2,2'-(naphthalene-1,5-diylbis(oxy))diacetic acid | 92423-99-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 2,2'-(naphthalene-1,5-diylbis(oxy))diacetic acid
• 英文别名: (5-carboxymethoxy-naphthalen-2-yloxy)-acetic acid；naphthalene-1,5-diyldioxy-di-acetic acid；Naphthalin-1,5-diyldioxy-di-essigsaeure；2,2'-[Naphthalene-1,5-diylbis(oxy)]diacetic acid；2-[5-(carboxymethoxy)naphthalen-1-yl]oxyacetic acid
• CAS: 92423-99-9
• 化学式: C₁₄H₁₂O₆
• 分子量: 276.246
• InChiKey: HAMZDAPGNZNQHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 2,2'-(naphthalene-1,5-diylbis(oxy))diacetic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到bis(2,5-dioxopyrrolidin-1-yl)-2,2'-(naphthalene-1,5-diylbis(oxy))diacetate
  参考文献：
  名称：

  来自水中供体-受体动态组合库的萘二甲酰亚胺基受体的模板化扩增。

  摘要：

  我们报告了一个动态的组合库，结合电子互补的来宾后，可产生高产量的四聚体受体，该受体具有平坦的疏水性，电子缺陷表面和柔性的，水溶性的含二硫化物的连接基；文库组成对模板浓度依赖性的分析可以深入了解所涉及物种的结合行为。

  DOI：

  10.1039/b816979a
• 作为产物：
  描述：

  <<5-<(methoxycarbonyl)-methoxy>-1-naphthylenyl>oxy>acetic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以87%的产率得到2,2'-(naphthalene-1,5-diylbis(oxy))diacetic acid
  参考文献：
  名称：

  来自水中供体-受体动态组合库的萘二甲酰亚胺基受体的模板化扩增。

  摘要：

  我们报告了一个动态的组合库，结合电子互补的来宾后，可产生高产量的四聚体受体，该受体具有平坦的疏水性，电子缺陷表面和柔性的，水溶性的含二硫化物的连接基；文库组成对模板浓度依赖性的分析可以深入了解所涉及物种的结合行为。

  DOI：

  10.1039/b816979a

文献信息

• Synthetic pores with sticky π-clamps
  作者：Hiroyuki Tanaka、Guillaume Bollot、Jiri Mareda、Svetlana Litvinchuk、Duy-Hien Tran、Naomi Sakai、Stefan Matile

  DOI：10.1039/b702255g

  日期：——

  In this report, we describe design, synthesis, evaluation and molecular dynamics simulations of synthetic multifunctional pores with π-acidic naphthalenediimide clamps. Experimental evidence is provided for the formation of unstable but inert, heterogeneous and acid-insensitive dynamic tetrameric pores that are sensitive to base and ionic strength. Blockage experiments reveal that the introduction of aromatic electron donor–acceptor interactions provides access to the selective recognition of π-basic intercalators within the pore. This breakthrough is important for the application of synthetic pores as multianalyte sensors.

  在本报告中，我们描述了具有π-酸性萘二酰亚胺夹具的合成多功能孔的设计、合成、评估和分子动力学模拟。实验证据表明，形成了不稳定但惰性、异质和抗酸动态四聚孔，这些孔对碱和离子强度敏感。阻塞实验揭示，引入芳香电子给体-接受体相互作用使得可以选择性识别孔内的π-碱性插层物。这一突破对于将合成孔应用于多分析物传感器具有重要意义。
• Janczewski et al., Przemysl Chemiczny, 1958, vol. 37, p. 784,786
  作者：Janczewski et al.

