2-(2-(1H-indol-3-yl)vinyl)-3-(4-(diethylamino)phenyl)-4-oxo-3,4-dihydroquinazoline-6-carbonitrile | 1357307-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(2-(1H-indol-3-yl)vinyl)-3-(4-(diethylamino)phenyl)-4-oxo-3,4-dihydroquinazoline-6-carbonitrile
• CAS: 1357307-26-6
• 化学式: C₂₉H₂₅N₅O
• 分子量: 459.55
• InChiKey: GRLZJBHJCMEQHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(2-(1H-indol-3-yl)vinyl)-3-(4-(diethylamino)phenyl)-4-oxo-3,4-dihydroquinazoline-6-carbonitrile 、 四丁基氟化铵 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  A new indole incorporated chemosensor exhibiting selective colorimetric and fluorescence ratiometric signaling of fluoride

  摘要：

  We have synthesized an internal charge transfer based chemosensor. Q-1 utilizing it-rich indole as the Hdonor and the cyano-quinazolinone ring as the it-acceptor. The probe is the first example of an indole incorporated receptor that exhibits both absorbance and emission red shifts in the presence of fluoride, offering dual naked eye detection (yellow to red) as well as fluorescence ratiometric capability. The 'H NMR study supports the F--induced deprotonation of the indole N-H bond, a process that significantly perturbs both the ground as well as the excited states of the probe via the electronic charge shift. It is noteworthy that in contrast to fluoride, the commonly competing AcO- and H2PO4- as well as HSO4-, Cl-, Br-, I-, NO; and SCN- induced none or relatively negligible optical perturbation even at significantly higher concentrations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.139
• 作为产物：
  描述：

  N,N-二乙基对苯二胺 在 哌啶 、 三氯氧磷 作用下， 以 邻二甲苯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 56.0h， 生成 2-(2-(1H-indol-3-yl)vinyl)-3-(4-(diethylamino)phenyl)-4-oxo-3,4-dihydroquinazoline-6-carbonitrile
  参考文献：
  名称：

  A new indole incorporated chemosensor exhibiting selective colorimetric and fluorescence ratiometric signaling of fluoride

  摘要：

  We have synthesized an internal charge transfer based chemosensor. Q-1 utilizing it-rich indole as the Hdonor and the cyano-quinazolinone ring as the it-acceptor. The probe is the first example of an indole incorporated receptor that exhibits both absorbance and emission red shifts in the presence of fluoride, offering dual naked eye detection (yellow to red) as well as fluorescence ratiometric capability. The 'H NMR study supports the F--induced deprotonation of the indole N-H bond, a process that significantly perturbs both the ground as well as the excited states of the probe via the electronic charge shift. It is noteworthy that in contrast to fluoride, the commonly competing AcO- and H2PO4- as well as HSO4-, Cl-, Br-, I-, NO; and SCN- induced none or relatively negligible optical perturbation even at significantly higher concentrations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.139