CN106800543A - A kind of burnt fragrant and sweet type compound of furans alkoxide and its synthetic method - Google Patents
A kind of burnt fragrant and sweet type compound of furans alkoxide and its synthetic method Download PDFInfo
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- CN106800543A CN106800543A CN201710052594.4A CN201710052594A CN106800543A CN 106800543 A CN106800543 A CN 106800543A CN 201710052594 A CN201710052594 A CN 201710052594A CN 106800543 A CN106800543 A CN 106800543A
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- compound
- furans
- alkoxide
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- burnt fragrant
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Abstract
The invention discloses a kind of burnt fragrant and sweet type compound of furans alkoxide and its synthetic method, the structural formula of such compound is as follows：Wherein：A represents H or CH3；B is represented
Description
Technical field
The present invention relates to a kind of burnt fragrant and sweet type compound of furans alkoxide and its synthetic method, belong to burnt fragrant and sweet type compound
Preparation field.
Background technology
Burnt fragrant and sweet type compound is that a class can reduce bitter taste and sour pungent taste, increases the spices chemical combination of sweet taste and roasting fragrance
Thing, can be used to improve the local flavor of food, be particularly well-suited to the product of coffee, chocolate and caramel type local flavor.Research shows this
The class compound generally planar structure unit with enolization, the compound for meeting the design feature is respectively provided with burnt sweet fragrance, such as
Compound maltol, ethylmaltol for being used as flavorant etc. are had allowed for, wherein furfuran compound is important
The burnt sweet flavor compounds of one class.
Furfuran compound is five-membered ring nitrogen-containing heterocycle compound, be constitute wholefood odor characteristic it is important micro into
/ mono-, it is prevalent in food flavor, such as coffee, nut, barbecue；Furfuran compound is widely used in as fumet
The industries such as food, beverage, cosmetics, tobacco, nearly hundred kinds of furans spices have obtained the approval of the international organizations such as FEMA, COE, IOFI
Use；Furfuran compound odor characteristic is protruded, and fragrance effects are favourable, but there is also volatile, effect not lasting, single taste
The problems such as, have impact on effect.
In order to overcome disadvantage mentioned above, the present invention with furan alcohol be a series of furan alcohol ester type compounds of Material synthesis, to obtain
Obtain the burnt sweet fragrant perfume that stable in properties, effect is lasting, flavouring essence quality is high.
The content of the invention
Technical problem：It is an object of the invention to provide a kind of burnt fragrant and sweet type compound of furans alkoxide, the furans alkoxide
The aroma property stabilization of burnt fragrant and sweet type compound, effect are lasting, quality is high；
Another object of the present invention provides a kind of synthetic method of the burnt fragrant and sweet type compound of furans alkoxide, and the method is with furan
Alcohol of muttering is raw material, and hydroxyl is used as active group, and it is appropriate to be carried out by chemical reaction with organic acid of the another kind containing fragrance component
Structure of modification, the burnt fragrant and sweet type compound of furans alkoxide of synthesizing new.
Technical scheme：The invention provides a kind of burnt fragrant and sweet type compound of furans alkoxide, the structural formula of compound is as follows：
Wherein：A represents H or CH3；
B is represented
Wherein：
Shown in burnt fragrant and sweet type structural formula of compound such as formula (the I-1)~formula (I-6) of described furans alkoxide：As A for H, B areWhen, shown in structural formula of compound such as formula (I-1), when A is CH3, B be C7H15When, the structural formula of compound such as formula
(I-2) shown in, when A is CH3, B beWhen, shown in structural formula of compound such as formula (I-3), when A is CH3, B beWhen, shown in structural formula of compound such as formula (I-4), when A is CH3, B beWhen, the structural formula of compound
As shown in formula (I-5), when A is CH3, B beWhen, shown in structural formula of compound such as formula (I-6).
Present invention also offers a kind of synthetic method of the burnt fragrant and sweet type compound of furans alkoxide, the method is with furan alcohol
Raw material is synthesized, and reaction equation is as follows：
Comprise the following steps that：
The acylation of step 1, organic acid：Organic acid B-COOH is dissolved in thionyl chloride, after through backflow, vacuum distillation return
After receiving thionyl chloride, weak yellow liquid, i.e. acyl chlorides are obtained：B-COCl；
The alcoholysis of step 2, acyl chlorides：The B-COCl that step 1 is obtained is dissolved in dichloromethane, carbonic acid is sequentially added afterwards
Sodium, furan alcohol, triethylamine, room temperature reaction overnight (TLC detection reactions carry out degree), obtain reaction solution；
The reaction solution that step 3, step 2 are obtained is pure through saturated sodium bicarbonate washing, anhydrous sodium sulfate drying, precipitation, separation
Change obtains the burnt fragrant and sweet type compound of furans alkoxide of the invention.
