CN120004874A - A kind of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and its synthesis method - Google Patents
A kind of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and its synthesis method Download PDFInfo
- Publication number
- CN120004874A CN120004874A CN202311273134.6A CN202311273134A CN120004874A CN 120004874 A CN120004874 A CN 120004874A CN 202311273134 A CN202311273134 A CN 202311273134A CN 120004874 A CN120004874 A CN 120004874A
- Authority
- CN
- China
- Prior art keywords
- oxetane
- oxymethyl
- synthesis method
- bis
- nitro
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
- C06B23/005—Desensitisers, phlegmatisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明提供了一种3,3‑二(4‑叠氮基呋咱‑3‑氧甲基)氧杂环丁烷及其合成方法，该方法包括：将3‑硝基‑4‑羟基呋咱、3,3‑二溴甲基氧杂环丁烷、碱性供体和相转移催化剂加入极性非质子溶剂中，在60～100℃下搅拌反应0.5～4h，然后经萃取、水洗、干燥、过滤、蒸干溶剂和重结晶，得到中间体3,3‑二(4‑硝基呋咱‑3‑氧甲基)氧杂环丁烷；将3,3‑二(4‑硝基呋咱‑3‑氧甲基)氧杂环丁烷和叠氮化试剂加入极性非质子溶剂中，在室温下搅拌反应0.5～1.5h，然后经萃取、水洗、干燥、过滤、蒸干溶剂和重结晶即得。本发明方法通过控制反应条件能够经由中间体硝基取代产物完全转化为3,3‑二(4‑叠氮基呋咱‑3‑氧甲基)氧杂环丁烷，产率高、纯度高，反应路线高效省时，便于工业化连续生产。
The invention provides 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and a synthesis method thereof. The method comprises: adding 3-nitro-4-hydroxyfurazan, 3,3-dibromomethyloxetane, an alkaline donor and a phase transfer catalyst into a polar aprotic solvent, stirring and reacting at 60-100 DEG C for 0.5-4h, then extracting, washing, drying, filtering, evaporating the solvent and recrystallizing to obtain an intermediate 3,3-bis(4-nitrofurazan-3-oxymethyl)oxetane; adding 3,3-bis(4-nitrofurazan-3-oxymethyl)oxetane and an azidation agent into a polar aprotic solvent, stirring and reacting at room temperature for 0.5-1.5h, then extracting, washing, drying, filtering, evaporating the solvent and recrystallizing to obtain the intermediate. The method of the present invention can completely convert the intermediate nitro-substituted product into 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane by controlling the reaction conditions, has high yield and purity, and the reaction route is efficient and time-saving, and is convenient for industrial continuous production.
Description
Technical Field
The invention belongs to the technical field of energetic materials, and particularly relates to 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane and a synthesis method thereof.
Background
The efficiency of high-precision ammunition in anti-terrorism wars is seen, but the existing capacity of high-precision ammunition is difficult to cope with the great demands, so that the modular energetic material which can be combined with other units to form products through different forms of processing modes, has relatively independent functions, can be decomposed and combined and is generally interchanged is produced, and the modular energetic material can be produced in batches and manufactured in series on the basis of standardization. Based on modular energetic material designs, custom made and synthetic research has recently received attention.
The oxetane is used as a saturated four-membered ring ether monomer with double active sites, can simultaneously load two energetic groups to form a high polymer skeleton, is an important branch of an energetic polymer, and has wide application prospect. The furazan compound is different from the traditional energetic compound, on one hand, the molecular structure of the furazan compound contains a large number of C-N, C =N and N=N bonds, the furazan compound has very high formation enthalpy, the furazan ring has aromaticity, so that the thermal stability of the furazan derivative is enhanced, the furazan ring has coplanarity, so that the furazan compound has higher density, and on the other hand, the furazan compound has the property of insensitive and heat-stable because the electronegativity of nitrogen and oxygen atoms is higher, and the aza-aromatic ring system of the furazan compound can form a large pi bond of a benzene-like structure. Therefore, many of the furazan energetic derivatives have the advantages of high energy density, high standard enthalpy of formation (delta Hf), high nitrogen content, excellent heat resistance and the like. The oxetane polymer with excellent mechanical properties and the stable furazan-based energetic groups are very suitable for the application requirements of the modularized energetic material.
