3-苯甲酰氧基苯甲酸 | 28547-22-0

• 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: 3-苯甲酰氧基苯甲酸
• 英文名称: 3-(benzoyloxy)benzoic acid
• 英文别名: Benzoic acid, 3-(benzoyloxy)-；3-benzoyloxybenzoic acid
• CAS: 28547-22-0
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: MEUAICCVSAZKMX-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  433.7±28.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-苯甲酰氧基苯甲酸 在 苄胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以51%的产率得到间羟基苯甲酸
  参考文献：
  名称：

  Bell, Kevin H., Australian Journal of Chemistry, 1987, vol. 40, # 10, p. 1723 - 1735

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯甲酰咪唑 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 96.0h， 生成 3-苯甲酰氧基苯甲酸
  参考文献：
  名称：

  Kinetic and structural consequences of the leaving group in substrates of a class C β-lactamase

  摘要：

  The class C beta-lactamase of Enterobacter cloacae P99 is known to catalyze the hydrolysis of certain acyclic (thio)esters. Previous experiments have employed thioglycolate, in-hydroxybenzoate, and phenylphosphate leaving groups. The relative effectiveness of these leaving groups has now been quantitatively assessed by employment of a series of compounds with common acyl groups, and found to rank in the order phenylphosphate > m-hydroxybenzoate > thioglycolate. Structural models suggest that these leaving groups interact during acylation principally with Tyr 150, Lys 315, and Thr 316 of the beta-lactamase active site. The positions of the leaving group carboxylates in these models is compared with those in published crystal structures of complexes of class C beta-lactamases with beta-lactams. The particular effectiveness of the acyl phosphate indicates the positions of two oxyanions that strongly interact with the active site. This information should be useful in the design of inhibitors of class C beta-lactamases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.042

文献信息

• Mapping the S1 and S1’ subsites of cysteine proteases with new dipeptidyl nitrile inhibitors as trypanocidal agents
  作者：Lorenzo Cianni、Carina Lemke、Erik Gilberg、Christian Feldmann、Fabiana Rosini、Fernanda dos Reis Rocho、Jean F. R. Ribeiro、Daiane Y. Tezuka、Carla D. Lopes、Sérgio de Albuquerque、Jürgen Bajorath、Stefan Laufer、Andrei Leitão、Michael Gütschow、Carlos A. Montanari

  DOI：10.1371/journal.pntd.0007755

  日期：——

  treatment of cutaneous leishmaniasis. The synthesized compounds are dipeptidyl nitriles designed based on the most promising combinations of different moieties in P1 (ten), P2 (six), and P3 (four different building blocks). Eight compounds exhibited a Ki smaller than 20.0 nM for Cz, whereas three compounds met these criteria for LmCPB. Three inhibitors had an EC50 value of ca. 4.0 μM, thus being equipotent

  半胱氨酸蛋白酶Cruzipain被认为是治疗南美锥虫病的有效治疗靶标。设计，合成了一系列26种新化合物，并针对重组Cruzain（Cz）进行了测试，以绘制其S1 / S1´子位图。在一组四个人类半胱氨酸蛋白酶（CatB，CatK，CatL，CatS）和墨西哥利什曼原虫CPB（一组可能是治疗皮肤利什曼病的潜在靶标）上对同一系列进行了评估。合成的化合物是基于P1（十个），P2（六个）和P3（四个不同的结构单元）中不同部分最有希望的组合而设计的二肽基腈。八个化合物的Cz的Ki小于20.0 nM，而三个化合物的LmCPB符合这些标准。三种抑制剂的EC50值为ca。4.0微米 因此，根据其抗胰锥作用，与苯硝唑相当。我们的作图方法和各自的结构活性关系为治疗相关的半胱氨酸蛋白酶的特定配体-靶标相互作用提供了见识。
• ANOMALOUS ORIENTATIONAL EFFECTS DURING BENZOYLOXYLATIONS BY “SILVER BROMIDE DIBENZOATE”
  作者：Derek Bryce-Smith、Neil S. Isaacs、Seddeg O. Tumi

  DOI：10.1246/cl.1984.1471

  日期：1984.9.5

  formed from bromine and silver benzoate reacts with both arenes and alkanes to form aryl and alkyl benzoates, respectively. Highly unusual substituent effects are observed in the benzoyloxylations of arenes. Electron-withdrawing groups (e.g. –NO2, –CN, –CO–) on the aromatic ring facilitate reaction though directing the attacking reagent exclusively to the meta position. In alkanes, tertiary positions are

  由溴和苯甲酸银形成的固体络合物分别与芳烃和烷烃反应形成芳基苯甲酸酯和烷基苯甲酸酯。在芳烃的苯甲酰氧基化中观察到非常不寻常的取代基效应。芳环上的吸电子基团（例如–NO2、–CN、–CO–）通过将攻击试剂专门导向间位来促进反应。在烷烃中，三级位置最容易受到攻击。
• Effects of neutral and charged substituents on the infrared carbonyl stretching frequencies in phenyl and alkyl benzoates in DMSO
  作者：Vilve Nummert、Mare Piirsalu、Signe Vahur、Lauri Toom、Ivo Leito、Ilmar A. Koppel

  DOI：10.1002/poc.3608

  日期：2017.3

  reported by Hoefnagel and Wepster and those determined from the log k values of the alkaline hydrolysis in 4.4 M NaCl solution at 50 °C. Thus, the values of substituent constants for ion pairs of charged substituents estimated on the basis of aqueous data could be successfully used in non‐aqueous solution (DMSO) simultaneously with neutral substituents in case the charged substituents were not completely

  57个间位，对位和邻位取代的苯甲酸酯C 6 H 5 CO 2 C 6 H 4- X和烷基苯甲酸酯C 6 H 5 CO 2 R的羰基红外拉伸频率，除中性取代基外，还包含带电荷的取代基记录了二甲基亚砜（DMSO）中的苯氧基和烷氧基部分。羰基伸缩频率，ν CO，为元-和对发现在中性取代基的情况下，苯甲酸的预取代苯基酯与取代基常数σ °很好地相关。在ν CO为值邻衍生物与感应取代基常数相关，σ我只。常数的电荷取代基的值，σ ° ±，所述的基础上计算ν CO和13角C NMR化学位移，δ CO，在DMSO中与吻合σ ° ±由Hoefnagel和Wepster报告的相应离子对的最大电离值，以及从50°C下4.4 M NaCl溶液中碱性水解的log k值确定的值。因此，在带电取代基未完全电离且处于离子对中的情况下，基于水性数据估算的带电荷取代基离子对的取代基常数值可以成功地用于非水溶液（DMSO）和中性取代基形成。版权所有©2016
• Dearomatising cyclisation of lithiated allyl phenyl ethers: the role of an oxazoline substituent
  作者：Rebecca A. Harvey、Ol’ga Karlubíková、Sean Parris、Jonathan Clayden

  DOI：10.1016/j.tetlet.2013.05.098

  日期：2013.7

  Treatment of 3-allyloxyphenyl oxazolines with organolithium bases leads to allyllithiums which undergo dearomatising cyclisation. The resulting dearomatised anions may be quenched with electrophiles to form partially saturated benzopyran derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
• Shah; Shah, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1949, vol. 18/3 A, p. 25,27
  作者：Shah、Shah

  DOI：——

  日期：——