2-[4-(Dibutylamino)phenyl]-6-(ethoxymethyl)-3-hydroxychromen-4-one | 1234679-38-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-[4-(Dibutylamino)phenyl]-6-(ethoxymethyl)-3-hydroxychromen-4-one
• CAS: 1234679-38-9
• 化学式: C₂₆H₃₃NO₄
• 分子量: 423.552
• InChiKey: MHPDLPKYELZBRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-(Dibutylamino)phenyl]-6-(ethoxymethyl)-3-hydroxychromen-4-one 在 氢溴酸 、 碳酸氢钠 作用下， 反应 3.0h， 生成 6-(bromomethyl)-2-(4-(dibutylamino)phenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of 3-hydroxyflavone fluorescent probes and study of their fluorescence properties

  摘要：

  Direct measurement of dipole potential in biological membranes has been impossible and 3-hydroxyflavones (3HFs) have allowed detection of changes in dipole potential in biological systems. In the present study, sixteen derivatives of 3HF with aliphatic hydrocarbon chains of different lengths at 4'-position and 6-position were synthesized The basic fluorescence properties of 3HFs are maintained in all the probes in terms of strong blue shift in maximum fluorescence emission wavelength and >100 fold increase in quantum yield in organic solvents and in dioleoylphosphatidylcholine (DOPC) small unilamellar vesicles (SUV) in comparison to in aqueous Hepes buffer (15 mmol/L, pH 7.4). More importantly, the ability of the new compounds to report dipole potential changes in biological systems are also maintained, since all the new probes showed spectrum properties that are similar to yet different from that of F4N1. which potentially may allow more sensitive measurement of the dipole potential change in membranes. (C) 2009 Wen Bao Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.12.003
• 作为产物：
  描述：

  乙醇 、 2-羟基-5-氯甲基苯乙酮 、 4-(二丁基氨基)苯甲醛 在 sodium hydroxide 、 双氧水 、 硫酸 作用下， 以 水 、 乙醇 为溶剂， 反应 0.5h， 生成 2-[4-(Dibutylamino)phenyl]-6-(ethoxymethyl)-3-hydroxychromen-4-one
  参考文献：
  名称：

  Synthesis of 3-hydroxyflavone fluorescent probes and study of their fluorescence properties

  摘要：

  Direct measurement of dipole potential in biological membranes has been impossible and 3-hydroxyflavones (3HFs) have allowed detection of changes in dipole potential in biological systems. In the present study, sixteen derivatives of 3HF with aliphatic hydrocarbon chains of different lengths at 4'-position and 6-position were synthesized The basic fluorescence properties of 3HFs are maintained in all the probes in terms of strong blue shift in maximum fluorescence emission wavelength and >100 fold increase in quantum yield in organic solvents and in dioleoylphosphatidylcholine (DOPC) small unilamellar vesicles (SUV) in comparison to in aqueous Hepes buffer (15 mmol/L, pH 7.4). More importantly, the ability of the new compounds to report dipole potential changes in biological systems are also maintained, since all the new probes showed spectrum properties that are similar to yet different from that of F4N1. which potentially may allow more sensitive measurement of the dipole potential change in membranes. (C) 2009 Wen Bao Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.12.003

文献信息

• Synthesis of 3-hydroxyflavone fluorescent probes and study of their fluorescence properties
  作者：Xiao Dong Zhao、Chang Jun Sun、Qing Qiang Yao、Wen Bao Li

  DOI：10.1016/j.cclet.2009.12.003

  日期：2010.5

  Direct measurement of dipole potential in biological membranes has been impossible and 3-hydroxyflavones (3HFs) have allowed detection of changes in dipole potential in biological systems. In the present study, sixteen derivatives of 3HF with aliphatic hydrocarbon chains of different lengths at 4'-position and 6-position were synthesized The basic fluorescence properties of 3HFs are maintained in all the probes in terms of strong blue shift in maximum fluorescence emission wavelength and >100 fold increase in quantum yield in organic solvents and in dioleoylphosphatidylcholine (DOPC) small unilamellar vesicles (SUV) in comparison to in aqueous Hepes buffer (15 mmol/L, pH 7.4). More importantly, the ability of the new compounds to report dipole potential changes in biological systems are also maintained, since all the new probes showed spectrum properties that are similar to yet different from that of F4N1. which potentially may allow more sensitive measurement of the dipole potential change in membranes. (C) 2009 Wen Bao Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.