苯基2-(三氟甲基)苯甲酸酯 | 216585-44-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 苯基2-(三氟甲基)苯甲酸酯
• 英文名称: Phenyl 2-(trifluoromethyl)benzoate
• 英文别名: 2-Trifluoromethylbenzoic acid, phenyl ester
• CAS: 216585-44-3
• 化学式: C₁₄H₉F₃O₂
• 分子量: 266.219
• InChiKey: ZHFBGJIMMTZRIC-UHFFFAOYSA-N

物化性质

• 沸点：
  125-126 °C(Press: 0.795 Torr)
• 密度：
  1.290±0.06 g/cm3(Predicted)
• 保留指数：
  1686

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  苯基2-(三氟甲基)苯甲酸酯 在 sodium perchlorate 、 水 、 sodium hydroxide 作用下， 生成 邻三氟甲基苯甲酸
  参考文献：
  名称：

  溶剂对取代苯甲酸苯基酯碱水解中邻位取代基作用的影响

  摘要：

  二阶速率常数ķ（DM 3 摩尔-1 小号-1为苯基酯的碱性水解）间位- ，对位和-邻-取代的苯甲酸在含水为5.3μm的NaClO 4和1.0M卜4测定NBR通过在25℃下的UV / Vis分光光度法。使用在各种介质中对苯甲酸的苯基酯进行碱水解的数据，研究了邻位感应，邻位共振以及间位和对极效应随溶剂参数的变化。的依赖邻上溶剂取代效果可通过下面的等式来精确描述的：Δlog ķ邻 =登录ķ邻 -日志ķ ħ  = 0.059 + 2.19 σ我 + 0.304 σ ° - [R  + 2.79 ë  - 0.016Δ Eσ我 - 0.085Δ Eσ ° ř，其中ΔE是溶剂的亲电性，ΔE  =  E S  -  E H2O，表征了溶剂的氢键给体能力。在增加元和随着溶剂氢键供体容量（亲电子性）的降低，对极性取代基的影响与邻位取代基的共振项大致相同（-0.068ΔEσ ° m，p）。邻取代基的空间术语与

  DOI：

  10.1002/poc.1628
• 作为产物：
  描述：

  2-三氟甲基苯甲酰氯 、 苯酚 在 sodium hydroxide 作用下， 生成 苯基2-(三氟甲基)苯甲酸酯
  参考文献：
  名称：

  Synthesis of benzoyl hydrazones having 4-hydroxy-3,5-dimethoxy phenyl ring, their biological activities and moleculer modeling studies on enzyme inhibition activities

  摘要：

  腙类化合物具有很高的抗氧化活性和酶抑制活性，如抗胆碱酯酶、酪氨酸酶和脲酶。本研究以 3,5-二甲氧基-4-羟基苯甲醛为原料，合成了苯甲酰肼化合物（7a-7m）。对合成化合物的抗氧化活性进行了评估。在 β-胡萝卜素-亚油酸和 ABTS 阳离子自由基清除活性方面，化合物 7j、7e 和 7m 分别是活性最高的化合物。在抗胆碱酯酶抑制活性结果中，化合物 7f 对 AChE 和 BChE 酶的活性是合成系列中最好的。此外，还进行了分子对接分析，以从原子水平了解合成化合物与目标酶的抑制机理。从生物活性和硅学研究的角度来看，它有可能指导未来阿尔茨海默病新药的开发研究。

  DOI：

  10.3906/kim-2107-7

文献信息

• Substituent Effects on the Base-Catalysed Hydrolysis of Phenyl Esters of ortho-Substituted Benzoic Acids
  作者：Ingrid Bauerová、Miroslav Ludwig

  DOI：10.1135/cccc20010770

  日期：——

  Fourteen model phenyl esters of 2-substituted benzoic acids were synthesised. Structures and purity of model compounds were confirmed by ¹H and ¹³C NMR spectroscopy, as well as by HPLC and elemental analysis. Kinetics of base-catalysed hydrolysis of model phenyl esters occurring by the BAc2 mechanism were measured by UV spectrophotometry in 50% (v/v) aqueous dimethyl sulfoxide solutions at 25 °C under pseudo-first-order reaction conditions (c(NaOH) = 0.001-1.0 mol l^-1). Linear relation between J_-^E and log k_obs with the slope close to unity was found for all model compounds. Neither one-parameter nor multiparameter Hammett-type description of variability of experimental data obtained for phenyl esters of 2-substituted benzoic acids was found. Two groups (conjugating and non-conjugating) were created by division of ortho-substituents in ortho-position using the AISE theory, based on their interaction with the reaction centre.