  DOI：——

  日期：——
• Different geometrical arrangements in carboxylate coordination polymers of flexible dicarboxylic acid
  作者：Himangshu Deka、Rupam Sarma、Satchi Kumari、Alika Khare、Jubaraj B. Baruah

  DOI：10.1016/j.jssc.2011.05.004

  日期：2011.7

  Dicarboxylate coordination polymers (1-5) of Mn(II), Ni(II), Cu(II), Zn(II) and Cd(II), respectively, derived from (7-carboxymethoxy-naphthalen-2-yloxy)-acetic acid (L1H2) are synthesized and characterized. Depending on the coordination sites around the metal centers and coordination mode of the ligand, dimensionality of these polymers varies. The dicarboxylates adopt three spatial orientations: in-plane linear coordination, out-of-plane cis coordination and out-of-plane trans coordination mode. Both the cis and trans out-of-plane coordination modes are found to exist only if the ancillary ligand pyridine is coordinated to the metal ion. When the aquoligand coordinates the in-plane linear coordination mode of L-1 predominates. The coordination polymers 4 and 5 show photoluminescence in solution. The dicarboxylate of (5-carboxymethoxy-naphthalen-1-yloxy)-acetic acid (L2H2) does not form coordination polymer under ambient conditions, but prefers to remain as uncoordinated anion providing hydrophobic confinement to hexa-aquometal(II) cation. Compound 3 crystallizes in P2(1) space group and it shows broadband ultra-violet fluorescence centered at 352.9 nm on focusing 632.8 nm He:Ne laser. (C) 2011 Elsevier Inc. All rights reserved.
• Syntheses, characterization and crystal structure of d10 coordination architectures: From 1D to 3D complexes based on mixed ligands
  作者：Lian-Jie Li、Xin-Long Wang、Kui-Zhan Shao、Zhong-Min Su、Qiang Fu

  DOI：10.1016/j.ica.2012.05.037

  日期：2012.9

  Three coordination polymers, namely, [Zn-2(ndd)(2)(2,2'-bpy)(2)center dot 2H(2)O](n) (1) [Cd(ndd)(2,2'-bpy)](n) (2), and [Cd(ndd)(1,4-pyb)](n) (3), where H(2)ndd = 2,2'-(naphthalene-1,5-diylbis(oxy))diacetic acid, 1,4-pyb = 1,4-bis(pyridin-4-ylmethoxy)benzene and 2,2'-bpy = 2,2'-bipyridine, have been synthesized under hydrothermal conditions and characterized by single-crystal X-ray diffraction analyses, powder X-ray diffraction and thermogravimetric analysis. Compound 1 can be considered as a 1D chain, which is further linked through the strongly multiple pi-pi interactions into a 3D supramolecular structure. By changing the metal ions, compound 2 is the 2D square structure (10.96 x 15.20 angstrom) with the 4(4).6(2) topology. By changing the auxiliary ligand, compound 3 presents a new (4,5)-connected 3D network with the point symbol of (4(2).6(5).8(3))(2).(6(6)). Furthermore, compounds 1-3 show good fluorescence properties in the solid state at room temperature. Crown Copyright (C) 2012 Published by Elsevier B. V. All rights reserved.
• Effect of metal ions on the structures of metal–organic frameworks based on mixed ligands
  作者：Lian-Jie Li、Xin-Long Wang、Liang Zhao、Kui-Zhan Shao、Hai-Ning Wang、Gang Yuan、Zhong-Min Su

  DOI：10.1016/j.inoche.2011.11.004

  日期：2012.1

  Two metal-organic frameworks, namely, [Zn(L)(phen)(H2O)](n) (1) and [Cd(L)(phen)](n) (2), where H2L = 2,2'-(naphthalene-1,5-diylbis(oxy))diacetic acid and phen = 1,10-phenanthroline, have been synthesized under hydrothermal conditions and characterized by single crystal X-ray diffraction analyses, powder X-ray diffraction and thermogravimetric analysis. Compound 1 can be described as a 3D supramolecular architecture formed via the strong pi-pi interactions. While, compound 2, obtained by changing the metal ions, exhibits a 3D metal-organic frameworks of PtS topology with the square window (the dimensions is 11.454 x 25.847 angstrom). The different structures between 1 and 2 indicate that metal ions have significant effects on the final complexes. Moreover, compounds 1 and 2 show good luminescent properties in the solid state at room temperature. (C) 2011 Elsevier B.V. All rights reserved.