2,6-dinitrophenyl benzoate | 1523-16-6

• 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
• 英文名称: 2,6-dinitrophenyl benzoate
• 英文别名: (2.6-Dinitro-phenyl)-benzoat；(2,6-dinitrophenyl) benzoate
• CAS: 1523-16-6
• 化学式: C₁₃H₈N₂O₆
• 分子量: 288.216
• InChiKey: KLZNCAYLXQDTIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-dinitrophenyl benzoate 、 L-脯氨酸 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-苯甲酰基-l-脯氨酸
  参考文献：
  名称：

  Reactivity of Tyrosyl–Proline toward Benzoylation in Aqueous 1,4-Dioxane

  摘要：

  The kinetics of the reaction of L-tyrosyl-L-proline (Tyr-Pro) with di- and trinitrophenyl benzoates in aqueous 1,4-dioxane (40 wt % of water) were studied in the temperature range 298-313 K. The reaction rate constant k(298) was found to vary in the range from 0.035 to 0.564 L.mol(-1).s(-1), and the activation barrier changed from 39 to 51 kJ/mol. The neutral and anionic forms of the dipeptide were simulated by the DFT/B3LYP/cc-pVTZ method. Natural bond orbital analysis of the electron density distribution in these forms showed that the preferred nucleophilic center in the dipeptide molecule is the nitrogen atom of the primary amino group rather than the oxygen atom of the phenolic hydroxy group.

  DOI：

  10.1134/s1070428020060111
• 作为产物：
  描述：

  2,6-二硝基苯酚 、 苯甲酸 在 吡啶 、 氯化亚砜 作用下， 生成 2,6-dinitrophenyl benzoate
  参考文献：
  名称：

  17O NMR study of ortho and alkyl substituent effects in substituted phenyl and alkyl esters of benzoic acids

  摘要：

  记录了在乙腈中的自然丰度下44个邻、间和对位取代苯基和烷基苯甲酸酯（C6H5CO2C6H4-X，C6H5CO2R）的17O NMR光谱。研究了取代基对羰基氧和单键的苯氧基（OPh）和烷氧基（OR）氧的17O NMR化学位移δ（17O）的影响。对于对位衍生物的羰基氧的δ（17O）值与σ°常数呈良好的相关性。发现如果对于电子捐赠+R和电子吸引-R取代基分别进行数据处理，则对于对位衍生物的羰基氧的δ（17O）值可以用包含电感σI、共振σ°R和空间位阻EsB取代基常数的Charton方程来描述。取代苯甲酸酯中的电子捐赠+R对于邻、对位取代基引起屏蔽，而电子吸引-R取代基则导致O信号失屏蔽。邻位取代基与酯基的空间相互作用降低了羰基氧的电子密度。在烷基苯甲酸酯中，δ（17O）值可以用电感σI和空间位阻EsB取代基常数来描述。

  DOI：

  10.1135/cccc2011100

文献信息

• Belousova; Simanenko; Savelova, Russian Journal of Organic Chemistry, 2000, vol. 36, # 11, p. 1656 - 1664
  作者：Belousova、Simanenko、Savelova、Suprun

  DOI：——

  日期：——
• Ph3P-I2 mediated aryl esterification with a mechanistic insight
  作者：Wong Phakhodee、Chuthamat Duangkamol、Mookda Pattarawarapan

  DOI：10.1016/j.tetlet.2016.03.105

  日期：2016.5

  In order to better understand the reaction mechanism and to obtain optimal conditions, the Ph3P-I-2/Et3N mediated aryl esterification reaction was thoroughly investigated. Using a specific reagent addition sequence, the reaction proceeds remarkably well especially with acidic substrates. P-31 NMR studies revealed that the formation of an aryloxyphosphonium salt is crucial in governing the reaction path toward the formation of phenolic esters. (C) 2016 Elsevier Ltd. All rights reserved.
• Reactivity of α-amino acids in the N-acylation with benzoic acid esters in aqueous dioxane
  作者：N. R. Ishkulova、L. E. Oparina、L. B. Kochetova、T. P. Kustova、N. V. Kalinina、L. V. Kuritsin

  DOI：10.1134/s1070363210050178

  日期：2010.5

  The effect of the nitro group as a substituent in the phenoxide part of phenyl benzoate on the rate of N-acylation of glycine, L-proline, and L-valine in the water (40 wt %)-dioxane solvent was studied. The activation parameters of glycine reactions with the esters were measured. The existence of compensation effect and the linear relation of the logarithms of the acylation constants to the Hammett constants were revealed. The energy of the LUMO of esters can serve as the descriptors of the easters reactivity.
• Fromm; Ebert, Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 108, p. 75
  作者：Fromm、Ebert

  DOI：——

  日期：——
• Acylation of piperidine and morpholine with phenyl benzoates in the mixtures water-2-propanol and water-dioxane
  作者：L. B. Kochetova、N. V. Kalinina、L. V. Kuritsyn、T. P. Kustova

  DOI：10.1134/s1070363215060109

  日期：2015.6

  Kinetics of acylation of piperidine and morpholine with 4-nitro- and 2,6-dinitrophenyl benzoates was studied in binary systems water-2-propanol and water-dioxane. Structural and energy characteristics of solvate complexes of morpholine and piperidine with the components of the mixed solvents were calculated. Kinetic regularities of acylation are considered from the viewpoint of specific solvation of amines.