(S)-2-butyl-6-((2-((2-((tert-butyldimethylsilyl)oxy)-1-phenylethyl)amino)pyridin-4-yl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1375415-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (S)-2-butyl-6-((2-((2-((tert-butyldimethylsilyl)oxy)-1-phenylethyl)amino)pyridin-4-yl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• CAS: 1375415-31-8
• 化学式: C₃₅H₄₂N₄O₃Si
• 分子量: 594.829
• InChiKey: MMKMHGSSHVHMKO-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  83.56
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-butyl-6-((2-((2-((tert-butyldimethylsilyl)oxy)-1-phenylethyl)amino)pyridin-4-yl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 四丁基氟化铵 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Reaction-Based Fluorescent Probe for Selective Discrimination of Thiophenols over Aliphaticthiols and Its Application in Water Samples

  摘要：

  The development of highly sensitive and selective detection techniques for the discrimination of relevant toxic benzenethiols and biologically active aliphatic thiols is of considerable importance in the fields of chemical, biological, and environmental sciences. In this article, we describe a new design of reaction-based fluorescent probe for discrimination of thiophenols over aliphaticthiols through intramolecular charge transfer pathways using N-butyl-4-amino-1,8-naphthalimide as a fluorophore, the strongly electron-withdrawing 2,4-dinitrobenzenesulfonamide group as a recognition unit, and 2,3-dihydroimidazo-[1,2-a] pyridine moiety as a linker. This rational design not only affords finely tunable spectroscopic properties by adding 2,3-dihydroimidazo-[1,2-a] pyridine moiety but also provides the chance to regulate the selectivity and sensitivity of the probe due to the formation of a new type of potentially reversible sulfonamide bond through 4-dimethylaminopyridine-like resonance. The developed probe displayed high off/on signal ratios, good selectivity, and sensitivity with a detection limit of 20 nM and a relative standard deviation of 1.7% for 11 replicate detections of 0.33 mu M thiophenol and was successfully applied to the determination of thiophenols in water samples with quantitative recovery (from 94% to 97%) demonstrating its application prospect for thiophenols sensing in environmental and biological sciences.

  DOI：

  10.1021/ac300512b
• 作为产物：
  描述：

  (S)-N-(2-((tert-butyldimethylsilyl)oxy)-1-phenylethyl)-4-nitropyridin-2-amine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲醇 、 甲苯 为溶剂， 60.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 生成 (S)-2-butyl-6-((2-((2-((tert-butyldimethylsilyl)oxy)-1-phenylethyl)amino)pyridin-4-yl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Reaction-Based Fluorescent Probe for Selective Discrimination of Thiophenols over Aliphaticthiols and Its Application in Water Samples

  摘要：

  The development of highly sensitive and selective detection techniques for the discrimination of relevant toxic benzenethiols and biologically active aliphatic thiols is of considerable importance in the fields of chemical, biological, and environmental sciences. In this article, we describe a new design of reaction-based fluorescent probe for discrimination of thiophenols over aliphaticthiols through intramolecular charge transfer pathways using N-butyl-4-amino-1,8-naphthalimide as a fluorophore, the strongly electron-withdrawing 2,4-dinitrobenzenesulfonamide group as a recognition unit, and 2,3-dihydroimidazo-[1,2-a] pyridine moiety as a linker. This rational design not only affords finely tunable spectroscopic properties by adding 2,3-dihydroimidazo-[1,2-a] pyridine moiety but also provides the chance to regulate the selectivity and sensitivity of the probe due to the formation of a new type of potentially reversible sulfonamide bond through 4-dimethylaminopyridine-like resonance. The developed probe displayed high off/on signal ratios, good selectivity, and sensitivity with a detection limit of 20 nM and a relative standard deviation of 1.7% for 11 replicate detections of 0.33 mu M thiophenol and was successfully applied to the determination of thiophenols in water samples with quantitative recovery (from 94% to 97%) demonstrating its application prospect for thiophenols sensing in environmental and biological sciences.

  DOI：

  10.1021/ac300512b