The 3, 3-bis (4-azidofuroazan-3-oxymethyl) oxetane energetic monomer contains furazan groups and oxetane matrix, has higher energy density and has application prospect as a multifunctional modularized energetic material, but the existing synthetic route adopts the raw material 3-azido-4-hydroxyfurazan, the preparation route is as long as four steps, the steps are long and the yield is low, the screening and purification of four byproducts are involved in the first-step substitution reaction, and the corrosive strong acid trifluoromethanesulfonic acid and the corrosive strong base DBU are involved in the second-step cyclization reaction. Experiments show that the operation steps of the route are complicated, the environmental pollution is serious, the nitro base is easy to hydrolyze due to the existence of the organic strong base DBU, the yield of the product is low, and the practical application is difficult.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane and a synthesis method thereof, which solve the technical problems of lengthy preparation steps and low yield of the 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane existing in the prior art.
In order to solve the technical problems, the invention adopts the following technical scheme:
A method for synthesizing 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane, comprising the steps of:
Step 1, adding 3-nitro-4-hydroxyfurazan, 3-dibromo methyl oxetane, an alkaline donor and a phase transfer catalyst into a polar aprotic solvent, stirring and reacting for 0.5-4 hours at 60-100 ℃, and then extracting, washing, drying, filtering, evaporating the solvent and recrystallizing to obtain an intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane;
And 2, adding the intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane and an azide reagent obtained in the step 1 into a polar aprotic solvent, stirring at room temperature for reaction for 0.5-1.5 h, and then extracting, washing, drying, filtering, evaporating the solvent and recrystallizing to obtain the product.
The invention also has the following technical characteristics:
Specifically, the alkaline donor in step1 includes anhydrous potassium carbonate, cesium carbonate and ferric hydroxide.
Still further, the phase transfer catalyst described in step 1 includes tetrabutylammonium bromide, benzyltriethylammonium chloride, methyltrialkylammonium chloride, and 18-crown-6.
Further, in the step 1, the molar ratio of 3, 3-dibromo-methyl oxetane to 3-nitro-4-hydroxyfurazan is 1 (2-3.5).
Further, the molar ratio of the 3-nitro-4-hydroxyfurazan to the alkaline donor in the step 1 is 1 (1.5-3).
Still further, the azide reagent in the step 2 includes sodium azide, azido trimethylsilane, p-toluenesulfonyl azide, ethyl azide, tetrabutylammonium azide, and tri-n-butyltin azide.
Further, in the step 2, the molar ratio of the intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane to the azide reagent is1 (2.5-3.5).
Still further, the polar aprotic solvent includes DMF, meCN, acetone and DMSO.
The invention also protects the 3, 3-di (4-azidofuranazan-3-oxymethyl) oxetane prepared by the synthesis method
Compared with the prior art, the invention has the following technical effects:
(I) The synthesis method of the invention takes cheap and easily available 3-nitro-4-hydroxyfurazan and commercial 3, 3-dibromo-methyl oxetane as raw materials, and the 3, 3-di (4-nitrofurazan-3-oxymethyl) oxetane can be obtained by heating in an alkaline solvent system in the presence of a catalytic amount of a phase transfer catalyst, and then the 3, 3-di (4-azidofuran-3-oxymethyl) oxetane can be obtained by reacting with sodium azide in a DMF solvent. The method has the advantages of easily obtained raw materials, simple and convenient reaction conditions and little environmental pollution.
(2) The synthesis method can completely convert the intermediate nitro substitution product into the azide substitution product 3, 3-bis (4-azidofuroazan-3-oxymethyl) oxetane by controlling the reaction conditions, and the final product has high yield and purity, is easy to post-treat, has high efficiency and time saving reaction route, and is convenient for industrial continuous production.
The following examples illustrate the invention in further detail.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane;
FIG. 3 is a FTIR spectrum of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane;
FIG. 4 is a high resolution mass spectrum of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane;
FIG. 5 is a DSC of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane.
The following examples illustrate the invention in further detail.
Detailed Description
All the raw materials in the present invention, unless otherwise specified, are known in the art.
The synthetic route for 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane disclosed in the prior art is as follows:
The energetic monomer contains furazan groups and oxetane matrix, has higher energy density and has application prospect as a multifunctional modularized energetic material, but the preparation route of the raw material 3-azido-4-hydroxyfurazan is selected in the synthetic route, the steps are long, the yield is low, the second cyclization reaction involves corrosive strong acid trifluoro methanesulfonic acid and corrosive strong base DBU, and the energetic oxetane monomer needs to be separated from four products to obtain a disubstituted product in the synthetic route, and then cyclizes, so that the steps are complicated, the operation is complex, and the method is difficult to practically apply.
