(Z)-3-(2-oxo-2-phenylethylidene)-6-methoxy-3,4-dihydroquinoxalin-2-one | 1393599-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-3-(2-oxo-2-phenylethylidene)-6-methoxy-3,4-dihydroquinoxalin-2-one
• 英文别名: (3Z)-6-methoxy-3-phenacylidene-1,4-dihydroquinoxalin-2-one
• CAS: 1393599-45-5
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: BBEXKDJSTIAHDN-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,4-二氧代-4-苯基-丁酸 、 4-甲氧基邻苯二胺 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-3-(2-oxo-2-phenylethylidene)-6-methoxy-3,4-dihydroquinoxalin-2-one 、 (Z)-3-(2-oxo-2-phenylethylidene)-7-methoxy-3,4-dihydroquinoxalin-2-one
  参考文献：
  名称：

  The effect of substituents on the response of 3,4-dihydro-3-(2-oxo-2-phenylethylidene)-quinoxalin-2(1H)-one derivatives toward binding of Cu2+

  摘要：

  A new series of fluorogenic chelating reagents based on phenylethylidene-3,4-dihydro-1H-quinoxalin-2-one with different substituents (attached either to the quinoxaline-2-one (3) or phenyl ring (4)) have been investigated to examine the effect of the substituent (nature/position) on the spectral properties and response toward Cu2+ in the presence of other metal cations, in ethanol. It was found that all of the examined ligands exhibit a pronounced response to Cu2+ addition resulting in a red-shift in the UV-vis spectra and a strong quenching in the fluorescence spectra. Among the ligands examined, 3a exhibits the highest selectivity toward various metal cations. In general it appears that the best response selectivity of these ligands toward Cu2+ ion is obtained by either EDG in 3 or EWG in 4. For example, the fluorescence intensity of 3a (with OMe substituent) increases to about three times that of the unsubstituted derivative. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.071

文献信息

• The effect of substituents on the response of 3,4-dihydro-3-(2-oxo-2-phenylethylidene)-quinoxalin-2(1H)-one derivatives toward binding of Cu2+
  作者：Efrat Korin、Beny Cohen、Yue-Xia Bai、Cheng-Chu Zeng、James Y. Becker

  DOI：10.1016/j.tet.2012.06.071

  日期：2012.9

  A new series of fluorogenic chelating reagents based on phenylethylidene-3,4-dihydro-1H-quinoxalin-2-one with different substituents (attached either to the quinoxaline-2-one (3) or phenyl ring (4)) have been investigated to examine the effect of the substituent (nature/position) on the spectral properties and response toward Cu2+ in the presence of other metal cations, in ethanol. It was found that all of the examined ligands exhibit a pronounced response to Cu2+ addition resulting in a red-shift in the UV-vis spectra and a strong quenching in the fluorescence spectra. Among the ligands examined, 3a exhibits the highest selectivity toward various metal cations. In general it appears that the best response selectivity of these ligands toward Cu2+ ion is obtained by either EDG in 3 or EWG in 4. For example, the fluorescence intensity of 3a (with OMe substituent) increases to about three times that of the unsubstituted derivative. (C) 2012 Elsevier Ltd. All rights reserved.