CN112280617A - Clathrate compound of column [5] arene and anethole, preparation method and application thereof - Google Patents

Clathrate compound of column [5] arene and anethole, preparation method and application thereof Download PDF

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CN112280617A
CN112280617A CN202011403574.5A CN202011403574A CN112280617A CN 112280617 A CN112280617 A CN 112280617A CN 202011403574 A CN202011403574 A CN 202011403574A CN 112280617 A CN112280617 A CN 112280617A
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anethole
column
arene
inclusion compound
inclusion
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刘晶
王海琨
杨波
王保兴
李忠
卢伟
苏丹丹
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China Tobacco Yunnan Industrial Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00—Preparing tobacco in the factory
    • A24B3/12—Steaming, curing, or flavouring tobacco

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Abstract

The invention discloses a column [5]]The inclusion compound of aromatic hydrocarbon and anethole and its preparation process and application include the following steps: will column [5]Mixing aromatic hydrocarbon and anethole, stirring to obtain mixed solution, dripping the mixed solution into organic solvent, stirring to perform inclusion reaction, separating the reaction product into upper and lower layers, suction filtering or centrifuging to remove the lower layer precipitate, drying the precipitate in oven to obtain column [5]]Inclusion compounds of aromatic hydrocarbons and anethole; the anethole is cis-anethole or trans-anethole, and the column [5]]The structural formula of the aromatic hydrocarbon is
Figure 100004_DEST_PATH_IMAGE002
Wherein R is-CH3，‑CH2OH，‑CH2NH2，‑CH2Br，‑CH2CH3，‑H，‑CH2COOH，‑CH2COOCH3，‑CH2COOCH2CH3One or more of the above ingredients can realize the slow release function of anethole in the inclusion compound, has good stability, and is free from burnt flavor when applied to tobacco products.

Description

Clathrate compound of column [5] arene and anethole, preparation method and application thereof
Technical Field
The invention relates to the technical field of tobacco flavors and fragrances, in particular to a clathrate compound of pillared [5] arene and anethole, a preparation method and application thereof.
Background
Anethole (Anethole), also known as Anethole (natural), is found in essential oils of burley tobacco leaf and anise oil, fennel oil and anise oil. Fennel fruit (Foenicuzu vulgareMill) is a dried mature fruit of Foeniculum vulgare of Umbelliferae, and is not only a flavoring agent, but also a traditional Chinese medicine. Anethole is widely used in food, beverage, toothpaste, gargle, as well as in the flavor correction agent and smell correction agent of medicine, the perfume of cosmetics and perfumed soap, the raw material of synthetic medicine and the sensitizer for color photography. Meanwhile, research shows that the anethole has a certain bacteriostatic action on the ring rot of apple, but the anethole monomer is volatile and unstable, and is difficult to be directly applied to the field of tobacco.
With the continuous development of economy, consumers put higher demands on cigarette brand value, harm and tar reduction, novel taste, safe product quality and the like. Therefore, the production of reconstituted tobacco has received extensive attention and research. Compared with the traditional non-high-quality tobacco leaf raw material, the reconstituted tobacco leaf is easy to control in product quality, and different spices can be added to produce cigarettes with different tastes to meet different requirements of the market. However, the traditional essence and sesame oil has volatility at normal temperature, is difficult to be applied to cigarette production as an aroma additive and ensure the quality, and how to apply the anethole as the aroma additive to the field of tobacco and maintain the stability of the anethole at high temperature is a problem to be solved by the prior art.
In the prior art, Zhao Xinghua and the like research 'a preparation process for researching a natural anethole beta-cyclodextrin inclusion compound by applying a uniform design method', the anethole is included by taking beta-cyclodextrin as an inclusion compound carrier, the slow release effect of the anethole is attempted to be increased, but the release temperature is low, the anethole is burnt when being released at a high temperature, and the anethole cannot be directly applied to the field of tobacco.
Disclosure of Invention
In order to solve the problems, the invention provides the inclusion compound of the column [5] arene and the anethole, the preparation method and the application thereof, which realize the slow release function of the anethole in the inclusion compound, have good stability and have no burnt flavor when being applied to tobacco products.
