3',6'-dibromofluoran | 87021-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3',6'-dibromofluoran
• 英文别名: 3′,6′-dibromofluoran；3',6'-Dibromospiro[2-benzofuran-3,9'-xanthene]-1-one
• CAS: 87021-26-9
• 化学式: C₂₀H₁₀Br₂O₃
• 分子量: 458.106
• InChiKey: RHZAZSCCHJXGKN-UHFFFAOYSA-N

物化性质

• 熔点：
  280-281 °C(Solv: methanol (67-56-1))
• 沸点：
  560.5±50.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3',6'-dibromofluoran 在 劳森试剂 、 sodium hypochlorite 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 水 、 双氧水 、 potassium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 84.5h， 生成 fluorescein disodium salt
  参考文献：
  名称：

  A Highly Specific Fluorescent Probe for Hypochlorous Acid and Its Application in Imaging Microbe-Induced HOCl Production

  摘要：

  Oxidative stress induced by reactive oxygen species (ROS) plays crucial roles in a wide range of physiological processes and is also implicated in various diseases, including cancer, chronic inflammatory diseases, and neurodegenerative disorders. Among the various ROS, hypochlorous acid (HOCl) plays as a powerful microbicidal agent in the innate immune system. The regulated production of microbicidal HOCl is required for the host to control the invading microbes. However, as a result of the highly reactive and diffusible nature of HOCl, its uncontrolled production may lead to an adverse effect on host physiology. Because of its biological importance, many efforts have been focused on developing selective fluorescent probes to image ROS. However, it is still challenging to design a fluorescent probe with exclusive selectivity toward a particular member of ROS. In the current work, we designed FBS as. a new fluorescent HOCl probe which has high selectivity, sensitivity, and short response time in a broad range of pH. Compared with other sensors, the "dual-lock" structure of FBS has an advantage of eliminating interferences from other ROS/RNS. Importantly, we further showed that our HOCl probe could be applied for the in vivo imaging of physiological HOCl production in the mucosa of live animals. This probe provides a promising tool for the study of HOCl production.

  DOI：

  10.1021/ja404649m
• 作为产物：
  描述：

  双(三氟甲磺酸)荧光素 在 [Cp*Ru(CH3CN)3]OTf 、 lithium bromide 作用下， 反应 15.0h， 以93%的产率得到3',6'-dibromofluoran
  参考文献：
  名称：

  抗氧化光蓝的三芳基甲烷荧光团

  摘要：

  多色荧光成像数据的正确解释和再现需要小分子荧光探针的光谱稳定性，特别是在超分辨率成像的高（去）激发光强度下或在单分子应用中。我们提出了一种基于连续 Ru 和 Cu 催化转化的一系列光谱稳定罗丹明荧光团的合成方法，使用化学计量分析在其他荧光团的背景下评估它们对光漂白和光转换的稳定性，并证明了荧光团光产物的化学反应性。已经确定了提供抗光转换三芳基甲烷荧光团的取代模式，并证明了非蓝色标记在活细胞 STED 纳米显微镜中的适用性。

  DOI：

  10.1021/jacs.8b11036

文献信息

• UV–vis absorption and fluorescence spectra, solvatochromism, and application to pH sensors of novel xanthene dyes having thienyl and thieno[3,2- b ]thienyl rings as auxochrome
  作者：Masaki Matsui、Takaya Yamamoto、Kenta Kakitani、Siddanagouda Biradar、Yasuhiro Kubota、Kazumasa Funabiki

  DOI：10.1016/j.dyepig.2016.11.013

  日期：2017.4

  Novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome have been synthesized. The UV–vis absorption maximum in dichloromethane was in the order of the auxochrome: NEt2 (Rhodamine B, 558 nm) < 2-thienyl (569 nm) < 5-thieno[3,2-b]thienyl (608 nm). These new xanthene dyes colored only in non-hydrogen-bond accepting solvents such as chloroform and dichloromethane. The lactone precursors

  合成了具有噻吩基和噻吩并[3,2- b ]噻吩基环作为辅助色素的新型x吨染料。在二氯甲烷中，UV-vis的最大吸收量为辅助色素的顺序：NEt 2（若丹明B，558 nm）<2-噻吩基（569 nm）<5-噻吩并[3,2- b ]噻吩基（608 nm）。这些新的x吨染料仅在非氢键接受溶剂（如氯仿和二氯甲烷）中着色。的噻吩基和噻吩并[3,2-的内酯前体b ]通过添加强酸，其p着色噻吩基衍生物ķ值小于-2.2低和0.23，分别，而通过添加弱酸其p着色若丹明B的ķ值低于4.7。这些结果源自杂芳族化合物比二乙氨基辅助色素对彩色阳离子染料的稳定性差。
• Synthesis of isomerically pure carboxylate- and sulfonate-substituted xanthene fluorophores
  作者：Carolyn C. Woodroofe、Mi Hee Lim、Weiming Bu、Stephen J. Lippard

