4-甲氧基苯基对氟苯磺酸盐 | 161912-34-1

• 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-甲氧基苯基对氟苯磺酸盐
• 英文名称: 4-Methoxyphenyl p-fluorobenzenesulfonate
• 英文别名: 4-methoxyphenyl 4-fluorobenzenesulfonate；(4-methoxyphenyl) 4-fluorobenzenesulfonate
• CAS: 161912-34-1
• 化学式: C₁₃H₁₁FO₄S
• 分子量: 282.292
• InChiKey: HTHDRBATKQIQKB-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C(Solv: toluene (108-88-3); hexane (110-54-3))
• 沸点：
  411.9±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯基对氟苯磺酸盐 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71%的产率得到4,4-二甲氧基联苯
  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 、 4-甲氧基苯酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到4-甲氧基苯基对氟苯磺酸盐
  参考文献：
  名称：

  钯催化的甲苯磺酸芳基酯和甲磺酸酯的羰基化

  摘要：

  已经使用衍生自 Pd(OAc)2 和庞大的双齿 dcpp 配体的催化剂系统开发了钯催化的甲苯磺酸芳基酯和甲磺酸酯羰基化形成酯的通用方案。该系统在温和的条件下运行：大气 CO 压力和 80-110 摄氏度的温度。 广泛的底物范围已被证明允许富电子、缺电子和杂环甲苯磺酸酯和甲磺酸酯羰基化，反应显示出广泛的官能团宽容。

  DOI：

  10.1021/ja711449e

文献信息

• 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.