4-甲苯基对氟苯磺酸盐 | 1858-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲苯基对氟苯磺酸盐
• 英文名称: 4-Tolyl p-fluorobenzenesulfonate
• 英文别名: (4-Methylphenyl) 4-fluorobenzenesulfonate
• CAS: 1858-67-9
• 化学式: C₁₃H₁₁FO₃S
• 分子量: 266.293
• InChiKey: DFPDUYBNXUPJSP-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  387.7±42.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲苯基对氟苯磺酸盐 在 bis(triphenylphosphine)nickel(II) chloride 、 四乙基碘化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到4,4'-二甲基联苯
  参考文献：
  名称：

  Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

  摘要：

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.

  DOI：

  10.1021/jo00106a031
• 作为产物：
  描述：

  4-氟苯磺酰氯 在 三乙胺 、 四甲基胍 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 4-甲苯基对氟苯磺酸盐
  参考文献：
  名称：

  使用硫-三唑交换化学在蛋白质上配体功能性酪氨酸位点

  摘要：

  调节硫亲电试剂的反应性是推进点击化学和化学探针发现的关键。迄今为止，用于蛋白质修饰的硫亲电子试剂的活化主要归因于在磺酰氟和芳基氟硫酸盐的共价反应中氟化物离去基团 (LG) 的稳定化。我们最近引入了硫三唑交换 (SuTEx) 化学，以证明三唑是一种有效的 LG，用于激活蛋白质酪氨酸位点上的亲核取代反应。在这里，我们通过用具有不同给电子和吸电子特性的官能团修饰加合物基团 (AG) 和 LG 来探测 SuTEx 用于基于片段的配体发现的可调性。我们发现硫亲电试剂对修饰位置高度敏感（AG 与 LG），这使得溶液和蛋白质组活动的粗略和精细调整成为可能。我们应用这些反应性原理来鉴定蛋白质 (~44%) 上的大部分酪氨酸位点 (~30%)，这些位点可以通过化学蛋白质组学量化的 >1500 个探针修饰位点进行配体。我们的蛋白质组学研究确定了非催化酪氨酸和磷酸酪氨酸位点，这些位点可以与 SuTEx 片段配位

  DOI：

  10.1021/jacs.0c00648

文献信息

• Synthesis of aryloxysulphoxonium salts
  作者：G. R. Chalkley、D. J. Snodin、G. Stevens、M. C. Whiting

  DOI：10.1039/j39700000682

  日期：——

  Aryloxysulphoxonium salts (tetrafluoroborates and hexafluorophosphates) have been prepared by the decomposition of arenediazonium salts in an excess of various compounds containing the sulphonyl grouping: sulphones and aryl esters, and alkylated amides of alkane- and arene-sulphonic acids and of sulphuric acid.

  芳氧磺鎓盐（四氟硼酸盐和六氟磷酸盐）是通过在过量的各种含磺酰基的化合物（包括砜和芳基酯，以及链烷烃和芳烃磺酸的烷基化酰胺）中分解芳构氮鎓盐而制得的。
• An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates
  作者：Chaoxian Cai、Nelo R. Rivera、Jaume Balsells、Rick R. Sidler、J. Christopher McWilliams、C. Scott Shultz、Yongkui Sun

  DOI：10.1021/ol062208g

  日期：2006.10.1

  Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates.
• SULFUR-HETEROCYCLE EXCHANGE CHEMISTRY AND USES THEREOF
  申请人：University of Virginia Patent Foundation

  公开号：EP3924348A2

  公开（公告）日：2021-12-22
• [EN] SULFUR-HETEROCYCLE EXCHANGE CHEMISTRY AND USES THEREOF<br/>[FR] CHIMIE D'ÉCHANGE SOUFRE-HÉTÉROCYCLE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV VIRGINIA PATENT FOUNDATION

  公开号：WO2020214336A2

  公开（公告）日：2020-10-22

  Sulfonyl-triazole compounds and related sulfonyl-heterocycle compounds are described. The compounds can be used to identify reactive nucleophilic amino acid residues, such as reactive tyrosines and reactive lysines, in proteins and to modify the activity of proteins with reactive nuclophilic amino acid residues via the formation of protein adducts comprising a fragment of the compounds. Methods are also described for screening the compounds to identify ligands of proteins comprising a reactive lysine or a reactive tyrosine.