CN108484552A - A kind of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative and preparation method thereof - Google Patents
A kind of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative and preparation method thereof Download PDFInfo
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- CN108484552A CN108484552A CN201810616462.4A CN201810616462A CN108484552A CN 108484552 A CN108484552 A CN 108484552A CN 201810616462 A CN201810616462 A CN 201810616462A CN 108484552 A CN108484552 A CN 108484552A
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- MIEYUUUDGKDHRE-UHFFFAOYSA-N NC(C(C(C1(C2c3ccccc3)Oc(cccc3)c3C1=O)c1ccccc1)(C#N)C#N)=C2C#N Chemical compound NC(C(C(C1(C2c3ccccc3)Oc(cccc3)c3C1=O)c1ccccc1)(C#N)C#N)=C2C#N MIEYUUUDGKDHRE-UHFFFAOYSA-N 0.000 description 1
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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
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
Abstract
The invention discloses a kind of polysubstituted 3 benzofuranone spiral shell cyclohexene derivatives and preparation method thereof, and the structural formula of the polysubstituted 3 benzofuranone spiral shell cyclohexene derivative is as shown in formula I：
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of polysubstituted 3- benzofuranones loop coil hexene derivative
Object and preparation method thereof.
Background technology
3- benzofuranones spiro-compound is widely present in nature, especially wide in medicine, pesticide etc. application
It is general.3- benzofuranones spiral shell cyclohexene derivative therein and people’s lives are in close relations, in many natural products and medicine
There are 3- benzofuranone loop coil hexene structural framings, such as：It is isolated natural with antibacterial activity from marine fungi
Product leptosphaerin c, antifungal antibiotic Griseofulvin etc..It is being cured based on 3- benzofuranones spiro-compound
Importance in medicine, pesticide, chemists develop a variety of methods for building such compound at present, but document report
The preparation method of 3- benzofuranone spiro-compounds is mainly concentrated and structure 3- benzofuranones spiro cyclopentane, 3- benzofurans
The compounds such as penta heterocycle of ketone loop coil, 3- benzofuranone loop coil hexanes, so obtained from these 3- benzofuranone spiro compounds
Species are limited, especially polysubstituted for the 3- benzofuranone spiral shell cyclohexene derivatives being widely present in natural products
The report of 3- benzofuranone spiral shell cyclohexene derivatives is less, and type is also limited.Therefore, one pot reaction, efficient structure are taken
The standby polysubstituted 3- benzofuranones spiral shell cyclohexene derivative with specific structure of organizational system, to develop wide variety, structure novel
Polysubstituted 3- benzofuranones spiral shell cyclohexene derivative to it is pharmaceutical chemical development have great importance.
Multi-component reaction for the treatment of different things alike mixes reactant, and a chain of multistep reaction occurs in a vessel, is high
Organic preparation of efficiency is reacted, the chemical constitution for obtaining having larger complexity using seldom step.With traditional chemistry
Reaction is compared, and multi-component reaction for the treatment of different things alike is reacted in a container, eliminates the separating step of intermediate, can be notable
Save the time, improve yield, it is all organic synthesis route preferred approach to treat different things alike, have efficient, convenient, atom economy, at
This low advantage.Better simply raw material can be conveniently transformed into complicated molecule by multi-component reaction for the treatment of different things alike.Especially
In the full preparation of labyrinth and natural products, multi-component reaction for the treatment of different things alike can usually play very crucial effect, because
This causes more and more concerns in recent years.
Invention content
For problems of the prior art, the present invention provides a kind of polysubstituted 3- benzofuranones loop coil hexene derivative
Object and preparation method thereof, this method have advantages, the application prospect such as efficient, convenient, at low cost good.
In order to solve the above technical problems, the present invention uses following technical scheme：
A kind of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative, the polysubstituted 3- benzofuranones loop coil hexene spread out
The structural formula of biology is as shown in formula I：
Wherein R1Structural formula be selected from：CN or CO2Me；
Wherein R2One kind in following structural formula of structural formula：
Wherein R3Structural formula be selected from selected from hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amine
One kind in base, amide groups, alkanoyloxy, cyano, aryl, alkenyl, halobenzyloxy, halogenated benzylamine base or halogenated phenoxy；
The R1＇, R2＇ is respectively and independently selected from hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amine
One kind in base, amide groups, alkanoyloxy, cyano, aryl, alkenyl, halobenzyloxy, halogenated benzylamine base or halogenated phenoxy；
The alkyl is the linear or branched alkyl group of C1-C18, carbocyclic ring or heterocycle (containing 1-3 oxygen, sulphur or nitrogen), substitution
Or the alkyl not replaced, wherein substituent group is halogen, hydroxyl, carboxyl, nitro, cyano, substituted amino, amide groups, carboxyl, ester
Base, alkoxy, alkylamino alkanoyloxy, aryl；
The aryl is the aromatic ring for replacing or not replacing, or the heteroaromatic for replacing or not replacing；
The aromatic ring is phenyl ring, naphthalene nucleus, anthracene nucleus, phenanthrene ring, quinoline ring, isoquinolin ring, pyrrole ring, pyridine ring, pyrimidine ring, furan
It mutters ring, thiphene ring；Substituent group is halogen, methyl, trifluoromethyl, hydroxyl, nitro, amino, substituted amino, carboxyl, ester group, alkane
Oxygroup, alkanoyloxy or cyano.
