CN114195787A - 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof - Google Patents
2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof Download PDFInfo
- Publication number
- CN114195787A CN114195787A CN202111626453.1A CN202111626453A CN114195787A CN 114195787 A CN114195787 A CN 114195787A CN 202111626453 A CN202111626453 A CN 202111626453A CN 114195787 A CN114195787 A CN 114195787A
- Authority
- CN
- China
- Prior art keywords
- azaadamantane
- triol
- reaction
- nitro
- acetyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/32—Compositions containing a nitrated organic compound the compound being nitrated pentaerythritol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and a preparation method thereof. The method takes 9-hydroxy bicyclo [3.3.1] nonane-2, 6-diketone as a raw material, and finally synthesizes the 2-nitro-2-aza adamantane-4, 6, 8-triol trinitrate through the steps of hydrazonation, elimination, epoxidation, cyclization, acetylation, nitration and the like.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a new compound 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and a synthesis method thereof.
Background
Adamantane has a three-dimensional cage-shaped carbon skeleton, a compact structure and good thermal stability, is an important organic compound, and can be widely applied to the fields of medicines, lubricants, functional polymers and the like. Wherein the nitro adamantane has the advantages of high energy, passivity and the like due to the unique molecular structure, and can be used for the compound containingThe material can be obtained, and research shows that the polynitro aza adamantane obtained by replacing carbon atoms on an adamantane ring by one or more nitrogen atoms has better detonation performance. For example, the results of the year 2018,
the adamantane is taken as a raw material to synthesize the adamantane-1, 3,5, 7-tetraol tetranitrate ester (
T M, chemplus chem,2018,83, 61). The calculation result shows that the detonation velocity is about 7282m.s < -1 > and the detonation pressure is about 22.9 GPa.
The azaadamantane derivative is widely applied to the fields of medicines, catalysis and energetic materials. Wherein the natural drug molecule Dapholdhamine B is 1-azaadamantane as a skeleton (Guo L D, J.Am.chem.Soc.,2019,141,11713); the 2-azaadamantane skeleton is another secondary amine type azaadamantane structure, and 2-azaadamantane-N-oxyl which is more researched can be used as a high-activity and high-selectivity catalytic oxidation reaction catalyst (Kawamata T, J.Am.chem.Soc.,2017,139,1814); the 2-azaadamantane-4, 8-diol backbone was used to synthesize a novel energetic compound, 2,4,4,8, 8-pentanitro-2-azaadamantane (Hou T, Eur.J.org.chem.,2017,6957). However, no report has been made on the method for constructing a 2-azaadamantane skeleton in a higher oxidation state.
Disclosure of Invention
The invention aims to provide 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and a synthesis method thereof, the compound has higher oxidation degree and introduces four nitro groups, and has higher density and energy than other adamantane derivatives containing four nitro groups, and the synthesis method has the advantages of easily available raw materials, simple operation, higher yield and the like.
The technical solution for realizing the purpose of the invention is as follows:
2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate, which has the following structure:
the preparation method of the compound comprises the following steps:
(1) the bicyclo [3.3.1]]Epoxidation reaction of nonane-2, 6-diene-9-ol and m-chloroperoxybenzoic acid to prepare 3, 8-dioxatetracyclo [4.4.1.02,4.07,9]A step of extracting undecane-11-ol,
(2) the 3, 8-dioxatetracyclo [4.4.1.0 ]2,4.07,9]A step of preparing 2-azaadamantane-4, 6, 8-triol by cyclization reaction of undecane-11-ol and methanol solution of saturated ammonia gas,
(3) the 2-azaadamantane-4, 6, 8-triol is subjected to acetylation reaction under the action of acetic anhydride and alkali to prepare 2-acetyl adamantane-4, 6, 8-triol;
(4) a step of preparing 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate by sequentially carrying out alcohol hydroxyl nitration and N-acetyl nitrohydrolysis on 2-acetyl-2-azaadamantane-4, 6, 8-triol in a mixed acid system of fuming nitric acid and fuming sulfuric acid,
further, in the step (1), the epoxidation reaction is carried out in the presence of an organic solvent dichloromethane; the molar ratio of bicyclo [3.3.1] nonane-2, 6-diene-9-ol to m-chloroperoxybenzoic acid is 1: 2.4-3.0; the epoxidation reaction temperature is 25-40 ℃; the epoxidation reaction time is 24-36 h.
