CN109810079A - A kind of synthetic method of polysubstituted dihydrofuran - Google Patents
A kind of synthetic method of polysubstituted dihydrofuran Download PDFInfo
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- CN109810079A CN109810079A CN201910090179.7A CN201910090179A CN109810079A CN 109810079 A CN109810079 A CN 109810079A CN 201910090179 A CN201910090179 A CN 201910090179A CN 109810079 A CN109810079 A CN 109810079A
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Abstract
The invention discloses a kind of new methods for synthesizing polysubstituted dihydrofuran class compound, the synthetic method carries out as follows: olefinic dicarbonyl compound, propiodal and oxidant shown in formula (I) are mixed in solvent, after reacting 8-12h at room temperature, the reaction solution is post-treated to obtain dihydrofuran class compound shown in formula (II)；The ratio between amount for the substance that feeds intake of olefinic dicarbonyl compound shown in the formula (I) and propiodal and oxidant is 1:0.5~1.1~2.5；The oxidant is tert-butyl hydroperoxide or hydrogen peroxide.Method of the present invention carries out intramolecular cyclization reaction directly using olefinic dicarbonyl compound as raw material；Whole process does not need metallic catalyst, avoids the residual of metal, and operation is simple, and reaction can carry out in a mild condition, and obtain good yield, more conducively its application in medicine synthesis.
Description
(1) technical field
The present invention relates to a kind of I2The preparation method for the polysubstituted dihydrofuran that/TBHP is mediated.
(2) background technique
Dihydrofuran class compound is a kind of critically important biological structure unit, is widely present in natural products and drug point
In son, and polysubstituted 2,3-dihydrofuran substance can be as the building block of many complicated heterocyclic compounds.
Such as dihydrofuran derivative Clerodin be from the chemical component for the natural neem extraction for being grown on India, they
With insect antifeedant activity, various pests can be effectively killed, for another example compound nepetaefolin is extracted from Caribbean region
Lip section plant Leonotis nepetaefolia, it have stronger inhibition cancer cell and antitumor activity.Although such
There are reports for the synthetic method of compound, but the synthetic method of these reported documents or the metal for having used valuableness
The disadvantages of catalyst or conditional operation complexity or not high atom utilization, so development is novel and meets Green Chemistry
Synthetic method has very important significance to scientific research tool.
(3) summary of the invention
The object of the present invention is to provide a kind of new methods for synthesizing polysubstituted dihydrofuran class compound.
The technical solution adopted by the invention is as follows:
A kind of synthetic method of dihydrofuran class compound shown in formula (II), the synthetic method as follows into
Row:
Olefinic dicarbonyl compound, propiodal and oxidant shown in formula (I) are mixed in solvent, react 8- at room temperature
After 12h, the reaction solution is post-treated to obtain dihydrofuran class compound shown in formula (II)；Olefinic shown in the formula (I)
The ratio between amount for the substance that feeds intake of dicarbonyl compound and propiodal and oxidant is 1:0.5~1.1~2.5；The oxidant is
Tert-butyl hydroperoxide or hydrogen peroxide；
In formula (I) or formula (II): R1Or R2Respectively stand alone as C1-4Alkyl, C1-4Alkoxy, phenyl or by halogen, first
Carbon between base, ethyl or methoxy-substituted phenyl or R1, R2 and R1, R2 forms six-membered carbon ring；
In formula (I) or formula (II): R3For hydrogen or methyl.
Further, it is preferred that in the formula (I) or formula (II): the R1For phenyl, 4- chlorphenyl, 4- aminomethyl phenyl,
4- bromophenyl, 4- methoxyphenyl, methoxyl group, ethyoxyl；The R2For phenyl, 4- chlorphenyl, 4- aminomethyl phenyl, 4- bromobenzene
Base, 4- methoxyphenyl or methyl；Or R1、R2And R1、R2Between carbon formed six-membered carbon ring；
The R3For methyl or hydrogen atom.
