2-(4-(ethylamino)-2-hydroxy-5-methylbenzoyl)benzoic acid | 88936-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-(ethylamino)-2-hydroxy-5-methylbenzoyl)benzoic acid
• 英文别名: Benzoic acid, 2-[4-(ethylamino)-2-hydroxy-5-methylbenzoyl]-；2-[4-(ethylamino)-2-hydroxy-5-methylbenzoyl]benzoic acid
• CAS: 88936-19-0
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: WNTBYRGDUJYEFC-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  545.2±50.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-(ethylamino)-2-hydroxy-5-methylbenzoyl)benzoic acid 在 硫酸 作用下， 反应 2.0h， 生成 2-(2-(9-(2-carboxyphenyl)-6-(N-ethylacetamido)-7-methyl-2,3-dihydro-1H-xanthen-4-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium perchlorate
  参考文献：
  名称：

  A Unique Class of Near-Infrared Functional Fluorescent Dyes with Carboxylic-Acid-Modulated Fluorescence ON/OFF Switching: Rational Design, Synthesis, Optical Properties, Theoretical Calculations, and Applications for Fluorescence Imaging in Living Animals

  摘要：

  Fluorescence imaging is one of the most powerful techniques for monitoring biomolecules in living systems. Fluorescent sensors with absorption and emission in the near-infrared (NIR) region are favorable for biological imaging . applications in living animals, as NIR light leads to minimum photodamage, deep tissue penetration, and minimum background autofluorescence interference. Herein, we have introduced a new strategy to design NIR functional dyes with the carboxylic-acid-controlled fluorescence on off switching mechanism by the spirocyclization. Based on the design strategy, we have developed a series of Changsha (CS1-6) NIR fluorophores, a unique new class of NIR functional fluorescent dyes, bearing excellent photophysical properties including large absorption extinction coefficients, high fluorescence quantum yields, high brightness, good photostability, and sufficient chemical stability. Significantly, the new CS1-6 NIR dyes are superior to the traditional rhodamine dyes with both absorption and emission in the NIR region while retaining the rhodamine-like fluorescence ON-OFF switching mechanism. In addition, we have performed quantum chemical calculations with the B3LYP exchange functional employing 6-31G* basis sets to shed light on the structure-optical properties of the new CS1-6 NIR dyes. Furthermore, using CS2 as a platform, we further constructed the novel NIR fluorescent TURN-ON sensor 7, which is capable of imaging endogenously produced HCIO in the living animals, demonstrating the value of our new CS NIR functional fluorescent dyes. We expect that the design strategy may be extended for development of a wide variety of NIR functional dyes with a suitable fluorescence-controlled mechanism for many useful applications in biological studies.

  DOI：

  10.1021/ja209292b
• 作为产物：
  描述：

  rhodamine 6G 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 2-(4-(ethylamino)-2-hydroxy-5-methylbenzoyl)benzoic acid
  参考文献：
  名称：

  一氧化氮供体、其制备及应用

  摘要：

  本发明涉及一氧化氮供体、其制备及应用。具体而言，本发明提供具有下式I所示结构的化合物，式中，R2为H、C3‑C8环烷基、或任选地被1－2个选自C1‑4烷氧基、‑S(O)2‑OH、和羟基的取代基取代的C1‑6烷基，其中，所述N连接到所述荧光团分子的苯环上。本发明还提供所述式I化合物的制备方法，含该式I化合物的组合物，以及式I化合物作为一氧化氮供体的用途。

  公开号：

  CN107459482B

文献信息

• [EN] NEW FLUORESCENT DYES AND THEIR USES AS BIOMARKERS<br/>[FR] NOUVEAUX COLORANTS FLUORESCENTS ET LEURS UTILISATIONS EN TANT QUE BIOMARQUEURS
  申请人：ILLUMINA CAMBRIDGE LTD

  公开号：WO2018060482A1

  公开（公告）日：2018-04-05

  The present application relates to new fluorescent dyes and their uses as fluorescent labels. The compounds may be used as fluorescent labels for nucleotides in nucleic acid sequencing applications.