The technical scheme for solving the problem is that the preparation method of the inclusion compound of the column [5] arene and the anethole comprises the following steps: mixing and stirring the column [5] arene and the anethole to obtain a mixed solution, dripping the mixed solution into an organic solvent, stirring to perform inclusion reaction, dividing a reaction product into an upper layer and a lower layer, taking a lower layer precipitate through suction filtration or centrifugation, and drying the precipitate in an oven to obtain an inclusion compound of the column [5] arene and the anethole;
the anethole is cis-anethole or trans-anethole, and the column [5]]The structural formula of the aromatic hydrocarbon is
Figure 71224DEST_PATH_IMAGE001
Wherein R is-CH3，-CH2OH，-CH2NH2，-CH2Br，-CH2CH3，-H，-CH2COOH，-CH2COOCH3，-CH2COOCH2CH3One or more of them, in this application, a column [5]]Aromatic hydrocarbons are obtained by known techniques, and are described in Ogoshi T, Kanai S, Sakakibara F, et al para-bridged systematic pillarl [5] arene, Their Lewis acid catalyzed synthesis and host-guest property [ J ]. J Am Chem Soc,2008,130 (15): 5022-: adding 7.3 g of p-dimethoxybenzene into a three-neck flask, adding 80 mL of dichloroethane, performing ultrasonic treatment until white solid is completely dissolved, adding 5g of paraformaldehyde, stirring for half an hour to fully dissolve, heating to 30 ℃, adding 6.5 mL of boron trifluoride diethyl etherate, continuously stirring until the color becomes dark green, adding 10 mL of methanol, and finally adding 10 mL of methanolThen adding a large amount of methanol until the product is precipitated. And (3) carrying out suction filtration separation, dissolving the filter residue in dichloromethane, filtering to remove insoluble impurities, and finally carrying out spin drying to obtain crude methoxy column [5] arene.
Preferably, the organic solvent is one or more of methanol, ethanol, propanol, isopropanol, butanol, n-pentanol, n-hexanol, n-heptanol, n-octanol, ethyl acetate, methyl acetate, propyl acetate, methyl chloride, dichloromethane, trichloromethane, tetrachloromethane, pentane, n-hexane, ethylene oxide, octane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, petroleum ether, diethyl ether, tert-butyl methyl ether, acetone, butanone and acetonitrile.
Preferably, the molar ratio of the anethole to the column [5] arene is 1-100: 1.
Preferably, the reaction temperature of the inclusion reaction is 20-100 ℃ and the reaction time is 1 hour-7 days.
Also provided is a column [5] prepared according to the above preparation method]An inclusion compound of aromatic hydrocarbon and anethole, the structural formula of the inclusion compound is shown in the specification
Figure 100002_DEST_PATH_IMAGE002
。
Further, the inclusion compound of the column [5] arene and anethole is also applied to the preparation of tobacco flavors and fragrances, and the specific references are as follows: a method for controlling the slow release of a cyclodextrin inclusion compound by a double-enzyme method.
Preferably, the inclusion complex of column [5] arene and anethole releases anethole at a temperature greater than 100 ℃.
Calixarene has attracted great attention due to its special structure and function, and has become a third-generation supramolecule, and the research based on the pillararene is developed like bamboo shoots in the spring after rain, including the research of a pillararene synthesis method, the functional modification of the pillararene molecules, the chemical research of a host and an object related to the pillararene molecules, the preparation of a molecular sensor based on the pillararene, and the like.
