3',6'-bis(diethylamino)-2-(pyridin-2-ylmethyl)spiro[isoindoline-1,9'-xanthen]-3-one | 1343487-71-7

• 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-(pyridin-2-ylmethyl)spiro[isoindoline-1,9'-xanthen]-3-one
• 英文别名: 3',6'-Bis(diethylamino)-2-(pyridin-2-ylmethyl)spiro[isoindole-3,9'-xanthene]-1-one；3',6'-bis(diethylamino)-2-(pyridin-2-ylmethyl)spiro[isoindole-3,9'-xanthene]-1-one
• CAS: 1343487-71-7
• 化学式: C₃₄H₃₆N₄O₂
• 分子量: 532.685
• InChiKey: MWLAKKHYTRKSFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',6'-bis(diethylamino)-2-(pyridin-2-ylmethyl)spiro[isoindoline-1,9'-xanthen]-3-one 、 mercury(II) nitrate 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  阴离子诱导的Hg 2+多信号探针及其在鱼肾和肝组织成像研究中的应用†

  摘要：

  合成了3'，6'-双（二乙氨基）-2-（吡啶-2-基甲基）螺[异吲哚啉-1,9'-黄嘌呤] -3-one（L），用于Hg 2的选择性荧光和比色识别+在pH 6.0下。此外，L还可用于使用荧光显微镜对鱼肾和肝脏组织中的Hg 2+进行成像。螺内酰胺开环的大号对Hg 2+识别强烈地受到汞盐的性质的影响，结果为NO 3 -诱导的。其他汞盐，例如HgCl 2，Hg（CH 3 COO）2和Hg（ClO 4）2在相同的实验条件下未能诱导L的荧光和比色反应。例如，前一种盐不显示螺内酰胺开环，而是形成了新的离子化合物（H 3 L）2 [Hg 6 Cl 18 ]·2H 2 O（1），其结构已通过单晶X射线衍射阐明。这可能由以下原因解释：（1）Hg 2+的共价性质较高，因此金属中心的酸度较低，并且无法引发开环反应；（2）在Hg情况下，体积较大的阴离子（二氧化氯4）2螺内酰胺开环后，它也是离子性的，面对空间位阻以容纳在N（Et）2基团内。

  DOI：

  10.1039/c5dt01854d
• 作为产物：
  描述：

  罗丹明B 在 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 28.0h， 生成 3',6'-bis(diethylamino)-2-(pyridin-2-ylmethyl)spiro[isoindoline-1,9'-xanthen]-3-one
  参考文献：
  名称：

  Rhodamine-based derivatives for Cu2+ sensing: Spectroscopic studies, structure-recognition relationships and its test strips

  摘要：

  A rhodamine spirolactam/2-hydrazinopyridine derivative was synthesized and characterized, which exhibited high selectivity to Cu2+ over other metal cations. The Cu2+ recognition of this rhodamine derivative could be detected by fluorescence spectra, absorption spectra and an obvious color change which was observed easily by naked-eyes. The binding of this rhodamine derivative to Cu2+ is instantaneous and sensitive. Moreover, a linear relationship was found between the fluorescence intensity at 575 nm from 0.5 x 10(-6) M to 3.0 x 10(-6) M of Cu2+ concentration, and the limit of detection (LOD) was at low concentration of 2.11 x 10(-8) M, this would benefit for the establishment of standard working curves in practical Cu2+ detection. Additionally, we synthesized rhodamine spirolactam/2-aminomethylpyridine derivative and rhodamine spirolactam/phenylhydrazine derivative as analogs for elucidate the structure-recognition relationships. Finally, we prepared the test strips of rhodamine spirolactam/2-hydrazinopyridine derivative for practical chromogenic the Cu2+ detection. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.05.016

文献信息

• Rhodamine-based fluorescent off–on sensor for Fe³⁺ – in aqueous solution and in living cells: 8-aminoquinoline receptor and 2 : 1 binding
  作者：Junhai Huang、Yufang Xu、Xuhong Qian

  DOI：10.1039/c3dt53159g

  日期：——

  A rhodamine-based Fe³⁺ sensor of a rigid 8-aminoquinoline receptor shows a 2 : 1 binding according to 1D and 2D-¹HNMR experiments.

