2,3-dimercaptobenzoic acid | 174577-69-6

• 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: 2,3-dimercaptobenzoic acid
• 英文别名: Dithiosalicylsaure；2,3-bis(sulfanyl)benzoic acid
• CAS: 174577-69-6
• 化学式: C₇H₆O₂S₂
• 分子量: 186.255
• InChiKey: CUUWAGAEOZKKCW-UHFFFAOYSA-N

物化性质

• 沸点：
  367.4±32.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dimercaptobenzoic acid 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 N-tert-butyl-2,3-dimercaptobenzamide
  参考文献：
  名称：

  Selective and Effective Stabilization of Mo^VI═O Bonds by NH···S Hydrogen Bonds via Trans Influence

  摘要：

  A monooxomolybdenum(IV) complex containing two intramolecular NH center dot center dot center dot S hydrogen bonds, (NEt4)(2)[(MoO)-O-IV-(1,2-S-2-3-t-BuNHCOC6H3)(2)], was synthesized. The trans isomer was crystallized as the major product, and the molecular structure was determined by X-ray analysis. The trans isomer was isomerized by heating in solution to give a 1:1 mixture of trans and cis isomers. Oxidation of these isomers by Me3NO afforded (NEt4)(2)[(MoO2)-O-VI(1,2-S-2-3-t-BuNHCOC6H3)(2)]. H-1 NMR analysis revealed that the dioxomolybdenum(VI) complex existed as a single isomer where both oxo ligands were trans to each of the two hydrogen-bonded thiolate ligands. The Mo-VI=O bond was effectively stabilized by the NH center dot center dot center dot S hydrogen bond via trans influence, which was determined using resonance Raman spectroscopy. These results were supported by preliminary density functional theory calculations.

  DOI：

  10.1021/ic301597d
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以93%的产率得到2,3-dimercaptobenzoic acid
  参考文献：
  名称：

  合成受保护的3,4-和2,3-二巯基苯丙氨酸作为Fmoc-肽合成的基础材料，并通过固相合成将3,4-类似物掺入十肽中

  摘要：

  3，4-二巯基苯丙氨酸和2，3-二巯基苯丙氨酸是通过3，4-和2，3-二巯基苄基溴衍生物上受保护的氨基丙二酸酯的亲核取代首次合成的。二硫醇官能团被保护为硫缩酮，关键的前体，二苯硫基缩酮保护的二巯基苄基溴，是通过两条不同的路线由二羟基苯甲酸酯或甲苯3,4-二硫醇合成的。通过手性HPLC将完全保护的氨基酸的外消旋混合物分离成相应的对映异构体。可以基于X射线晶体学和VCD / DFT测量来分配3,4-和2,3-模拟的绝对构型。与氧化汞和四氟硼酸水溶液反应后，噻托金属基团脱保护，然后用H 2处理在氩气氛下用S气获得相应的二巯基氨基酸。使用标准的固相肽合成法将光学纯的1 - Fmoc保护的3，4-类似物（S-对映异构体）成功地掺入十肽中。因此，现在可以通过简单的合成方法获得二硫代烯官能化的肽，这将为催化，诊断和纳米技术领域的研究提供新的分子工具。

  DOI：

  10.1021/acs.joc.0c02359

文献信息

• Strong NH⋯S hydrogen bonds in molybdoenzyme models containing anilide moieties
  作者：Taka-aki Okamura、Kumiko Kunisue、Yui Omi、Kiyotaka Onitsuka

  DOI：10.1039/c3dt50139f

  日期：——

  Monooxomolybdenum(IV) and dioxomolybdenum(VI) benzenedithiolate derivatives containing anilide moieties were synthesized and characterized by 1H NMR, UV-visible, IR, and Raman spectroscopies. These complexes exhibit very strong intramolecular NH⋯S hydrogen bonds formed by the acidic anilide NH proton and the desired coplanar structure, resulting in significantly positive redox potential and remarkable acceleration in the reduction of Me3NO in DMF.