The ring-opened cucurbituril with benzene ring and naphthalene ring can not include anethole, and part of cyclodextrin can well include the anethole, and the difference of the effects depends on the cavity ruler between the host and the objectSize matching and the strength of intermolecular forces, column [5]]The inclusion of the aromatic hydrocarbon and the anethole is a column [5] on the premise that the cavities of the host and the guest are matched relatively]The benzene ring on the aromatic hydrocarbon structure and the benzene ring on the anethole structure generate pi-pi accumulation acting force, the boiling point of the anethole is 234-237 ℃, and the anethole is close to the boiling point of the object at 200 ℃, so that the gasification escape capability of anethole molecules after heat absorption is obviously enhanced, and the column [5] can be quickly released]The aromatic hydrocarbon is composed of 5 p-dimethoxybenzenes, has regular shape and highly symmetrical, looks like a pentagonal columnar pattern, and is close to SP due to the included angle between bridge carbons3The hybrid orbital key causes the tension of the ring to be small and has a very stable structure due to the column [5]]Highly symmetrical structure and characteristic cavity depth of aromatic hydrocarbons, therefore columns [5]]The aromatic hydrocarbon can generate stable inclusion with anethole molecules, and the reaction process is as follows by taking trans-anethole as an example:
Figure 440895DEST_PATH_IMAGE003
through the inclusion of the column [5] arene and the anethole substance, the anethole can be effectively stored, the stability of the anethole at high temperature is increased, the molecular basis of burnt smell generation is a series of small molecular mixtures generated by the decomposition of carbohydrate compounds or protein substances at high temperature, the column [5] arene can not generate decomposition at the temperature of releasing the anethole, no burnt smell is generated, the harm to the environment can be effectively reduced when the anethole is used in the tobacco field, and the anethole has wide economic, social and ecological benefits.
The invention has the beneficial effects that:
1. the inclusion compound prepared by the scheme has good thermal stability and high safety, overcomes the instability and volatility of anethole at normal temperature, and can be applied to the field of preparation of tobacco flavors and fragrances as slow-release anethole;
2. the preparation method of the inclusion compound is simple, convenient and feasible, has mild conditions and is suitable for industrial production;
3. in the scheme, the column [5] arene has a highly symmetrical structure and a special cavity depth, and the column [5] arene can be stably included with anethole molecules, so that the release temperature of the anethole is increased, and the limitation of the anethole in the preparation of the tobacco essence and spice field is removed.
Drawings
FIG. 1 shows a methoxy column [5] in example 1]Nuclear magnetic hydrogen spectrum of aromatic hydrocarbon (1H NMR) pattern;
FIG. 2 is a nuclear magnetic hydrogen spectrum comparison chart of methoxy pillar [5] arene (a), inclusion compound (b) and trans-anethole (c) in example 1;
FIG. 3 is a graph comparing the characteristic peak of trans-anethole in example 1 with the hydrogen spectrum of the characteristic peak of trans-anethole in the clathrate;
FIG. 4 is a graphical representation of the extent of anethole release at different temperatures for the clathrate prepared in example 1;
FIG. 5 is a graphical representation of the extent of anethole release at different temperatures for the clathrate prepared in example 2;
FIG. 6 is a graphical representation of the extent of anethole release at different temperatures for the clathrate prepared in example 3;
FIG. 7 is a graph showing the extent of anethole release at different temperatures from the clathrate prepared in comparative example 4;
FIG. 8 is a graph showing the extent of anethole release at different temperatures from the clathrate prepared in comparative example 5;
FIG. 9 is a graph comparing the extent of anethole release at different temperatures.
Detailed Description
In order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
Example 1: preparation of methoxy pillar [5] arene and anethole inclusion compound
Adding 7.3 g of p-dimethoxybenzene into a three-neck flask, adding 80 mL of dichloroethane, performing ultrasonic treatment until white solids are completely dissolved, adding 5g of paraformaldehyde, stirring for half an hour to fully dissolve the paraformaldehyde, heating to 30 ℃, adding 6.5 mL of boron trifluoride diethyl etherate, continuously stirring until the color becomes dark green, adding 10 mL of methanol, and finally adding a large amount of methanol until products are precipitated. And (3) carrying out suction filtration separation, dissolving the filter residue in dichloromethane, filtering to remove insoluble impurities, and finally carrying out spin drying to obtain a crude methoxy column [5] arene with the yield of 90%. The nuclear magnetic hydrogen spectrum is shown in fig. 1, and aromatic hydrogen, methylene hydrogen and methyl hydrogen =10:10: 30.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)3) And 0.1 mmol of trans-anethole, stirring for 20 hours at 20 ℃, then dripping the mixed solution into 20 mL of ethanol to separate out a precipitate, performing suction filtration or centrifugation to separate the solution and the precipitate, and drying the precipitate to obtain the clathrate compound with the yield of 95%. The nuclear magnetic hydrogen spectrum is shown in fig. 2 and fig. 3, and the characteristic peak of trans-anethole appears in the inclusion compound, and the chemical potential shift of the characteristic peak is shifted by 0.03 ppm in a high field, thereby proving that the synthesis of the inclusion compound by the scheme is successful.
