3',6'-bis(diethylamino)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9'-xanthen]-3-one | 1341198-48-8

• 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'-bis(diethylamino)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9'-xanthen]-3-one
• CAS: 1341198-48-8
• 化学式: C₃₉H₄₅N₅O₃
• 分子量: 631.818
• InChiKey: BZTJPAAUZLOWDS-UHFFFAOYSA-N

物化性质

• 沸点：
  791.2±70.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.85
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3',6'-bis(diethylamino)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9'-xanthen]-3-one 、 copper dichloride 以 aq. phosphate buffer 、 乙腈 为溶剂， 以97%的产率得到
  参考文献：
  名称：

  Label-free sensing platform for miRNA-146a based on chromo-fluorogenic pyrophosphate recognition

  摘要：

  In this study we applied the dual-responsive chromo-fluorescent Cu2+ chelate IC for the recognition of miRNA-146a through a pyrophosphate (PPi) sensing strategy in a rolling circle amplification (RCA) process. This approach for the recognition of miRNA-146a was highly robust, selective, and sensitive down to the attomolar (fluorogenic) and sub-micromolar (chromogenic) ranges under modified biochemical conditions at elevated temperature. Probe 1 selectively recognized Cu2+ and PPi ions in a sequential manner, as evidenced by colorless -> pink -> colorless transitions; the fluorescence emissions centered at 480 nm underwent a corresponding on off on sequence in the bluish-green region. We attribute this reversible switching upon the addition of Cu2+/PPi ions to effective chelation-induced ligand-to-metal charge/electron transfer that resulted in opening of the lactam ring upon complexation and closing of the lactam ring upon decomplexation. We also report a label-free approach for monitoring miRNA-146a amplification in an RCA process under modified T4 ligase and phi(29) buffer conditions, using the Cu2+ ensemble 1C at pH 7.0 (4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid: HEPES, 10 mM MgCl2); the time required to perform this process (40-50 min) was relatively shorter than conventional RCA process. This ensemble 1C could recognize miRNA-146a coorimetrically (from pink to colorless) and fluorimetrically ("turn-on" mode) at concentrations within the highly sensitive atto-/nanomolar range under physiological conditions. This cost-effective label-free sensing strategy appears to be a universal method for detecting miRNAs according to the specified length of the template.

  DOI：

  10.1016/j.jinorgbio.2019.110867
• 作为产物：
  描述：

  罗丹明B 在 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 23.5h， 生成 3',6'-bis(diethylamino)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9'-xanthen]-3-one
  参考文献：
  名称：

  The synthesis and mercury-recognizing skill of two emission “turn-on” rhodamine derivatives excited by rare earth up-conversion lattice

  摘要：

  The present paper focused on the synthesis and Hg(II)-sensing behavior of two rhodamine derived probes. Up-conversion NaYF4 nanocrystals were constructed and applied as the excitation host so that those probes could be lightened by the 980 nm excited up-conversion emission, aiming at better probe photostability. The efficient energy transfer between the up-conversion host and the probes was analyzed and confirmed by spectral analysis and emission decay lifetime comparison. The probes followed a simple complexation stoichiometry of 1:1 with Hg(II) ions. Then two sensing composite systems containing the up-conversion host and the probes were established. Their sensing performance, including spectral response, Stern-Volmer plots, emission stability and selectivity, was explored in detail. It was found that the probe emission linearly increased with increasing Hg(II) ions while was immune to other common metal ions, showing emission "turn-on" effect towards Hg(II) ions with good selectivity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.07.007

文献信息

• 一种新型罗丹明类探针及其合成方法和应用
  申请人：临沧永旭生物科技有限公司

  公开号：CN113200991A

  公开（公告）日：2021-08-03

  本发明涉及一种新型罗丹明类探针及其合成方法和应用。所述新型罗丹明类探针为罗丹明B与水合肼合成中间产物罗丹明B酰肼，罗丹明B酰肼与与4‑(乙二氨基)水杨醛在无水甲醇溶剂中，加入冰醋酸后，回流反应，所得反应物过滤，得到新型罗丹明类探针。具有选择性高，灵敏度比较高，可以应用于检测铜离子的探针试剂，其成本低廉，检测过程操作简单。
• Fluorescent salicylaldehyde hydrazone as selective chemosensor for Zn2+ in aqueous ethanol: a ratiometric approach
  作者：Na Li、Weixin Tang、Yu Xiang、Aijun Tong、Peiyuan Jin、Yong Ju