The invention is characterized in that 3-nitro-4-hydroxyfurazan with the synthesis difficulty far smaller than that of 3-azido-4-hydroxyfurazan is combined with an oxetane matrix to obtain an intermediate through Williamson ether formation reaction under alkaline condition and nucleophilic attack of oxyanion, and furazan nitro is converted into azido through mature azido reaction to prepare 3, 3-bis (4-azido furazan-3-oxymethyl) oxetane. This route allows successful synthesis of the target compound, but the reaction time in the first step of preparing the intermediate is longer (3-4 h) and the yield is lower (60%). Accordingly, the inventors have searched for a catalyst for accelerating the reaction by using inexpensive and easily available N, N-Dimethylformamide (DMF), acetonitrile (MeCN), acetone (Acetone), dimethyl sulfoxide (DMSO), or the like as a solvent.
The invention provides a synthetic method of 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane, which comprises the following synthetic route:
the method comprises the following steps:
Step 1, adding 3-nitro-4-hydroxyfurazan, 3-dibromo methyl oxetane, an alkaline donor and a phase transfer catalyst into a polar aprotic solvent, stirring and reacting for 0.5-4 hours at 60-100 ℃, and then extracting, washing, drying, filtering, evaporating the solvent and recrystallizing to obtain an intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane;
wherein the alkaline donor comprises anhydrous potassium carbonate, cesium carbonate and ferric hydroxide.
The phase transfer catalyst comprises tetrabutylammonium bromide, benzyl triethyl ammonium chloride, methyl trialkyl ammonium chloride and 18-crown ether-6.
Preferably, the molar ratio of 3, 3-dibromo-methyl oxetane to 3-nitro-4-hydroxyfurazan is 1 (2-3.5).
Preferably, the molar ratio of the 3-nitro-4-hydroxyfurazan to the alkaline donor is 1 (1.5-3).
Preferably, the polar aprotic solvent comprises DMF, meCN, acetone and DMSO.
The polar aprotic solvent includes DMF, meCN, acetone and DMSO.
And 2, adding the intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane and an azide reagent obtained in the step 1 into a polar aprotic solvent which comprises DMF, meCN, acetone and DMSO, stirring at room temperature for reaction for 0.5-1.5 h, and then extracting, washing, drying, filtering, evaporating the solvent and recrystallizing to obtain the product.
Still further, the azide reagent includes sodium azide, azido trimethylsilane, p-toluenesulfonyl azide, ethyl azide, tetrabutylammonium azide, tri-n-butyltin azide.
Further, the molar ratio of the intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane to the azide reagent is 1 (2.5-3.5).
The following specific embodiments of the present application are provided, and it should be noted that the present application is not limited to the following specific embodiments, and all equivalent changes made on the basis of the technical scheme of the present application fall within the protection scope of the present application.
Example 1
The embodiment provides a synthetic method of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane, which comprises the following steps:
Step 1, adding 3-nitro-4-hydroxyfurazan (2.62 g,0.02 mol), 3-dibromomethyl oxetane (2.44 g,0.01 mol), anhydrous potassium carbonate (2.76 g,0.02 mol) and a phase transfer catalyst 18-crown ether-6 (0.05 g,0.0002 mol) into dimethylformamide DMF (30 ml) at room temperature, fully stirring, reacting for 1.5h at 75 ℃, adding water and dichloromethane for extraction after the reaction is finished, and then washing, drying by anhydrous magnesium sulfate, filtering, evaporating the solvent, and recrystallizing to finally obtain light yellow crystals (2.8 g, yield 81%);
Step 2, the intermediate (1.72 g,0.005 mol) obtained in step 1 and sodium azide (0.65 g,0.01 mol) were added to 3ml of DMF, and the mixture was stirred at room temperature for 0.5h, and then extracted with ethyl acetate, washed with water, dried, filtered, evaporated in suspension, and recrystallized from ethanol to give the desired product as white crystals (1.51 g, yield 90%).
