3-aminobenzanthrone | 13456-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-aminobenzanthrone
• 英文别名: 3-ABA；3-amino-7H-benzo[d,e]anthracen-7-one；3-amino-benz[de]anthracen-7-one；3-Amino-7-oxo-7H-benz[de]anthracen；3-Amino-benz[de]anthracen-7-on；Amino-peribenzanthron；3-aminobenzo[b]phenalen-7-one
• CAS: 13456-80-9
• 化学式: C₁₇H₁₁NO
• 分子量: 245.28
• InChiKey: ZXPXRBDYCANCCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-aminobenzanthrone 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-acetoxy-N-acetyl-3-aminobenzanthrone
  参考文献：
  名称：

  An Unusual DNA Adduct Derived from the Powerfully Mutagenic Environmental Contaminant 3-Nitrobenzanthrone

  摘要：

  The covalent binding of an N-hydroxy metabolite of the powerfully mutagenic 3-nitrobenzanthrone (NBA) to 2'-deoxyguanosine (dG) and calf thymus DNA has been investigated in vitro. The major adduct obtained from the reaction of the N-acetoxy-N-acetyl derivative (N-Aco-N-Ac-ABA) of 3-aminobenzanthrone (ABA) and dG was identified as N-acetyl-3-amino-2-2'-deoxyguanosin-8-yl) benzanthrone (dG-N-Ac-ABA) by H-1 NMR and mass spectroscopies as well as by the reaction of N-Aco-N-Ac-ABA with the double-stranded calf thymus DNA. The coupling with the dG moiety occurred exclusively at C-2 of benzanthrone (BA), suggesting a significant contribution of a resonance-stabilized arenium ion intermediate derived from BA to the production of this new type of adduct. The preferred conformation of the adduct has been shown to be syn by H-1 and C-13 NMR.

  DOI：

  10.1021/tx980104b
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 、 乙醇 作用下， 生成 3-aminobenzanthrone
  参考文献：
  名称：

  DE592202

  摘要：

  公开号：

文献信息

• Fluorescent substituted amidines of benzanthrone: Synthesis, spectroscopy and quantum chemical calculations
  作者：Svetlana Gonta、Maris Utinans、Georgii Kirilov、Sergey Belyakov、Irena Ivanova、Mendel Fleisher、Valerij Savenkov、Elena Kirilova

  DOI：10.1016/j.saa.2012.09.104

  日期：2013.1

  reaction from 3-aminobenzo[de]anthracen-7-one and appropriate aromatic and aliphatic amides. The obtained derivatives have a bright yellow or orange fluorescence in organic solvents and in solid state. The novel benzanthrone derivatives were characterized by TLC analysis, (1)H NMR, IR, MS, UV/vis, and fluorescence spectroscopy. The solvent effect on photophysical behaviors of these dyes was investigated

  通过3-氨基苯并[蒽] -7-one与适当的芳族和脂族酰胺的缩合反应合成了几种新的苯并蒽酮取代的AM衍生物。所获得的衍生物在有机溶剂中和处于固态时具有亮黄色或橙色荧光。通过TLC分析，（1）1 H NMR，IR，MS，UV / vis和荧光光谱表征了新的苯并蒽酮衍生物。研究了溶剂对这些染料光物理行为的影响，结果表明斯托克位移增加，而量子产率随着溶剂极性的增加而降低。通过X射线单晶结构分析确认了某些染料的结构。使用高斯软件对AM1，ZINDO / S和从头算进行了计算，以估计结构的电子系统。计算显示这些化合物的芳族核的平面构型和AM基取代基的两个可能的方向。计算结果与化合物的红移吸收光谱和发射光谱密切相关。
• Experimental and theoretical study on structure and spectroscopic properties of 2‐bromo‐3‐N‐(N′,N′‐dimethylformamidino) benzanthrone
  作者：Elena Kirilova、Artur Yanichev、Aleksandrs Puckins、Mendel Fleisher、Sergey Belyakov

  DOI：10.1002/bio.3538

  日期：2018.11

  The goal of present research is a theoretical and experimental investigation of geometrical structure, electronic properties, absorption and fluorescence spectra prediction for 2-bromo-3-N-(N',N'-dimethylformamidino)benzanthrone. As a result of conformational analysis, two rotamers have been found with a rotational barrier of 5.45 kcal/mol. Absorption and fluorescence spectra maxima in the solvent

