苯基 2-氨基苯甲酸 | 10268-69-6

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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-氨基苯甲酸
• 中文别名: 苯基2-氨基苯甲酸
• 英文名称: phenyl anthranilate
• 英文别名: phenyl o-aminobenzoate；2-aminobenzoic acid phenyl ester；N-phenyl anthranilic acid；Phenyl 2-aminobenzoate；phenyl anthranylate；anthranilic acid phenyl ester
• CAS: 10268-69-6
• 化学式: C₁₃H₁₁NO₂
• mdl: MFCD00060603
• 分子量: 213.236
• InChiKey: ZBFSYQBEXZGTAX-UHFFFAOYSA-N

物化性质

• 熔点：
  70°C
• 沸点：
  382.7±25.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)
• 溶解度：
  Insoluble in water, poorly soluble in cold alcohol. Soluble in most perfume oils.

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922439000
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  苯基 2-氨基苯甲酸 在 碳酸氢钠 作用下， 以 氯仿 、 苯 为溶剂， 反应 5.33h， 生成 2-chloroacetylamino-2'-hydroxybenzophenone
  参考文献：
  名称：

  Algarra, Felipe; Miranda, Miguel A., Heterocycles, 1993, vol. 36, # 10, p. 2335 - 2344

  摘要：

  DOI：
• 作为产物：
  描述：

  phenyl 2-nitrobenzoate 在 盐酸 、 tin 、 乙醇 作用下， 生成 苯基 2-氨基苯甲酸
  参考文献：
  名称：

  Rule; Bretscher, Journal of the Chemical Society, 1927, p. 926

  摘要：

  DOI：

文献信息

• Intramolecular General Base Catalyzed Ester Hydrolysis. The Hydrolysis of 2-Aminobenzoate Esters
  作者：Thomas H. Fife、Randhir Singh、Ramesh Bembi

  DOI：10.1021/jo0103017

  日期：2002.5.1

  with the phenyl ester is 10(5)-fold. Intramolecular general base catalyzed reactions are assessed in respect to their relative advantages and disadvantages in enzyme catalysis. A general base catalyzed reaction can be more rapid at low pH than a nucleophilic reaction that has a marked dependence on pH and the leaving group.

  已经获得了在50°C下于H（2）O中水解2-氨基苯甲酸的三氟乙基，苯基和对硝基苯基酯的速率常数。拟一级反应速率常数k（obsd）与pH无关，与pH 8至pH 4（胺基共轭酸的pK（a））无关。2-氨基苯甲酸酯在不依赖pH的反应中以相似的速率常数水解，在D（2）O中，这些水反应比H（2）O中的反应慢约2倍。最可能的机制涉及相邻胺基团在分子内的一般碱催化作用。与相应的对位取代的酯或苯甲酸酯的不依赖pH的水解相比，不依赖pH的反应的速率提高了50-100倍。与氢氧根离子催化的反应相比，用苯酯在pH 4下k（obsd）的增强是10（5）倍。就其在酶催化中的相对优点和缺点，评估了分子内一般碱催化的反应。一般的碱催化反应在低pH条件下比对pH和离去基团有明显依赖性的亲核反应更快。
• 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）。
• Metal‐Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of <i>ortho</i> ‐Carbonyl Anilines
  作者：Alankrita Garia、Jatin Grover、Nidhi Jain

  DOI：10.1002/ejoc.202100756

  日期：2021.8.6

  A metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole reagent under ambient conditions is described. No external additives are required, the reaction has broad substrate scope and delivers anthranils in excellent yields via oxidative heterocyclization.

  描述了在环境条件下使用 PhIO 作为唯一试剂从邻羰基苯胺无金属合成邻氨基苯甲酸。不需要外部添加剂，该反应具有广泛的底物范围，并通过氧化杂环化以优异的产率提供邻氨基苯甲酸。
• Derivative of saccharide and physiologically active agent containing the
  申请人：Kureha Kagaku Kogyo Kabushiki Kaisha

  公开号：US04372948A1

  公开（公告）日：1983-02-08

  The novel derivatives of saccharide obtained by bringing a saccharide into reaction with an ester of aminobenzoic acid, an aminobenzoic acid amide, an aminophenylacetic acid or an ester thereof have various physiological activities.

  将糖与氨基苯甲酸酯、氨基苯甲酰胺、氨基苯乙酸或其酯类化合物反应得到的糖的新型衍生物具有各种生理活性。
• 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-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）以及苯甲酸苯酯的取代苯酯 C6H5CO2C6H4-X（X = 2-I、2-CF3、2-C(CH3)3、4-Cl、4-CH3、4-OCH3、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。

表征谱图