Further, in the step (2), the cyclization reaction temperature is 110-140 ℃; the cyclization reaction time is 24-48 h; 3, 8-dioxatetracyclo [4.4.1.0 ] -2,4.07,9]The molar ratio of the undecane-11-ol to the ammonia gas is 1: 40-50.
Further, in the step (3), acetylation is carried out in the presence of an organic solvent dichloromethane, and the molar ratio of 2-azaadamantane-4, 6, 8-triol to acetic anhydride is 1: 1.0-1.2; the base is triethylamine; the temperature of acetylation reaction is 0-30 ℃; the acetylation reaction time is 8-16 h.
Further, in the step (4), the volume ratio of fuming sulfuric acid to fuming nitric acid is 1: 1.5-2.5; the temperature of the alcohol hydroxyl nitration reaction is 0-25 ℃, and the reaction time is 0.5-1 h; the temperature of the N-acetyl nitrohydrolysis reaction is 60-80 ℃, and the reaction time is 4-8 h; the molar ratio of the 2-acetyl adamantane-4, 6, 8-triol to the fuming nitric acid is 1: 20-30.
Compared with the prior art, the invention has the following advantages: (1) the method has the advantages of easily obtained raw materials, simple synthesis steps, easy operation, high yield and easy scale-up preparation; (2) the invention introduces nitrogen heteroatom and nitroxyl radical on the basis of tetranitroadamantane, improves oxygen balance and enables the tetranitroadamantane to have higher density and energy.
Drawings
FIG. 1 shows a bicyclo [3.3.1] ring of the invention]Process for preparing nonane-2, 6-dien-9-ols1H NMR spectrum.
FIG. 2 shows a bicyclo [3.3.1] ring of the invention]Process for preparing nonane-2, 6-dien-9-ols13C NMR spectrum.
FIG. 3 shows a 3, 8-dioxatetracyclo [4.4.1.0 ] of the present invention2,4.07,9]Process for preparing undecane-11-ol1H NMR spectrum.
FIG. 4 shows a 3, 8-dioxatetracyclo [4.4.1.0 ] of the present invention2,4.07,9]Process for preparing undecane-11-ol13C NMR spectrum.
FIG. 5 is a drawing showing the preparation of 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate according to the present invention1H NMR spectrum.
FIG. 6 is a drawing showing 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate of the present invention13C NMR spectrum.
FIG. 7 is a FT-IR spectrum of 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate of the present invention.
FIG. 8 is a TG-DSC of 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate of the present invention.
Detailed Description
The invention is described in further detail below with reference to the figures and examples.
The general synthetic route of the 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate ester is as follows:
the synthesis method comprises the following specific steps:
(1) dissolving bicyclo [3.3.1] nonane-2, 6-dione and p-toluenesulfonyl hydrazide in an organic solvent methanol, stirring for 2-6 h at 65-75 ℃, and carrying out a hydrazonation reaction to synthesize 9-hydroxybicyclo [3.3.1] nonane-2, 6-diylidene bis (4-methylbenzenesulfonyl hydrazide);
(2) sequentially adding diisopropylamine and n-butyllithium into an organic solvent tetrahydrofuran at low temperature, then adding 9-hydroxybicyclo [3.3.1] nonane-2, 6-diylidene bis (4-methylbenzenesulfonyl hydrazide) into a reaction solvent in batches, stirring for 18-24 hours at the temperature of-68 to-78 ℃, and carrying out elimination reaction to synthesize bicyclo [3.3.1] nonane-2, 6-diene-9-ol;
(3) the bicyclo [3.3.1]]Dissolving nonane-2, 6-diene-9-alcohol and m-chloroperoxybenzoic acid in an organic solvent dichloromethane, stirring for 24-36 h at 25-40 ℃, and carrying out epoxidation reaction to synthesize 3, 8-dioxatetracyclo [4.4.1.0 ]2,4.07,9]Undecane-11-ol;
(4) the 3, 8-dioxatetracyclo [4.4.1.0 ]2,4.07,9]Adding undecane-11-ol into a methanol solution of saturated ammonia gas, stirring and reacting for 24-48 h at 110-140 ℃, and carrying out cyclization reaction to synthesize 2-azaadamantane-4, 6, 8-triol;
(5) dissolving 2-azaadamantane-4, 6, 8-triol in a solvent dichloromethane, adding acetic anhydride, adding triethylamine to neutralize acetic acid generated in the reaction process, stirring and reacting for 8-16 h at 0-30 ℃, and performing acetylation reaction to synthesize 2-acetyl-2-azaadamantane-4, 6, 8-triol;
(6) under the ice bath condition, fuming sulfuric acid and fuming nitric acid in a volume ratio of 1: 1.5-2.5 are mixed and stirred uniformly, then the fuming nitric acid and fuming sulfuric acid are added into 2-acetyl-2-azaadamantane-4, 6, 8-triol, and the mixture is stirred and reacted for 0.5-1 h at the temperature of 0-25 ℃ to generate nitration reaction of alcoholic hydroxyl; and then heating to 60-80 ℃, stirring and reacting for 4-8 h, and carrying out N-acetyl nitrohydrolysis reaction to synthesize 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate.
