(2,4,5-tris-carboxymethylsulfanyl-3,6-dihydroxy-phenylsulfanyl)-acetic acid | 6285-66-1

• 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: (2,4,5-tris-carboxymethylsulfanyl-3,6-dihydroxy-phenylsulfanyl)-acetic acid
• 英文别名: 2,3,5,6-tetrakis-(carboxymethylthio)-benzenediol；(3,6-dihydroxy-benzene-1,2,4,5-tetrayltetramercapto)-tetra-acetic acid；3,6-Dihydroxy-1,2,4,5-tetrakis-carboxymethylmercapto-benzol；(3,6-Dihydroxy-benzen-1,2,4,5-tetrayltetramercapto)-tetra-essigsaeure；2,3,5,6-Tetrakis-carboxymethylmercapto-hydrochinon；2,2',2'',2'''-[(3,6-Dihydroxybenzene-1,2,4,5-tetrayl)tetrasulfanediyl]tetraacetic acid；2-[2,4,5-tris(carboxymethylsulfanyl)-3,6-dihydroxyphenyl]sulfanylacetic acid
• CAS: 6285-66-1
• 化学式: C₁₄H₁₄O₁₀S₄
• 分子量: 470.523
• InChiKey: MOYCBOGJZXVOLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  288-289 °C (decomp)
• 沸点：
  689.5±55.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  291
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2,4,5-tris-carboxymethylsulfanyl-3,6-dihydroxy-phenylsulfanyl)-acetic acid 在 硝酸 作用下， 生成 (3,6-dioxo-cyclohexa-1,4-diene-1,2,4,5-tetrayltetramercapto)-tetra-acetic acid
  参考文献：
  名称：

  The Interaction of Thiols and Quinones¹

  摘要：

  DOI：

  10.1021/ja01195a513
• 作为产物：
  描述：

  巯基乙酸 、 对苯醌 以 水 为溶剂， 反应 0.5h， 以56%的产率得到(2,4,5-tris-carboxymethylsulfanyl-3,6-dihydroxy-phenylsulfanyl)-acetic acid
  参考文献：
  名称：

  Synthesis and photophysical study of an octahedral silver(I) 1-D coordination polymer with thiocarboxylic-acid-based ligands

  摘要：

  We describe the synthesis of a unique 1-D silver coordination polymer, in which the silver metal center is, unusually, six-coordinated. The reaction of 2,3,5,6-tetrakis-(carboxymethylthio)-benzenediol (H2L) and AgNO3 in a 1:2 ratio resulted in the esterification of the carboxylic acid groups and the oxidation of quinol to quinone. As a result, a methylesterthioquinone ligand (L-1) was obtained. By increasing the molar ratio of Ag to four equivalents, a 1-D coordination polymer, [AgL1(NO3)](n) (1), was obtained. The simple reaction of L-1 and AgNO3 in a 1:2 ratio also produced complex 1 in quantitative yield. Both the esterified ligand L-1 and the coordination polymer 1 were fully characterized by infrared and H-1 NMR spectroscopy, elemental analysis, electrospray ionization mass spectrometry, and single crystal X-ray crystallography. The single crystal X-ray diffraction measurements revealed that the Ag metal center has an octahedral geometry with eta(2)-nitrate ligands. The photophysical properties of complexes are also explored. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.08.035

文献信息

• [EN] HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES<br/>[FR] QUINONES ROBUSTES SOLUBLES DANS L'EAU À POTENTIEL FAIBLE ET ÉLEVÉ
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2018160618A1

  公开（公告）日：2018-09-07

  Substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, and anthrahydroquinones are disclosed herein. The substituted hydroquinones and catechols have the formula: while the substituted 1,4-quinones or 1,2-have the corresponding oxidized structure (1,4- benzoquinones and 1,2-benzoquinones). One or more of R1, R2, R3 and R4 include a sulfonate moiety, a sulfonimide moiety, or a phosphonate moiety, and any of R1, R2, R3 and R4 that do not include one of these moieties include an alkyl, a cycloalkyl, a thioether, a sulfoxide, a sulfone, a haloalkyl, a halogen, a nitrile, an imide, a pyrazole, or combinations thereof. The substituted anthraquinones have the formula: while the substituted anthrahydroquinones have the corresponding reduced structure. One or more of R1-R8 have a sulfonate or phosphate tethered to the ring by a thi other, amine, or ether including one or more alkyl groups. Any of R1-R8 that do not contain one of these moieties include an alkyl, a cycloalkyl, a thiother, a sulfoxide, a sulfone, a haloalkyl, a halogen, a hydroxyl, an alkoxyl, an ether, an amine, or hydrogen The substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, or anthrahydroquinones are soluble in water, stable in aqueous acid solutions, and have useful reduction potentials in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.

