5-(piperidin-1-yl)benzene-1,3-diol | 855874-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-(piperidin-1-yl)benzene-1,3-diol
• 英文别名: 5-Piperidin-1-ylbenzene-1,3-diol
• CAS: 855874-79-2
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD10478330
• 分子量: 193.246
• InChiKey: TVAXHZFAJHFMHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(piperidin-1-yl)benzene-1,3-diol 在 高氯酸 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 86.0h， 生成
  参考文献：
  名称：

  Brightly fluorescent purple and blue labels for amines and proteins

  摘要：

  Novel amino-reactive phenoxazines were obtained by reasonably simple synthetic protocols and characterized in terms of their use as fluorescent labels for amines, amino acids and proteins in general. Purple labels (alternatives to Texas Red) and blue labels (alternatives to Cy-1) were obtained by this strategy. The absorption/emission maxima, in aqueous solution, are at around 589/630 nm and 648/670 nm, respectively, thus indicating larger Stokes' shifts than those of common cyanine-type of labels. The new labels are compatible with commercial diode laser light sources. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.133
• 作为产物：
  描述：

  哌啶 、 间苯三酚 以 四氢呋喃 为溶剂， 反应 3.0h， 以39%的产率得到5-(piperidin-1-yl)benzene-1,3-diol
  参考文献：
  名称：

  Brightly fluorescent purple and blue labels for amines and proteins

  摘要：

  Novel amino-reactive phenoxazines were obtained by reasonably simple synthetic protocols and characterized in terms of their use as fluorescent labels for amines, amino acids and proteins in general. Purple labels (alternatives to Texas Red) and blue labels (alternatives to Cy-1) were obtained by this strategy. The absorption/emission maxima, in aqueous solution, are at around 589/630 nm and 648/670 nm, respectively, thus indicating larger Stokes' shifts than those of common cyanine-type of labels. The new labels are compatible with commercial diode laser light sources. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.133

文献信息

• Clickable fluorophores for biological labeling—with or without copper
  作者：Péter Kele、Xiaohua Li、Martin Link、Krisztina Nagy、András Herner、Krisztián Lőrincz、Szabolcs Béni、Otto S. Wolfbeis

  DOI：10.1039/b907741c

  日期：——

  for fluorescent labeling of biomolecules is presented by examples on model frameworks representing major biopolymer building blocks. The versatility of these dyes is presented in cell labeling experiments as well as by labeling the azide modified surface glycans of CHO-cells either by copper catalyzed or copper-free click reaction. These dyes are expected to have a large variety of applications in (bio)orthogonal

  本文介绍了一组新的可点击的荧光团的合成，这些荧光团实际上覆盖了到达近红外区域的整个可见光谱。除了能够参与具有相应功能的经典铜催化的1,3-偶极环加成反应的染料外，我们还制备了含有环辛炔部分的炔烃染料，该炔烃衍生物能够使铜自由键合到叠氮化物上。在代表主要生物聚合物构件的模型框架上，通过实例说明了这些染料对生物分子进行荧光标记的适用性。这些染料的多功能性在细胞标记实验中以及通过铜催化的或无铜的点击反应标记CHO细胞的叠氮化物修饰的表面聚糖上呈现出来。体内和体外。
• Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels
  作者：Martin Link、Xiaohua Li、Jana Kleim、Otto S. Wolfbeis

  DOI：10.1002/ejoc.201001085

  日期：2010.12

  Maleinimides are widely used to label proteins and to derivatize thiols. The so-called click reaction was shown to allow the efficient introduction of the maleinimido group into azido-modified fluorophores (benzoxazines) by reacting them with an alkyne-modified maleinimide to yield new thiol-reactive fluorescent labels 5–7. The reaction proceeds under mild experimental conditions and provides a new

  马来酰亚胺广泛用于标记蛋白质和衍生硫醇。所谓的点击反应被证明允许将马来酰亚胺基团有效地引入叠氮基改性的荧光团（苯并恶嗪），方法是通过将它们与炔烃改性的马来酰亚胺反应产生新的硫醇反应性荧光标记 5-7。该反应在温和的实验条件下进行，并提供了一种引入马来酰亚胺基团的新策略，如此处针对荧光团的示例。可以想象，它可以扩展到放射性、电活性、同位素或自旋标记。以前报道的从开环前体开始形成这种马来酰亚胺的方法需要相当苛刻的条件。新的苯并恶嗪 5-7 的特点是在发色团和马来酰亚胺官能团之间有一个相当长且灵活的接头，并且它们的荧光可以用二极管激光器（这是荧光测定中的首选光源）进行光激发。它们与：(a) 氨基硫醇半胱胺、(b) 肽谷胱甘肽和 (c) 与人血清白蛋白偶联。吩恶嗪酮 5 的荧光是强溶剂致变色的，这表明它可用作极性敏感探针。
• Novel Method for the Synthesis of Merocyanines: New Photophysical Possibilities for a Known Class of Fluorophores
  作者：Brunella Bardi、Katerina V. Vygranenko、Beata Koszarna、Olena Vakuliuk、Łukasz Dobrzycki、Daniel T. Gryko、Francesca Terenziani、Anna Painelli

  DOI：10.1002/chem.202300979

  日期：2023.8.10

  Friedel–Crafts reaction followed by nucleophilic aromatic substitution enables the assembly of rhodols and novel strongly emitting merocyanines from simple substrates.

  弗里德尔-克来福特反应随后进行亲核芳香族取代，使得能够从简单的底物组装对甲酚和新型强发射部花青。
• JP6281975
  申请人：——

  公开号：——

  公开（公告）日：——
• Brightly fluorescent purple and blue labels for amines and proteins
  作者：Martin Link、Péter Kele、Daniela E. Achatz、Otto S. Wolfbeis

  DOI：10.1016/j.bmcl.2011.06.133

  日期：2011.9

  Novel amino-reactive phenoxazines were obtained by reasonably simple synthetic protocols and characterized in terms of their use as fluorescent labels for amines, amino acids and proteins in general. Purple labels (alternatives to Texas Red) and blue labels (alternatives to Cy-1) were obtained by this strategy. The absorption/emission maxima, in aqueous solution, are at around 589/630 nm and 648/670 nm, respectively, thus indicating larger Stokes' shifts than those of common cyanine-type of labels. The new labels are compatible with commercial diode laser light sources. (C) 2011 Elsevier Ltd. All rights reserved.