Wherein：
Described reaction solution refers to that reaction solution is washed to bubble-free product through saturated sodium bicarbonate through saturated sodium bicarbonate washing
It is raw；
Described isolating and purifying refers to that column chromatography silica gel is isolated and purified, and detailed process is as follows：Will through anhydrous sodium sulfate drying,
Residue after precipitation is splined on silicagel column, through elution after, precipitation obtains the burnt fragrant and sweet type chemical combination of furans alkoxide again
Thing；The eluent is petroleum ether and ethyl acetate according to volume ratio 10:1-40:1 mixed solvent being mixed to get.
Beneficial effect：Compared with prior art, the present invention has advantages below：
1st, the present invention passes through compound obtained in acyl chloride esterification method, features simple and practical process, low cost, yield using furan alcohol
Height, with the important market development and application prospect.
2nd, using the burnt fragrant and sweet type compound property stabilization of furans alkoxide of present invention synthesis, can produce pleasant
Burnt fragrant and sweet rhythm and flowers and fruits note and effect is lasting, quality is high.
Specific embodiment
Embodiment 1：The preparation of compound I-1
1. in 100mL round-bottomed flasks, 20-30mmol strawberriffs are added, be subsequently adding 15-20ml thionyl chlorides, flowed back
Reaction 3-5h, after Distillation recovery thionyl chloride, obtains yellow liquid, i.e. acyl chlorides；
2. in 250mL round-bottomed flasks, add the acyl chlorides that obtains of step 1, sequentially add 80-100mL dichloromethane,
40-50mmol sodium carbonate, then adds 10-20mmol furfuryl alcohols, 2-3 drop triethylamines under stirring at room temperature, finishes, and continues to stir anti-
Should overnight (TLC detection reactions carry out degree)；Question response terminates, and is washed 2-3 times with saturated sodium bicarbonate, is produced to bubble-free,
After isolated and purified through anhydrous sodium sulfate drying, precipitation, column chromatography silica gel, be dried to obtain target product 1.65g, yield 70%,
It is petroleum ether and ethyl acetate according to volume ratio 10 that wherein column chromatography silica gel isolates and purifies eluent used:1 is mixed to get
Mixed solvent.
Analysis products therefrom：
Proton nmr spectra：1H NMR(400MHz,CDCl3) δ 7.41 (d, J=1.4Hz, 1H), 6.39 (d, J=3.2Hz,
1H),6.37–6.32(m,1H),5.05(s,2H),2.36–2.30(t,2H),1.70–1.50(m,7H),1.25–1.10(m,
4H), 0.86 (dt, J=13.8,7.0Hz, 2H).
Embodiment 2：The preparation of compound I-2
1. in 100mL round-bottomed flasks, (20-30mmol) octanoic acid is added, be subsequently adding 15-20ml thionyl chlorides, flowed back
Reaction 3-5h, after Distillation recovery thionyl chloride, obtains yellow liquid, i.e. acyl chlorides；；
2. in 250mL round-bottomed flasks, the acyl chlorides of above-mentioned preparation is added, sequentially add 80-100mL dichloromethane, 40-
50mmol sodium carbonate, then adds 10-20mmol furfuryl alcohols, 2-3 drop triethylamines under stirring at room temperature, finishes, and continues stirring reaction
Overnight (TLC detection reactions carry out degree)；Question response terminates, and is washed 2-3 times with saturated sodium bicarbonate, is produced to bubble-free, it
Isolated and purified by anhydrous sodium sulfate drying, precipitation, column chromatography silica gel, be dried to obtain target product 1.90g, yield 80%, its
It is petroleum ether and ethyl acetate according to volume ratio 20 that middle column chromatography silica gel isolates and purifies eluent used:1 be mixed to get it is mixed
Bonding solvent.