Example 1
Preparation of (mono) 9-hydroxybicyclo [3.3.1] nonane-2, 6-diylidenebis (4-methylbenzenesulfonyl hydrazide)
504mg (3.00mmol) of 9-hydroxybicyclo [3.3.1] nonane-2, 6-dione are added to 25mL of methanol, 1.34g (7.2mmol) of p-toluenesulfonylhydrazide is added thereto, and the mixture is heated to 68 ℃ and refluxed for 4 hours. The solvent was distilled off under reduced pressure, washed with cold absolute ethanol, and dried under vacuum to give 1.36g of a white solid. The yield thereof was found to be 90%.
Example 2
Preparation of (di) bicyclo [3.3.1] nonane-2, 6-dien-9-ol
At low temperature, adding 5.6mL (3.50mmol) of diisopropylamine and n-butyllithium into 15mL of tetrahydrofuran in sequence, adding 1.008g (2.00mmol) of raw materials in batches after the dropwise addition is finished, slowly raising the temperature to 25 ℃ after the raw materials are added, and continuing stirring and reacting for 12 hours. And dropwise adding 30mL of water under ice bath to quench the reaction, extracting with ethyl acetate, adjusting the pH to 4-5 with 10% diluted hydrochloric acid, washing with saturated saline solution, carrying out reduced pressure distillation to obtain 300mg of a golden yellow oily substance, and carrying out silica gel column chromatography to obtain 240mg of a white solid with the yield of 88%. Its characteristic map is shown in figure 1 andas shown in fig. 2.1H NMR(500MHz,CDCl3)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.13C NMR(126MHz,CDCl3)δ:130.51,127.49,125.70,124.83,68.40,35.85,34.58,31.93,25.65ppm.。
Example 3
(III) 3, 8-dioxatetracyclo [4.4.1.02,4.07,9]Preparation of undecane-11-ol
272mg (2.00mmol) of bicyclo [3.3.1]Dissolving nonane-2, 6-dien-9-ol in 10mL of dichloromethane, adding 863mg (4.81mmol) of mCPBA, reacting at 25 ℃ for 24h, and dropwise adding 20mL of 10% NaHSO3The reaction was quenched with aqueous solution, extracted with dichloromethane, the combined organic phases were chromatographed on silica gel column to give 289mg of a white solid in 86% yield. The characterization maps are shown in fig. 3 and 4.1H NMR(500MHz,CDCl3)δ:3.81(s,1H),3.42(s,1H),3.32(t,J＝4.7Hz,1H),3.17(d,J＝8.4Hz,2H),3.11(t,J＝4.4Hz,1H),2.51-2.43(m,2H),2.37(d,J＝7.0Hz,1H),2.29(dd,J＝15.9,6.9Hz,1H),2.05-1.95(m,2H)ppm.13C NMR(126MHz,CDCl3)δ:66.21,59.05,58.11,50.93,49.32,31.53,30.94,26.92,22.79ppm.。
Example 4
Preparation of (tetra) 2-azaadamantane-4, 6, 8-triol
336mg (2.00mmol) of 3, 8-dioxatetracyclo [4.4.1.0 ]2,4.07,9]Adding 5mL of saturated ammonia gas methanol solution into undecane-11-ol, heating to 120 ℃ for reaction for 48h, cooling, filtering, washing with cold ethanol for 2-3 times, and distilling under reduced pressure to obtain 300mg of light yellow solid with the yield of 81%.
