3,5-dinitro-benzoic acid isopropyl ester | 10477-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dinitro-benzoic acid isopropyl ester
• 英文别名: iso-propyl 3,5-dinitrobenzoate；isopropyl 3,5-dinitrobenzoate；3,5-Dinitro-benzoesaeure-isopropylester；Isopropyl-(3.5-dinitro-benzoat)；3,5-dinitro-benzoic acid, 1-methylethyl ester；Isopropyl-<3,5-dinitro-benzoat>；Propan-2-yl 3,5-dinitrobenzoate
• CAS: 10477-99-3
• 化学式: C₁₀H₁₀N₂O₆
• 分子量: 254.199
• InChiKey: FAYNAMQMBONHIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  371.0±22.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)
• 保留指数：
  1783;1788;1800;1785.4;1785

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-dinitro-benzoic acid isopropyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以94%的产率得到异丙基3,5-二氨基苯甲酸酯
  参考文献：
  名称：

  Heterocycles in Organic Materials Chemistry. Synthesis of Di-, Tri-, and Tetraimide Polycarboxylic Acids for Use in Organic Network Assembly

  摘要：

  DOI：

  10.3987/com-01-9242
• 作为产物：
  描述：

  3,5-二硝基苯甲酸 、 异丙醇 在 吡啶 、 2,4,6-三硝基氯苯 作用下， 反应 3.0h， 以98%的产率得到3,5-dinitro-benzoic acid isopropyl ester
  参考文献：
  名称：

  以2-氯-1,3,5-三硝基苯为缩合剂的醇酯化羧酸

  摘要：

  当羧酸或其钠盐和醇的混合物在吡啶存在下在温和条件下用 2-氯-1,3,5-三硝基苯处理时，形成相应的羧酸酯。酯形成的产率和速率取决于所使用的酸和醇的类型。

  DOI：

  10.1246/bcsj.54.1470
• 作为试剂：
  描述：

  1-Boc-四氢吡咯 在 仲丁基锂 、 鹰爪豆碱 、 3C₆H₁₄S*CuI 、 3,5-dinitro-benzoic acid isopropyl ester 作用下， 以 乙醚 、 环己烷 、 四氢呋喃 为溶剂， 反应 4.0h， 以63%的产率得到
  参考文献：
  名称：

  Method for Highly Enantioselective Ligation of Two Chiral C(sp³) Stereocenters

  摘要：

  A method is described for the joining of two alpha-lithiated C(sp(3)) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R2CuLi, by i-propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at -90 degrees C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.

  DOI：

  10.1021/jacs.7b07366

文献信息

• Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD)
  作者：Sivaraman Dandapani、Jeffery J. Newsome、Dennis P. Curran

  DOI：10.1016/j.tetlet.2004.07.009

  日期：2004.8

  context of the Mitsunobu reaction with adamantyl tags. HPLC experiments showed that molecules containing adamantyl groups were especially well retained on Sumichiral OA7500 β-methylated cyclodextrin bonded silica columns relative to many other types of molecules. Two new Mitsunobu reagents, bis-(1-adamantylmethyl) azodicarboxylate (BadMAD) and bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD), were prepared

  引入了一种新的分离带有环糊精结合基团的标签的方法，并在具有金刚烷基标签的Mitsunobu反应的背景下进行了举例说明。HPLC实验表明，相对于许多其他类型的分子，含有金刚烷基的分子在Sumichiral OA7500β-甲基化的环糊精键合硅胶柱上的保留特别好。制备了两种新的Mitsunobu试剂，双（1-金刚烷基甲基）偶氮二羧酸酯（BadMAD）和双（2-（1-金刚烷基）乙基）偶氮二羧酸酯（BadEAD），用于典型的Mitsunobu反应，并与β-甲基化的环糊精分离键合二氧化硅和标准二氧化硅。
• Fluorous Mitsunobu reagents and reactions
  作者：Sivaraman Dandapani、Dennis P. Curran

  DOI：10.1016/s0040-4020(02)00205-3

  日期：2002.5

  A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H4)2PPh] and new [C8F17CH2CH2C6H4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)NNCOOCH2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction

  引入了完全氟的Mitsunobu反应程序。它既使用现有的[（C 6 F 13 CH 2 CH 2 C 6 H 4）2 PPh]，又使用新的[C 8 F 17 CH 2 CH 2 C 6 H 4 PPh 2 ]氟膦和新的氟偶氮二羧酸酯（C 6 ˚F 13 CH 2 CH 2 OC（O）NNCOOCH 2 CH 2 C ^ 6 ˚F 13）。该过程涉及在典型的Mitsunobu条件下在THF中与代表性的亲核试剂和醇进行平行反应，然后在氟硅石上进行快速固相萃取（spe），从而提供了具有优良收率的清洁产品。可以容易地分离出包含氧化的氧化膦和还原的酰肼的氟级分，并且可以通过适当的氧化还原反应以高收率再生起始试剂，以供再利用。
• Esterification of Aromatic Carboxylic Acids with Alcohols Using 2-Chloro-3,5-dinitropyridine as a Condensing Agent
  作者：Seiji Takimoto、Naomi Abe、Yasushi Kodera、Hiroshi Ohta

  DOI：10.1246/bcsj.56.639

  日期：1983.2

  The reaction of 2-chloro-3,5-dinitropyridine (CDNP) with carboxylic acids and alcohols was examined, and it was found that CDNP was a useful condensing agent. Various esters were prepared in good yields.

  研究了 2-氯-3,5-二硝基吡啶 (CDNP) 与羧酸和醇的反应，发现 CDNP 是一种有用的缩合剂。以良好的收率制备了各种酯。
• 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.