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2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof

A technology of triol trinitrate and azaadamantane, applied in the direction of nitrated pentaerythritol composition, organic chemistry, etc., can solve the problems that have not been reported, and achieve the effects of high yield, easy scale-up preparation, and easy operation

Pending Publication Date: 2022-03-18
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the method of constructing a 2-azadamantane framework with a higher oxidation state has not been reported so far.

Method used

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  • 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof
  • 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof
  • 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof

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preparation example Construction

[0033] Synthetic method of the present invention, its concrete steps are as follows:

[0034] (1) Dissolve bicyclo[3.3.1]nonane-2,6-dione and p-toluenesulfonyl hydrazide in methanol, an organic solvent, and stir at 65-75°C for 2-6 hours to synthesize 9- Hydroxybicyclo[3.3.1]nonane-2,6-diylidenebis(4-methylbenzenesulfonylhydrazide);

[0035] (2) Add diisopropylamine and n-butyllithium to the organic solvent tetrahydrofuran sequentially at low temperature, and then add 9-hydroxybicyclo[3.3.1]nonane-2,6-diylidene bis(4-methylbenzenesulfonate Hydrazide) was added to the reaction solvent in batches, stirred at -68 to -78°C for 18 to 24 hours, and an elimination reaction occurred to synthesize bicyclo[3.3.1]nonane-2,6-dien-9-ol;

[0036] (3) Dissolve bicyclo[3.3.1]nonan-2,6-dien-9-ol and m-chloroperoxybenzoic acid in the organic solvent dichloromethane, stir at 25~40°C for 24~36h, and Synthesis of 3,8-dioxa-tetracyclo[4.4.1.0 by epoxidation reaction 2,4 .0 7,9 ]undecan-11-ol;

...

Embodiment 1

[0041] (1) Preparation of 9-hydroxybicyclo[3.3.1]nonane-2,6-diylidene bis(4-methylbenzenesulfonylhydrazide)

[0042]

[0043]Add 504mg (3.00mmol) of 9-hydroxybicyclo[3.3.1]nonane-2,6-dione into 25mL of methanol, then add 1.34g (7.2mmol) of p-toluenesulfonyl hydrazide, heat up to 68°C for reflux reaction 4h. The solvent was distilled off under reduced pressure, washed with cold absolute ethanol, and dried in vacuo to obtain 1.36 g of a white solid. Yield 90%.

Embodiment 2

[0045] (2) Preparation of bicyclo[3.3.1]nonane-2,6-dien-9-ol

[0046]

[0047] Add 5.6mL (3.50mmol) of diisopropylamine and n-butyllithium to 15mL of tetrahydrofuran successively at low temperature. After the dropwise addition is completed, add 1.008g (2.00mmol) of raw materials in batches. After the addition of raw materials is completed, slowly rise to The stirring reaction was continued at 25°C for 12h. Add 30 mL of water dropwise in an ice bath to quench the reaction, extract with ethyl acetate, adjust the pH to 4-5 with 10% dilute hydrochloric acid, wash with saturated saline, distill under reduced pressure to obtain 300 mg of golden yellow oil, and obtain 240 mg of white solid by silica gel column chromatography , yield 88%. Its characteristic graph is as figure 1 and figure 2 shown. 1 H NMR (500MHz, CDCl 3 )δ:5.92-5.51(m,4H),3.95(d,J=5.9Hz,1H),2.62-2.33(m,4H),2.07(dd,J=17.8,4.7Hz,1H),1.94-1.80 (m,2H)ppm. 13 C NMR (126MHz, CDCl 3 )δ: 130.51, 127.49, 125.70, 1...

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Abstract

The invention discloses 2-nitro-2-aza adamantane-4, 6, 8-triol trinitrate and a preparation method of the 2-nitro-2-aza adamantane-4, 6, 8-triol trinitrate. According to the method, 9-hydroxyl bicyclo [3.3. 1] nonane-2, 6-diketone is used as a raw material, the 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate is finally synthesized through the steps of hydrazone formation, elimination, epoxidation, cyclization, acetylation, nitration and the like, the compound has higher density and energy, the synthesis method is simple, the yield is high, and the performance is stable.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a novel compound 2-nitro-2-azaadamantane-4,6,8-triol trinitrate and a synthesis method thereof. Background technique [0002] Adamantane has a three-dimensional cage-like carbon skeleton, compact structure, and good thermal stability. It is an important class of organic compounds and can be widely used in the fields of drugs, lubricants, and functional polymers. Among them, nitroadamantane has the advantages of high energy and insensitivity due to its unique molecular structure, and can be used in energetic materials. Studies have shown that replacing the carbon atoms on the adamantane ring with one or more nitrogen atoms can result in polynitroadaptane Azaadamantane has better detonation performance. For example, in 2018, synthesized adamantane-1,3,5,7-tetraol tetranitrate ( TM, ChemPlusChem, 2018, 83, 61). Calculation results show that the detonation velocit...

Claims

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Application Information

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IPC IPC(8): C07D471/08C06B25/32
CPCC07D471/08C06B25/32
Inventor 罗军郭广帅刘运芝周琪蔡荣斌
Owner NANJING UNIV OF SCI & TECH
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