Analysis products therefrom：
Proton nmr spectra：1H NMR(400MHz,CDCl3) δ 6.28 (d, J=3.0Hz, 1H), 5.94 (d, J=2.3Hz,
1H),5.00(s,2H),2.35–2.30(m,2H),2.29(s,3H),1.66–1.59(m,2H),1.33–1.23(m,8H),
0.87 (t, J=6.8Hz, 3H).
Embodiment 3：The preparation of compound I-3
With embodiment 2, benzenpropanoic acid replaces octanoic acid to preparation method, is dried to obtain target product 1.83g, yield 75%, wherein
It is petroleum ether and ethyl acetate according to volume ratio 30 that column chromatography silica gel isolates and purifies eluent used:1 mixing being mixed to get
Solvent.
Analysis products therefrom：
Proton nmr spectra：1H NMR(400MHz,CDCl3) δ 7.29-7.24 (m, 2H), 7.19 (m, J=8.7,7.1Hz,
3H), 6.27 (d, J=3.1Hz, 1H), 5.94 (d, J=2.4Hz, 1H), 5.00 (s, 2H), 2.95 (t, J=7.8Hz, 2H),
2.65 (t, J=7.8Hz, 2H), 2.29 (s, 3H).
Embodiment 4：The preparation of compound I-4
With embodiment 2, phenylacetic acid replaces octanoic acid to preparation method, is dried to obtain target product 1.80g, yield 78%, wherein
It is petroleum ether and ethyl acetate according to volume ratio 40 that column chromatography silica gel isolates and purifies eluent used:1 mixing being mixed to get
Solvent.
Analysis products therefrom：
Proton nmr spectra：1H NMR(400MHz,CDCl3) δ 7.35-7.22 (m, 5H), 6.27 (d, J=3.1Hz, 1H),
5.93 (d, J=2.3Hz, 1H), 5.02 (s, 2H), 3.64 (s, 2H), 2.29 (s, 3H).
Embodiment 5：The preparation of compound I-5
With embodiment 2, pineapple acid replaces octanoic acid to preparation method, is dried to obtain target product 1.80g, yield 72%, wherein
It is petroleum ether and ethyl acetate according to volume ratio 25 that column chromatography silica gel isolates and purifies eluent used:1 mixing being mixed to get
Solvent.
Analysis products therefrom：
Proton nmr spectra：1H NMR(400MHz,CDCl3) δ 6.27 (d, J=3.0Hz, 1H), 5.94 (d, J=2.5Hz,
1H), 4.99 (s, 2H), 2.36-2.31 (t, 2H), 2.29 (s, 3H), 1.68 (d, J=10.8Hz, 4H), 1.60 (s, 1H),
1.53 (dd, J=15.3,7.2Hz, 2H), 1.25-1.09 (m, 4H), 0.86 (dt, J=13.7,6.9Hz, 2H).
Embodiment 6：The preparation of compound I-6
With embodiment 2, cinnamic acid replaces octanoic acid to preparation method, is dried to obtain target product 1.84g, yield 76%, wherein
It is petroleum ether and ethyl acetate according to volume ratio 35 that column chromatography silica gel isolates and purifies eluent used:1 mixing being mixed to get
Solvent.
Analysis products therefrom：
Proton nmr spectra：1H NMR(400MHz,CDCl3) δ 7.72 (d, J=16.0Hz, 1H), 7.51 (dd, J=6.8,
2.7Hz, 2H), 7.44-7.34 (m, 3H), 6.46 (d, J=16.0Hz, 1H), 6.34 (d, J=3.1Hz, 1H), 5.96 (d, J=
2.4Hz,1H),5.14(s,2H),2.32(s,3H)。
Claims (6)
1. the burnt fragrant and sweet type compound of a kind of furans alkoxide, it is characterised in that：The structural formula of compound is as follows：
Wherein：A represents H or CH3；
B is represented
2. the burnt fragrant and sweet type compound of a kind of furans alkoxide as claimed in claim 1, it is characterised in that：Described furans alcohol ester
Shown in burnt fragrant and sweet type structural formula of compound such as formula (the I-1)~formula (I-6) of class：As A for H, B areWhen, the compound knot
Shown in structure formula such as formula (I-1), when A is CH3, B be C7H15When, shown in structural formula of compound such as formula (I-2), when A is CH3, B beWhen, shown in structural formula of compound such as formula (I-3), when A is CH3, B beWhen, the structural formula of compound
As shown in formula (I-4), when A is CH3, B beWhen, shown in structural formula of compound such as formula (I-5), when A is CH3, B beWhen, shown in structural formula of compound such as formula (I-6)：
3. the synthetic method of the burnt fragrant and sweet type compound of a kind of furans alkoxide as claimed in claim 1, it is characterised in that：The party
Method is synthesized by raw material of furan alcohol, and reaction equation is as follows：
Comprise the following steps that：
The acylation of step 1, organic acid：Organic acid B-COOH is dissolved in thionyl chloride, after through backflow, vacuum distillation removed
The thionyl chloride of amount, obtains weak yellow liquid, i.e. acyl chlorides：B-COCl；
The alcoholysis of step 2, acyl chlorides：The B-COCl that step 1 is obtained is dissolved in dichloromethane, sequentially add afterwards sodium carbonate,
Furan alcohol, triethylamine, room temperature reaction overnight, obtain reaction solution；
The reaction solution that step 3, step 2 are obtained through saturated sodium bicarbonate washing, anhydrous sodium sulfate drying, precipitation, isolate and purify
To the burnt fragrant and sweet type compound of described furans alkoxide.