  2-取代苯甲酸的十四种模型苯基酯已合成。通过¹H和¹³C核磁共振波谱、高效液相色谱和元素分析确认了模型化合物的结构和纯度。在25°C下，通过UV分光光度法在50%（体积分数）水溶性二甲基亚砜溶液中测量了模型苯基酯的碱催化水解动力学，反应条件为伪一级反应条件（c(NaOH) = 0.001-1.0 mol l^-1）。发现所有模型化合物的J_-^E与log k_obs之间存在线性关系，斜率接近于单位。未发现适用于2-取代苯甲酸苯基酯实验数据变异性的单参数或多参数Hammett类型描述。通过使用AISE理论，根据它们与反应中心的相互作用，将邻位取代基分为两组（共轭和非共轭）。
• Kinetic Study of Hydrolysis of Benzoates. Part XXV. Ortho Substituent Effect in Alkaline Hydrolysis of Phenyl Esters of Substituted Benzoic Acids in Water
  作者：Vilve Nummert、Mare Piirsalu、Vahur Mäemets、Ilmar Koppel

  DOI：10.1135/cccc20060107

  日期：——

  The second-order rate constants k₂ for alkaline hydrolysis of phenyl esters of meta-, para- and ortho-substituted benzoic acids, X-C₆H₄CO₂C₆H₅ (X = H, 3-Cl, 3-NO₂, 3-CH₃, 4-NO₂, 4-Cl, 4-F, 4-CH₃, 4-OCH₃, 4-NH₂, 2-NO₂, 2-CN, 2-F, 2-Cl, 2-Br, 2-I, 2-CH₃, 2-OCH₃, 2-CF₃, 2-NH₂), and of substituted phenyl esters of benzoic acid, C₆H₅CO₂C₆H₄-X (X = 2-I, 2-CF₃, 2-C(CH₃)₃, 4-Cl, 4-CH₃, 4-OCH₃, 4-NH₂), have been measured spectrophotometrically in water at 25 °C. The substituent effect in alkaline hydrolysis of phenyl esters of para-substituted benzoic acids, similar to that for ethyl esters of para-substituted benzoic acids, was found to be precisely described by the Hammett relationship (ρ = 1.7 in water). The log k value for alkaline hydrolysis of phenyl and ethyl esters of meta-, para- and ortho-substituted benzoic acids, X-C₆H₄CO₂R, was nicely correlated with log k_m,p,ortho = log k_o + (ρ)_m,pσ + (ρ_I)_orthoσ_I + (ρ°_R)_orthoσ°_R + δ_orthoE_s^B where σ, σ_I, σ°_R are the Hammett polar, Taft inductive and Taft resonance (σ°_R = σ° - σ_I) substituent constants, respectively. E_s^B is the steric scale for ortho substituents calculated on the basis of the log k values for the acid hydrolysis of ortho- substituted phenyl benzoates in water owing to the ortho substituent in the phenyl of phenyl benzoates. In water, the main factors responsible for changes in the ortho substituent effect in alkaline hydrolysis of phenyl and ethyl esters of ortho-substituted benzoic acids, X-C₆H₄CO₂R, were found to be the inductive and steric factors while the role of the resonance term was negligible ((ρ°_R)_ortho ca. 0.3). In alkaline hydrolysis of substituted benzoates in neat water, the ortho inductive effect appeared to be 1.5 times and steric influence 2.7 times higher than the corresponding influences from the ortho position in the phenyl of phenyl benzoates. The contributions of the steric effects in alkaline hydrolysis of esters of ortho-substituted benzoic acids was found to be approximately the same as in acid hydrolysis of esters of ortho-substituted benzoic and acid esterification of ortho-substituted benzoic acids.

