3',6'-bis(diethylamino)-2-(phenylamino)spiro[isoindoline-1,9'-xanthen]-3-one | 90457-20-8

• 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-(phenylamino)spiro[isoindoline-1,9'-xanthen]-3-one
• 英文别名: rhodamine B phenyl hydrazine；RBPH；2-anilino-3',6'-bis-diethylamino-spiro[isoindoline-1,9'-xanthen]-3-one；2-Anilino-3',6'-bis-diaethylamino-spiro[isoindolin-1,9'-xanthen]-3-on；2-Anilino-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
• CAS: 90457-20-8
• 化学式: C₃₄H₃₆N₄O₂
• 分子量: 532.685
• InChiKey: WFZKDAYHQMKSJT-UHFFFAOYSA-N

物化性质

• 沸点：
  691.3±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  48
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',6'-bis(diethylamino)-2-(phenylamino)spiro[isoindoline-1,9'-xanthen]-3-one 在 peroxynitrite anion 作用下， 以 aq. phosphate buffer 、 水 、 乙腈 为溶剂， 生成 C.I.颜料紫1
  参考文献：
  名称：

  Bioimaging of Peroxynitrite in MCF-7 Cells by a New Fluorescent Probe Rhodamine B Phenyl Hydrazide

  摘要：

  过氧化亚硝酸盐是一种强效氧化剂和硝化剂，会改变细胞内生物大分子的结构和功能，从而对细胞产生有害影响。荧光探针罗丹明 B 苯酰肼（RBPH）具有氧化特性，可将 RBPH 转化为粉红色的高荧光罗丹明 B，因此被提议用于 MCF-7 细胞中的过亚硝酸（ONOO-）成像。在 2-20 nM 的浓度范围内，该方法符合比尔定律，检测限为 1.4 nM。通过光谱证据讨论了亚硝酸过氧化物与 RBPH 生成罗丹明 B 的可能反应机制。在接近生理 pH 值的 pH 值 6-8 范围内，该探针对过亚硝酸盐具有选择性。荧光显微镜研究表明，该探针具有细胞渗透性，因此可以对 MCF-7 细胞中的亚硝酸过氧化物进行成像。

  DOI：

  10.1007/s10895-013-1205-y
• 作为产物：
  描述：

  罗丹明B 、 苯肼 以 乙醇 为溶剂， 反应 4.0h， 以88%的产率得到3',6'-bis(diethylamino)-2-(phenylamino)spiro[isoindoline-1,9'-xanthen]-3-one
  参考文献：
  名称：

  A Fluorescent Chemodosimeter for Hg2+Based on a Spirolactam Ring-Opening Strategy and its Application Towards Mercury Determination in Aqueous and Cellular Media

  摘要：

  设计并合成了一种新型 Hg2+ 荧光化学传感器罗丹明 B 苯酰肼（RBPH）。该探针对 Hg2+ 具有高度灵敏性、选择性和不可逆性，并在 580 nm 波长处显示荧光响应。经 Hg2+ 处理后，RBPH 的颜色也会从无色变为粉红色。这一特性已被用于肉眼检测各种工业样品中的 Hg2+。荧光显微实验表明，这种化学传感器具有细胞渗透性，可用于细胞介质中 Hg2+ 的荧光成像。该探针可以检测 1 至 100 nM 范围内的 Hg2+，线性关系良好，r = 0.99983；在 10 nM 浓度下，检测限为 0.019 nM，RSD 为 ± 0.91 %。

  DOI：

  10.1007/s10895-013-1271-1

文献信息

• Turn-On Type Fluorogenic and Chromogenic Probe for the Detection of Trace Amount of Nitrite Ion in Water
  作者：Muhammad Saleem、Razack Abdullah、In Seok Hong、Ki-Hwan Lee

  DOI：10.5012/bkcs.2013.34.2.389

  日期：2013.2.20

  A rhodamine B-based fluorescent probe for nitrite ion ($NO_2}^-$) has been designed, synthesized, characterized and its properties for recognition of $NO_2}^-$ were studied. Nearly non fluorescent probe upon reaction with nitrite ion significantly triggered the fluorescence. Fluorescence response is based on ring opening of the spirolactam of rhodamine B phenyl hydrazide showing maximum absorbance at 552 nm and maximum emission at 584 nm. Probe 3 exhibited high sensitivity and extreme selectivity for nitrite ion over other common ions and oxidants ($Cl^-$, $ClO^-$, $ClO_2}^-$, $ClO_3}^-$, $ClO_4}^-$, $SO_4}^2-}$, $SiO_3}^2-}$, $NO_3}^2-}$, $CO_3}^2-}$) examined in methanol water (1:1, v/v) at pH 7.0. The probe might be a new efficient tool for detection of nitrite ion in natural water and biological system.

  我们设计、合成并鉴定了一种基于罗丹明 B 的亚硝酸离子（$NO_2}^-$）荧光探针，并研究了其识别 $NO_2}^-$ 的特性。近乎无荧光的探针与亚硝酸根离子反应后会显著引发荧光。荧光反应是基于罗丹明 B 苯酰肼的螺内酰胺开环，在 552 纳米波长处显示最大吸光度，在 584 纳米波长处显示最大发射度。与其他常见离子和氧化剂（$Cl^-$、$ClO^-$、$ClO_2}^-$、$ClO_3}^-$、$ClO_4}^-$、$SO_4}^2-}$、$SiO_3}^2-}$、$NO_3}^2-}$、$CO_3}^2-}$）在甲醇水（1：1，v/v）中进行检测，pH 值为 7.0.该探针可能是检测天然水和生物系统中亚硝酸根离子的一种新的有效工具。
• 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.
• DE85242
  申请人：——

  公开号：——

  公开（公告）日：——
• Utilisation pour la coloration des fibres kératiniques d'une composition comprenant un composé halochromique et / ou le colorant correspondant à ce composé
  申请人：L'Oréal

  公开号：EP1972327B1

  公开（公告）日：2010-04-07
• Composition for the coloring of keratinous fibers comprising a halochromic compound and/or the dye corresponding to this compound, and method of use thereof
  申请人：Guerin Frederic

  公开号：US20080244838A1

  公开（公告）日：2008-10-09

  Disclosed herein is the use, in the coloring of keratinous fibers, such as human keratinous fibers, such as the hair, of a composition comprising at least one compound chosen from the compounds of formula (I) comprising a cyclic group G including a ring H capable of opening, the dyes corresponding to the compounds of formula (I) wherein the ring H is open, and the addition salts thereof: and a method for treating keratinous fibers employing this composition.