Example 5
Preparation of (penta) 2-acetyl-2-azaadamantane-4, 6, 8-triol
370mg (2.00mmol) of 2-azaadamantane-4, 6, 8-triol are dissolved in 7mL of dichloromethane, then 0.21mL (2.22mmol) of acetic anhydride and 0.56mL (4.05mmol) of triethylamine are added, the mixture is reacted for 8h at 25 ℃, 480mg of yellow oily matter is obtained by reduced pressure distillation, 364mg of white solid is obtained by silica gel column chromatography, and the yield is 80%.
Example 6
Preparation of (hexa) 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate
Under the ice bath condition, 2mL fuming nitric acid and 1.0mL fuming sulfuric acid are respectively added into a single-mouth bottle to be stirred and reacted for 20min, then the fuming nitric acid and the fuming sulfuric acid are added into 454mg (2.00mmol) of 2-acetyl-2-azaadamantane-4, 6, 8-triol, the mixture is stirred and reacted for 0.5h under the ice bath condition, then the temperature is increased to 65 ℃ to be reacted for 6h, the mixture is poured into ice water to be filtered, washed by cold ethanol and dried in vacuum, and 497mg of white solid is obtained, and the yield is 68%. The characterization maps are shown in FIGS. 5-7.1H NMR(500MHz,(CD3)2CO)δ:5.60-5.09(m,3H),5.05-4.89(m,1H),4.49(dd,J＝7.2,3.6Hz,1H),2.97(s,1H),2.86(d,J＝4.7Hz,1H),2.45-2.32(m,2H),2.15(d,J＝4.6Hz,2H)ppm.13C NMR(126MHz,(CD3)2CO)δ:80.93,80.51,79.37,79.02,78.46,48.07,47.87,42.29,42.09,32.44,32.39,31.87,31.82,24.65,23,20.51,20.47ppm.IR(thin film,υcm-1):2925,1624,1426,1267,1000,970,931,831.
The density of the compound is 1.79g.cm by theoretical calculation-3The detonation velocity was 8060m.s-1The detonation pressure was 28.73 GPa.
The thermal stability of the compound was studied by a thermogravimetric analyzer (TG) and a Differential Scanning Calorimeter (DSC), and its characterization map is shown in fig. 8. As can be seen from FIG. 8, there is a distinct endothermic peak at 175 ℃ indicating a melting point of 175 ℃ and a distinct exothermic peak at 196 ℃ indicating a sharp exotherm at 196 ℃. The total weight loss from the beginning to the end of the decomposition is 68 percent, and the results show that the 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate has better thermal stability.
Claims (7)
1. A 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate having the structure:
2. a preparation method of 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate is characterized by comprising the following steps:
(1) the bicyclo [3.3.1]]Epoxidation reaction of nonane-2, 6-diene-9-ol and m-chloroperoxybenzoic acid to prepare 3, 8-dioxatetracyclo [4.4.1.02,4.07,9]A step of extracting undecane-11-ol,
(2) the 3, 8-dioxatetracyclo [4.4.1.0 ]2,4.07,9]A step of preparing 2-azaadamantane-4, 6, 8-triol by cyclization reaction of undecane-11-ol and methanol solution of saturated ammonia gas,
(3) the 2-azaadamantane-4, 6, 8-triol is subjected to acetylation reaction under the action of acetic anhydride and alkali to prepare 2-acetyl adamantane-4, 6, 8-triol;
(4) a step of preparing 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate by sequentially carrying out alcohol hydroxyl nitration and N-acetyl nitrohydrolysis on 2-acetyl-2-azaadamantane-4, 6, 8-triol in a mixed acid system of fuming nitric acid and fuming sulfuric acid,
3. the process according to claim 2, wherein in step (1), the epoxidation reaction is carried out in the presence of an organic solvent, dichloromethane; the molar ratio of bicyclo [3.3.1] nonane-2, 6-diene-9-ol to m-chloroperoxybenzoic acid is 1: 2.4-3.0; the epoxidation reaction temperature is 25-40 ℃; the epoxidation reaction time is 24-36 h.