  DOI：10.1016/j.tet.2005.01.024

  日期：2005.3

  fluorophores such as fluorescein and rhodamine are typically prepared by acid-catalyzed condensation of the appropriate resorcinol or 3-aminophenol with phthalic anhydride. Condensation of substituted phthalic anhydride species results in functionalized fluorophores that are formed as mixed isomers. Crystallization approaches to isomer separation have been reported elsewhere for symmetric fluorescein carboxylates

  基于吨的荧光团，例如荧光素和若丹明，通常通过适当的间苯二酚或3-氨基苯酚与邻苯二甲酸酐的酸催化缩合而制备。取代的邻苯二甲酸酐物质的缩合导致官能化的荧光团形成为混合异构体。在别处已经报道了用于对称荧光素羧酸盐的用于异构体分离的结晶方法。我们描述了基于结晶的受保护的荧光素磺酸盐的分离和偶联条件，以形成磺酰胺，羧酸取代的若丹明的前体，以及不对称取代的荧光素和Rhodafluors的前体。
• Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives
  作者：Hossein Eshghi、Narges Mirzaie

  DOI：10.2478/s11696-011-0024-3

  日期：2011.1.1

  Polycondensation reactions of phenols with phthalic anhydride were carried out in the presence of ferric hydrogensulphate under melt conditions. The reactions proceeded in short reaction times by using a catalytic amount of Fe(HSO4)3 and the corresponding fluorescein derivatives were obtained in high yields. The simplicity, scale-up, along with the use of an inexpensive, non-toxic, recyclable catalyst of an environmentally benign nature, are other remarkable features of the procedure. The absorption and emission properties of these fluorescein derivatives were studied.

  摘要：在熔融条件下，在硫酸亚铁的存在下，苯酚与邻苯二甲酸酐发生了聚缩反应。通过使用少量Fe(HSO4)3催化剂，反应在短时间内进行，并且获得了高产率的相应荧光素衍生物。该程序的其他显著特点包括简单易行、可扩展性强，以及使用成本低廉、无毒、可回收的环保催化剂。这些荧光素衍生物的吸收和发射特性也得到了研究。
• Boronate ester cross-linked PVA hydrogels for the capture and H₂O₂-mediated release of active fluorophores
  作者：George T. Williams、Adam C. Sedgwick、Sajal Sen、Lauren Gwynne、Jordan E. Gardiner、James T. Brewster、Jennifer R. Hiscock、Tony D. James、A. Toby A. Jenkins、Jonathan L. Sessler

  DOI：10.1039/d0cc01904f

  日期：——

  A new set of H₂O₂-responsive PVA hydrogels were formed using the boronate fluorescent probe PF1 and the novel boronate fluorescent probe PT1 as the covalent crosslinkers.

  一组新的H₂O₂响应性PVA水凝胶是使用硼酸荧光探针PF1和新型硼酸荧光探针PT1作为共价交联剂形成的。
• Donor–Acceptor–Donor NIR II Emissive Rhodindolizine Dye Synthesized by C–H Bond Functionalization
  作者：Chathuranga S. L. Rathnamalala、Jacqueline N. Gayton、Austin L. Dorris、Shane A. Autry、William Meador、Nathan I. Hammer、Jared H. Delcamp、Colleen N. Scott

  DOI：10.1021/acs.joc.9b01860

  日期：2019.10.18

  A NIR II emissive dye was synthesized by the C-H bond functionalization of 1-methyl-2-phenylindolizine with 3,6-dibromoxanthene. The rhodindolizine (RhIndz) spirolactone product was nonfluorescent; however, upon opening of the lactone ring by the formation of the ethyl ester derivative, the fluorophore absorbs at 920 nm and emits at 1092 nm, which are both in the NIR II region. In addition, 4-cyanophenyl-

  通过1-甲基-2-苯基吲哚嗪与3,6-二溴并氧杂蒽的CH键官能化合成了NIR II发光染料。罗丹多利嗪（RhIndz）螺内酯产品不发荧光；然而，当通过形成乙酯衍生物而打开内酯环时，荧光团在920nm处吸收并在1092nm处发射，它们均在NIR II区域中。另外，还可以通过CH活化反应来制备4-氰基苯基-（CNRhIndz）和4-甲氧基苯基取代的罗丹二嗪（MeORhIndz）。