  通过 1H NMR、紫外-可见光谱、红外光谱和拉曼光谱，合成并表征了含有苯胺分子的单氧杂钼(IV)和二氧杂钼(VI)苯二硫酸盐衍生物。这些配合物表现出非常强的分子内 NH'S 氢键（由酸性苯胺 NH 质子和所需的共面结构形成），因而在 DMF 中还原 Me3NO 时具有明显的正氧化还原电势和显著的加速度。
• Carboxy‐thioether‐thiolato titanium–graphene oxide nanocomposite as drug delivery system for targeted cancer therapy: Design, characterization, bovine serum albumin binding study, and biological evaluation
  作者：Hanan A. Mohamed、Mohamed M. Ibrahim、Ibrahim M. El‐Mehasseb、Abd El‐Motaleb M. Ramadan、Shaban Y. Shaban

  DOI：10.1002/aoc.7009

  日期：2023.3

  investigate the interactions of CTT, TiCTT, GO, and GO–TiCTT nanocomposite with bovine serum albumin (BSA). The results revealed that the intrinsic fluorescence quenching of BSA resulting from low concentrations was caused by the formation of stable BSA adducts via the binding interaction with BSA. The stable adduct had a stoichiometry of 1:1 and binding constants (Kb) in the order of 105 M1 at 310 K for CTT

  制备并表征了羧基-硫醚-硫醇钛（IV）络合物（TiCTT）及其氧化石墨烯纳米复合材料（GO-TiCTT），用于开发具有增强抗菌和抗癌能力的新型化合物，发现 TiCTT 的负载比为约33.3%。热研究和 zeta 电位表明 GO-TiCTT 比 GO 更稳定，而 SEM 和 TEM 表明 TiCTT 在 GO 表面有效吸附。各种生物物理程序用于研究 CTT、TiCTT、GO 和 GO-TiCTT 纳米复合材料与牛血清白蛋白 (BSA) 的相互作用。结果表明，低浓度 BSA 的固有荧光猝灭是通过与 BSA 的结合相互作用形成稳定的 BSA 加合物引起的。稳定加合物的化学计量为 1：b ) 大约 10 5CTT、TiCTT 和 GO–TiCTT 的 M1 在 310 K，表明与 BSA 的结合相互作用非常强。根据自由能变化 (G#) 的符号和大小，可以得出结论，与 BSA 的结合过程是自发的，范
• Scllmann, Dieter; Backer, Thomas; Enoch, Falk, Chemische Berichte, 1996, vol. 129, # 5, p. 509 - 519
  作者：Scllmann, Dieter、Backer, Thomas、Enoch, Falk

  DOI：——

  日期：——
• Synthesis, structure and DFT calculation of a hexanuclear mixed-valence copper cluster supported by 2,3-disulfidobenzoate and 3-carboxybenzene-1,2-bis(thiolate)
  作者：Kuntal Pal、Satoshi Takamizawa、Kazushi Mashima

  DOI：10.1016/j.ica.2011.03.055

  日期：2011.7

  A homoleptic hexanuclear Cu cluster, [(Cu(DSB)(CBT))(2)(Cu2Br)(2)][PPh4](2) (1-PPh4) [DSB = 2,3-disulfidobenzoate; CBT = 3-carboxybenzene-1,2-bis(thiolate)] was synthesized as dark green crystals by the reaction of CuCl2 with 2,3-dimercaptobenzoic acid in acetate buffer solution. The X-ray crystal study of 1-PPh4 revealed its unique structural features: (1) one of two types of crystallographically distinct Cu centers adopted a square planer geometry and the other center had a tetrahedral geometry, and (2) intermolecular H-bonding interactions connected between carboxylic acid group of CBT and the carboxylate group of DSB led to the construction of an unprecedented topologic architecture of a zigzag patterned infinite sheet. In addition, taking into account the total charge of the molecule, which contained 2,3-disulfidobenzoate and 3-carboxybenzene-1,2-bis(thiolate), and the diamagnetic nature of 1-PPh4, 1-PPh4 led to it is assignment as a mixed-valence Cu(I)/Cu(III) cluster. Such mixed valence states of Cu atoms were also examined by density functional theory calculation. (C) 2011 Elsevier B.V. All rights reserved.
• Hahn, F. Ekkehardt; Seidel, Wolfram W., Angewandte Chemie, 1995, vol. 107, # 23/24, p. 2938 - 2941
  作者：Hahn, F. Ekkehardt、Seidel, Wolfram W.

  DOI：——

  日期：——