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative, its step are as follows：By benzaldehyde,
Malononitrile and 3- benzofuranones react under conditions of potassium carbonate is catalyst, dichloromethane is solvent, temperature is 20-80 DEG C
1-72 hours, polysubstituted 3- benzofuranones spiral shell cyclohexene derivative is made through column chromatography for separation.
The ratio between amount of substance of the benzaldehyde, malononitrile and 3- benzofuranones is 2:2:1~3:3:1.
On the basis of the amount of the substance of 3- benzofuranones, the amount of the substance of potassium carbonate is the amount of 3- benzofuranone substances
10%-80%.
Preferred 30-60 DEG C of the reaction temperature.
The eluent petroleum ether and ethyl acetate of the column chromatography, the petroleum ether with and ethyl acetate volume ratio be 15:1
To 1:1.
Beneficial effects of the present invention：The present invention provides it is a kind of simple, efficiently, easily polysubstituted 3- benzofuranones spiral shell
It is that solvent prepares polysubstituted 3- benzofuranones that cyclohexene derivative preparation method, which is using potassium carbonate as catalyst, dichloromethane,
Spiral shell cyclohexene derivative, has many advantages, such as efficient, convenient, at low cost, and application prospect is good.
Specific implementation mode
With reference to specific embodiment, the present invention will be further described.It should be understood that following embodiment is merely to illustrate this
The person skilled in the art of the range of invention and is not intended to limit the present invention, the field can make one according to the content of foregoing invention
A little nonessential modifications and adaptations.
Embodiment 1
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the turbine-like phthalazine derivatives of the present embodiment is：By 20.1mg (0.15mmol) 3- benzofurans
The dichloro of ketone, 31.8mg (0.3mmol) benzaldehyde, 19.8mg (0.3mmol) malononitrile, 8.3mg (40%eq) potassium carbonate, 1mL
Methane is added in reaction tube, and 2h is stirred to react under conditions of 20~80 DEG C, uses column chromatography to obtain target product (elution
Agent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
Embodiment 2
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 45.3mg (0.3mmol) 4- nitrobenzaldehydes, 19.8mg (0.3mmol) malononitrile,
8.3mg (40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 5h under conditions of 20~80 DEG C,
Using column chromatography to obtain target product, (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR(400MHz,CDCl3)δ7.51–7.35(m,4H),7.31–7.23(m,2H),7.23-7.03(m,7H),
6.79 (t, J=7.4Hz, 1H), 5.22 (s, 2H), 4.34 (s, 1H), 3.98 (s, 1H)
Embodiment 3
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 37.2mg (0.3mmol) 4- fluorobenzaldehydes, 19.8mg (0.3mmol) malononitrile, 8.3mg
(40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 72h under conditions of 20~80 DEG C, use column
Chromatography obtains target product, and (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR (400MHz, DMSO) δ 7.71-7.56 (m, 3H), 7.40 (dd, J=8.8,5.3Hz, 2H), 7.21 (d, J
=8.4Hz, 1H), 7.17 (d, J=7.7Hz, 1H), 7.11 (t, J=8.4Hz, 2H), 6.91 (t, J=7.4Hz, 3H), 4.98
(s,1H),4.41(s,1H),3.40(s,2H).
Embodiment 4
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 40.5mg (0.3mmol) 4-methoxybenzaldehyde, 19.8mg (0.3mmol) malononitrile,
8.3mg (40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react under conditions of 20~80 DEG C
72h, using column chromatography to obtain target product, (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR (400MHz, CDCl3) δ 7.49-7.43 (m, 1H), 7.31 (d, J=9.0Hz, 2H), 7.23-6.97 (m,
4H), 6.94 (s, 1H), 6.81 (t, J=7.4Hz, 1H), 6.67 (t, J=8.9Hz, 3H), 5.13 (s, 2H), 4.27 (s, 1H),
3.91(s,1H),3.69(s,3H),3.63(s,3H).
Embodiment 5
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 55.5mg (0.3mmol) 4- bromobenzaldehydes, 19.8mg (0.3mmol) malononitrile, 8.3mg
(40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 72h under conditions of 20~80 DEG C, use column
Chromatography obtains target product, and (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR(400MHz,CDCl3) δ 7.73 (dd, J=8.0,1.7Hz, 1H), 7.65 (dd, J=8.1,1.4Hz,
1H),7.51–7.47(m,1H),7.33–7.28(m,1H),7.19–7.12(m,3H),7.06–6.96(m,2H),6.85(t,J
=7.4Hz, 1H), 6.77 (tt, J=7.4,1.2Hz, 1H), 6.70 (d, J=7.6Hz, 1H), 5.22 (s, 2H), 5.20 (s,
1H),5.10(s,1H).
