2-[2-(6-methoxyanthracenyl)]-4,4-dimethyl-2-oxazoline

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-[2-(6-methoxyanthracenyl)]-4,4-dimethyl-2-oxazoline
• 英文别名: 2-[2-(6-methoxyanthryl)]-4,4-dimethyl-2-oxazoline；2-[9-(6-Methoxyanthranyl)]-4,4-dimethyl-2-oxazoline；2-(6-methoxyanthracen-2-yl)-4,4-dimethyl-5H-1,3-oxazole
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: WXXQNAZQMYALFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-methoxy-2-anthracene carboxylic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-[2-(6-methoxyanthracenyl)]-4,4-dimethyl-2-oxazoline
  参考文献：
  名称：

  Anthryl-Substituted Heterocycles as Acid-Sensitive Fluorescence Probes

  摘要：

  Four pH-sensitive fluorescence probes are presented which consist of an anthracene fluorophore and a pi-conjugated oxazoline, benzoxazole, or pyridine substituent. The protonation of the heterocycles increases their acceptor properties and results in significant red-shifts of the absorption and emission maxima of the anthracene chromophore. The comparison between 2-[2'-(6'-methoxy-anthryl)]-4,4-dimethyl-2-oxazoline and 2-[2'-(anthryl)]-4,4-dimethyl-2-oxazoline reveals that the donor-acceptor substitution pattern of the fluorophore is not required to achieve a red shift upon protonation. The benzoxazole and pyridine substituents offer a particular advantage due to their persistence under acidic conditions. Thus, these compounds may be used as efficient pH-sensitive fluorescence switches. Nevertheless, the switching of benzoxazole 2c requires relatively strong acidic conditions. The anthrylpyridinium exhibits a red-shifted emission in chloroform; however, it is nonfluorescent in aqueous or alcoholic solution. Although the oxazoline is not persistent under permanent acidic conditions, this heterocycle may be useful as a substituent in fluorescence indicators since it may be used to detect acid concentrations of 10(-4)-10(-5) M, which are close to the biologically relevant range.

  DOI：

  10.1021/jo047841z

文献信息

• Novel Fluorescence Probes Based on 2,6-Donor−Acceptor-Substituted Anthracene Derivatives
  作者：Heiko Ihmels、Andreas Meiswinkel、Christian J. Mohrschladt

  DOI：10.1021/ol006291y

  日期：2000.9.1

  The fluorescence properties of selected derivatives of 6-methoxyanthracene-2-carboxylic acid were studied. The corresponding ester and oxazoline derivatives exhibit a moderate solvatochromism, which is caused by the donor-acceptor interplay, The fluorescence band shift and intensity of oxazoline If may be reversibly modulated by protonation or complexation with silver ions; thus, the oxazoline heterocycle serves as a useful substituent with switchable acceptor strength.
• Anthryl-Substituted Heterocycles as Acid-Sensitive Fluorescence Probes
  作者：Heiko Ihmels、Andreas Meiswinkel、Christian J. Mohrschladt、Daniela Otto、Michael Waidelich、Michael Towler、Rick White、Martin Albrecht、Alexander Schnurpfeil

  DOI：10.1021/jo047841z

  日期：2005.5.1

  Four pH-sensitive fluorescence probes are presented which consist of an anthracene fluorophore and a pi-conjugated oxazoline, benzoxazole, or pyridine substituent. The protonation of the heterocycles increases their acceptor properties and results in significant red-shifts of the absorption and emission maxima of the anthracene chromophore. The comparison between 2-[2'-(6'-methoxy-anthryl)]-4,4-dimethyl-2-oxazoline and 2-[2'-(anthryl)]-4,4-dimethyl-2-oxazoline reveals that the donor-acceptor substitution pattern of the fluorophore is not required to achieve a red shift upon protonation. The benzoxazole and pyridine substituents offer a particular advantage due to their persistence under acidic conditions. Thus, these compounds may be used as efficient pH-sensitive fluorescence switches. Nevertheless, the switching of benzoxazole 2c requires relatively strong acidic conditions. The anthrylpyridinium exhibits a red-shifted emission in chloroform; however, it is nonfluorescent in aqueous or alcoholic solution. Although the oxazoline is not persistent under permanent acidic conditions, this heterocycle may be useful as a substituent in fluorescence indicators since it may be used to detect acid concentrations of 10(-4)-10(-5) M, which are close to the biologically relevant range.