  本研究的目的是对2-溴-3-N-（N'，N'-二甲基甲酰胺基）苯并蒽醌的几何结构，电子性质，吸收和荧光光谱预测进行理论和实验研究。构象分析的结果是，发现了两个旋转势垒为5.45 kcal / MOl的旋转异构体。已使用Jablonsky图的概念计算了溶剂（乙醇）中的吸收光谱和荧光光谱最大值。所获得的吸收最大值和荧光最大值（分别为437和679 nm）对应于实验值（447和659 nm）。异常大的斯托克斯位移与电子密度的重新分布以及激发态下分子结构的平坦化有关。根据额叶分子轨道分析数据，吸收光谱的长波部分中的峰是由从最高占据分子轨道（HOMO）到最低占据分子轨道（LUMO）（π→π*）的电子跃迁产生的）。替代基团不参与吸收光谱和荧光光谱的形成。
• Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy
  作者：Natalja Orlova、Irena Nikolajeva、Aleksandrs Pučkins、Sergey Belyakov、Elena Kirilova

  DOI：10.3390/molecules26092570

  日期：——

  azomethines of benzanthrone with heterocyclic substituents were synthesized by condensation reaction of 3-aminobenzo[de]anthracen-7-one with appropriate aromatic aldehydes. The resulting imines were reduced with sodium borohydride to the corresponding amines, the luminescence of which is more pronounced in comparison with the initial azomethines. The novel benzanthrone derivatives were characterized by

  通过3-氨基苯并[蒽]蒽-7-一与适当的芳族醛的缩合反应，合成了具有杂环取代基的苯并蒽酮新的取代的甲亚胺。用硼氢化钠将所得的亚胺还原成相应的胺，与最初的偶氮甲胺相比，其发光更为明显。通过NMR，IR，MS，UV / Vis和荧光光谱对新型苯并蒽醌衍生物进行了表征。通过X射线单晶结构分析研究了三种染料的结构。研究了溶剂对合成的亚胺和胺的光物理行为的影响。获得的化合物在420-525 nm处吸收，斯托克斯位移相对较大（在乙醇中可达150 nm），并在500-660 nm处发射。结果证明，所研究化合物的发射对溶剂极性敏感，对于合成的偶氮甲胺表现出负氟溶剂变色性，对于所获得的胺表现出正氟溶剂变色性。所得结果表明，合成的化合物有望用作发光染料。
• Functional properties of azomethine substituted benzanthrone dyes for use in nematic liquid crystals
  作者：I.K. Grabtchev、V.B. Bojinov、I.T. Moneva

  DOI：10.1016/s0022-2860(98)00400-1

  日期：1998.11

  Abstract The spectral properties in organic solvents, solid polymer film and nematic liquid crystal (LC) of new benzanthrone dyes substituted with azomethine derivative groups at position 3 and their utility for liquid crystal displays of the guest-host type are reported. In particular, the effect of substitutes upon the phase transition and orientational order of LC in surface stabilized display cells

  摘要 报道了在 3 位被偶氮甲碱衍生物基团取代的新型苯并蒽酮染料在有机溶剂、固体聚合物膜和向列液晶 (LC) 中的光谱特性及其在客-主型液晶显示器中的应用。特别讨论了替代物对表面稳定显示单元中 LC 的相变和取向顺序的影响。
• The synthesis of novel heterocyclic 3-acetamide derivatives of benzanthrone
  作者：Elena M. Kirilova、Irena D. Nikolaeva、Evita Romanovska、Aleksandrs I. Pučkins、Sergey V. Belyakov

  DOI：10.1007/s10593-020-02644-1

  日期：2020.2

  Novel luminescent derivatives of benzanthrone were obtained in nucleophilic substitution reactions of 3-(2-chloroacetamido)-benzanthrone with a number of heterocyclic amines. The structures of the obtained compounds were confirmed by spectral data. Target products, due to pronounced luminescent properties, can be used to visualize biological objects.

  在3-（2-氯乙酰胺基）-苯并蒽酮与许多杂环胺的亲核取代反应中获得了苯并蒽酮的新型发光衍生物。所得化合物的结构通过光谱数据确认。由于具有显着的发光特性，目标产品可用于可视化生物对象。