And (3) structural identification:
(1) Nuclear magnetic resonance carbon spectrum analysis
As shown in FIG. 2, the comparison of the obtained spectrum with the intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane shows that the characteristic peaks at 158.77ppm and 152.65ppm of 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane shift to 159.26ppm and 145.23ppm respectively at low-high fields, the peak type changes from the high-low peak type of the nitrofurazan characteristic to the approximate equal-high peak type of the azidofuranazan characteristic, which indicates the disappearance of furazan nitro and the formation of azidofuranazan, and the characteristic peaks of the methyl oxetane at 73.42ppm, 73.33ppm and 42.68ppm have little change, which indicates that the methyl oxetane main body has not changed. The corresponding hydrogen spectrum is shown in FIG. 1, the area obtained by integrating the corresponding peaks is 1:1, and successful synthesis of 3, 3-bis (4-azidofuranazan-3-oxymethyl) oxetane is also demonstrated.
(2) Infrared spectrogram analysis
The resulting spectrum and intermediate 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane pairs such as shown in FIG. 3, shows that the characteristic peak of oxetane at 835cm -1 is still present, indicating that the oxetane structure is still present in the pure monomer, whereas the infrared absorption peak of nitro group at 1624cm -1 is disappeared, indicating that no nitro group is present in the product, whereas the occurrence of the characteristic absorption peaks of azido groups at 2100cm -1 and 2150cm -1 indicates successful synthesis of 3, 3-bis (4-azidofurofurazan-3-oxymethyl) oxetane.
(3) High resolution mass spectrometry
As shown in FIG. 4, the highest peak m/z in the high resolution mass spectrum is 337.08619, which is well matched with the predicted hydrogenation peak 337.0757, indicating successful synthesis of 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane.
(4) Single crystal X-ray diffraction results
The single crystal X-ray diffraction results obtained are shown in the following table:
The 3, 3-bis (4-azidofuroazan-3-oxymethyl) oxetane prepared by the embodiment leads the oxetane to obtain good detonation performance and extremely high stability by introducing furazan groups into the oxetane, has the functions of simple substance explosive and energetic plasticizer, simultaneously leads the introduced oxetane structure to endow the oxetane with good polymerization capability, greatly expands the application field of the oxetane, can be polymerized as a structural energetic material or an energetic adhesive, can also be used as an energetic initiator/chain extender, and is a multifunctional insensitive energetic material with great application prospect
Example 2
The synthesis method and procedure used in this example were the same as those of example 1 except that in step 1, the reaction was carried out at 65℃for 1.5 hours to give pale yellow crystals (1.9 g, yield 55%) as an intermediate, and the final product was 1.51g, yield 90%.
The structure identification result of this example was the same as that of example 1.
Example 3
The synthesis method and procedure used in this example were the same as those of example 1 except that in step 1, the reaction was carried out at 75℃for 2.5 hours to give pale yellow crystals (2.9 g, yield 84%) as an intermediate, and the final product was 1.51g, yield 90%.
The structure identification result of this example was the same as that of example 1.
Example 4
The synthesis method and procedure used in this example were the same as those of example 1 except that in step 1, the amount of 3-nitro-4-hydroxyfurazan added was 3.93g,0.03mol, to give pale yellow crystals (3.0 g, yield 58%) as an intermediate, and the final product was 1.51g, yield 90%.
The structure identification result of this example was the same as that of example 1.
Example 5
The synthesis method and procedure used in this example were the same as those of example 1 except that in step 1, the polar aprotic solvent used was DMSO to give pale yellow crystals (2.1 g, yield 61%) as intermediates, and the product obtained in final step 2 was 1.51g, yield 90%.
The structure identification result of this example was the same as that of example 1.
Example 6
The synthesis method and procedure used in this example were the same as those of example 1 except that in step 2, the reaction was stirred at room temperature for 1.5 hours to give a white crystal (1.55 g, yield 92%) of the final product.
The structure identification result of this example was the same as that of example 1.
Example 7
The synthesis method and procedure used in this example were the same as those of example 1 except that in step 2, the added amount of sodium azide was 0.975g and 0.015mol, and white crystals (1.56 g, yield 93%) were obtained as the final product.
The structure identification result of this example was the same as that of example 1.
Example 9
The synthesis method and procedure used in this example were the same as those of example 1 except that tetrabutylammonium bromide was used as the phase transfer catalyst, and 0.92g of pale yellow crystals was obtained in 54.8% yield.
The structure identification result of this example was the same as that of example 1.
Example 10
The synthesis method and procedure used in this example were the same as those of example 1 except that the phase transfer catalyst was benzyltriethylammonium chloride, to give 1.23g of pale yellow crystals, and the yield was 73.2%.
The structure identification result of this example was the same as that of example 1.