4. The method according to claim 2, wherein in the step (2), the cyclization reaction temperature is 110-140 ℃; the cyclization reaction time is 24-48 h; 3, 8-dioxatetracyclo [4.4.1.0 ] -2,4.07,9]The molar ratio of the undecane-11-ol to the ammonia gas is 1: 40-50.
5. The method according to claim 2, wherein in the step (3), the acetylation reaction is carried out in the presence of an organic solvent dichloromethane, and the molar ratio of 2-azaadamantane-4, 6, 8-triol to acetic anhydride is 1: 1.0-1.2; the base is triethylamine; the temperature of acetylation reaction is 0-30 ℃; the acetylation reaction time is 8-16 h.
6. The method according to claim 2, wherein in step (4), the volume ratio of fuming sulfuric acid to fuming nitric acid is 1: 1.5-2.5; the temperature of the alcohol hydroxyl nitration reaction is 0-25 ℃, and the reaction time is 0.5-1 h; the temperature of the N-acetyl nitrohydrolysis reaction is 60-80 ℃, and the reaction time is 4-8 h; the molar ratio of the 2-acetyl adamantane-4, 6, 8-triol to the fuming nitric acid is 1: 20-30.
7. Use of 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate according to claim 1 as an energetic material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111626453.1A CN114195787A (en) | 2021-12-28 | 2021-12-28 | 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111626453.1A CN114195787A (en) | 2021-12-28 | 2021-12-28 | 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114195787A true CN114195787A (en) | 2022-03-18 |
Family
ID=80657048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111626453.1A Pending CN114195787A (en) | 2021-12-28 | 2021-12-28 | 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114195787A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115490698A (en) * | 2022-09-22 | 2022-12-20 | 南京理工大学 | 6-nitro-2-oxa-6-azaadamantane-4,8-diol dinitrate and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001026591A (en) * | 1999-07-09 | 2001-01-30 | Agency Of Ind Science & Technol | Azoniaadamantane compound, production of azaadamantane compound from the same and production of the azoniaadamantane compound |
| US8853220B1 (en) * | 2011-02-25 | 2014-10-07 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis of 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-diene intermediates toward the preparation of polyaza-adamantanes |
| CN106478604A (en) * | 2015-08-28 | 2017-03-08 | 南京理工大学 | 2,4,9- trinitro- -2,4,9- three azepine -7- adamantanol nitrate and its synthetic method |
| CN109516986A (en) * | 2017-09-19 | 2019-03-26 | 南京理工大学 | Five nitros of 2,4,4,8,8- -2-aza-adamantane and its synthetic method |
| CN110885330A (en) * | 2018-09-11 | 2020-03-17 | 南京理工大学 | Nitro derivative and synthetic method thereof |
-
2021
- 2021-12-28 CN CN202111626453.1A patent/CN114195787A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001026591A (en) * | 1999-07-09 | 2001-01-30 | Agency Of Ind Science & Technol | Azoniaadamantane compound, production of azaadamantane compound from the same and production of the azoniaadamantane compound |
| US8853220B1 (en) * | 2011-02-25 | 2014-10-07 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis of 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-diene intermediates toward the preparation of polyaza-adamantanes |
| CN106478604A (en) * | 2015-08-28 | 2017-03-08 | 南京理工大学 | 2,4,9- trinitro- -2,4,9- three azepine -7- adamantanol nitrate and its synthetic method |
| CN109516986A (en) * | 2017-09-19 | 2019-03-26 | 南京理工大学 | Five nitros of 2,4,4,8,8- -2-aza-adamantane and its synthetic method |