4. the synthetic method of the burnt fragrant and sweet type compound of a kind of furans alkoxide as claimed in claim 3, it is characterised in that：It is described
Reaction solution through saturated sodium bicarbonate washing, to refer to reaction solution wash to bubble-free through saturated sodium bicarbonate produces.
5. the synthetic method of the burnt fragrant and sweet type compound of a kind of furans alkoxide as claimed in claim 3, it is characterised in that：It is described
To isolate and purify refer to that column chromatography silica gel is isolated and purified, detailed process is as follows：By through the residual after anhydrous sodium sulfate drying, precipitation
Thing is splined on silicagel column, through elution after, obtain the burnt fragrant and sweet type compound of furans alkoxide.
6. the synthetic method of the burnt fragrant and sweet type compound of a kind of furans alkoxide as claimed in claim 5, it is characterised in that：It is described
Eluent is petroleum ether and ethyl acetate according to volume ratio 10:1-40:1 mixed solvent being mixed to get.
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| CN201710052594.4A CN106800543A (en) | 2017-01-24 | 2017-01-24 | A kind of burnt fragrant and sweet type compound of furans alkoxide and its synthetic method |
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| CN201710052594.4A CN106800543A (en) | 2017-01-24 | 2017-01-24 | A kind of burnt fragrant and sweet type compound of furans alkoxide and its synthetic method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299359A (en) * | 2018-03-20 | 2018-07-20 | 东南大学 | A kind of furans esters of gallic acid tobacco aromaticss and preparation method thereof and the application in cigarette |
| CN108440618A (en) * | 2018-03-14 | 2018-08-24 | 郑州轻工业学院 | The preparation method and application of 5- methyl furfuryl alcohols-β-D-Glucose glycosides |
| CN108516998A (en) * | 2018-03-14 | 2018-09-11 | 郑州轻工业学院 | A kind of preparation method and application of coke sweet tea fragrance emitting agent for cigarettes active ingredient |
-
2017
- 2017-01-24 CN CN201710052594.4A patent/CN106800543A/en active Pending
Non-Patent Citations (3)
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| -: "RN 328119-23-9，RN 98407-48-8，RN948834-57-9，RN 36707-28-5，RN 39252-03-4", 《STN REGISTRY》 * |
| 刘秀娟等: "羧酸糠醇酯的合成研究", 《化学世界》 * |
| 张维成等: "糠酸和糠醇醋类香料的研究", 《精细化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440618A (en) * | 2018-03-14 | 2018-08-24 | 郑州轻工业学院 | The preparation method and application of 5- methyl furfuryl alcohols-β-D-Glucose glycosides |
| CN108516998A (en) * | 2018-03-14 | 2018-09-11 | 郑州轻工业学院 | A kind of preparation method and application of coke sweet tea fragrance emitting agent for cigarettes active ingredient |
| CN108516998B (en) * | 2018-03-14 | 2020-06-02 | 郑州轻工业学院 | Preparation method and application of effective components of aroma releasing agent for burnt sweet type cigarettes |
| CN108299359A (en) * | 2018-03-20 | 2018-07-20 | 东南大学 | A kind of furans esters of gallic acid tobacco aromaticss and preparation method thereof and the application in cigarette |
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Application publication date: 20170606 |
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