Further, synthetic method of the present invention, olefinic dicarbonyl compound shown in the preferably described formula (I) are selected from
It is one of following: 2- allyl -1,3- diphenyl -1,3- propanedione, bis- (4- the chlorphenyl) -1,3- propanedione of 2- allyl -1,3-,
Bis- (4- the aminomethyl phenyl) -1,3- propanedione of 2- allyl -1,3-, 2- allyl -1,3- bis- (4- bromophenyl) -1,3- propanedione, 2-
Bis- (4- the methoxyphenyl) -1,3- propanedione of allyl -1,3-, 2- (2- methacrylic) -1,3- diphenyl -1,3- propanedione,
2- allyl-hydroresorcinol, 2- allyl -3- benzoyl -1- ethyl propionate or 2- acetyl group -4- pentenoic acid ethyl ester.
Further, the propiodal is preferably iodine.
Further, the preferably described oxidant is tert-butyl hydroperoxide.
Further, the solvent is selected from one of following: water, ethyl acetate, dimethyl sulfoxide, acetone, acetonitrile, dichloromethane
Alkane, n,N-Dimethylformamide or 1,2- dichloroethanes, preferably acetonitrile.
Further, the additional amount of the solvent is with olefinic dicarbonyl compound substance shown in the formula (I)
Amount is calculated as 5-15ml/mmol.
Further, the substance that feeds intake of olefinic dicarbonyl compound shown in the preferably described formula (I) and propiodal and oxidant
The ratio between amount be 1:0.5:2.
Synthetic method of the present invention, preferable reaction temperature are room temperature, reaction time 8-12.
Further, recommend the reaction solution post-processing approach are as follows: after reaction, the reaction solution is passed through into decompression
It is concentrated to get crude product, then carries out column chromatography for separation, the petrol ether/ethyl acetate mixed liquor for being 50~1:1 with volume ratio is to wash
De- agent, collects the eluent for merging target compound, and dry, i.e., the dihydrofuran class compound described in gained after solvent is evaporated off.
More specifically, recommend the synthetic method of the dihydrofuran class compound are as follows:
Olefinic dicarbonyl compound, propiodal and oxidant shown in formula (I) are mixed in solvent and react 8- at room temperature
After 12h reacts completely, obtained reaction solution is carried out to be concentrated under reduced pressure to give crude product, then carries out column chromatography for separation；With volume
Than being eluant, eluent for the petrol ether/ethyl acetate mixed liquor of 50~1:1, the eluent for merging target compound is collected, is evaporated off molten
Dihydrofuran class compound dry after agent, i.e., described in gained；Olefinic dicarbonyl compound shown in the formula (I) and propiodal and
The ratio between amount for the substance that feeds intake of oxidant is 1:0.5:2；The additional amount of the solvent is with olefinic dicarbapentaborane shown in formula (I)
The amount for closing object substance is calculated as 10ml/mmol；Olefinic dicarbonyl compound shown in the formula (I) is selected from one of following: 2- allyl
Base -1,3- diphenyl -1,3- propanedione, bis- (4- chlorphenyl) -1, the 3- propanedione of 2- allyl -1,3-, 2- allyl -1,3- are bis-
(4- aminomethyl phenyl) -1,3- propanedione, bis- (4- bromophenyl) -1, the 3- propanedione of 2- allyl -1,3-, 2- allyl -1,3- are bis-
(4- methoxyphenyl) -1,3- propanedione, 2- (2- methacrylic) -1,3- diphenyl -1,3- propanedione, allyl -1 2-,
Hydroresorcinol, 2- allyl -3- benzoyl -1- ethyl propionate, 2- acetyl group -4- pentenoic acid ethyl ester；The propiodal is
Iodine；The oxidant is tert-butyl hydroperoxide；The solvent is acetonitrile.
Compared with prior art, the invention has the following advantages that
(1) Atom economy is high, and reagent is inexpensively environmentally friendly, easy to operate, the more mild feature of reaction condition.
(2) substrate adaptability is good, and a variety of substituent groups can realize the synthesis of corresponding dihydrofuran class compound.
(3) directly using olefinic dicarbonyl compound as raw material, intramolecular cyclization reaction is carried out；Whole process does not need metal
Catalyst avoids the residual of metal, and operation is simple, and reaction can carry out in a mild condition, and obtain good yield,
More conducively its application in medicine synthesis.