  本申请涉及新的荧光染料及其作为荧光标记物的用途。这些化合物可用作核酸测序应用中核苷酸的荧光标记物。
• A General Method To Increase Stokes Shift by Introducing Alternating Vibronic Structures
  作者：Tian-Bing Ren、Wang Xu、Wei Zhang、Xing-Xing Zhang、Zhi-Yao Wang、Zhen Xiang、Lin Yuan、Xiao-Bing Zhang

  DOI：10.1021/jacs.8b04404

  日期：2018.6.20

  common fluorophores. By simply appending a 1,4-diethyl-decahydro-quinoxaline (DQ) moiety onto the conjugated structure, we introduced a vibronic backbone that could facilely expand the Stokes shifts, emission wavelength, and photostability of 11 different fluorophores by more than 3-fold. This generalizable method could significantly improve the imaging efficiency of commercial fluorophores. As a demonstration

  荧光染料在广泛的生物医学领域取得了很大进展。然而，许多市售染料都存在小的斯托克斯位移，导致当前显微镜配置的信噪比和自淬火较差。在这项工作中，我们开发了一种通用方法来显着增加常见荧光团的斯托克斯位移。通过简单地将 1,4-二乙基-十氢-喹喔啉 (DQ) 部分附加到共轭结构上，我们引入了一个振动骨架，可以轻松地将 11 种不同荧光团的斯托克斯位移、发射波长和光稳定性扩大 3 倍以上. 这种可推广的方法可以显着提高商业荧光团的成像效率。作为示范，我们表明半花青的 DQ 衍生物在小鼠模型中产生了超过吲哚菁绿的 5 倍信号。此外，DQ 修饰的荧光团可以与其母分子配对进行单激发、多发射成像，使我们能够更稳健地研究细胞行为。这种方法有望产生适用于超分辨率显微镜和第二窗口近红外成像的染料。
• 一氧化氮供体、其制备及应用
  申请人：华东理工大学

  公开号：CN107459482B

  公开（公告）日：2020-11-17

  本发明涉及一氧化氮供体、其制备及应用。具体而言，本发明提供具有下式I所示结构的化合物，式中，R2为H、C3‑C8环烷基、或任选地被1－2个选自C1‑4烷氧基、‑S(O)2‑OH、和羟基的取代基取代的C1‑6烷基，其中，所述N连接到所述荧光团分子的苯环上。本发明还提供所述式I化合物的制备方法，含该式I化合物的组合物，以及式I化合物作为一氧化氮供体的用途。
• Molecular engineering of ultra-sensitive fluorescent probe with large Stokes shift for imaging of basal HOCl in tumor cells and tissues
  作者：Peng Lu、Xingxing Zhang、Tianbing Ren、Lin Yuan

  DOI：10.1016/j.cclet.2020.08.016

  日期：2020.11

  Abstract Fluorescent probes have been widely employed in biological imaging and sensing. However, it is always a challenge to design probes with high sensitivity. In this work, based on rhodamine skeleton, we developed a general strategy to construct sensitivity-enhanced fluorescent probe with the help of theoretical calculation for the first time. As a proof of concept, we synthesized a series of

  摘要荧光探针已广泛应用于生物成像和传感。但是，设计高灵敏度的探头始终是一个挑战。在这项工作中，我们基于罗丹明骨架，首次借助理论计算开发了一种构建灵敏度增强型荧光探针的通用策略。作为概念验证，我们合成了一系列HOC1探针。实验结果表明，通过电子给体基团稳定了若丹明的丙酮酸部分的C-9，探针DQF-S对HOCl的灵敏度（LOD：0.2 nmol / L）显着提高，并且响应时间（650 nm）和快速大斯托克斯班次。生物成像研究表明，DQF-S不仅可以有效检测各种类型细胞中的基础HOCl，而且还可以成功地应用于体内肿瘤组织的成像。
• Multicolor Chromism from a Single Chromophore through Synergistic Coupling of Mechanochromic and Photochromic Subunits
  作者：Weiye He、Yuan Yuan、Mengjiao Wu、Xinxin Li、Yanbing Shen、Zhiyu Qu、Yulan Chen

  DOI：10.1002/anie.202218785

  日期：2023.3.6

  bis-mechanophore featuring light-regulable multicolor mechanochromism has been developed, by synergistically coupling the mechanochromic and photochromic subunits (bis-rhodamine and bisthienylethene) into one chromophore. Consecutively and/or orthogonally triggered mechanochemical and photochemical reactions of the chromophore-centered polymers enabled vividly detectable, multicolor switches and gradient optical

  通过将机械变色和光致变色亚基（双罗丹明和双噻吩乙烯）协同耦合到一个生色团中，开发了一种具有光调节多色机械变色的新型双机械变色团。以发色团为中心的聚合物的连续和/或正交触发的机械化学和光化学反应能够实现生动可检测的多色开关和梯度光学响应。