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Compound containing nitrate functional group and synthesis method of compound

A synthesis method and technology of nitrate esters, which are applied in the field of compounds containing nitrate ester functional groups and their synthesis, can solve problems such as complex reaction steps, and achieve the effects of easy installation and removal, avoiding pre-activation, and wide applicability of substrates

Active Publication Date: 2021-05-11
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Or perform a halogen substitution reaction (Journal of Medicinal Chemistry, 2004, 47(3):711-719) to generate a nitrate ester structure, but it requires activation to install other functional groups, and the reaction steps are complicated
The completely inert C(sp3)-H bond direct site-selective conversion strategy to nitrate group has not been reported

Method used

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  • Compound containing nitrate functional group and synthesis method of compound
  • Compound containing nitrate functional group and synthesis method of compound
  • Compound containing nitrate functional group and synthesis method of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] E)-3-Methyl-2-(((quinoline-8-methylene)amino)oxy)butyl nitrate

[0031] Accurately weigh E)-quinoline formaldehyde-(3-methylbutane-2-yl)oxime (24.2mg, 0.1mmol), palladium acetate (2.2mg, 0.01mmol), silver nitrite (46.2mg, 0.3mmol), selective fluorine reagent (53.1mg, 0.15mmol), tetrabutylammonium bisulfate (33.9mg, 0.1mmol) were transferred to the reaction vessel, 1.5ml 1,2-dichloroethane was added, and the bottle was screwed Plug, react at 80°C for 18h. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, extracted 3 times with ethyl acetate and water, and extracted 1 time with brine, and the organic phase was removed from the solvent to obtain a crude product, which was separated by column chromatography ( Eluent: ethyl acetate / petroleum ether=1:10) to obtain a pure and dry product with a yield of 72%. 1 H NMR (500MHz, CDCl 3 )δ9.44(s,1H),8.92(dd,J=4.1,1.7Hz,1H),8.26(dd,J=7.3,0.8...

Embodiment 2

[0033] E)-2-cyclohexyl-2-(((quinoline-8-methylene)amino)oxy)ethyl nitrate

[0034] Accurately weigh E)-quinoline-8-formaldehyde O-(1-cyclohexylethyl)oxime (28.2mg, 0.1mmol), palladium acetate (2.2mg, 0.01mmol), silver nitrite (46.2mg, 0.3mmol ), selective fluorine reagent (53.1mg, 0.15mmol), tetrabutylammonium bisulfate (33.9mg, 0.1mmol) were transferred to the reaction vessel, 1.5ml 1,2-dichloroethane was added, and the stopper was tightened. Reaction at 80°C for 18h. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, extracted 3 times with ethyl acetate and water, and extracted 1 time with brine, and the organic phase was removed from the solvent to obtain a crude product, which was separated by column chromatography ( Eluent: ethyl acetate / petroleum ether=1:10), a pure and dry product was obtained with a yield of 63%. 1H NMR (500MHz, Chloroform-d) δ9.42(s, 1H), 8.94(dd, J=4.1, 1.8Hz, ...

Embodiment 3

[0036] E)-4-Phenyl-2-(((quinoline-8-methylene)amino)oxy)butyl nitrate

[0037] Accurately weigh E)-quinoline-8-carbaldehyde O-(4-phenylbutane-2-yl)oxime (30.4mg, 0.1mmol), palladium acetate (2.2mg, 0.01mmol), silver nitrite ( 46.2mg, 0.3mmol), selective fluorine reagent (53.1mg, 0.15mmol), tetrabutylammonium bisulfate (33.9mg, 0.1mmol) were transferred to the reaction vessel, 1.5ml 1,2-dichloroethane was added, Tighten the cork and react at 80°C for 18h. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, extracted 3 times with ethyl acetate and water, and extracted 1 time with brine, and the organic phase was removed from the solvent to obtain a crude product, which was separated by column chromatography ( Eluent: ethyl acetate / petroleum ether=1:10), a pure and dry product was obtained with a yield of 67%. 1 H NMR (500MHz, CDCl 3 )δ9.50(s,1H),8.95(dd,J=4.1,1.7Hz,1H),8.31–8.24(m,1H),8.17...

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Abstract

The invention discloses a compound containing a nitrate functional group and a synthesis method of the compound. According to the compound containing the nitrate functional group, an alcohol substrate of an oxime quinoline guiding group is subjected to a one-pot heating reaction to prepare a beta-position nitric acid esterification product under the catalytic action of palladium acetate and under the conditions that silver nitrite serves as a nitrate source, a selective fluorine reagent serves as an oxidizing agent, tetrabutylammonium hydrogen sulfate serves as a phase transfer catalyst, 1,2-dichloroethane serves as a solvent. The method is mild in condition, carbon-oxygen atom chemical bonds of specific reaction sites can be effectively constructed in one step, the pre-functionalization process is omitted, reaction steps are reduced, and high atom economy is achieved. Meanwhile, the substrate is wide in application range, the alcohol molecular structure is modified, and the generated nitrate functional group-containing compound has a wide application prospect in the fields of medicines and energetic materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and relates to a compound containing a nitrate functional group and a synthesis method thereof. Background technique [0002] Transition metal-catalyzed C–H bond functionalization strategies provide a concise route to directly convert C–H bonds into various more value-added carbon–carbon and carbon–heteroatom bonds (e.g., C-halogen, C–O, C–N and C-S, etc.), which would simplify many synthetic steps and reduce the formation of unwanted by-products. The regioselectivity and stereoselectivity of the reaction are also well controlled by the construction of the directing group-directing strategy in the system. Nitrate compounds have important applications in the fields of medicine and energetic materials, such as general coronary heart disease, angina pectoris, and energetic material propellants. The traditional synthesis method of nitrate esters is to use a mixture of concentrat...

Claims

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Application Information

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IPC IPC(8): C07D217/14
CPCC07D217/14
Inventor 姜超赵婷婷
Owner NANJING UNIV OF SCI & TECH
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