(4) specific embodiment
The present invention is described in further detail combined with specific embodiments below, but protection scope of the present invention and not only
It is limited to this.
Embodiment 1
By 2- allyl -1,3- diphenyl -1,3- propanedione (52.8mg, 0.2mmol), iodine (25.4mg,
0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) is added in reaction flask, is finally added again
Enter acetonitrile 2ml, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petrol ether/ethyl acetate
Volume ratio 50:1) isolated compound 1 (56.7mg), yield 72.7%.
Characterization of The Products: white solid；m.p.104-106℃；1H NMR(500MHz,CDCl3) δ/ppm=7.46-7.44
(dd, J=1.2Hz, 8.4Hz, 2H), 7.24-7.16 (m, 4H), 7.09-7.04 (dd, J=7.5Hz, 15Hz, 2H), 4.90-
4.85 (m, 1H), 3.53-3.46 (m, 3H), 3.10-3.05 (dd, J=7Hz, 15.4Hz, 1H)
Embodiment 2
By bis- (4- the methoxyphenyl) -1,3- propanedione (64.8mg, 0.2mmol) of 2- allyl -1,3-, iodine
(25.4mg, 0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) are added in reaction flask,
Acetonitrile 2ml is finally added, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petroleum ether/
Ethyl acetate volume ratio 20:1) isolated compound 2 (65.9mg), yield 73.2%.
Characterization of The Products: colourless oil liquid；1H NMR(500MHz,CDCl3) δ=7.53-7.51 (dt, J=2Hz,
8.9Hz, 2H), 7.23-7.21 (dt, J=2Hz, 8.9Hz, 2H), 6.65-6.61 (m, 4H), 4.87-4.81 (m, 1H), 3.74
(s, 3H), 3.72 (s, 3H), 3.48-3.46 (d, J=5.8Hz, 2H), 3.45-3.43 (t, J=5.3Hz, 10Hz, 1H),
3.06-3.01 (dd, J=7Hz, 15.4Hz, 1H)
Embodiment 3
By bis- (4- the aminomethyl phenyl) -1,3- propanedione (58.4mg, 0.2mmol) of 2- allyl -1,3-, iodine
(25.4mg, 0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) are added in reaction flask,
Acetonitrile 2ml is finally added, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petroleum ether/
Ethyl acetate volume ratio 20:1) isolated compound 3 (58.6mg), yield 70.1%.
Characterization of The Products: colourless oil liquid；1H NMR(500MHz,CDCl3) δ=7.41-7.39 (d, J=8.2Hz, 2H),
7.14-7.12 (d, J=8.2Hz, 2H), 6.92-6.88 (m, 4H), 4.88-4.82 (m, 1H), 3.48-3.47 (d, J=
5.8Hz, 2H), 3.46-3.43 (t, J=5.3Hz, 10Hz, 1H), 3.07-3.03 (dd, J=7Hz, 15.4Hz, 1H), 2.24
(s,3H),2.23(s,3H).
Embodiment 4
By bis- (4- the chlorphenyl) -1,3- propanedione (66.6mg, 0.2mmol) of 2- allyl -1,3-, iodine (25.4mg,
0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) is added in reaction flask, is finally added again
Enter acetonitrile 2ml, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petrol ether/ethyl acetate
Volume ratio 10:1) isolated compound 4 (64.5mg), yield 70.2%.
Characterization of The Products: white solid: m.p.120-122 DEG C；1H NMR(500MHz,CDCl3) δ/ppm=7.42-7.40
(dt, J=1.9Hz, 8.5Hz, 2H), 7.18-7.16 (dt, J=1.9Hz, 8.5Hz, 2H), 7.12-7.08 (m, 4H), 4.88-
4.82 (m, 1H), 3.52-3.43 (m, 3H), 3.06-3.02 (dd, J=7Hz, 15.6Hz, 1H)
Embodiment 5
By bis- (4- the bromophenyl) -1,3- propanedione (84.4mg, 0.2mmol) of 2- allyl -1,3-, iodine (25.4mg,
0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) is added in reaction flask, is finally added again
Enter acetonitrile 2ml, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petrol ether/ethyl acetate
Volume ratio 10:1) isolated compound 5 (74.2mg), yield 67.7%.
