pyrido[2,1-c][1,2,4]benzotriazin-11-ium perchlorate | 1018945-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: pyrido[2,1-c][1,2,4]benzotriazin-11-ium perchlorate
• 英文别名: 9,10-diaza-4a-azonia-phenanthrene perchlorate
• CAS: 1018945-57-7
• 化学式: C₁₁H₈N₃*ClO₄
• 分子量: 281.655
• InChiKey: RWHOEYXZLBRQEB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.39
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122.12
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  pyrido[2,1-c][1,2,4]benzotriazin-11-ium perchlorate 、 乙烷,三氯氟- 以 乙腈 为溶剂， 反应 1.0h， 以35%的产率得到6-p-tolylamino-9,10-diaza-4a-azonia-phenanthrene perchlorate
  参考文献：
  名称：

  Sinan, Mominul; Ghosh, Pradip; Goswami, Sreebrata, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2011, vol. 50, # 9-10, p. 1273 - 1280

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氟-2-亚硝基苯 在 sodium perchlorate 、 sodium hydroxide 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 0.42h， 生成 pyrido[2,1-c][1,2,4]benzotriazin-11-ium perchlorate
  参考文献：
  名称：

  Synthesis and structural, spectroscopic, and electrochemical characterization of benzo[c]quinolizinium and its 5-aza-, 6-aza, and 5,6-diaza analogues

  摘要：

  Four heterocyclic salts 1a-d were prepared by Ca2+-assisted cyclization of fluoro derivatives 3, and investigated by spectroscopic (NMR and UV), electrochemical, and computational (DFT and MP2) methods. The mechanism for the formation of the cations was investigated at the DFT level of theory. 2-D NMR spectroscopy for 1[ClO4] in DMSO-d(6) aided with DFT results permitted the assignment of H-1 and C-13 NMR signals in cations 1. The molecular and crystal structures for 1a[ClO4] [C13H10ClNO4 triclinic, P-1, a=9.6517(12) angstrom, 6=11.0470(13) angstrom, c=12.2373(15) angstrom, alpha=67.615(1)degrees, beta=78.845(2)degrees, gamma=87.559(2)degrees; V=1183.0(2) angstrom(3). Z=4] and 1d[ClO4] [C12H9ClN2O4 triclinic, P-1, alpha=5.9525(6) angstrom, b=8.3141(9) angstrom, c=12.2591 (13) angstrom, alpha=73.487(1)degrees, beta=83.814(1)degrees, gamma=83.456(1)degrees; V=576.07(10) angstrom(3), Z=2] were determined by X-ray crystallography and compared with results of DFT and MP2 calculations. Electrochemical analysis gave the reduction potential order (1b>1c similar to 1d>1a), which is consistent with computational results. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.023

文献信息

• Mild Synthesis of a Family of Planar Triazinium Cations via Proton-Assisted Cyclization of Pyridyl Containing Azo Compounds and Studies on DNA Intercalation
  作者：M. Sinan、M. Panda、A. Ghosh、K. Dhara、P. E. Fanwick、D. J. Chattopadhyay、S. Goswami

  DOI：10.1021/ja710211u

  日期：2008.4.1

  An efficient synthesis of a family of heteroaromatic triazinium compounds, [2a]X-[2g]X (X= Cl, ClO4, NO3, and HSO4), from 2-(arylazo)pyridines via proton-catalyzed heterocyclization is described. Characterization of the compounds is made by different spectroscopic, electrochemical techniques, as well as single-crystal structure determination of the triflate salt of a representative compound, [2a]CF3SO3. The bond parameters indicate that the tricyclo compound, 2a(+), is planar and aromatic with a N-N bond length of 1.275(6) angstrom. These exhibited fluorescence with an emission maximum in the range of 540-535 nm with moderate quantum yields. The triazinium salts can be reduced in two successive one-electron steps as probed by cyclic voltammetry and coulometry. The paramagnetic radical intermediate 2a(center dot) is distinguished by a sharp and intense EPR spectrum. Fluorescence spectroscopy, circular dichroism, cyclic voltammetry, viscosity measurements, together with DNA melting studies have been used to characterize the binding of 2a+ with calf thymus DNA. The emission quenching of the compound by [Fe(CN)(6)](4-) decreased when bound to DNA. As determined by a MTT assay, 2a+ exhibited significant cytotoxicity at a higher concentration range of 1 mg/mL to 1 mu g/mL; however, the % survival ratio increased with dilution. Cellular uptake studies of the referenced compound were followed by FACS analysis.