阅读说明：本技术 一种鉴别试剂的制备方法及其应用 (Preparation method and application of identification reagent ) 是由 张海龙 于 2021-06-26 设计创作，主要内容包括：本发明为一种鉴别试剂的制备方法及其应用,涉及5,6-二甲基四氢-1,3-恶嗪-2-硫酮合成方法及其的应用。本发明公开了一种5,6-二甲基四氢-1,3-恶嗪-2-硫酮,及其合成方法,该合成方法路线短,无其他杂质,反应产率高,目标产物纯度高。另外,本发明提供了合成化合物的新用途。(The invention relates to a preparation method and application of an identification reagent, in particular to a synthesis method and application of 5,6-dimethyl tetrahydro-1, 3-oxazine-2-thioketone. The invention discloses 5,6-dimethyl tetrahydro-1, 3-oxazine-2-thioketone and a synthetic method thereof, and the synthetic method has the advantages of short route, no other impurities, high reaction yield and high purity of target products. In addition, the invention provides a new use of the synthetic compounds.)

1. A compound of formula (1), wherein the compound of formula (1) is as follows:

2. the compound of claim 1, wherein the compound of formula (1) is prepared by a process comprising: reacting a compound represented by the structural formula (2) with a compound represented by the structural formula (3) to obtain a compound represented by the structural formula (1):

3. the compound of claim 1, wherein the reaction molar ratio of the compound of formula 2 to the compound of formula 3 is 0.5:1 to 1.5: 1.

4. The compound of claim 1, wherein the reaction temperature of the compound of formula 2 with the compound of formula 3 is 10 ℃ to 50 ℃.

5. Use of a compound of formula (1) according to claim 1 as an identification of mustard.

6. The use of a compound of formula 1 as an identifying reagent in a mustard assay procedure comprises: extracting; and LC-MS detection.

7. The compound of claim 6, wherein the extraction solvent comprises n-butane, pentane.

8. The compound of claim 6, wherein ethanol is added to the reaction mixture after the extraction is completed.

9. The compound of claim 8, wherein the reaction time is from 10 minutes to 30 hours.

Technical Field

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of an identification reagent and application thereof.

Background

The compound shown in the structural formula 1 is a 5,6-dimethyl tetrahydro-1, 3-oxazine-2-thioketone, 5,6-dimethyl tetrahydrochysene-1, 3-oxazine-2-thione organic compound, can be used as an identification reagent, reacts with ethanol to generate the 5,6-dimethyl tetrahydro-1, 3-oxazine-2-thioketone, and is used for identifying whether mustard or mustard sauce contains allyl isothiocyanate.

The mustard is slightly bitter, spicy and aromatic, has strong stimulation to mouth and tongue, has unique taste, has fragrance after being wetted, has strong lacrimatory pungent taste, and has stimulation to taste and smell. Can be used as seasoning for sauerkraut, pickled raw meat or salad. The mustard sauce is a common seasoning prepared by fermenting and blending mustard powder or horseradish, horseradish or other powders, has strong pungent smell and fresh taste feeling, and can be used as a seasoning of cold vegetable in summer.

Allyl isothiocyanate (Allyl isothiocyanate) is colorless to light yellow transparent oily liquid, has strong pungent smell, and is easy to be discolored and decomposed with light. Slightly soluble in water and soluble in alcohols, ethers and carbon disulphide. Allyl isothiocyanate is a food flavor, and is also used in the aspects of raw materials of organic synthesis intermediates, auxiliary agents of heavy ammonia sensitive paper, pesticide and the like. It can also be used for chili sauce, meat (processed meat), vinegar-pickled food, and other flavoring agents.

Allyl isothiocyanate is an important component of mustard or wasabi. Can be used for identifying mustard quality. The mustard with good quality has high content of allyl isothiocyanate. In the case of the pseudo mustard and wasabi, allyl isothiocyanate was negligible. Therefore, the principle of reaction of allyl isothiocyanate and other substances can be used for identifying the quality of mustard or wasabi.

Disclosure of Invention

Aiming at the problems of long synthesis route, high cost and the like of the existing 5,6-dimethyl tetrahydro-1, 3-oxazine-2-thioketone. The invention provides 5,6-dimethyl tetrahydro-1, 3-oxazine-2-thioketone and a synthetic method thereof, and the synthetic method has the advantages of short route, no other impurities, high reaction yield and high purity of target products. In addition, new uses of the synthetic compounds for identifying mustard or wasabi are provided.

