2-(1H-benzo[d]imidazol-1-yl)-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)acetamide | 1083091-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(1H-benzo[d]imidazol-1-yl)-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)acetamide
• CAS: 1083091-32-0
• 化学式: C₂₃H₁₅N₃O₃
• 分子量: 381.39
• InChiKey: ZDTDAYIBMJPORY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  81.06
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苯并咪唑 、 2-氯-N-(9,10-二氧代-9,10-二氢-2-蒽基)乙酰胺 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到2-(1H-benzo[d]imidazol-1-yl)-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)acetamide
  参考文献：
  名称：

  Synthesis, optical and electrochemical properties of new receptors and sensors containing anthraquinone and benzimidazole units

  摘要：

  Novel anion receptors and sensors, HBIMANQ and BIMANQ fabricated from the imidazolole unit and anthraquinone moieties were synthesized. H-1 NMR spectroscopy and UV-vis titrations in DMSO-d(6) and DMSO, respectively, showed that both receptors underwent deprotonation at the NH- moiety of the amide-anthraquinone unit in the presence of basic anions such as F- and AcO-. These phenomena gave a dramatic color change due to charge transfer transition corresponding to the shift of lambda(max) from 371 nm to 489 nm. Redox chemistry of HBIMANQ and BIMANQ in the presence of anions (F-, Cl-, AcO-, BzO(-), and H2PO4-) using cyclic voltammetry showed the different CV responses upon addition of various anions. In the case of HBIMANQ with various anions, the CV changes are dependent on the basic strength of anions in order of F-> AcO-, BzO(-)> H2PO4-> Cl-, Br-. Interestingly, the CV responses of BIMANQ with H2PO4- exhibited the most significant changes. BIMANQ, thus, has an excellent electrochemical selectivity toward H2PO4-. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.073