班德罗夫斯基碱 | 20048-27-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 班德罗夫斯基碱
• 中文别名: 班德罗斯基碱
• 英文名称: N,N'-bis(4-aminophenyl)-2,5-diammino-1,4-quinone-diimine
• 英文别名: Bandrowski’s base；Bandrowski's base；BB；2,5-diamino-[1,4]benzoquinone-bis-(4-amino-phenylimine)；2,5-Diamino-[1,4]benzochinon-bis-(4-amino-phenylimin)；3,6-bis[(4-aminophenyl)imino]cyclohexa-1,4-diene-1,4-diamine
• CAS: 20048-27-5
• 化学式: C₁₈H₁₈N₆
• 分子量: 318.381
• InChiKey: KKJZEUXMWDXPAU-UHFFFAOYSA-N

物化性质

• 沸点：
  523.5±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  班德罗夫斯基碱 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到N,N'-(2,5-diaminocyclohexa-2,5-diene-1,4-diylidene)bis(4-aminobenzenaminium) dichloride
  参考文献：
  名称：

  Bandrowski’s Base Revisited: Toward a Unprecedented Class of Quinonediimines or New Two-Way Chromophoric Molecular Switches

  摘要：

  Temperature-con trolled reactivity places Bandrowski's base 3 at the crossroads of a new versatile strategy for the preparation of two different categories of chromophores. We describe the access to a new class of quinonediimines (8) with an extended pi-conjugation owing to the presence of imine functions. Under slightly different conditions, Bandrowski's base appears to be the precursor of choice in the preparation of a novel pH- and liglit-dependent binary molecular switch. This molecule (11) is constituted of a benzobis(imidazole) core that can be reversibly protonated and a diarylethene unit which can be reversibly converted into its closed form upon irradiation. Triggered by two independent variables, 11 provides four distinct optical states for molecular number processing.

  DOI：

  10.1021/jo902437u
• 作为产物：
  描述：

  对苯二胺 在 ammonium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 反应 24.0h， 以15%的产率得到班德罗夫斯基碱
  参考文献：
  名称：

  轻松合成寡聚苯胺作为永久染发剂：化学修饰如何赋予颜色并避免毒性†

  摘要：

  许多用于持久染发的染料都含有芳香胺，这些胺会发生氧化聚合反应，从而导致过敏性接触性皮炎，并可能产生严重的毒性作用。在这些胺中，对苯二胺（PPD）是苯胺的小分子形式，尽管它是人类已知的过敏原，但通常用于美容产品中。因此，在这项研究中，我们通过合成寡聚PPD和在PPD上引入庞大的侧链来设计和合成更安全的PPD类似物，以克服PPD染料的毒性。我们假设（a）通过在游离胺上添加PPD单体单元来增加PPD的分子大小，以及（b）在邻位进行战略性官能化具有强供电子大基团的PPD的位置能够保持染发性能，并增加与皮肤蛋白结合的抵抗力，因此减少了皮肤致敏的机会。合成了13种低聚物，目的是生产更安全的染发剂，同时最大程度地减少对人体的最终毒性。尤其是，带有大侧链的低聚物，PPD 6（13），PPD 7（14）和PPD 8（15）表现出弱至中度（27.1％，24.1％和34.0％）的敏化潜能。该结果证实了具有大而强

  DOI：

  10.1039/c9nj03362a

文献信息

• Eco-friendly synthesis of indo dyes mediated by a bacterial laccase
  作者：Ana Catarina Sousa、M. Fátima M. M. Piedade、Lígia O. Martins、M. Paula Robalo

  DOI：10.1039/c6gc02050j

  日期：——

  An enzymatic route was identified for the production of indo dyes, through oxidative coupling mediated by the bacterial CotA-laccase.

  一种酶催化途径被发现用于通过细菌CotA-漆酶介导的氧化偶联来生产印度染料。
• Liquid chromatography–mass spectrometry analysis of dyes formed by in situ oxidative methods then purified by absorption and extraction from hair wefts
  作者：M John Plater、Andrea Raab

  DOI：10.1177/1747519820978621

  日期：2021.5

  The dye mixtures formed from three commercial hair colour formers were purified by absorption onto human hair wefts, washed and dried, extracted with dichloromethane:trifluoroacetic acid (75:25) and then analysed by liquid chromatography–mass spectrometry. Only 1–2 dyes were identified from each complex mixture of commercial aromatic amines along with a broad UV absorption mainly consisting of mixtures of quaternary ammonium salts from shampoos and some surfactants. Mecetronium ethyl sulfate and didecyldimethylammonium chloride were the main ammonium salts.

  三种商业染发剂混合物被吸附到人类头发上，经过清洗和干燥后，用二氯甲烷：三氟乙酸（75:25）提取，并通过液相色谱-质谱分析。每个商业芳香胺复合混合物中仅鉴定出1-2种染料，同时还有广谱的紫外吸收，主要由洗发水中的季铵盐混合物和一些表面活性剂组成。甲基乙基硫酸甲铵和十二烷基二甲基铵盐是主要的铵盐。
• Benzo[1,2‐ <i>d</i> :4,5‐ <i>d</i> ′]bisimidazoles as a Convenient Platform Towards Dyes that are Capable of Excited‐State Intramolecular Proton Transfer and of Two‐Photon Absorption
  作者：Mariusz Tasior、Vincent Hugues、Mireille Blanchard‐Desce、Daniel T. Gryko

  DOI：10.1002/asia.201200539

  日期：2012.11

  New, strongly fluorescent benzo[1,2‐d:4,5‐d′]bisimidazoles have been prepared by the reaction of Bandrowski′s base with various aldehydes. Their structures were carefully designed to achieve efficient excited‐state intramolecular proton transfer and good two‐photon‐absorption (2PA) cross‐sections. Functional dyes that possessed both high fluorescence quantum yields and large Stokes shifts were prepared

  新的强荧光苯并[1,2- d：4,5- d' ]双咪唑是通过Bandrowski碱与各种醛反应制得的。它们的结构经过精心设计，以实现有效的激发态分子内质子转移和良好的双光子吸收（2PA）截面。制备了兼具高荧光量子产率和大斯托克斯位移的功能性染料。该所具有的π膨胀d-A-d衍生物Φ FL = 50％和σ 2对于生物成像而言，感兴趣的光谱区域中的= 230 GM是荧光探针的绝佳候选者。由于存在两个反应性氨基，因此此类化合物可轻松转化为生物偶联探针。所有这些苯并[1,2- d：4,5- d ']双咪唑在固态时也发出强烈的荧光。
• Laccase-Catalysed Homocoupling of Primary Aromatic Amines towards the Biosynthesis of Dyes
  作者：Ana Catarina Sousa、Lígia O. Martins、M. Paula Robalo

  DOI：10.1002/adsc.201300501

  日期：2013.10.11

  AbstractColoured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p‐electron donor primary aromatic amines using two different laccases, CotA‐laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange‐red to purple products, presenting high molar extinction coefficients, presumably result from oxidative homocoupling reactions, through the formation of NC bonds at positions 2 and 5, of the laccase oxidised intermediate as showed in the proposed oxidative pathway. The product of 1,4‐phenylenediamine is shown to be the trimer known as Bandrowski’s base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p‐electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data contribute for (i) understanding key features of laccase reactivity with p‐substituted aromatic amines and (ii) establishing enzymatic processes that lead to the synthesis of coloured bio‐products under mild conditions with potential impact in the cosmetic and dye industries.magnified image
• Crippa, Gazzetta Chimica Italiana, 1930, vol. 60, p. 644,646
  作者：Crippa

  DOI：——

  日期：——