4-hydroxy-benzoic acid phenacyl ester | 55153-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-benzoic acid phenacyl ester
• 英文别名: 2-(4-Hydroxy-benzoyloxy)-1-phenyl-aethanon-(1)；4-Hydroxy-benzoesaeure-phenacylester；Benzoic acid, 4-hydroxy-, 2-oxo-2-phenylethyl ester；phenacyl 4-hydroxybenzoate
• CAS: 55153-15-6
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: PJFZYVHBWQRRIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-benzoic acid phenacyl ester 在 乙酰胺 、 三氟化硼乙醚 作用下， 以73%的产率得到4-(4-phenyloxazol-2-yl)phenol
  参考文献：
  名称：

  Convenient Syntheses of 2-Alkyl(Aryl)-4,5-diphenyloxazoles and 2-Alkyl(Aryl)-4-phenyloxazoles

  摘要：

  DOI：

  10.1055/s-1998-6093
• 作为产物：
  描述：

  2-溴苯乙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 4-hydroxy-benzoic acid phenacyl ester
  参考文献：
  名称：

  PHENACYL AND p-BROMOPHENACYL ESTERS OF MONOSUBSTITUTED BENZOIC ACIDS¹

  摘要：

  DOI：

  10.1021/ja01350a037

文献信息

• Kinetics of reaction of triethylammonium carboxylates with α-halogenocarbonyl compounds in organic solvents
  作者：M.Krishna Pillay、K. Kannan、P. Ramasubramanian

  DOI：10.1016/s0040-4020(01)90893-2

  日期：1983.1

  of the reaction of phenacyl bromide with triethylammonium p-substituted benzoates and phenoxyacetates at 25°, 30° and 35° in acetone suggest a rigid cyclic transition state involving a hydrogen bonded ion-pair as the active nucleophile. The effect of addition of water on the rate constant is rationalized. Regression analysis on single parameter treatment on benzoates shows that the reaction obeys the

  苯甲酰溴与三乙基铵对位取代的苯甲酸酯和苯氧乙酸酯在丙酮中在25°，30°和35°下反应的动力学表明，刚性环过渡态涉及氢键结合的离子对作为活性亲核试剂。加水对速率常数的影响是合理的。对苯甲酸酯进行单参数处理的回归分析表明，该反应符合哈米特方程（ϱ值+ 0.37，r = 0.993）。
• Protecting Groups That Can Be Removed through Photochemical Electron Transfer:  Mechanistic and Product Studies on Photosensitized Release of Carboxylates from Phenacyl Esters
  作者：Anamitro Banerjee、Daniel E. Falvey

  DOI：10.1021/jo970495j

  日期：1997.9.1

  Photolysis of electron-donating photosensitizers in the presence of various phenacyl esters (PhCOCH2-OCOR) results in C-O bond scission leading to the formation of acetophenone (PhCOCH3) and the corresponding carboxylic acid(RCO2H). Preparative experiments showed that the carboxylic acids are generated in high or quantitative isolated yields. It is argued that this reaction is initiated by a photoinduced electron transfer from the excited state sensitizer to the phenacyl ester. The latter process forms the anion radical of the phenacyl ester which in turn undergoes rapid C-O bond scission leading to the phenacyl radical and the corresponding carboxylate anion. This mechanism is supported by the following observations. (1) The phenacyl esters quench fluorescence from the sensitizers. (2) Analysis of the redox potentials of the sensitizer excited states and the substrates shows that the proposed electron transfer step is exergonic by 15-20 kcal/mol. (3) The byproducts are indicative of the proposed ion radical intermediates. In particular N-methylaniline is detected when N,N-dimethylaniline is used as a sensitizer. (4) Competing processes are observed in phenacyl esters whose acid components are themselves labile to single-electron transfer. For example, phenacyl 4-bromophenylacetate showed bromide elimination in competition with deprotection.
• Potassium fluoride assisted derivatization of carboxylic acids to phenacyl esters for determination by high-performance liquid chromatography
  作者：Jack M. Miller、Ian D. Brindle、Stephen R. Cater、Kwok-Hung. So、James H. Clark

  DOI：10.1021/ac50064a047

  日期：1980.12.1
• Convenient Syntheses of 2-Alkyl(Aryl)-4,5-diphenyloxazoles and 2-Alkyl(Aryl)-4-phenyloxazoles
  作者：Weiwei Pei、Shaohui Li、Xiaoping Nie、Yiwei Li、Jian Pei、Bingzi Chen、Jie Wu、Xiulin Ye

  DOI：10.1055/s-1998-6093

  日期：1998.9
• PHENACYL AND p-BROMOPHENACYL ESTERS OF MONOSUBSTITUTED BENZOIC ACIDS¹
  作者：T. Leonard Kelly、Hartley W. Howard

  DOI：10.1021/ja01350a037

  日期：1932.11