  对苯酸酯碱水解的二阶速率常数 k2，对邻、对、间取代苯甲酸的苯酯 X-C6H4CO2C6H5（X = H、3-Cl、3-NO2、3-CH3、4- 、4-Cl、4-F、4- 、4-O 、4-NH2、2- 、2-CN、2-F、2-Cl、2-Br、2-I、2- 、2-O 、2-CF3、2-NH2）以及苯甲酸苯酯的取代苯酯 C6H5CO2C6H4-X（X = 2-I、2- 、2-C( )3、4-Cl、4- 、4-O 、4-NH2）在25°C的水中进行了分光光度测定。对邻取代苯甲酸的苯酯碱水解的取代基效应，类似于对邻取代苯甲酸的乙酯，被发现可以精确地由 Hammett 关系描述（ρ = 1.7 在水中）。对邻、对、间取代苯甲酸的苯酯和乙酯 X-C6H4CO2R 的碱水解的 log k 值与 log km,p,ortho = log ko + (ρ)m,pσ + (ρI)orthoσI + (ρ°R)orthoσ°R + δorthoE sB 相关联，其中σ、σI、σ°R 是 Hammett 极性、Taft 归纳和Taft 共振（σ°R = σ° - σI）取代基常数，E sB 是基于对苯甲酸苯酯的苯基中取代基的酸水解 log k 值计算的对位取代基的立体规模。在水中，对苯酸酯碱水解的对取代基效应的主要因素被发现为归纳和立体因素，而共振项的作用微乎其微（（ρ°R）ortho 约为0.3）。在水中，对苯酸酯碱水解的对位取代基的立体影响似乎比对苯甲酸苯酯的苯基中的对位影响高出1.5倍，而归纳影响则高出2.7倍。对苯酸酯碱水解的对位取代基的立体效应的贡献与对苯酸酯碱水解的酸和对位取代基酯化的酸酯化大致相同。
• Kinetic study of hydrolysis of benzoates. part xxvii. ortho substituent effect in alkaline hydrolysis of phenyl esters of substituted benzoic acids in aqueous Bu4NBr
  作者：Vilve Nummert、Mare Piirsalu、Signe Vahur、Oksana Travnikova、Ilmar A. Koppel

  DOI：10.1135/cccc2008019

  日期：——

  The second-order rate constants k (in dm³ mol^–1 s^–1) for alkaline hydrolysis of phenyl esters of meta-, para- and ortho-substituted benzoic acids, X-C6H₄CO₂C₆H_5, have been measured spectrophotometrically in aqueous 0.5 and 2.25 M Bu₄NBr at 25 °C. The substituent effects for para and meta derivatives were described using the Hammett relationship. For the ortho derivatives the Charton equation was used. For ortho-substituted esters two steric scales were involved: the E_sB and the Charton steric (υ) constants. When going from pure water to aqueous 0.5 and 2.25 M Bu₄NBr, the meta and para polar effects, the ortho inductive and resonance effects in alkaline hydrolysis of phenyl esters of substituted benzoic acids, became stronger nearly to the same extent as found for alkaline hydrolysis of C₆H₅CO₂C₆H₄-X. The steric term of ortho-substituted esters was almost independent of the media considered. The rate constants of alkaline hydrolysis of ortho-, meta- and para-substituted phenyl benzoates (X-C₆H₄CO₂C₆H₅, C₆H₅CO₂C₆H₄-X) and alkyl benzoates, C₆H₅CO₂R, in water, 0.5 and 2.25 M Bu₄NBr were correlated with the corresponding IR stretching frequencies of carbonyl group, (Δν_CO)_X.

  对苯甲酸酯的碱水解的二阶速率常数 k（以 dm³ mol⁻¹ s⁻¹ 计量），在25°C下，在水溶液中0.5和2.25 M Bu₄NBr下，用分光光度法测定了对位、间位和邻位取代苯甲酸的苯基酯的速率常数。对于对位和间位衍生物，取代基效应使用 Hammett 关系描述。对于邻位衍生物，使用了 Charton 方程。对于邻位取代酯，涉及两种立体参数：EsB 和 Charton 立体（υ）常数。从纯水到水溶液0.5和2.25 M Bu₄NBr，对苯基酯的碱水解中，对位和间位极性效应，对苯甲酸酯的碱水解中的邻位感应和共振效应，几乎与对 C₆H₅CO₂C₆H₄-X 的碱水解发现的情况一样强。邻位取代酯的立体项几乎独立于考虑的介质。对苯基苯甲酸酯（X-C₆H₄CO₂C₆H₅，C₆H₅CO₂C₆H₄-X）和烷基苯甲酸酯 C₆H₅CO₂R 在水、0.5和2.25 M Bu₄NBr中的碱水解速率常数与羰基的对应 IR 伸缩频率（ΔνCO）X 相关联。