2,1,3-Benzoselenadiazol-5-carbaldehyd | 112608-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,1,3-Benzoselenadiazol-5-carbaldehyd
• 英文别名: 2,1,3-benzoselenadiazole-5-carbaldehyde
• CAS: 112608-12-5
• 化学式: C₇H₄N₂OSe
• 分子量: 211.082
• InChiKey: PPVGIZQKXPFHEU-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  333.5±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,1,3-Benzoselenadiazol-5-carbaldehyd 在 氢氧化钾 、 硫酸肼 作用下， 以 水 为溶剂， 反应 0.5h， 以88%的产率得到2,1,3-benzoselenadiazole-5-carbaldazine
  参考文献：
  名称：

  Morkved, Eva H.; Bjorlo, Olav; Schilf, Wojciech, Bulletin of the Polish Academy of Sciences: Chemistry, 2000, vol. 48, # 1, p. 47 - 56

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Methyl-benzo[1,2,5]selenadiazole 在 selenium(IV) oxide 作用下， 以 xylene 为溶剂， 反应 2.5h， 以36%的产率得到2,1,3-Benzoselenadiazol-5-carbaldehyd
  参考文献：
  名称：

  甲基取代2,1,3-苯并噻二唑和2,1,3-苯并硒二唑的氧化还原反应

  摘要：

  甲基取代的2,1,3-苯并噻二唑和2,1,3-苯并硒二唑与二氧化硒的氧化反应

  DOI：

  10.1002/hlca.19870700411

文献信息

• The determination of thiols based using a probe that utilizes both an absorption red-shift and fluorescence enhancement
  作者：Baocun Zhu、Xiaoling Zhang、Hongying Jia、Yamin Li、Shutang Chen、Sichun Zhang

  DOI：10.1016/j.dyepig.2009.11.011

  日期：2010.6

  A pyridylvinylene derivative containing piazselenole displayed high selectivity toward glutathione in the presence of other biorelevant analytes. The compound exhibited a 19 run red-shift in absorption spectra and similar to 3-fold fluorescence intensity enhancement: in addition, it was possible to detect micromolar amounts of glutathione quantitatively using both red-shift absorbance and enhanced fluorescence. The mechanism of the reaction between the modified pyridylvinylene derivative and glutathione was confirmed using ESI-MS and absorption/fluorescence spectra. (C) 2009 Elsevier Ltd. All rights reserved.
• NEIDLEIN, R.;KNECHT, D., HELV.-CHIM. ACTA, 70,(1987) N 4, 997-1000
  作者：NEIDLEIN, R.、KNECHT, D.

  DOI：——

  日期：——
• Dynamic Chalcogen Squares for Material and Topological Control over Macromolecules
  作者：Aaron H. Bui、Anne D. Fernando Pulle、Aaron S. Micallef、Jacob J. Lessard、Bryan T. Tuten

  DOI：10.1002/anie.202404474

  日期：2024.5.27

  Herein we introduce chalcogen squares via selenadiazole motifs as a new class of dynamic supramolecular bonding interactions for the modification and control of soft matter materials. We showcase selenadiazole motifs in supramolecular networks of varying primary chain length prepared through polymerization using tandem step‐growth/Passerini multicomponent reactions (MCRs). Compared to controls lacking the selenadiazole motif, these networks display increased glass transition temperatures and moduli due to the chalcogen bonding linkages formed between chains. These elastomeric networks were shown to autonomously heal at room temperature, retaining up to 83 % of the ultimate tensile strength. Lastly, we use post‐polymerization modification via the Biginelli MCR to add selenadiazole motifs to narrowly dispersed polymers for controlled topology in solution. Chalcogen squares via selenadiazoles introduce an exciting exchange mechanism to the realm of dynamic materials.