Comparative example 1
The synthesis method used in this comparative example was the same as in example 1 except that no phase transfer catalyst was added in step 1, and 0.69g of pale yellow crystals were finally obtained in a yield of 41.3%.
The structure identification result of this comparative example is the same as that of example 1.
From examples 1 to 12, and comparative examples 1 to 3, it can be seen that:
firstly, under the condition that raw material components are the same, a phase transfer catalyst is added to have catalytic capability on the reaction, secondly, the yield of the product is in an ascending trend along with the rise of the reaction temperature, but after 75 ℃, the rise of the yield is not obvious, meanwhile, the influence of safety is considered, the 75 ℃ is the optimal temperature of the reaction, and the polar aprotic solvent, especially DMF, has obvious solvation effect on the reaction to promote the reaction, because the polar aprotic solvent with high boiling point can not only provide energy to help the reaction to cross the energy barrier by heating, but also can greatly improve the reaction speed and yield by adopting the special solvation action of the polar aprotic solvent.
Compared with the existing method for preparing 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane by taking pentaerythritol which is an easily explosive dangerous product and 3-azido-4-hydroxyfurazan which is complicated and low-efficiency to prepare as raw materials in the presence of corrosive strong alkali DBU and corrosive acid trifluoromethanesulfonic acid, the method provided by the invention has the advantages that the 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane which is cheap and easy to obtain and the 3, 3-dibromomethyl oxetane which is commercially available is taken as the raw materials, the 3, 3-bis (4-nitrofurazan-3-oxymethyl) oxetane can be obtained by heating in an alkaline solvent system in the presence of a catalytic amount of a phase transfer catalyst, and then the final product 3, 3-bis (4-azidofuran-3-oxymethyl) oxetane can be obtained by reacting with sodium azide in a DMF solvent.
Compared with the existing method for obtaining 3-azido-4-hydroxyfurazan through complicated post-treatment by a four-step reaction of diaminofurazan, and then obtaining four azidofuranazan substituted pentaerythritol, the method still needs to pass through a complicated separation process, screens out di-substituted pentaerythritol and tri-substituted pentaerythritol to continue cyclization reaction, and finally can obtain the 3, 3-di (4-azidofuran-3-oxymethyl) oxetane product.
In conclusion, the method has the advantages of easily available raw materials, simple and convenient reaction conditions and little environmental pollution, can completely convert an intermediate nitro-substituted product into an azide substituted product 3, 3-bis (4-azidofuroazan-3-oxymethyl) oxetane by controlling the reaction conditions, has high product yield and purity, shorter reaction time, and is easier to post-treat, thereby being convenient for industrial continuous production.
The preferred embodiments of the present disclosure have been described in detail above with reference to the accompanying drawings, but the present disclosure is not limited to the specific details of the embodiments described above, and various simple modifications may be made to the technical solutions of the present disclosure within the scope of the technical concept of the present disclosure, and all the simple modifications belong to the protection scope of the present disclosure.
In addition, the specific features described in the foregoing embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, the present disclosure does not further describe various possible combinations.
Moreover, any combination between the various embodiments of the present disclosure is possible as long as it does not depart from the spirit of the present disclosure, which should also be construed as the disclosure of the present disclosure.