Characterization of The Products: white solid: m.p.124-125 DEG C；1H NMR(500MHz,CDCl3) δ/ppm=7.35-7.31
(dt, J=1.8Hz, 8.5Hz, 2H), 7.30-7.26 (m, 4H), 7.11-7.09 (dt, J=1.8Hz, 8.5Hz, 2H), 4.89-
4.84 (m, 1H), 3.54-3.44 (m, 3H), 3.07-3.02 (dd, J=7Hz, 15.6Hz, 1H)
Embodiment 6
By 2- allyl-hydroresorcinol (30.4mg, 0.2mmol), iodine (25.4mg, 0.1mmol) and uncle
Butylhydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) is added in reaction flask, finally adds acetonitrile 2ml, then
8h is reacted at room temperature.After reaction, it is separated with column chromatography chromatogram method (eluent: petrol ether/ethyl acetate volume ratio 1:1)
To compound 6 (36.4mg), yield 65.4%.
Characterization of The Products: white solid: m.p.85-86 DEG C；1H NMR(500MHz,CDCl3) δ/ppm=4.85-4.79 (m,
1H), 3.36-3.30 (m, 2H), 2.97-2.94 (ddt, J=1.8Hz, 10Hz, 15Hz, 1H), 2.60-2.55 (ddt, J=
1.9Hz,7Hz,15Hz,1H),2.45-2.41(m,2H),2.34-2.32(m,3H),2.06-2.00(m,2H).
Embodiment 7
By 2- allyl -3- benzoyl -1- ethyl propionate (46.4mg, 0.2mmol), iodine (25.4mg,
0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) is added in reaction flask, is finally added again
Enter acetonitrile 2ml, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petrol ether/ethyl acetate
Volume ratio 20:1) isolated compound 7 (35.6mg), yield 49.7%.
Characterization of The Products: colorless oil；1H NMR(500MHz,CDCl3) δ/ppm=7.79-7.77 (dd, J=1.2Hz,
7.9Hz, 2H), 7.44-7.37 (m, 3H), 4.84-4.78 (m, 1H), 4.16-4.12 (q, J=7.2Hz, 14.3Hz, 2H),
3.44-3.38 (m, 2H), 3.31-3.26 (dd, J=10.3Hz, 15.6Hz, 1H), 2.94-2.89 (dd.J=7Hz, 15.6Hz,
1H), 1.23-1.20 (t, J=7.1Hz, 3H)
Embodiment 8
By 2- (2- methacrylic) -1,3- diphenyl -1,3- propanedione (55.6mg, 0.2mmol), iodine
(25.4mg, 0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) are added in reaction flask,
Acetonitrile 2ml is finally added, then reacts 12h at room temperature.After reaction, with column chromatography chromatogram method (eluent: petroleum ether/
Ethyl acetate volume ratio 20:1) isolated compound 8 (69.4mg), yield 86.3%.
Characterization of The Products: colorless oil；1H NMR(500MHz,CDCl3) δ/ppm=7.45-7.43 (dd, J=1.1Hz,
8.1Hz, 2H), 7.22-7.15 (m, 4H), 7.08-7.04 (m, 4H), 3.57-3.55 (d, J=10.5Hz, 1H), 3.52-3.50
(d, J=10.5Hz, 1H), 3.32-3.29 (d, J=15.4Hz, 1H), 3.25-3.22 (d, J=15.4Hz, 1H), 1.74 (s, 3H)
Embodiment 9
By 2- acetyl group -4- pentenoic acid ethyl ester (34mg, 0.2mmol), iodine (25.4mg, 0.1mmol) and tertiary fourth
Base hydrogen peroxide (51.4mg, 0.4mmol, 70% aqueous solution) is added in reaction flask, finally adds acetonitrile 2ml, then in room
Temperature is lower to react 12h.After reaction, it is separated with column chromatography chromatogram method (eluent: petrol ether/ethyl acetate volume ratio 10:1)
To compound 9 (69.4mg), yield 89.7%.