In order to solve the problems, the invention adopts the following technical scheme:

synthesis method of structural formula 1

The method comprises the following steps:

I. a compound of the formula 2,

with a compound of structure 3, and reacting,

to give a compound of formula 1:

preferably, in the step (I), the reaction molar ratio of the compound of formula 2 to the compound of formula 3 is 0.5:1 to 1.5:1, and more preferably 0.8:1 to 1.2: 1.

Preferably, in the step (I), the reaction temperature is 10-50 ℃, preferably 20-30 ℃.

Preferably, in the step (I), the reaction solvent is ethanol.

The compounds of the present invention having the structural formulae 1 and 2 can be directly purchased through commercial sales channels.

Another object of the present invention is to provide a novel use of the compound of formula 1 as a discrimination reagent for mustard or wasabi.

The use of a compound of formula 1 as an identifying reagent in a mustard assay procedure comprises:

1. extracting mustard with n-butane, and collecting extractive solution.

2. Adding ethanol, shaking uniformly, reacting for 10 minutes to 30 hours,

3. then LC-MS detection is carried out.

The synthesis method of the compound with the structural formula 1 has the beneficial effects that: short synthetic route, cheap reagent, simple operation steps and high yield. Can be used for

Drawings

FIG. 1 LC-MS diagram of Compound 2 of example 1.

FIG. 2. Mass spectrum of Compound 2 of example 1.

FIG. 3 LC-MS diagram of the synthesis of Compound 1 of example 1.

FIG. 4. Mass spectrum of synthetic Compound 1 of example 2.

Detailed Description

The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.

Example 1

10mL of ethanol (99%) and 10mL of allyl isothiocyanate (a compound of formula 2) were put into a single-neck flask, and stirred overnight at 20 ℃ to 35 ℃. Collecting the target product. To obtain the compound of formula 1.

The product structure was analyzed by GC-MS. The calculated molecular weight value is 145, the mass spectrum detection value M/Z is 145, and the mass spectrum detection result is consistent with the theoretical value.

Example 2

30mL of ethanol (95%) and 30mL of allyl isothiocyanate (a compound of formula 2) were put into a single-neck flask, and stirred at 30 ℃ for 40 hours, to collect the desired product. To obtain the compound of formula 1. The product structure was analyzed by GC-MS. The calculated molecular weight value is 145, the mass spectrum detection value M/Z is 145, and the mass spectrum detection result is consistent with the theoretical value.

Example 3

30mL of ethanol (95%) and 30mL of allyl isothiocyanate (a compound of formula 2) were put into a single-neck flask, and stirred at 25 ℃ for 10 hours to collect the desired product. To obtain the compound of formula 1. The product structure was analyzed by GC-MS. The calculated molecular weight value is 145, the mass spectrum detection value M/Z is 145, and the mass spectrum detection result is consistent with the theoretical value.

Example 4

Synthesizing a compound of structure 1 as a mustard identification reagent. The mustard paste was extracted with n-hexane, followed by addition of ethanol for 30 minutes for GC-MS routine. The temperature is programmed to 50-250 ℃ for 50 minutes.

The detection result shows that the structural formula 1 is detected after the identification reagent is added and identification reaction is carried out. The synthesis of the compound of the structural formula 1 is shown to be used as a mustard sauce identification reagent.

Example 5

Synthesizing a compound of structure 1 as a mustard identification reagent. The mustard paste was extracted with n-hexane, then reacted with ethanol for 60 minutes for conventional detection by GC-MS. The temperature is programmed to 50-250 ℃ for 50 minutes.

The detection result shows that the structural formula 1 is detected after the identification reagent is added and identification reaction is carried out. The synthesis of the compound of the structural formula 1 is shown to be used as a mustard sauce identification reagent.

Example 6

Synthesizing a compound of structure 1 as a mustard identification reagent. The mustard paste was extracted with n-hexane, then reacted with ethanol for 90 minutes for GC-MS routine. The temperature is programmed to 50-250 ℃ for 50 minutes.

The detection result shows that the structural formula 1 is detected after the identification reagent is added and identification reaction is carried out. The synthesis of the compound of the structural formula 1 is shown to be used as a mustard sauce identification reagent.