6-diethylaminobenzo[b]furan-2-carbaldehyde | 126174-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-diethylaminobenzo[b]furan-2-carbaldehyde
• 英文别名: 6-(diethylamino)benzofuran-2-carbaldehyde；6-(diethylamino)-1-benzofuran-2-carbaldehyde
• CAS: 126174-13-8
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: SAGKXCUOXIGTNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-diethylaminobenzo[b]furan-2-carbaldehyde 生成 7-(diethylamino)-3-[(E)-3-[6-(diethylamino)-1-benzofuran-2-yl]prop-2-enoyl]chromen-2-one
  参考文献：
  名称：

  CHEN, C. H.;FOX, J. L.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxymethyl-6-diethylaminobenzo[b]furan 在 四氯苯醌 作用下， 以 氯仿 为溶剂， 以77%的产率得到6-diethylaminobenzo[b]furan-2-carbaldehyde
  参考文献：
  名称：

  Preparation of Cyan Dyes from 6-Diethylaminobenzo[b]furan-2-carboxaldehyde

  摘要：

  6-Diethylaminobenzo[b]furan-2-carboxaldehyde was synthesized in four steps and 48% overall yield starting from 4-diethylaminosalicylaldehyde. Five cyan dyes were made from this aldehyde using malononitrile dimer and 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran. The crystal structures of two dyes are included.

  DOI：

  10.1080/00397910903351568

文献信息

• Clickable Long-Wave “Mega-Stokes” Fluorophores for Orthogonal Chemoselective Labeling of Cells
  作者：Krisztina Nagy、Erika Orbán、Szilvia Bősze、Péter Kele

  DOI：10.1002/asia.200900477

  日期：2010.4.1

  Dyes that can easily be tied: The synthesis of water‐soluble far‐red/NIR emitting polymethine‐based dyes with clickable functionalities (azide, alkyne) and their application in cell‐surface labeling are presented.

  易于结合的染料：介绍了具有可点击功能的水溶性远红外/ NIR聚亚甲胺基染料的合成（叠氮化物，炔烃）及其在细胞表面标记中的应用。
• Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents
  作者：Andrey S. Klymchenko、Vasyl G. Pivovarenko、Turan Ozturk、Alexander P. Demchenko

  DOI：10.1039/b302965d

  日期：——

  electron-donor substituents, introduced on opposite sides of the chromophore, were compared in solvents of different polarities. The substitution of 2-phenyl for 2-(2-benzo[b]furanyl) and introduction of electron donors on the 2-aryl group not only shift the absorption and fluorescence spectra to the red, but also strongly modulate the ESIPT behavior, resulting in a dramatic increase of the intensity ratio of the

  3-Hydroxychromones（3HCs）是 荧光染料，以回应 溶剂通过在发射光谱中两个分离良好的谱带的相对强度的变化和变化来扰动。这些条带源自分子内的激发态质子转移 （ESIPT）反应，可以通过不同的因素进行调节，包括3HC的修饰 发色团。鉴于3HC作为分子传感器的潜在基本元素的重要性，我们对3HC结构与光谱性质之间的相关性进行了首次系统研究。在电子束的相反侧引入了两个系列的已知和新合成的2-苯基-3-羟基色酮和具有不同电子给体取代基的2-（2-苯并[ b ]呋喃基）-3-羟基色酮。发色团，在中进行了比较 溶剂不同的极性。用2-苯基取代2-（2-苯并[ b ]呋喃基）并引入电子给体 在2-芳基上不仅会改变吸收和 荧光光谱为红色，但也强烈调节ESIPT行为，导致两个发射带I N * / I T *的强度比急剧增加。相反，引入7-甲氧基导致完全相反的光谱效应。所有研究过的3HC染料证明ln（I
• Fluorescence Turn On of Coumarin Derivatives by Metal Cations:  A New Signaling Mechanism Based on C=N Isomerization
  作者：Jia-Sheng Wu、Wei-Min Liu、Xiao-Qing Zhuang、Fang Wang、Peng-Fei Wang、Si-Lu Tao、Xiao-Hong Zhang、Shi-Kang Wu、Shuit-Tong Lee

  DOI：10.1021/ol062518z

  日期：2007.1.1

  [reaction: see text] A new sensing mechanism based on C=N isomerization, which shows a very significant fluorescence enhancement to the metal cations in a simple and efficient way, is demonstrated. A coumarin derivative (L) containing a C=N group was designed as an example for illustration. The free ligand L is almost nonfluorescent due to the isomerization of C=N double bond in the excited state. However

  [反应：见正文]展示了一种基于C = N异构化的新传感机制，该机制以简单有效的方式显示了对金属阳离子的非常显着的荧光增强。以含有C ＝ N基团的香豆素衍生物（L）为例进行说明。游离配体L由于处于激发态的C ＝ N双键的异构化而几乎不发荧光。但是，配体溶液在添加Zn（ClO4）2后，荧光量子产率提高了约200倍（约30％）。
• Compound, especially marker-dye on the basis of polymethines
  申请人：Dyomics GmbH

  公开号：US20040260093A1

  公开（公告）日：2004-12-23

  The invention relates to fluorescent dyes (fluorophores) based on polymethines for use in optical measurement and detection procedures, in particular those employing fluorescence, for example in medicine, in pharmacology and in the biological, materials and environmental sciences. The objective was to create fluorophores based on polymethines that have a large Stokes shift, high photostability, long storage life and a high fluorescent quantum yield, and that can be excited in the simplest possible manner by white-light sources or laser radiation in the UV, visible or NIR spectral region. According to the invention dyes on the basis of polymethines having the general formulas I, II or III 1 are employed.

  本发明涉及基于聚甲烯蓝的荧光染料（荧光团）用于光学测量和检测程序，特别是那些使用荧光的程序，例如在医学、药理学和生物、材料和环境科学中。其目的是创建基于聚甲烯蓝的荧光团，具有大的斯托克斯位移、高光稳定性、长期储存寿命和高荧光量子产率，可以通过白光源或紫外、可见或近红外光激发。根据本发明，基于聚甲烯蓝的染料具有I、II或III1通用公式。
• Compound, especially marker-dye, on the basis of polymethines
  申请人：Dyomics GmbH

  公开号：US20030165942A1

  公开（公告）日：2003-09-04

  The invention relates to fluorescent dyes (fluorophores) based on polymethines for use in optical measurement and detection procedures, in particular those employing fluorescence, for example in medicine, in pharmacology and in the biological, materials and environmental sciences. The objective was to create fluorophores based on polymethines that have a large Stokes shift, high photostability, long storage life and a high fluorescent quantum yield, and that can be excited in the simplest possible manner by white-light sources or laser radiation in the UV, visible or NIR spectral region. According to the invention dyes on the basis of polymethines having the general formulas I, II and III 1 are employed.

  本发明涉及基于聚甲烯的荧光染料（荧光物质）的使用，用于光学测量和检测程序，特别是那些使用荧光的程序，例如在医学、药理学以及生物、材料和环境科学中。本发明的目的是创建基于聚甲烯的荧光物质，具有大的Stokes位移、高光稳定性、长期存储寿命和高荧光量子产率，并且可以通过白光源或紫外、可见或近红外光谱区的激光辐射以最简单的方式激发。根据本发明，采用具有一般式I、II和III1的聚甲烯基染料。