1,2-bis[4-(formyl)phenyl]disulfane | 100538-31-6

• 物质功能分类: 有机原料 - 醛类化合物
• 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: 1,2-bis[4-(formyl)phenyl]disulfane
• 英文别名: 4,4’-dithiodibenzaldehyde；bis(4-formylphenyl) disulfide；4,4'-dithiobis(benzaldehyde)；4,4'-Dithiodibenzaldehyde；4,4'-disulfanediyl-di-benzaldehyde；4,4'-Disulfandiyl-di-benzaldehyd；4,4'-Disulfanediyldibenzaldehyde；4-[(4-formylphenyl)disulfanyl]benzaldehyde
• CAS: 100538-31-6
• 化学式: C₁₄H₁₀O₂S₂
• 分子量: 274.364
• InChiKey: GSPKFDVCAFADTI-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: ethanol (64-17-5))
• 沸点：
  443.4±30.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1,2-bis[4-(formyl)phenyl]disulfane 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 4-(benzylaminomethyl)thiophenol
  参考文献：
  名称：

  Polyvalent Interactions in Unnatural Recognition Processes

  摘要：

  The synthesis of two cluster compounds, one containing six secondary dialkylammonium ion centers and the other possessing six benzo-m-phenylene[25]crown-8 (BMP25C8) macrocycles, both appended to hexakis(thiophenyl)benzene cores, is described. The binding of these clusters with complementary mono- and divalent ligands is investigated with NMR spectroscopy to probe polyvalency in these unnatural recognition systems. The ability of the two different families of clusters to bind complementary monovalent ligands is compared with that of the monovalent receptor pair, namely the dibenzylammonium ion and BMP25C8. This comparison is made possible by determining an average association constant (K-AVE) for the binding of each recognition site on the cluster with the corresponding monovalent ligand. We have found that the clustering of recognition sites together in one molecule is detrimental to their individual abilities to bind monovalent ligands. In the case of the polyvalent interaction between the hexakisBMP25C8 cluster and divalent dialkylammonium ions, an association constant, K-POLY, was calculated from the value of K-AVE determined for the complexation of the individual component recognition sites. This polyvalent interaction is significantly stronger than that associated with the averaged monovalent interactions.

  DOI：

  10.1021/jo030283o
• 作为产物：
  描述：

  4-(叔丁基磺酰基)苯甲醛 在 氢溴酸 、 二甲基亚砜 作用下， 以 溶剂黄146 为溶剂， 以92%的产率得到1,2-bis[4-(formyl)phenyl]disulfane
  参考文献：
  名称：

  Oxidative Cleavage of Aryl or Alkyltert-Butyl Sulfides with Dimethyl Sulfoxide/Hydrobromic Acid to Form Symmetrical Aryl or Alkyl Disulfides

  摘要：

  本文讨论了如何使用二甲基亚砜和氢溴酸作为试剂，将（叔丁硫基）苯甲醛、芳基或烷基叔丁基硫醚氧化裂解为相应的对称二硫化物。在几个对照实验的基础上，简要介绍了机理原理。

  DOI：

  10.1055/s-1993-25907

文献信息

• Efficient Syntheses of Thiophenol Derivatives
  作者：Frédéric Dumur、Valérie Roubaud、Eddy Dumas、Cédric Mayer

  DOI：10.1055/s-0030-1258058

  日期：2010.10

  The photochemical bromination of 4-methylthiophenol with N-bromosuccinimide is reported. Depending on the amount of NBS, mono or bis bromination of the methyl group was obtained. Conversion of brominated derivatives to dialdehydes is also discussed. Improvement of synthetic routes towards thiophenol derivatives is motivated by their key role for the functionalization of metal nanoparticles and surfaces

  报道了 4-甲基苯硫酚与 N-溴代琥珀酰亚胺的光化学溴化。根据 NBS 的量，获得甲基的单溴化或双溴化。还讨论了溴化衍生物向二醛的转化。苯硫酚衍生物合成路线的改进是由于它们在金属纳米颗粒和表面功能化方面的关键作用。
• Haloacid/dimethyl sulfoxide-catalyzed synthesis of symmetrical disulfides by oxidation of thiols
  作者：Palani Natarajan、Himani Sharma、Mandeep Kaur、Pooja Sharma

  DOI：10.1016/j.tetlet.2015.08.041

  日期：2015.10

  A novel method is developed for the oxidation of thiols to the corresponding disulfides using 20 mol % haloacid (HBr or HI) in combination with dimethyl sulfoxide. A tentative mechanism is proposed for the oxidation. In addition to the advantages of cost-effectiveness, simple processes, and broad functional group tolerance, the exclusive formation of disulfides is the principle reward of this methodology

