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Cyclo-alpha-enaminone compound, synthetic method and application thereof, and tobacco product

The technology of a cyclomethenamine and a synthesis method, which is applied in the field of heterocyclic compounds and cooling agents, can solve the problems of unpleasant smell amine substances, low cooling effect, poor stability, etc., and achieve obvious cooling taste and improved Quality, good stability effect

Active Publication Date: 2020-04-14
ZHENGZHOU TOBACCO RES INST OF CNTC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in practical applications, the cooling effect of the existing methenaminoketones is far lower than expected, mainly due to the poor stability of these compounds during use and storage. It is easily hydrolyzed in complex systems and produces amines with unpleasant odor

Method used

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  • Cyclo-alpha-enaminone compound, synthetic method and application thereof, and tobacco product
  • Cyclo-alpha-enaminone compound, synthetic method and application thereof, and tobacco product
  • Cyclo-alpha-enaminone compound, synthetic method and application thereof, and tobacco product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The cyclomethanaminoketone compound of this embodiment has the structure shown in formula I, and is named 3-(3-pyrrolinyl)-5-methyl-2H-pyran-2-one:

[0035]

[0036] The embodiment of the synthetic method of cyclomethanyl ketone compound

Embodiment 2

[0038] The present embodiment has the synthetic route of the cyclic methyl enamino ketone compound of the structure shown in formula I as follows:

[0039]

[0040] The specific synthetic method comprises the following steps:

[0041] 1) Synthesis of 3-(3-pyrrolinyl)-5-bromo-2H-pyran-2-one (the compound represented by formula II)

[0042] Under nitrogen protection, 254 mg (1 mmol) of 3,5-dibromo-2-pyrone, 7 mg (0.03 mmol) of palladium acetate, and 1,1'-binaphthalene-2,2' were successively added to a dry Schlenk reaction tube. - 37 mg (0.06 mmol) of bisdiphenylphosphine, 207 mg (1.5 mmol) of potassium carbonate, 83 mg (1.2 mmol) of 3-pyrroline, and 3 mL of anhydrous toluene, the reaction solution was stirred at 80°C for 1 hour under nitrogen atmosphere. The reaction solution was cooled to room temperature, filtered through a short silica gel column, the eluent was 40 mL of diethyl ether, and the filtrate was evaporated under reduced pressure to remove the solvent to obtain ...

Embodiment 3

[0048] The application of the cyclomethanamine compound as a cooling agent in this embodiment is specifically the application of the cyclomethanaminone compound having the structure shown in formula I as a cooling agent in cigarettes.

[0049] In another embodiment of the application of the cyclomethicone compound of the present invention as a cooling agent, it is the application of the compound of formula I as a cooling agent in chewing gum, beverage, toothpaste or cosmetics.

[0050] Examples of Tobacco Products

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Abstract

The invention relates to a cyclo-alpha-enaminone compound, a synthesis method and application thereof and a tobacco product, and belongs to the technical field of heterocyclic compounds and cooling agents. The cyclo-alpha-enaminone compound disclosed by the invention is 3-(3-pyrrolinyl)-5-methyl-2H-pyran-2-one, and has a structure as shown in a formula I which is described in the specification. The cyclo-alpha-enaminone compound with the structure shown in the formula I is odorless and tasteless, can be used as a cooling agent, has better stability than the existing cyclo-alpha-enaminone cooling agent, is used for perfuming tobacco shreds of cigarettes, and can obviously improve the comfort of the cigarettes.

Description

technical field [0001] The invention relates to a cyclic methyl enaminone compound, a synthesis method, application and tobacco products thereof, and belongs to the technical field of heterocyclic compounds and cooling agents. Background technique [0002] Cooling agent is a substance that can bring coolness or freshness to the skin or mucous membranes. The physiological effect of cooling agent on the skin is not caused by temperature changes, but by the interaction between chemical substances and trigeminal nerve endings. produced by special interactions. Compounds with cooling properties have become indispensable additives in people's daily life, especially in products such as food (eg, beverages, chewing gum), toothpaste, cosmetics, and cigarettes. [0003] Menthol is the most familiar cooling agent. It has the advantages of fresh cooling taste, low price and easy availability. However, menthol also has obvious disadvantages, such as volatile, not resistant to high tempe...

Claims

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Application Information

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IPC IPC(8): C07D405/04A23L29/00
CPCA23V2002/00A23L29/035C07D405/04A23V2200/14A23V2200/16A23V2250/30
Inventor 范武柴国璧张启东刘俊辉史清照姬凌波王丁众毛健崔凯马骥
Owner ZHENGZHOU TOBACCO RES INST OF CNTC
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