  DOI：10.1002/bio.1175

  日期：2010.11

  4-N,N-diethylaminosalicylaldehyde hydrazone Schiff base (1) and its analogues (2-6) were synthesized and characterized by NMR, MS and elemental analysis. Compound 1 exhibited ratiometric fluorescent response to Zn2+ over other metal ions in aqueous ethanol solution with neutral buffer. The complexation ratio, site and constant and the effect of pH value and water fraction on its fluorescent response to Zn2+ were investigated. Copyright © 2009 John Wiley & Sons, Ltd.

  合成了4-N,N-二乙氨基水杨醛腙席夫碱(1)及其类似物(2-6)，并通过NMR、MS和元素分析对其进行了表征。在含有中性缓冲液的乙醇水溶液中，化合物 1 对 Zn2+ 表现出相对于其他金属离子的比率荧光响应。研究了络合比、位点和常数以及pH值和水含量对其对Zn2+荧光响应的影响。版权所有 © 2009 约翰·威利父子有限公司
• Reversible Photochromic System Based on Rhodamine B Salicylaldehyde Hydrazone Metal Complex
  作者：Kai Li、Yu Xiang、Xiaoyan Wang、Ji Li、Rongrong Hu、Aijun Tong、Ben Zhong Tang

  DOI：10.1021/ja411689w

  日期：2014.1.29

  photostability in its ring-open form. It is an ideal chromophore for the development of new photochromic systems. However, known photochromic rhodamine derivatives, such as amides, exhibit only millisecond lifetimes in their colored ring-open forms, making their application very limited and difficult. In this work, rhodamine B salicylaldehyde hydrazone metal complex was found to undergo intramolecular ring-open

  光致变色分子广泛应用于化学、物理学、生物学和材料科学。虽然之前已经开发了一些光致变色系统，但它们的应用仍然受到合成复杂、耐疲劳性低或光转换不完全的限制。罗丹明是一类具有优异光学性能的染料，包括长波长吸收、大吸收系数和开环形式的高光稳定性。它是开发新光致变色系统的理想发色团。然而，已知的光致变色罗丹明衍生物，例如酰胺，在其有色开环形式中仅显示毫秒寿命，这使得它们的应用非常有限且困难。在这项工作中，发现罗丹明 B 水杨醛腙金属络合物在紫外线照射下发生分子内开环反应，导致溶液和固体基质中的颜色和荧光发生明显变化。该配合物在可逆光致变色方面表现出良好的抗疲劳性，在开环状态下表现出长寿命。有趣的是，热漂白率可以通过使用不同的金属离子、温度、溶剂和化学取代进行调节。有人提出紫外光促进罗丹明 B 衍生物从烯醇形式异构化为酮形式，从而诱导复合物中的罗丹明螺内酰胺开环产生颜色。该光致变色系统成功地应用于光印
• New fluorescent probe based on rhodamine derivative for detection of both Cu2+ and L-Methionine and living cells imaging
  作者：Yuliang Jiang、Ronghua Shen、Guo Wei、Yixiang Cheng、Bingxiang Wang

  DOI：10.1016/j.tet.2016.03.052

  日期：2016.5

  This paper developed a new fluorescent rhodamine-based derivatives (RAD) probe for highly sensitive and selective detection of Cu2+ and L-Methionine (L-Met). The detection limits can reach as low as 12 nM for Cu2+ and 5 nM for L-Met, In addition, the RAD probe can be further applied to cell imaging owing to its photostability and low cytotoxicity. (C) 2016 Elsevier Ltd. All rights reserved.