  开发了一种新颖的方法，用于将硫醇氧化为相应的二硫化物，方法是使用20 mol％的卤代酸（HBr或HI）与二甲基亚砜结合使用。提出了一种初步的氧化机理。除了具有成本效益，简单的方法和广泛的官能团耐受性的优点外，与已知的方法进一步将二硫化物进一步氧化为S-氧化物和其他副产物相比，仅形成二硫化物是该方法的主要优点。
• Convergent Synthesis of <i>N</i>-Linked Glycopeptides via Aminolysis of ω-Asp <i>p</i>-Nitrophenyl Thioesters in Solution
  作者：Jing-Jing Du、Xiao-Fei Gao、Ling-Ming Xin、Ze Lei、Zheng Liu、Jun Guo

  DOI：10.1021/acs.orglett.6b02288

  日期：2016.10.7

  An efficient N-linked glycosylation reaction between glycosylamines and p-nitrophenyl thioester peptides has been developed. The reaction conditions are mild and compatible with the C-terminal free carboxylic acid group and the unprotected N-linked sialyloligosaccharide. By means of this convergent strategy, a versatile N-glycopeptide fragment containing an N-terminal Thz and a C-terminal thioester

  已经开发了糖胺和对硝基苯基硫酯肽之间的有效的N-联糖基化反应。反应条件温和并且与C端游离羧酸基团和未保护的N-连接的唾液酸寡糖相容。通过这种收敛策略，可以容易地制备出包含N端Thz和C端硫酯的通用N糖肽片段，该片段可用于使用天然化学连接方案合成长糖肽和糖蛋白。
• Unsymmetrical aryl disulfides with excellent transparency in the visible region for second order nonlinear optics
  作者：Ramanathan Sudharsanam、Srinivasan Chandrasekaran、Puspendu Kumar Das

  DOI：10.1039/b204034d

  日期：2002.9.26

  Several unsymmetrically substituted aromatic donor–acceptor disulfides have been synthesized and analysed for their second order nonlinear optical properties. These molecules exhibit moderately high first hyperpolarizability (β) with excellent transparency in the visible region. Most of the unsymmetrical disulfides have a cut-off wavelength below 420 nm. Calculations show that the molecules have an asymmetric charge distribution around the disulfide bond which is responsible for their high β values. These results provide motivation for the design and synthesis of nonlinear optical chromophores with multiple disulfide bonds for large second order nonlinearity and excellent visible transparency.

  我们合成了几种不对称取代的芳香族供体-受体二硫化物，并分析了它们的二阶非线性光学特性。这些分子表现出中等程度的第一超极化率 (β)，在可见光区域具有极佳的透明度。大多数非对称二硫化物的截止波长低于 420 纳米。计算表明，这些分子在二硫键周围具有不对称的电荷分布，这也是它们具有高 β 值的原因。这些结果为设计和合成具有多个二硫键的非线性光学发色团提供了动力，使其具有较大的二阶非线性和出色的可见光透明度。
• New organic picolylamine-type ligands and electrochemical study of their complexation with Cu(MeCN)4ClO4
  作者：A. G. Majouga、R. B. Romashkina、A. S. Kashaev、E. K. Beloglazkina、A. A. Moiseeva、N. V. Zyk

  DOI：10.1007/s11172-011-0044-8

  日期：2011.2

  A series of novel organic ligands with dipicolylamine and disulfide groups connected by polymethylene, alkylaryl, alkoxyaryl, or alkoxycarbonyl linker was synthesized. The electrochemical study by cyclic voltammetry was carried out for two synthesized ligands, and the formation of the complexes with Cu(MeCN)ClO4 in the solution or on the gold electrode surface was established. The complex of CuI with 1,24-bis[N,N-bis(2-pyridylmethyl)-glycinoyloxy]-12,13-dithiatetracosane chemisorbed on the Au electrode is capable of binding molecular oxygen from solution.

  合成了一系列新型有机配体，这些配体带有二二甲苯胺基和二硫化物基团，并通过聚亚甲基、烷基芳基、烷氧基芳基或烷氧基羰基连接。通过循环伏安法对两种合成配体进行了电化学研究，确定了在溶液中或金电极表面与 Cu(MeCN)ClO4 形成的配合物。CuI 与 1,24-双[N,N-双（2-吡啶基甲基）-甘氨酰氧基]-12,13-二硫代四碳烷的配合物化学吸附在金电极上，能够结合溶液中的分子氧。