Example 2: preparation of ethyoxyl column [5] arene and anethole inclusion compound
Putting 3.78 g, 10mmoL ethoxy-2, 5-dibenzyloxy methylbenzene into a three-neck flask, adding 80 mL dichloromethane, carrying out ultrasonic treatment until white solid is completely dissolved, then adding 0.172 g p-toluenesulfonic acid, stirring for half an hour to fully dissolve the white solid, heating to 40 ℃, and continuing stirring for two hours. The extract was separated, and the organic phase was washed with water and saturated brine, followed by drying over anhydrous sodium sulfate. And (3) after spin-drying, passing through a silica gel column, using petroleum ether and ethyl acetate as a developing agent to =40:1, and finally spin-drying to obtain a crude product of the ethoxy column [5] arene with the yield of 95%.
0.2 mmol of ethoxy column [5]]Aromatic hydrocarbon (R is-CH)2CH3) Mixing with 0.5mmol trans-anethole at 50 deg.C under stirring for 1 hr, dropping the mixture into 20 mL organic solvent such as ethanol to precipitate, filtering or centrifuging to separate the solution and precipitate, and drying the precipitate to obtain clathrate with yield of 97%.
Example 3: preparation of hydroxy column [5] arene and anethole inclusion compound
Putting 0.34 g of p-methoxy pillar [5] arene into a flask, adding 20 mL of trichloromethane, adding 2.4 g of boron tribromide, stirring at room temperature for 96 hours, carrying out suction filtration, and washing filter residues with water. Passing through silica gel column, developing solvent with dichloromethane acetone =1:1, and spin-drying to obtain white solid 0.21g, 0.36 mmoL, yield 90%.
Stirring 0.1 mmol of hydroxylated column [5] arene (R is-H) and 0.1 mmol of trans-anethole at 50 ℃ for 5 hours, then dropping the mixed liquid into 30mL of methanol to separate out a precipitate, performing suction filtration or centrifugation to separate the solution and the precipitate, and drying the precipitate to obtain the clathrate, wherein the yield is 98%.
Example 4: preparation of ethyl acetate column [5] arene and anethole inclusion compound
2.4 g, 3.93 mmoL of hydroxylated column [5] arene is dissolved in 30mL of DMF and 30mL of THF, then 3.0 g, 125 mmoL of sodium hydroxide is added, and the reaction solution is reacted for half an hour under the protection of nitrogen. Then 9.0 mL of 81.0 mmoL of ethyl bromoacetate was added, and the mixture was heated to 60 ℃ to react for 48 hours. Removing solution, dissolving precipitate into dichloromethane and water, drying organic phase with anhydrous sodium sulfate, spin drying, passing through column, developing solvent with dichloromethane: acetone =95:5, precipitating the first part as product, dropping into acetone for precipitation, and oven drying to obtain product 4.34g with yield of 74.9%.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)2COOCH2CH3) And 0.3 mmol of cis-anethole, stirring for 5 days at 30 ℃, then dripping the mixed solution into 10 mL of ether to separate out a precipitate, performing suction filtration or centrifugation to separate the solution and the precipitate, and drying the precipitate to obtain the clathrate compound with the yield of 97%.
Example 5: preparation of water-soluble carboxylic acid column [5] arene and anethole inclusion compound
0.15g, 0.102 mmoL of ethyl acetate column [5] arene, 0.35g sodium hydroxide, 15 mL ethanol, 15 mL water and 15 mL tetrahydrofuran were stirred under reflux for 24 hours. Adding certain diluted hydrochloric acid to generate precipitate, performing suction filtration, washing filter residue with water for several times, and drying to obtain 0.175 g, wherein the yield is 72.0%.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)2COOH) and 2mmol of cis-anethole are stirred for 48 hours at 50 ℃, then the mixed solution is dripped into 20 mL of acetone to separate out a precipitate, the solution and the precipitate are separated by suction filtration or centrifugation, and the precipitate is dried to obtain the clathrate compound with the yield of 94 percent.