  本文披露了取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌和蒽氢醌。取代的对苯二酚和邻苯二酚的化学式为：而取代的1,4-喹啉醌或1,2-喹啉醌具有相应的氧化结构（1,4-苯醌和1,2-苯醌）。R1、R2、R3和R4中的一个或多个包括磺酸酯基、磺酰胺基或膦酸酯基，而不包括这些基团之一的R1、R2、R3和R4包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、腈、酰亚胺、吡唑或其组合。取代的蒽醌的化学式为：而取代的蒽氢醌具有相应的还原结构。R1-R8中的一个或多个通过硫醚、胺或醚与环相连，包括一个或多个烷基。不含这些基团之一的R1-R8包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、羟基、烷氧基、醚、胺或氢的任何基团。取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌或蒽氢醌在水中溶解，在水酸性溶液中稳定，并且在氧化形式中具有有用的还原电位。因此，它们可以用作新兴技术中的氧化还原中介体，例如在介导燃料电池或有机介质流动电池中。
• High solubility thioether quinones
  申请人：Wisconsin Alumni Research Foundation

  公开号：US11021441B2

  公开（公告）日：2021-06-01

  Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R1, R2, R3 and R4 comprise a thioether moiety and a sulfonate moiety, and wherein each R1, R2, R3 and R4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.

  本文公开了取代的氢醌和醌类化合物以及合成此类化合物的方法。取代的对苯二酚具有以下式子 而取代的醌类具有相应的氧化结构（1,4-苯醌）。R1、R2、R3 和 R4 中的一、二、三或全部四个包含硫醚分子和磺酸分子，其中每个不包含硫醚分子和磺酸分子的 R1、R2、R3 和 R4 独立地是氢、烷基或取电子基团。 取代的对苯二酚和醌类可溶于水，在酸性水溶液中稳定，在氧化形式下具有较高的还原电位。因此，它们可用作新兴技术中的氧化还原介质，如介导燃料电池或有机介质液流电池。
• High-Solubility Thioether Quinones
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20190055193A1

  公开（公告）日：2019-02-21

  Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydrroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R 1 , R 2 , R 3 and R 4 comprise a thioether moiety and a sulfonate moiety, and wherein each R 1 , R 2 , R 3 and R 4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.
• High Solubility Thioether Quinones
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20200223794A1

  公开（公告）日：2020-07-16

  Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R 1 , R 2 , R 3 and R 4 comprise a thioether moiety and a sulfonate moiety, and wherein each R 1 , R 2 , R 3 and R 4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.
• Synthesis and photophysical study of an octahedral silver(I) 1-D coordination polymer with thiocarboxylic-acid-based ligands
  作者：Ume Farwa、Moumita Pait、Ji Yeon Ryu、Sunwoo Lee、Youngjo Kim、Hyoung-Ryun Park、Junseong Lee

  DOI：10.1016/j.poly.2017.08.035

  日期：2017.11

  We describe the synthesis of a unique 1-D silver coordination polymer, in which the silver metal center is, unusually, six-coordinated. The reaction of 2,3,5,6-tetrakis-(carboxymethylthio)-benzenediol (H2L) and AgNO3 in a 1:2 ratio resulted in the esterification of the carboxylic acid groups and the oxidation of quinol to quinone. As a result, a methylesterthioquinone ligand (L-1) was obtained. By increasing the molar ratio of Ag to four equivalents, a 1-D coordination polymer, [AgL1(NO3)](n) (1), was obtained. The simple reaction of L-1 and AgNO3 in a 1:2 ratio also produced complex 1 in quantitative yield. Both the esterified ligand L-1 and the coordination polymer 1 were fully characterized by infrared and H-1 NMR spectroscopy, elemental analysis, electrospray ionization mass spectrometry, and single crystal X-ray crystallography. The single crystal X-ray diffraction measurements revealed that the Ag metal center has an octahedral geometry with eta(2)-nitrate ligands. The photophysical properties of complexes are also explored. (C) 2017 Elsevier Ltd. All rights reserved.