3',6'-bis(diethylamino)-2-(2-hydroxyethylamino)spiro[iso-indoline-1,9'-xanthen]-3-one | 1167601-09-3

• 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-(2-hydroxyethylamino)spiro[iso-indoline-1,9'-xanthen]-3-one
• 英文别名: N-hydroxyl ethyl-N′-rhodamine hydrazide；3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino)spiro[isoindoline-1,9'-xanthen]-3-one；3',6'-bis(diethylamino)-2-(2-hydroxyethylamino)spiro[isoindole-3,9'-xanthene]-1-one
• CAS: 1167601-09-3
• 化学式: C₃₀H₃₆N₄O₃
• 分子量: 500.641
• InChiKey: VKDXWGAWFLVOJC-UHFFFAOYSA-N

物化性质

• 沸点：
  682.4±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',6'-bis(diethylamino)-2-(2-hydroxyethylamino)spiro[iso-indoline-1,9'-xanthen]-3-one 在 Cu⁺ 作用下， 生成 罗丹明B
  参考文献：
  名称：

  Rhodamine-based ‘turn-on’ fluorescent probe for Cu(II) and its fluorescence imaging in living cells

  摘要：

  A novel rhodamine spirolactam derivative 3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino) spiro[iso-indoline-1,9'-xanthen]-3-one (RO1) was synthesized, and characterized by high-resolution mass spectrometry (HRMS), X-ray crystallography, Infrared spectroscopy (IR), and H-1 NMR and C-13 NMR spectroscopy. RO1 exhibited highly sensitive and exclusively selective fluorescence response toward Cu2+ over other metal ions with a detection limit of 0.56 ppb in mixed aqueous solution. The fluorescence was pH-independent in the wide range pH 3.1-11.6. The turn-on fluorescence enhancement of the probe is based on Cu2+ induced ring-opening mechanism of the rhodamine spirolactam. Moreover, by means of fluorescence microscopy experiments, it was demonstrated that RO1 could monitor trace Cu2+ changes by live cell imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.052
• 作为产物：
  描述：

  2-[[3',6'-bis(diethylamino)-3-oxospiro[1-isoindole-1,9'-xanthen]-2-yl]imino]acetaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以89.9%的产率得到3',6'-bis(diethylamino)-2-(2-hydroxyethylamino)spiro[iso-indoline-1,9'-xanthen]-3-one
  参考文献：
  名称：

  Rhodamine-based ‘turn-on’ fluorescent probe for Cu(II) and its fluorescence imaging in living cells

  摘要：

  A novel rhodamine spirolactam derivative 3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino) spiro[iso-indoline-1,9'-xanthen]-3-one (RO1) was synthesized, and characterized by high-resolution mass spectrometry (HRMS), X-ray crystallography, Infrared spectroscopy (IR), and H-1 NMR and C-13 NMR spectroscopy. RO1 exhibited highly sensitive and exclusively selective fluorescence response toward Cu2+ over other metal ions with a detection limit of 0.56 ppb in mixed aqueous solution. The fluorescence was pH-independent in the wide range pH 3.1-11.6. The turn-on fluorescence enhancement of the probe is based on Cu2+ induced ring-opening mechanism of the rhodamine spirolactam. Moreover, by means of fluorescence microscopy experiments, it was demonstrated that RO1 could monitor trace Cu2+ changes by live cell imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.052

文献信息

• Fluorescent Polyamide-Based Rhodamine Hydrazide Moieties with Oxethyl as Spacer for Detection of Cr3+, Fe3+, and Hg2+ Ions in Water
  作者：Tong-Mou Geng、Xie Wang、Hui Jiang、Wan Song、Ruo-Fan Ni、Jian Chen、Yu Wang

  DOI：10.1007/s10895-016-1785-4

  日期：2016.5

  hydrazide (ARBHE) was synthesized from N-hydroxyl ethyl-N′-rhodamine hydrazide (RBHE) and acryloyl chloride (Ac) in the presence of triethylamine in dry dichloromethane (CH2Cl2) at room temperature. The synthesized ARBHE was identified by FTIR, 1H NMR spectra and elementary analysis. Copolymer poly(AM-ARBHE) of ARBHE and AM was synthesized with thermal initiator by free radical precipitation polymerization

  在干燥条件下，在三乙胺存在下，由N-羟乙基-N'-若丹明酰肼（RBHE）和丙烯酰氯（Ac）合成带有x吨基团的丙烯酸单体，丙烯酸N-氧乙酯-N'-若丹明B酰肼（ARBHE）在室温下为二氯甲烷（CH 2 Cl 2）。通过FTIR，1 H NMR光谱和元素分析鉴定合成的ARBHE 。用热引发剂通过自由基沉淀聚合反应合成了ARBHE和AM的共聚物聚（AM-ARBHE），并通过FTIR和1 H NMR对其进行了表征。其分子量（Mη）为7.03×10 3  g mol -1聚合物链中若丹明单元的含量以摩尔分数计为1.44％。聚（AM-ARBHE）检测不同金属阳离子（Ag +，Ba 2 +，Cd 2+ Co 2 +，Cr 3+，Cu 2 +，Co 2+ K +，La 3+，Mg 2的能力对水中的+，Na +，Ni 2 +，Pb 2 +，Fe 2 +，Fe 3+，Hg 2+和Zn 2+进行了研究。在添加Cr
• Rhodamine-based ‘turn-on’ fluorescent probe for Cu(II) and its fluorescence imaging in living cells
  作者：Mao-Zhong Tian、Ming-Ming Hu、Jiang-Li Fan、Xiao-Jun Peng、Jing-Yun Wang、Shi-Guo Sun、Rong Zhang

  DOI：10.1016/j.bmcl.2013.03.052

  日期：2013.5

  A novel rhodamine spirolactam derivative 3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino) spiro[iso-indoline-1,9'-xanthen]-3-one (RO1) was synthesized, and characterized by high-resolution mass spectrometry (HRMS), X-ray crystallography, Infrared spectroscopy (IR), and H-1 NMR and C-13 NMR spectroscopy. RO1 exhibited highly sensitive and exclusively selective fluorescence response toward Cu2+ over other metal ions with a detection limit of 0.56 ppb in mixed aqueous solution. The fluorescence was pH-independent in the wide range pH 3.1-11.6. The turn-on fluorescence enhancement of the probe is based on Cu2+ induced ring-opening mechanism of the rhodamine spirolactam. Moreover, by means of fluorescence microscopy experiments, it was demonstrated that RO1 could monitor trace Cu2+ changes by live cell imaging. (C) 2013 Elsevier Ltd. All rights reserved.