Ethyl 2-phenyl-2-(trifluoromethylsulfonyloxy)acetate | 178552-83-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Ethyl 2-phenyl-2-(trifluoromethylsulfonyloxy)acetate
• 英文别名: ethyl 2-phenyl-2-(trifluoromethylsulfonyloxy)acetate
• CAS: 178552-83-5
• 化学式: C₁₁H₁₁F₃O₅S
• 分子量: 312.267
• InChiKey: MKMHITJYOBEQCF-UHFFFAOYSA-N

物化性质

• 沸点：
  336.3±42.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-phenyl-2-(trifluoromethylsulfonyloxy)acetate 在 tetrabutylammonium fluoride hydrofluoride 作用下， 以 二氯甲烷 为溶剂， 生成 fluoro-phenyl-acetic acid ethyl ester
  参考文献：
  名称：

  Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride

  摘要：

  Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.

  DOI：

  10.1021/jo8015659
• 作为产物：
  描述：

  三氟甲磺酸酐 、 扁桃酸乙酯 以 二氯甲烷 为溶剂， 生成 Ethyl 2-phenyl-2-(trifluoromethylsulfonyloxy)acetate
  参考文献：
  名称：

  Versatile application of trifluoromethyl triflate

  摘要：

  Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F(-) sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.105

文献信息

• Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride
  作者：Kyu-Young Kim、Bong Chan Kim、Hee Bong Lee、Hyunik Shin

  DOI：10.1021/jo8015659

  日期：2008.10.17

  Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.
• Versatile application of trifluoromethyl triflate
  作者：Alexander A. Kolomeitsev、Mikhail Vorobyev、Hartmut Gillandt

  DOI：10.1016/j.tetlet.2007.11.105

  日期：2008.1

  Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F(-) sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely. (C) 2007 Elsevier Ltd. All rights reserved.