  一种基于罗丹明的Fe³⁺传感器，其受体为刚性的8-氨基喹啉，根据一维和二维¹HNMR实验，显示出2 : 1的络合比例。

• Smartphone‐Based Sensing of Cortisol by Functionalized Rhodamine Probes
  作者：Rossella Santonocito、Alessia Cavallaro、Roberta Puglisi、Andrea Pappalardo、Nunzio Tuccitto、Manuel Petroselli、Giuseppe Trusso Sfrazzetto

  DOI：10.1002/chem.202401201

  日期：——

  During a stress condition, the human body synthesizes catecholamine neurotransmitters and specific hormones (called “stress hormones”), the most important of which is cortisol. The monitoring of cortisol levels should be extremely important to control the stress levels, and for this reason, it shows important medical applications. The common analytical methods (HPLC, GC‐MS) cannot be used in real life, due to the bulky size of the instruments and the necessity of specialized personnel. Molecular probes solve these problems due to their fast and easy use. The synthesis of new fluorescent rhodamine probes, able to interact by non‐covalent interactions with cortisol, the recognition properties in solution as well as in solid state by Strip Test, using a smartphone as detector, are here reported. DFT calculations and FT‐IR measurements suggest the formation of supramolecular complexes through hydrogen bonds as main non‐covalent interaction. The present study represents one of the first sensor, based on synthetical chemical receptors, able to detect cortisol in a linear range from 1 mM to 1 pM, based on non‐covalent molecular recognition and paves the way to the realization of practical point‐of‐care device for the monitoring of cortisol in real live.
• An anion induced multisignaling probe for Hg²⁺ and its application for fish kidney and liver tissue imaging studies
  作者：Sandip Mandal、Arnab Banerjee、Debasree Ghosh、Dipak Kumar Mandal、Damir A. Safin、Maria G. Babashkina、Koen Robeyns、Mariusz P. Mitoraj、Piotr Kubisiak、Yann Garcia、Debasis Das

  DOI：10.1039/c5dt01854d

  日期：——

  exhibit spirolactam ring opening but forms a new ionic compound (H3L)2[Hg6Cl18]·2H2O (1), whose structure has been elucidated by single crystal X-ray diffraction. This might be explained by (1) the higher covalent nature of Hg2+ and, hence, the lower acidity of the metal center and its inability to induce the ring opening reaction, and (2) the bulky anion, in the case of Hg(ClO4)2, which is also ionic

  合成了3'，6'-双（二乙氨基）-2-（吡啶-2-基甲基）螺[异吲哚啉-1,9'-黄嘌呤] -3-one（L），用于Hg 2的选择性荧光和比色识别+在pH 6.0下。此外，L还可用于使用荧光显微镜对鱼肾和肝脏组织中的Hg 2+进行成像。螺内酰胺开环的大号对Hg 2+识别强烈地受到汞盐的性质的影响，结果为NO 3 -诱导的。其他汞盐，例如HgCl 2，Hg（CH 3 COO）2和Hg（ClO 4）2在相同的实验条件下未能诱导L的荧光和比色反应。例如，前一种盐不显示螺内酰胺开环，而是形成了新的离子化合物（H 3 L）2 [Hg 6 Cl 18 ]·2H 2 O（1），其结构已通过单晶X射线衍射阐明。这可能由以下原因解释：（1）Hg 2+的共价性质较高，因此金属中心的酸度较低，并且无法引发开环反应；（2）在Hg情况下，体积较大的阴离子（二氧化氯4）2螺内酰胺开环后，它也是离子性的，面对空间位阻以容纳在N（Et）2基团内。
• Rhodamine-based derivatives for Cu2+ sensing: Spectroscopic studies, structure-recognition relationships and its test strips
  作者：Yunxu Yang、Weiling Gao、Ruilong Sheng、Weili Wang、Hui Liu、Wumin Yang、Tianyi Zhang、Xuetao Zhang

  DOI：10.1016/j.saa.2011.05.016

  日期：2011.10

  A rhodamine spirolactam/2-hydrazinopyridine derivative was synthesized and characterized, which exhibited high selectivity to Cu2+ over other metal cations. The Cu2+ recognition of this rhodamine derivative could be detected by fluorescence spectra, absorption spectra and an obvious color change which was observed easily by naked-eyes. The binding of this rhodamine derivative to Cu2+ is instantaneous and sensitive. Moreover, a linear relationship was found between the fluorescence intensity at 575 nm from 0.5 x 10(-6) M to 3.0 x 10(-6) M of Cu2+ concentration, and the limit of detection (LOD) was at low concentration of 2.11 x 10(-8) M, this would benefit for the establishment of standard working curves in practical Cu2+ detection. Additionally, we synthesized rhodamine spirolactam/2-aminomethylpyridine derivative and rhodamine spirolactam/phenylhydrazine derivative as analogs for elucidate the structure-recognition relationships. Finally, we prepared the test strips of rhodamine spirolactam/2-hydrazinopyridine derivative for practical chromogenic the Cu2+ detection. (C) 2011 Elsevier B.V. All rights reserved.