3,5-二硝基苯甲酸异戊酯 | 10574-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二硝基苯甲酸异戊酯
• 英文名称: isopentyl 3,5-dinitrobenzoate
• 英文别名: 3,5-dinitro-benzoic acid isopentyl ester；3,5-Dinitro-benzoesaeure-isopentylester；3.5-Dinitro-benzoesaeure-isoamylester；Isoamyl-(3.5-dinitro-benzoat)；Isoamyl-<3,5-dinitro-benzoat>；3-methylbutyl 3,5-dinitrobenzoate
• CAS: 10574-12-6
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 282.253
• InChiKey: OVANGOIYCAFEOP-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C(Solv: ligroine (8032-32-4))
• 沸点：
  395.4±22.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)
• 保留指数：
  1995;2003;2018;2016.4;2015

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  3,5-二硝基苯甲酸异戊酯 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0~40.0 ℃ 、4.0 Pa 条件下， 反应 11.0h， 生成 diisopentyl 55,135-bis(((S)-1-butoxy-1-oxopropan-2-yl)carbamoyl)-3,7,11,15-tetraoxo-2,4,6,8,10,12,14,16-octaaza-1,5,9,13(1,3)-tetrabenzenacyclohexadecaphane-15,95-dicarboxylate
  参考文献：
  名称：

  One-Pot Formation of Aromatic Tetraurea Macrocycles

  摘要：

  Treating derivatives of m-phenylenediamine having different electron-richness and reactivities with triphosgene in the presence of triethylamine led to aromatic tetraurea rnacrocycles in high yields. Factors important for efficiently forming these macrocycles include the molar ratio (2:1) between the diamine and triphosgene, reaction temperature (-75 degrees C), and solvent (CH2Cl2). By controlling the order and rate for adding diamines, tetraurea macrocycles consisting of two different types of monomeric residues have also been obtained in high yields.

  DOI：

  10.1021/ol300684j
• 作为产物：
  描述：

  异戊醇 、 3,5-二硝基苯甲酰氯 在 potassium carbonate 、 sodium chloride 作用下， 70.0 ℃ 、420.01 kPa 条件下， 反应 0.03h， 以93%的产率得到3,5-二硝基苯甲酸异戊酯
  参考文献：
  名称：

  微波反应器中酚类和醇类的固相苯甲酰化：一种环保方案

  摘要：

  摘要 开发了一种在微波辐射下高效固相苯甲酰化苯酚和醇的方法。化学计量的苯甲酰氯足以进行反应。这种苯甲酰化反应的特点是反应时间短、产率高、后处理程序简单。此外，该反应的范围扩展到制备醇的 3,5-二硝基苯甲酰基衍生物。图形概要

  DOI：

  10.1080/00397911.2015.1078899

文献信息

• 3,5-Dinitrobenzoate and 3,5-Dinitrobenzamide Derivatives: Mechanistic, Antifungal, and In Silico Studies
  作者：Allana B. S. Duarte、Yunierkis Perez-Castillo、Patrícia Néris Andrade、Ricardo D. de Castro、Damião P. de Sousa

  DOI：10.1155/2022/2336175

  日期：2022.9.19

  Fungal infections, including those caused by Candida spp., are recognized in immunocompromised individuals for their high rates of morbidity and mortality. Microorganism resistance to conventional drugs compromises treatment effectiveness and yet also reveals the need to develop new drugs. In many compounds, nitro groups contribute to antimicrobial activity; thus, the inhibitory activity of a collection of twenty esters and amides (derived from 3,5-dinitrobenzoic acid) against Candida spp. was elucidated using microdilution methods to determine the Minimum Inhibitory Concentration (MIC) and Minimum Fungicide Concentration (MFC), as well as probable mechanisms of action. The structures of the synthesized compounds were characterized by FTIR spectroscopy, 1H-NMR, 13C NMR, and HRMS. Of the tested derivatives, ten presented fungicidal activity against at least one of the tested strains. Ethyl 3,5-dinitrobenzoate (2) exhibited the most potent antifungal activity against Candida albicans (MIC = 125 µg/mL; 0.52 mM), Candida krusei (MIC = 100 µg/mL; 4.16 mM), and Candida tropicalis (MIC = 500 µg/ml; 2.08 mM). The structure of the second most potent derivative (propyl 3,5-dinitrobenzoate (3) reveals that esters with short alkyl side chains exhibit better biological activity profiles. Compounds 2 and 3 presented a mechanism of action involving the fungal cell membrane. Though compound 2 modeling against C. albicans revealed a multitarget antifungal mechanism of action, involving various cellular processes, interference in the synthesis of ergosterol was observed. Our results demonstrate that certain ester derivatives containing aromatic ring nitro groups may be useful in the search for new antifungal drugs.