| CN110885330A (en) * | 2018-09-11 | 2020-03-17 | 南京理工大学 | Nitro derivative and synthetic method thereof |
Non-Patent Citations (6)
| Title |
|---|
| TIANJIAO HOU ET AL.: "2, 4, 4, 8, 8-Pentanitro-2-Azaadamantane: A High-Density Energetic Compound", EUR. J. ORG. CHEM., pages 6957 - 6960 * |
| 冯增国: "多面体含能材料的爆速和爆压预估", 含能材料, vol. 1, no. 2, pages 42 - 48 * |
| 杜耀 等: "多硝基金刚烷的合成及其理论研究进展", 化学推进剂与高分子材料, vol. 12, no. 2, pages 57 - 63 * |
| 郭广帅: "2-氮杂金刚烷-4, 6, 8-三醇骨架的构建", 南京理工大学硕士学位论文, pages 1 - 82 * |
| 阮宏伟 等: "2-硝基-2-氮杂金刚烷-4，8-二醇二硝酸酯的合成与表征", 含能材料, vol. 24, no. 6, pages 544 - 549 * |
| 阮宏伟: "2-氮杂金刚烷衍生物的合成研究及1, 2, 2, 5, 6, 6-六硝基金刚烷的合成探索", 中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑, no. 2, pages 014 - 254 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115490698A (en) * | 2022-09-22 | 2022-12-20 | 南京理工大学 | 6-nitro-2-oxa-6-azaadamantane-4,8-diol dinitrate and preparation method thereof |
| CN115490698B (en) * | 2022-09-22 | 2023-10-31 | 南京理工大学 | 6-nitro-2-oxa-6-azaadamantane-4, 8-diol dinitrate and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107235923B (en) | Preparation method of 3-aryl quinoxalinone derivatives | |
| Guo et al. | An unexpected multi-component one-pot cascade reaction to access furanobenzodihydropyran-fused polycyclic heterocycles | |
| CN108558692B (en) | Preparation method of amide compound | |
| CN114057578A (en) | Derivative of 2-trifluoromethyl cyclopentanone and preparation method thereof | |
| CN114751872A (en) | Column [5] arene N-heterocyclic carbene catalyst and preparation method and application thereof | |
| CN114195787A (en) | 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof | |
| CN112920066A (en) | Alpha-substituted-alpha-amino acid ester compound and preparation method thereof | |
| CN116283899A (en) | 3-perfluoroalkyl benzothiophene [ b ] cyclopentenone compound and synthesis method thereof | |
| CN109516986B (en) | 2,4,4,8, 8-pentanitro-2-azaadamantane and synthetic method thereof | |
| CN113061077B (en) | Alpha, alpha-dideuteroalcohol compounds, deuterated drugs and preparation method thereof | |
| CN115490698B (en) | 6-nitro-2-oxa-6-azaadamantane-4, 8-diol dinitrate and preparation method thereof | |
| Hernández-Guadarrama et al. | Synthesis of β-mono-and β, γ-di-substituted α-methylene-γ-lactams | |
| CN115353457B (en) | Asymmetric carbonate and preparation method thereof | |
| CN115197232A (en) | Cyclopropane fused oxygen bridge hexacyclic compound and synthesis method thereof | |
| CN113121357B (en) | 2-nitrovinyl cyclopropane compound and synthesis method thereof | |
| CN110734354B (en) | Method for preparing biaryl compound from alcohol compound | |
| CN108383754B (en) | Preparation method and application of aryl oxime ester compound | |
| Deng et al. | Regio-and diastereoselective synthesis of diverse spirocyclic indenes by cyclization with indene-dienes as two carbon building blocks | |
| CN112778199B (en) | Compound containing nitrate functional group and synthetic method thereof | |
| CN115322106B (en) | Synthesis method of trans-3-azido-1-methylcyclobutanol and trans-3-amino-1-methylcyclobutanol | |
| CN110467556B (en) | Nucleophilic reaction method for catalyzing imine ions and acetophenone by nickel | |
| CN114213440B (en) | 2-boron alkenyl oxygen ether compound and preparation method thereof | |
| CN113248418B (en) | 3-alkynyl-2, 4-diester-based pyrrole compound and preparation method thereof | |
| CN115583902B (en) | Preparation method of alkynyl thioether compound | |
| CN115784895B (en) | Method for preparing arylamine compound by nonmetal reduction of aryl nitro compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |