Ethyl 2-[1-[2-(2-ethoxy-2-oxoethoxy)naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetate | 1351952-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2-[1-[2-(2-ethoxy-2-oxoethoxy)naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetate
• CAS: 1351952-56-1
• 化学式: C₂₈H₂₆O₆S
• 分子量: 490.577
• InChiKey: ZALAKMLIZHAGGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[1-[2-(2-ethoxy-2-oxoethoxy)naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以95%的产率得到1,1'-thio-bis-(2-naphthoxy-acetic acid)
  参考文献：
  名称：

  Benzimidazole Conjugate of 1,1′-Thiobis(2-naphthol) as Switch-On Fluorescence Receptor for Ag⁺ and the Complex as Secondary Recognition Ensemble toward Cys, Asp, and Glu in Aqueous Methanolic Solution: Synthesis, Characterization, Ion and Amino Acid Recognition, Computational Studies, and Microscopy Features

  摘要：

  A new 1,1'-thiobis(2-naphthoxy)-based receptor molecule (L) containing a benzimidazole moiety has been synthesized and characterized by H-1 NMR, ESI-MS, and elemental analysis. The selectivity of L has been explored in aqueous methanol, resulting in selective (7.5 +/- 0.5)-fold switch-on fluorescence response toward Ag+ among 14 different transition, alkali, and alkaline earth metal ions studied. The complexation of Ag+ by L has been addressed by ESI-MS, H-1 NMR, and UV-vis spectra. Microstructural features of L and its Ag+ complex have been measured by AFM and TEM. The morphological features of L alone and L in the presence of Ag+ differ dramatically both in shape and size, and the ion induces the formation of chains owing to its coordinating ability toward benzimidazole. Further, the in situ [Ag+-L] complex was titrated against 20 naturally occurring amino acids and found that this complex acts as a secondary recognition ensemble toward Cys, Asp, and Glu by switch-off fluorescence.

  DOI：

  10.1021/jo201926q
• 作为产物：
  描述：

  1,1'-硫联二(2-萘酚) 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以85%的产率得到Ethyl 2-[1-[2-(2-ethoxy-2-oxoethoxy)naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetate
  参考文献：
  名称：

  Benzimidazole Conjugate of 1,1′-Thiobis(2-naphthol) as Switch-On Fluorescence Receptor for Ag⁺ and the Complex as Secondary Recognition Ensemble toward Cys, Asp, and Glu in Aqueous Methanolic Solution: Synthesis, Characterization, Ion and Amino Acid Recognition, Computational Studies, and Microscopy Features

  摘要：

  A new 1,1'-thiobis(2-naphthoxy)-based receptor molecule (L) containing a benzimidazole moiety has been synthesized and characterized by H-1 NMR, ESI-MS, and elemental analysis. The selectivity of L has been explored in aqueous methanol, resulting in selective (7.5 +/- 0.5)-fold switch-on fluorescence response toward Ag+ among 14 different transition, alkali, and alkaline earth metal ions studied. The complexation of Ag+ by L has been addressed by ESI-MS, H-1 NMR, and UV-vis spectra. Microstructural features of L and its Ag+ complex have been measured by AFM and TEM. The morphological features of L alone and L in the presence of Ag+ differ dramatically both in shape and size, and the ion induces the formation of chains owing to its coordinating ability toward benzimidazole. Further, the in situ [Ag+-L] complex was titrated against 20 naturally occurring amino acids and found that this complex acts as a secondary recognition ensemble toward Cys, Asp, and Glu by switch-off fluorescence.

  DOI：

  10.1021/jo201926q

文献信息

• Benzimidazole Conjugate of 1,1′-Thiobis(2-naphthol) as <i>Switch-On</i> Fluorescence Receptor for Ag⁺ and the Complex as Secondary Recognition Ensemble toward Cys, Asp, and Glu in Aqueous Methanolic Solution: Synthesis, Characterization, Ion and Amino Acid Recognition, Computational Studies, and Microscopy Features
  作者：Jayaraman Dessingou、Atanu Mitra、Khatija Tabbasum、Garima Singh Baghel、Chebrolu P. Rao

  DOI：10.1021/jo201926q

  日期：2012.1.6

  A new 1,1'-thiobis(2-naphthoxy)-based receptor molecule (L) containing a benzimidazole moiety has been synthesized and characterized by H-1 NMR, ESI-MS, and elemental analysis. The selectivity of L has been explored in aqueous methanol, resulting in selective (7.5 +/- 0.5)-fold switch-on fluorescence response toward Ag+ among 14 different transition, alkali, and alkaline earth metal ions studied. The complexation of Ag+ by L has been addressed by ESI-MS, H-1 NMR, and UV-vis spectra. Microstructural features of L and its Ag+ complex have been measured by AFM and TEM. The morphological features of L alone and L in the presence of Ag+ differ dramatically both in shape and size, and the ion induces the formation of chains owing to its coordinating ability toward benzimidazole. Further, the in situ [Ag+-L] complex was titrated against 20 naturally occurring amino acids and found that this complex acts as a secondary recognition ensemble toward Cys, Asp, and Glu by switch-off fluorescence.