Example 6: preparation of methyl acetate column [5] arene and anethole inclusion compound
4.8 g of hydroxylated column [5] arene is dissolved in 60mL of DMF and 60mL of THF, then 6.0 g of sodium hydroxide is added, and the reaction solution is reacted for half an hour under the protection of nitrogen. Then 18 mL of methyl bromoacetate was added, heated to 60 ℃ and reacted for 36 hours. Removing solution, dissolving precipitate in dichloromethane and water, drying organic phase with anhydrous sodium sulfate, spin drying, passing through column, developing solvent with dichloromethane acetone =95:5, precipitating the first part as product, dropping into acetone for precipitation, and oven drying to obtain product 8.8g with yield of 76%.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)2COOCH3) And 10mmol of cis-anethole are stirred for 7 days at 50 ℃, then the mixed solution is dripped into 20 mL of methanol to separate out a precipitate, the solution and the precipitate are separated by suction filtration or centrifugation, and the precipitate is dried to obtain the clathrate compound with the yield of 95.6 percent.
Example 7: preparation of ethanol-based column [5] arene and anethole inclusion compound
0.7 g of 0.5mmoL of methyl acetate column [5] arene was dissolved in 30mL of THF at 0 ℃ under nitrogen, and 380 mg of 10mmoL of lithium aluminum hydride was added. Subsequently, the mixture was stirred at 25 ℃ for 12 hours, and then refluxed for 4 hours, and the reaction solution was cooled and added dropwise to a 1M sodium hydroxide solution. And (4) carrying out suction filtration, concentrating the filtrate to obtain a white solid, washing with water, and finally drying to obtain 360 mg of a product with the yield of 72%.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)2CH2OH) and 1.0 mmol of trans-anethole are stirred for 20 hours at the temperature of 20 ℃, then the mixed solution is dripped into 20 mL of ethanol to separate out a precipitate, the solution and the precipitate are separated by suction filtration or centrifugation, and the precipitate is dried to obtain the clathrate compound with the yield of 99 percent.
Example 8: preparation of bromoethyl column [5] arene and anethole inclusion compound
290 mg of 0.28 mmoL of ethanol-based column [5] arene and 1.09g of 4.16mmoL of triphenylphosphine were added to 9 mL of acetonitrile, and 1.38g of 4.16mmoL of carbon tetrabromide was slowly added thereto with stirring at 0 ℃. Then, the temperature is raised to room temperature, and the mixture is stirred for 12 hours under the protection of nitrogen. Then 200 mL of water is added, and the precipitate is obtained by suction filtration, washed by methanol and dried to obtain 338 mg with the yield of 72 percent.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)2CH2Br) and 0.9 mmol of anethole are stirred for 20 hours at 50 ℃, then the mixed solution is dripped into 35 mL of ethylene glycol monoethyl ether to separate out a precipitate, the solution and the precipitate are separated by suction filtration or centrifugation, and the precipitate is dried to obtain the inclusion compound with the yield of 96 percent.
Example 9: preparation of aminoethyl column [5] arene and anethole clathrate
193 mg, 3 moL of sodium azide are added into 5 mL of DMF solution containing 100 mg, 0.06mmoL L of bromoethyl column [5] arene, stirred for 12 hours at 100 ℃ under the protection of nitrogen, cooled to room temperature, dropped into 80 mL of water, filtered to obtain precipitate, washed with water for 3 times, and dried to obtain white solid. Adding 900mg of white solid into methanol, adding triphenylphosphine, stirring for half an hour, adding strong ammonia water, stirring for 12 hours, concentrating the reaction solution, dripping chloroform to obtain a precipitate, performing suction filtration, and drying to obtain 655 mg of white solid with a yield of 92%.
0.1 mmol of column [5]]Aromatic hydrocarbon (R is-CH)2CH2NH2) And 0.7 mmol of anethole are stirred for 2 hours at the temperature of 90 ℃, then the mixed solution is dripped into 40 mL of n-octanol to separate out a precipitate, the solution and the precipitate are separated by suction filtration or centrifugation, and the precipitate is dried to obtain the clathrate compound with the yield of 98 percent.