Characterization of The Products: white solid: m.p.64-65 DEG C；1H NMR(500MHz,CDCl3) δ/ppm=4.70-4.64 (m,
1H), 4.17-4.13 (q, J=7Hz, 2H), 3.30-3.26 (m, 2H), 3.05-3.00 (m, 1H), 2.66-2.62 (m, 1H),
2.18-2.17 (t, J=1.6Hz), 1.17 (s, 3H)
Claims (9)
1. a kind of synthetic method of dihydrofuran class compound shown in formula (II), the synthetic method as follows into
Row:
Olefinic dicarbonyl compound, propiodal and oxidant shown in formula (I) are mixed in solvent, react 8-12h at room temperature
Afterwards, the reaction solution is post-treated obtains dihydrofuran class compound shown in formula (II)；Two carbonyl of olefinic shown in the formula (I)
The ratio between amount for the substance that feeds intake of based compound and propiodal and oxidant is 1:0.5~1.1~2.5；The oxidant is tertiary fourth
Base hydrogen peroxide or hydrogen peroxide；
In formula (I) or formula (II): R1Or R2Respectively stand alone as C1-4Alkyl, C1-4Alkoxy, phenyl or by halogen, methyl,
Ethyl or methoxy-substituted phenyl or R1、R2And R1、R2Between carbon formed six-membered carbon ring；
In formula (I) or formula (II): R3For hydrogen or methyl.
2. the method as described in claim 1, it is characterised in that: in the formula (I) or formula (II): the R1For phenyl, 4- chlorine
Phenyl, 4- aminomethyl phenyl, 4- bromophenyl, 4- methoxyphenyl, methoxyl group, ethyoxyl.
3. the method as described in claim 1, it is characterised in that: in the formula (I) or formula (II): the R2For phenyl, 4- chlorine
Phenyl, 4- aminomethyl phenyl, 4- bromophenyl, 4- methoxyphenyl or methyl.
4. the method as described in claim 1, it is characterised in that: olefinic dicarbonyl compound shown in the formula (I) is selected from down
One of column: 2- allyl -1,3- diphenyl -1,3- propanedione, 2- allyl -1,3- bis- (4- chlorphenyl) -1,3- propanedione, 2-
Bis- (4- the aminomethyl phenyl) -1,3- propanedione of allyl -1,3-, 2- allyl -1,3- bis- (4- bromophenyl) -1,3- propanedione, 2-
Bis- (4- the methoxyphenyl) -1,3- propanedione of allyl -1,3-, 2- (2- methacrylic) -1,3- diphenyl -1,3- the third two
Ketone, 2- allyl-hydroresorcinol, 2- allyl -3- benzoyl -1- ethyl propionate or 2- acetyl group -4- penetenoic acid second
Ester.
5. the method as described in claim 1, it is characterised in that: the propiodal is iodine.
6. the method as described in claim 1, it is characterised in that: the oxidant is tert-butyl hydroperoxide.
7. the method as described in claim 1, it is characterised in that: the solvent is selected from one of following: water, ethyl acetate, two
First sulfoxide, acetone, acetonitrile, methylene chloride, N,N-dimethylformamide or 1,2- dichloroethanes.
8. the method as described in claim 1, it is characterised in that: the additional amount of the solvent is shown in the formula (I)
The amount of olefinic dicarbonyl compound substance is calculated as 5-15ml/mmol.
9. the method as described in claim 1, it is characterised in that: the post-processing approach of the reaction solution are as follows: after reaction, will
The reaction solution is by being concentrated under reduced pressure to give crude product, then carries out column chromatography for separation, the petroleum for being 50~1:1 with volume ratio
Ether/ethyl acetate mixtures are eluant, eluent, collect the eluent for merging target compound, and drying after solvent, i.e. gained institute is evaporated off
The dihydrofuran class compound stated.
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| CN112159375A (en) * | 2020-09-14 | 2021-01-01 | 宁波大学 | Green preparation method of 2, 3-dihydrofuran compound |
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Application publication date: 20190528 |