4-(1-hydroxyethyl)phenyl trifluoromethanesulfonate | 838884-19-8

• 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: 4-(1-hydroxyethyl)phenyl trifluoromethanesulfonate
• 英文别名: [4-(1-Hydroxyethyl)phenyl] trifluoromethanesulfonate
• CAS: 838884-19-8
• 化学式: C₉H₉F₃O₄S
• 分子量: 270.229
• InChiKey: YVUSEXSZBVEQDK-UHFFFAOYSA-N

物化性质

• 沸点：
  92 °C(Press: 0.4 Torr)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxyethyl)phenyl trifluoromethanesulfonate 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到对羟基苯乙酮
  参考文献：
  名称：

  A polystyrene-supported triflating reagent for the synthesis of aryl triflates

  摘要：

  An insoluble polystyrene-supported triflating reagent has been prepared by suspension co-polymerization of N-(4-vinylphenyl)trifluoromethanesulphonimide, styrene and the JandaJel((R)) cross-linker. This reagent, in the presence of triethylamine, allows for the efficient synthesis of aryl triflates from a wide range of phenols in a process that permits the desired product to be isolated from the reaction mixture in essentially pure form via several filtration and concentration operations. Adding to the utility of this reagent is its ability to be easily recovered, regenerated and reused. Both soluble and insoluble bifunctional polymers containing trialkylamine moieties in addition to triflimide groups were also prepared and examined as triflating reagents. Unfortunately these reagents afforded only modest yields of the desired products in representative reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.108
• 作为产物：
  描述：

  4-乙酰苯基三氟甲烷磺酸酯 在 aluminum isopropoxide 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以83%的产率得到4-(1-hydroxyethyl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Direct Coupling Reaction between Alcohols and Silyl Compounds:  Enhancement of Lewis Acidity of Me₃SiBr Using InCl₃

  摘要：

  The combination of InCl3 and Me3SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced Lewis acidity of this system was measured by the C-13 NMR in terms of the coordination to an alcohol. Moreover, the interaction between Me3SiBr and the In(III) species was revealed by Si-29 NMR spectral analysis. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.

  DOI：

  10.1021/jo061512k

文献信息

• Direct Coupling Reaction between Alcohols and Silyl Compounds:  Enhancement of Lewis Acidity of Me₃SiBr Using InCl₃
  作者：Takahiro Saito、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1021/jo061512k

  日期：2006.10.1

  The combination of InCl3 and Me3SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced Lewis acidity of this system was measured by the C-13 NMR in terms of the coordination to an alcohol. Moreover, the interaction between Me3SiBr and the In(III) species was revealed by Si-29 NMR spectral analysis. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.
• A polystyrene-supported triflating reagent for the synthesis of aryl triflates
  作者：Cecilia Wan Ying Chung、Patrick H. Toy

  DOI：10.1016/j.tet.2004.10.108

  日期：2005.1

  An insoluble polystyrene-supported triflating reagent has been prepared by suspension co-polymerization of N-(4-vinylphenyl)trifluoromethanesulphonimide, styrene and the JandaJel((R)) cross-linker. This reagent, in the presence of triethylamine, allows for the efficient synthesis of aryl triflates from a wide range of phenols in a process that permits the desired product to be isolated from the reaction mixture in essentially pure form via several filtration and concentration operations. Adding to the utility of this reagent is its ability to be easily recovered, regenerated and reused. Both soluble and insoluble bifunctional polymers containing trialkylamine moieties in addition to triflimide groups were also prepared and examined as triflating reagents. Unfortunately these reagents afforded only modest yields of the desired products in representative reactions. (C) 2004 Elsevier Ltd. All rights reserved.