3-chlorophenyl trifluoroacetates | 57076-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-chlorophenyl trifluoroacetates
• 英文别名: 3-chlorophenyl trifluoroacetate；m-chlorophenyl trifluoroacetate；3-chlorophenyl 2,2,2-trifluoroacetate；3-Chlorphenyl-trifluoracetat；3-Chlorophenol, trifluoroacetate；(3-chlorophenyl) 2,2,2-trifluoroacetate
• CAS: 57076-48-9
• 化学式: C₈H₄ClF₃O₂
• 分子量: 224.567
• InChiKey: IVGWAFXWYCCNGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chlorophenyl trifluoroacetates 在 水 、 β-环糊精 作用下， 以 乙腈 为溶剂， 生成 3-氯苯酚
  参考文献：
  名称：

  β-环糊精对三氟乙酸酯水解的影响。

  摘要：

  在存在β-环糊精（β-CD）的情况下研究了pF，p-Cl和m-Cl苯基三氟乙酸酯的水解。在碱性溶液中催化反应时，pH为6的β-CD可以抑制反应。MM3计算重现了一些实验结果。底物与β-CD形成包合物，其稳定性与相应的乙酸盐相似。然而，在这些反应中，过渡态的缔合不如在乙酸盐中的缔合有利，因此观察到的催化作用更弱。

  DOI：

  10.1021/jo001691k
• 作为产物：
  描述：

  3-氯苯酚 、 三氟乙酸酐 生成 3-chlorophenyl trifluoroacetates
  参考文献：
  名称：

  Neuvonen, Helmi, Journal of the Chemical Society. Perkin transactions II, 1986, p. 1141 - 1146

  摘要：

  DOI：

文献信息

• Synthesis of 4-trifluoromethyl-2<i>H</i>-chromenes <i>via</i> the reaction of 2-(trifluoroacetyl)phenols with vinyltriphenylphosphonium chloride
  作者：Alexander S. Golubev、Petr N. Ostapchuk、Tatiana V. Strelkova、Nikolai D. Kagramanov、Kyrill Yu. Suponitsky、Rina U. Takazova、Nikolai D. Chkanikov

  DOI：10.1039/d2ob01177h

  日期：——

  Substituted on the benzene ring 4-CF3-2H-chromenes have been prepared from substituted 2-(trifluoroacetyl)phenols and vinyltriphenylphosphonium chloride according to the Schweizer protocol in moderate to excellent yields. The influence of the type and the position of aromatic ring substituents on yields of 4-CF3-2H-chromenes have been investigated. It has been shown that 4-CF3-2H-chromenes are convenient

  根据 Schweizer 协议，在苯环上取代的 4-CF 3 -2 H -色烯由取代的 2-(三氟乙酰基)苯酚和乙烯基三苯基氯化鏻以中等至优异的产率制备。研究了芳环取代基的类型和位置对4-CF 3 -2 H-色烯收率的影响。已经表明4-CF 3 -2 H-色烯是4-CF 3 -香豆素的方便前体。
• On the Mechanism of Ester Hydrolysis:  Trifluoroacetate Derivatives
  作者：Mariana A. Fernandez、Rita H. de Rossi

  DOI：10.1021/jo990550j

  日期：1999.8.1

  The hydrolysis rate of trifluoacetates of ArX (X = p-CH3, H, p-F, p-Cl, and m-Cl) was measured as function of pH and buffer concentration. All the reactions were catalyzed by the buffer bases, and the Bronsted plot showed a small upward curvature. The kinetic isotope effect is ca. 2.5-2.3 for the reactions of water. The Hammett plots as well as the plots of log Kg VS PKlg are linear. The slopes of these plots are remarkably similar to those corresponding to the hydrolysis of aryl acetates and aryl formates. From these results, we conclude that the reaction corresponds to general base-catalyzed addition of water and break of the leaving group with no intermediate with finite lifetime despite the fact that the trifluoromethyl group stabilized the intermediate considerably.
• Neuvonen, Helmi, Journal of the Chemical Society. Perkin transactions II, 1986, p. 1141 - 1146
  作者：Neuvonen, Helmi

  DOI：——

  日期：——
• Effect of β-Cyclodextrin on the Hydrolysis of Trifluoroacetate Esters
  作者：Mariana A. Fernández、Rita H. de Rossi、Enric Cervelló、Carlos Jaime

  DOI：10.1021/jo001691k

  日期：2001.6.1

  The hydrolysis of p-F, p-Cl, and m-Cl phenyl trifluoracetates was studied in the presence of beta-cyclodextrin (beta-CD). The reactions are inhibited by beta-CD at pH 6 while they are catalyzed in alkaline solution. MM3 calculations reproduce some of the experimental results. The substrates form inclusion complexes with beta-CD which are of similar stability as those of the corresponding acetates;

  在存在β-环糊精（β-CD）的情况下研究了pF，p-Cl和m-Cl苯基三氟乙酸酯的水解。在碱性溶液中催化反应时，pH为6的β-CD可以抑制反应。MM3计算重现了一些实验结果。底物与β-CD形成包合物，其稳定性与相应的乙酸盐相似。然而，在这些反应中，过渡态的缔合不如在乙酸盐中的缔合有利，因此观察到的催化作用更弱。