  真菌感染，包括由念珠菌属引起的感染，在免疫力低下的人群中发病率和死亡率都很高。微生物对传统药物的耐药性损害了治疗效果，同时也揭示了开发新药物的必要性。在许多化合物中，硝基都具有抗菌活性；因此，我们使用微量稀释法阐明了二十种酯类和酰胺类化合物（源自 3,5- 二硝基苯甲酸）对念珠菌属的抑制活性，以确定最低抑制浓度 (MIC) 和最低杀菌浓度 (MFC)，以及可能的作用机制。傅立叶变换红外光谱、1H-NMR、13C NMR 和 HRMS 对合成化合物的结构进行了表征。在测试的衍生物中，有十种对至少一种受试菌株具有杀菌活性。3,5-二硝基苯甲酸乙酯（2）对白色念珠菌（MIC = 125 µg/mL; 0.52 mM）、克鲁塞念珠菌（MIC = 100 µg/mL; 4.16 mM）和热带念珠菌（MIC = 500 µg/ml; 2.08 mM）具有最强的抗真菌活性。第二种最有效的衍生物（3,5-二硝基苯甲酸丙酯（3））的结构表明，具有短烷基侧链的酯类具有更好的生物活性。化合物 2 和 3 的作用机制涉及真菌细胞膜。虽然化合物 2 针对白僵菌的建模揭示了涉及各种细胞过程的多靶点抗真菌作用机制，但也观察到了对麦角甾醇合成的干扰。我们的研究结果表明，某些含有芳香环硝基的酯类衍生物可能有助于寻找新的抗真菌药物。
• “Healthy-Start”: Outcome of an Intervention to Promote a Heart Healthy Diet in Preschool Children
  作者：Christine L. Williams、Marguerite C. Bollella、Barbara A. Strobino、Arlene Spark、Theresa A. Nicklas、Laura B. Tolosi、Brian P. Pittman

  DOI：10.1080/07315724.2002.10719195

  日期：2002.2

  Objective: We evaluated the effects of a preschool nutrition education and food service intervention ''Healthy Start,'' on two-to-five-year-old children in nine Head Start Centers in upstate NY. The primary objective was to reduce the saturated fat (sat-fat) content of preschool meals to <10% daily energy (E) and to reduce consumption of sat-fat by preschoolers to <10% E.Methods: Six centers were assigned to the food service intervention and three to control condition. Food service intervention included training workshops for cooks and monthly site visits to review progress towards goals. Child dietary intake at preschool was assessed by direct observation and plate waste measurement. Dietary intake at home was assessed by parental food record and telephone interviews. Dietary data were collected each Fall/Spring over two years, including five days of menus and recipes from each center. Dietary data were analyzed with the Minnesota NDS software.Results: Consumption of saturated fat from school meals decreased significantly from 11.0%E to 10.4%E after one year of intervention and to 8.0%E after the second year, compared with an increase of 10.2% to 13.0% to 11.4%E, respectively, for control schools (p < 0.001). Total caloric intake was adequately maintained for both groups. Analysis of preschool menus and recipes over the two-year period of intervention showed a significant decrease in sat-fat content in intervention preschools (from 12.5 at baseline to 8.0%E compared with a change of 12.1%E to >11.6%E in control preschools (p < 0.001)). Total fat content of menus also decreased significantly in intervention schools (31.0% to >25.0%E) compared with controls (29.9% to >28.4%E).Conclusions: The Healthy Start food service intervention was effective in reducing the fat and saturated fat content of preschool meals and reducing children's consumption of saturated fat at preschool without compromising energy intake or intake of essential nutrients. These goals are consistent with current U.S. Dietary Guidelines for children older than two years of age.
• OELSCHLAEGER, H.;FRITSCH, H., ARCH. PHARM., 1985, 318, N 8, 759-763
  作者：OELSCHLAEGER, H.、FRITSCH, H.

  DOI：——

  日期：——
• Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol
  作者：Suchandra Chakraborty、Ahana Saha、Kaushik Basu、Chandan Saha

  DOI：10.1080/00397911.2015.1078899

  日期：2015.10.18

  Abstract An efficient solid-phase benzoylation of phenols and alcohols was developed under microwave irradiation. A stoichiometric amount of benzoyl chloride was sufficient to carry out the reaction. This benzoylation features short reaction time, good yields, and easy workup procedures. Furthermore, the scope of the reaction was extended to prepare 3,5-dinitrobenzoyl derivatives of alcohols. GRAPHICAL

  摘要 开发了一种在微波辐射下高效固相苯甲酰化苯酚和醇的方法。化学计量的苯甲酰氯足以进行反应。这种苯甲酰化反应的特点是反应时间短、产率高、后处理程序简单。此外，该反应的范围扩展到制备醇的 3,5-二硝基苯甲酰基衍生物。图形概要
• One-Pot Formation of Aromatic Tetraurea Macrocycles
  作者：Zehui Wu、Ting Hu、Lan He、Bing Gong

  DOI：10.1021/ol300684j

  日期：2012.5.18

  Treating derivatives of m-phenylenediamine having different electron-richness and reactivities with triphosgene in the presence of triethylamine led to aromatic tetraurea rnacrocycles in high yields. Factors important for efficiently forming these macrocycles include the molar ratio (2:1) between the diamine and triphosgene, reaction temperature (-75 degrees C), and solvent (CH2Cl2). By controlling the order and rate for adding diamines, tetraurea macrocycles consisting of two different types of monomeric residues have also been obtained in high yields.