Stability test
The inclusion compounds prepared in examples 1 to 9 and comparative examples 1 to 2 were used as test samples, and anethole monomer was used as a control, and the test samples were incubated at 95 deg.C, 100 deg.C, and 200 deg.C, respectively1HNMR detects, in order to obtain the release degree of anethole substance in the inclusion complex, the result is shown as fig. 4-9, it is shown that in this scheme, the inclusion complex of anethole substance has no release of anethole substance below 100 ℃, only slight release occurs at 100 ℃, but obvious quick release occurs at more than 100 ℃, especially more than 200 ℃, and the comparative example and the anethole monomer release degree are bigger at normal temperature, which can prove that the inclusion complex has good thermal stability at a certain temperature and can be quickly released at high temperature, can be well applied to essence and flavor and tobacco industry, as slow release type anethole substance, prepare essence and flavor additive and tobacco product, the concrete step is: application of the clathrate prepared in example 1 to cigaretteThe preparation process of the grass essence spice comprises the following steps: a methoxy column [5]]The inclusion compound of aromatic hydrocarbon and anethole is prepared into chloroform solution with the concentration of 10 percent, then the solution is sprayed on tobacco and dried, then the inclusion compound is attached to the surface of the tobacco, and in the test process, the inclusion compound prepared by the scheme has no burnt smell when the anethole is released, and the taste of the inclusion compound for tobacco products is good.
Specific embodiments of the present invention have been described above in detail.
It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, any technical solutions that can be obtained by a person skilled in the art through logical analysis, reasoning or limited experiments in the prior art based on the inventive concept should be within the scope of protection defined by the claims.

Claims (7)

1. Column [5]]The preparation method of the inclusion compound of aromatic hydrocarbon and anethole is characterized by comprising the following steps: will column [5]Mixing aromatic hydrocarbon and anethole, stirring to obtain mixed solution, dripping the mixed solution into organic solvent, stirring to perform inclusion reaction, collecting precipitate, and drying the precipitate to obtain column [5]]Inclusion compounds of aromatic hydrocarbons and anethole; the anethole is cis-anethole or trans-anethole, and the column [5]]The structural formula of the aromatic hydrocarbon is
Figure DEST_PATH_IMAGE002
Wherein R is-CH3，-CH2OH，-CH2NH2，-CH2Br，-CH2CH3，-H，-CH2COOH，-CH2COOCH3，-CH2COOCH2CH3One or more of them.
2. The method for preparing the inclusion compound of column [5] arene and anethole according to claim 1, wherein the organic solvent is one or more of methanol, ethanol, propanol, isopropanol, butanol, n-pentanol, n-hexanol, n-heptanol, n-octanol, ethyl acetate, methyl acetate, propyl acetate, methyl chloride, dichloromethane, trichloromethane, tetrachloromethane, pentane, n-hexane, ethylene oxide, octane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, petroleum ether, diethyl ether, tert-butyl methyl ether, acetone, butanone and acetonitrile.
3. The method for preparing the inclusion compound of column [5] arene and anethole according to claim 1, wherein the molar ratio of the anethole to the column [5] arene is 1-100: 1.
4. the preparation method of the inclusion compound of column [5] arene and anethole according to claim 1, wherein the reaction temperature of the inclusion reaction is 20-100 ℃, and the reaction time is 1 hour-7 days.
5. The clathrate of column [5] arene and anethole obtained by the production method according to any one of claims 1 to 4.
6. The use of the inclusion compound of column [5] arene and anethole according to claim 5 as slow-release anethole in preparing tobacco flavors and fragrances.
7. The application of the inclusion compound of column [5] arene and anethole as slow-release anethole in the preparation of tobacco flavors and fragrances according to claim 6, wherein the temperature of the inclusion compound of column [5] arene and anethole for releasing anethole is more than 100 ℃.
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张华承，等: "柱芳烃的合成与应用", 《有机化学》 *
赵星华: "应用均匀设计法研究天然大茴香脑β-环糊精包合物的制备工艺", 《食品研究与开发》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114085298A (en) * 2021-11-30 2022-02-25 扬州大学 Water-soluble supramolecular inclusion compound DPG and preparation method and application thereof
CN114085298B (en) * 2021-11-30 2022-09-16 扬州大学 Water-soluble supramolecular inclusion compound DPG and preparation method and application thereof
WO2023098271A1 (en) * 2021-11-30 2023-06-08 扬州大学 Water-soluble supramolecular inclusion dpg, and preparation method therefor and application thereof

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