1,1'-thio-bis-(2-naphthoxy-acetic acid) | 930598-37-1

• 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: 1,1'-thio-bis-(2-naphthoxy-acetic acid)
• 英文别名: 2-[1-[2-(Carboxymethoxy)naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxyacetic acid
• CAS: 930598-37-1
• 化学式: C₂₄H₁₈O₆S
• 分子量: 434.469
• InChiKey: JAIFUHCHBINYKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1'-thio-bis-(2-naphthoxy-acetic acid) 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Efficient Routes for the Synthesis of Dinaphthosulfide (BINOL Derivatives) and Dibenzosulfide Aza Podands Containing Ethanolamine

  摘要：

  Four new dinaphthosulfide and dibenzosulfide aza podands were synthesized. The synthesis of these podands was performed under three different reaction conditions: 1) diester, K(2)CO(3), methanol, and RT; 2) diester, ethanolamine, and microwave (MW); and 3) diacid dichloride, ethanolamine, Et(3)N, CH(2)Cl(2), RT. Two kinds of diester (dinaphthosulfide and dibenzosulfide) were used for the preparation of dihydroxy podands. These dihydroxy podands were reacted with thionyl chloride to afford dichloro podands. The second route gave excellent yields of dihydroxy podands. Dichloro podands are more soluble than dihydroxy podands in conventional solvents such as methanol, chloroform, and acetonitrile.

  DOI：

  10.1080/10426500802417059
• 作为产物：
  描述：

  1,1'-硫联二(2-萘酚) 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 36.0h， 生成 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

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.
• Efficient Routes for the Synthesis of Dinaphthosulfide (BINOL Derivatives) and Dibenzosulfide Aza Podands Containing Ethanolamine
  作者：Esmael Rostami、Davood Heidaryan、Hanif Fattahi、Abbas Shockravi、Mehdi Zarei、Farokh Rakhshanderu

  DOI：10.1080/10426500802417059

  日期：2009.7.13

  Four new dinaphthosulfide and dibenzosulfide aza podands were synthesized. The synthesis of these podands was performed under three different reaction conditions: 1) diester, K(2)CO(3), methanol, and RT; 2) diester, ethanolamine, and microwave (MW); and 3) diacid dichloride, ethanolamine, Et(3)N, CH(2)Cl(2), RT. Two kinds of diester (dinaphthosulfide and dibenzosulfide) were used for the preparation of dihydroxy podands. These dihydroxy podands were reacted with thionyl chloride to afford dichloro podands. The second route gave excellent yields of dihydroxy podands. Dichloro podands are more soluble than dihydroxy podands in conventional solvents such as methanol, chloroform, and acetonitrile.