2,5-Difluorophenyl trifluoromethanesulphonate | 211512-93-5

• 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: 2,5-Difluorophenyl trifluoromethanesulphonate
• 英文别名: (2,5-difluorophenyl) trifluoromethanesulfonate
• CAS: 211512-93-5
• 化学式: C₇H₃F₅O₃S
• 分子量: 262.157
• InChiKey: COJBXGYEVJLMTI-UHFFFAOYSA-N

物化性质

• 沸点：
  236.0±40.0 °C(Predicted)
• 密度：
  1.645±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-Difluorophenyl trifluoromethanesulphonate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 甲酸 、 二乙胺 、 三乙胺 、 lithium chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (Z)-3-(2-amino-3-propan-2-ylsulfonylbenzimidazol-5-yl)-3-(2,5-difluorophenyl)prop-2-enamide
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

  摘要：

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.

  DOI：

  10.1021/jo980235h
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2,5-二氟苯酚 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到2,5-Difluorophenyl trifluoromethanesulphonate
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

  摘要：

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.

  DOI：

  10.1021/jo980235h

文献信息

• Carbonylative coupling of aryl tosylates/triflates with arylboronic acids under CO atmosphere
  作者：Cheng Yi Hao、Dan Wang、Ya Wei Li、Lin Lin Dong、Ying Jin、Xiu Rong Zhang、He Yun Zhu、Sheng Chang

  DOI：10.1039/c6ra14678c

  日期：——

  The carbonylative Suzuki–Miyaura reaction between aryl tosylates/triflates with arylboronic acid is herein reported, using base-free conditions and a balloon pressure of carbon monoxide. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of oxybenzone and ketoprofen in good yields under mild conditions.

  本文报道了在无碱条件和一氧化碳的球囊压力下，芳基甲苯磺酸盐/三氟甲磺酸与芳基硼酸之间的羰基化Suzuki-Miyaura反应。在这些条件下，以中等至极好的收率获得了不对称的联芳基酮。该方法适合在温和条件下以高收率合成氧苯甲酮和酮洛芬。
• Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides
  作者：Lynne A. Hay、Thomas M. Koenig、Francis O. Ginah、James D. Copp、David Mitchell

  DOI：10.1021/jo980235h

  日期：1998.7.1

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.