Claims (9)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311273134.6A CN120004874A (en) | 2023-09-28 | 2023-09-28 | A kind of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and its synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311273134.6A CN120004874A (en) | 2023-09-28 | 2023-09-28 | A kind of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and its synthesis method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN120004874A true CN120004874A (en) | 2025-05-16 |
Family
ID=95672301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311273134.6A Pending CN120004874A (en) | 2023-09-28 | 2023-09-28 | A kind of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and its synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN120004874A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001005871A1 (en) * | 1999-07-16 | 2001-01-25 | Aerojet-General Corporation | Amorphous polyether glycols based on bis-substituted oxetane monomers |
| CN111247141A (en) * | 2017-10-23 | 2020-06-05 | 四国化成工业株式会社 | Epoxy-oxetane compound, method for its synthesis and utilization of the compound |
| WO2022202538A1 (en) * | 2021-03-23 | 2022-09-29 | 三菱ケミカル株式会社 | Compound, method for producing same, polymerizable composition, polymer, holographic recording medium, optical material, and optical component |
| US20230074558A1 (en) * | 2019-12-06 | 2023-03-09 | Mersana Therapeutics, Inc. | Dimeric compounds as sting agonists |
-
2023
- 2023-09-28 CN CN202311273134.6A patent/CN120004874A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001005871A1 (en) * | 1999-07-16 | 2001-01-25 | Aerojet-General Corporation | Amorphous polyether glycols based on bis-substituted oxetane monomers |
| CN111247141A (en) * | 2017-10-23 | 2020-06-05 | 四国化成工业株式会社 | Epoxy-oxetane compound, method for its synthesis and utilization of the compound |
| US20230074558A1 (en) * | 2019-12-06 | 2023-03-09 | Mersana Therapeutics, Inc. | Dimeric compounds as sting agonists |
| WO2022202538A1 (en) * | 2021-03-23 | 2022-09-29 | 三菱ケミカル株式会社 | Compound, method for producing same, polymerizable composition, polymer, holographic recording medium, optical material, and optical component |
Non-Patent Citations (4)
| Title |
|---|
| ALEKSEI B. SHEREMETEV等: ""Furazanyl Ethers of Pentaerythritol Derivates"", 28TH INTERNATIONAL ANNUAL CONFERENCE OF ICT, 31 December 1997 (1997-12-31), pages 1 - 8 * |
| JAMES V. CRIVELLO等: ""Kick-Starting" Oxetane Photopolymerizations", JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY, vol. 52, 31 December 2014 (2014-12-31), pages 2934 - 2946 * |
| LEONID L. FERSHTAT等: ""Ionic liquid-mediated synthesis of (1H-1, 2, 3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes"", MENDELEEV COMMUNICATIONS, vol. 25, no. 4, 31 December 2015 (2015-12-31), pages 257 - 259 * |
| 徐明辉等: ""无规嵌段型含氟PAMMO基热塑性弹性体的合成与表征"", 含能材料, vol. 25, no. 8, 31 December 2017 (2017-12-31), pages 651 - 655 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11891370B2 (en) | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof | |
| CN117603199A (en) | A kind of 3-(4-azidofurazan-3-oxymethyl)-3-azidomethyloxetane, synthesis method and application | |
| Li et al. | Sequential extraction and separation of soluble humins from fructose conversion for structural and evolutional understanding | |
| CN115490657B (en) | A kind of preparation method of 3,3`,4,4`-benzophenone tetracarboxylic dianhydride | |
| CN120004874A (en) | A kind of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane and its synthesis method | |
| CN106554338B (en) | A kind of method that furancarboxylic acid prepares 2,5- furandicarboxylic acids | |
| CN112759558B (en) | Process for the preparation of triazine rings | |
| CN107312114B (en) | A kind of azide polymer with polynorbornene main chain structure and preparation method thereof | |
| CN120004873A (en) | A kind of 3,3-bis(4-nitrofurazan-3-oxymethyl)oxetane and its synthesis method | |
| CN116554164B (en) | A preparation method of Remigipam | |
| CN115385822B (en) | Synthesis method of 1, 5-diazido-3-nitroazane | |
| CN119462630B (en) | Preparation method of 3- (4-nitrofurazan-3-oxymethyl) -3-azidomethyl oxetane | |
| CN117362246A (en) | Preparation method of 3-phenyl-1, 4, 2-dioxazole-5-ketone | |
| WO2019244166A1 (en) | Process development for 5-hydroxymethylfurfural (5-hmf) synthesis from carbohydrates | |
| CN119371415A (en) | Preparation method of 3,3-bis(4-azidofurazan-3-oxymethyl)oxetane | |
| CN111732562A (en) | Preparation method of intermediate of antitumor drug gemcitabine hydrochloride | |
| CN115925656B (en) | A method for industrial synthesis of 5-HMF and its derivatives | |
| CN113045572A (en) | Preparation method of doxofylline impurity A | |
| CN119462629A (en) | Preparation method of 3-(4-nitrofurazan-3-oxymethyl)-3-azidomethyloxetane | |
| CN111574540B (en) | A kind of preparation method of degotinib | |
| CN120040363B (en) | Preparation method of 2,4,6-tricyanethoxy-1,3,5-triazine | |
| RU2797180C2 (en) | Method for synthesis of 5-hydroxymethylfurfural (5-hmf) from carbohydrates | |
| CN114380781A (en) | Preparation method of 2-cyano-8-nitro-4-oxo-4H-1-benzopyran | |
| CN119118868A (en) | A kind of preparation method of 2-methoxy-4-cyanobenzaldehyde | |
| CN119569665A (en) | 1, 2-Bis (5-azido-3-nitro-1, 2, 4-triazole) diazene and synthesis method thereof |
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 |