent a 470-fold decrease in quantum yield upon conversion to the triazole While, 5-ethynyl-benzoxadiazole exhibited a 48-fold enhancement of quantum yield upon formation of tnazole The modulating effects of solvent polarity, conjugation, and attachment point of the fluorochrome to the tnazole were examined (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.05.007

文献信息

• Benzofurazane as a New Redox Label for Electrochemical Detection of DNA: Towards Multipotential Redox Coding of DNA Bases
  作者：Jana Balintová、Medard Plucnara、Pavlína Vidláková、Radek Pohl、Luděk Havran、Miroslav Fojta、Michal Hocek

  DOI：10.1002/chem.201301868

  日期：2013.9.16

  Benzofurazane has been attached to nucleosides and dNTPs, either directly or through an acetylene linker, as a new redox label for electrochemical analysis of nucleotide sequences. Primer extension incorporation of the benzofurazane‐modified dNTPs by polymerases has been developed for the construction of labeled oligonucleotide probes. In combination with nitrophenyl and aminophenyl labels, we have

  苯并呋喃烷已直接或通过乙炔连接子连接到核苷和dNTPs上，作为一种新的氧化还原标记，可用于核苷酸序列的电化学分析。已经开发了通过聚合酶将苯并呋喃烷修饰的dNTP进行引物延伸掺入的方法，用于构建标记的寡核苷酸探针。结合硝基苯基和氨基苯基标记，我们已经成功开发了DNA碱基的三电位编码，并探索了相关的电化学电位。苯并呋喃烷和硝基苯基可还原标记的组合已被证明对核苷酸序列的比例分析是极好的，并且适用于生物分析应用。
• Identification of fluorogenic and quenched benzoxadiazole reactive chromophores
  作者：Jessie A. Key、Christopher W. Cairo

  DOI：10.1016/j.dyepig.2010.05.007

  日期：2011.1

  The Sharpless-Meldal reaction was employed to generate triazole-substituted, alkynyl, azido and tri-azolyl-benzoxadiazole as well as nitro-benzoxadiazole fluorophores Linkage of the triazole to the benzoxadiazole ring at C4 gave chromophores which were fluorogenic, while attachment through NI resulted in quenching The 4-azalo-7-nitrobenzoxadiazole underwent a 470-fold decrease in quantum yield upon conversion to the triazole While, 5-ethynyl-benzoxadiazole exhibited a 48-fold enhancement of quantum yield upon formation of tnazole The modulating effects of solvent polarity, conjugation, and attachment point of the fluorochrome to the tnazole were examined (C) 2010 Elsevier Ltd. All rights reserved.