Embodiment 6
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 46.9mg (0.3mmol) 4- bromobenzaldehydes, 19.8mg (0.3mmol) malononitrile, 8.3mg
(40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 72h under conditions of 20~80 DEG C, use column
Chromatography obtains target product, and (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
isomer A:Isomer B=1:0.24.1H NMR(400MHz,CDCl3) δ 8.46 (d, J=9.1Hz, 1H, for
Isomer B), 8.37 (d, J=8.7Hz, 1H, for isomer A), 8.31 (d, J=8.7Hz, 1H, for isomer B),
8.02-7.93 (m, 2H, for isomer A and isomer B), 7.83 (d, J=8.2Hz, 1H, for isomer A and
isomer B),7.79–7.52(m,8H,isomer A and isomer B),7.43–7.30(m,4H,for isomer A
And isomer B), 7.22-7.06 (m, 2H, for isomer A and isomer B), 7.03 (d, J=8.4Hz, 1H,
For isomer A), 6.90 (d, J=7.0Hz, 1H, for isomer B), 6.70 (d, J=7.7Hz, 1H, for isomer
), B 6.65 (d, J=7.7Hz, 1H, for isomer A), 6.62-6.47 (m, 1H, for isomer A and isomer
B),5.54(s,1H,for isomer A),5.32(s,1H,for isomer A),5.29(s,1H,for isomer B),
5.24(s,1H,for isomer B),5.18(s,2H,for isomer B),5.16(s,2H,for isomer A).
Embodiment 7
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 46.9mg (0.3mmol) 1- naphthaldehydes, 19.8mg (0.3mmol) malononitrile, 8.3mg
(40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 48h under conditions of 20~80 DEG C, use column
Chromatography obtains target product, and (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR(400MHz,CDCl3) δ 8.24 (d, J=17.0Hz, 1H), 8.03 (dd, J=8.2,1.3Hz, 1H),
7.86-7.60 (m, 3H), 7.40 (d, J=7.1Hz, 1H), 7.29 (t, J=8.0Hz, 2H), 7.04 (dd, J=43.6,
14.1Hz, 3H), 6.77 (t, J=7.5Hz, 1H), 6.57 (d, J=14.1Hz, 2H), 4.68 (d, J=6.4Hz, 1H), 4.41
(d, J=5.0Hz, 1H), 3.85 (s, 3H), 3.31 (s, 3H)
Embodiment 8
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 42.2mg (0.3mmol) 4- chloromethanes aldehyde, 19.8mg (0.3mmol) malononitrile, 8.3mg
(40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 72h under conditions of 20~80 DEG C, use column
Chromatography obtains target product, and (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR(400MHz,CDCl3) δ 7.44-7.38 (m, 1H), 7.26 (d, J=8.6Hz, 2H), 7.15 (dd, J=
12.3,7.7Hz, 2H), 7.05 (d, J=8.7Hz, 3H), 6.94 (d, J=8.4Hz, 1H), 6.81 (dd, J=16.4,8.8Hz,
3H),6.34(s,2H),4.53(s,1H),4.21(s,1H),3.79(s,3H),3.31(s,3H).
Embodiment 9
The structural formula of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is as follows：
The preparation method of the polysubstituted 3- benzofuranones spiral shell cyclohexene derivative of the present embodiment is：By 20.1mg
(0.15mmol) 3- benzofuranones, 42.2mg (0.3mmol) 2 thiophene carboxaldehyde, 19.8mg (0.3mmol) malononitrile, 8.3mg
(40%eq) potassium carbonate, 1mL dichloromethane be added in reaction tube, be stirred to react 72h under conditions of 20~80 DEG C, use column
Chromatography obtains target product, and (eluant, eluent is：Petroleum ether and ethyl acetate volume ratio are 15:1 to 1:1).
1H NMR(400MHz,CDCl3) δ 7.75 (dd, J=8.1,1.7Hz, 1H), 7.45-7.40 (m, 2H), 7.16-
7.12(m,1H),6.92-6.99(m,5H),5.25(s,2H),5.18(s,1H),5.10(s,1H).
The basic principles and main features and advantages of the present invention of the present invention have been shown and described above.The skill of the industry
Art personnel it should be appreciated that the present invention is not limited to the above embodiments, the above embodiments and description only describe
The principle of the present invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these
Changes and improvements all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent thereof.
Claims (6)
1. a kind of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative, the polysubstituted 3- benzofuranones loop coil hexene derives
The structural formula of object is as shown in formula I：
Wherein R1It is selected from：CN or CO2Me；R2One kind in following structural formula：
R3Selected from selected from hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amido, amide groups, alkyloyloxyethyl
One kind in base, cyano, aryl, alkenyl, halobenzyloxy, halogenated benzylamine base or halogenated phenoxy；
The R1＇, R2＇ is respectively and independently selected from hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amido, acyl
One kind in amido, alkanoyloxy, cyano, aryl, alkenyl, halobenzyloxy, halogenated benzylamine base or halogenated phenoxy；
The alkyl is the linear or branched alkyl group of C1-C18, carbocyclic ring or heterocycle, the alkyl for replacing or not replacing, wherein substituent group
For halogen, hydroxyl, carboxyl, nitro, cyano, substituted amino, amide groups, carboxyl, ester group, alkoxy, alkylamino alkanoyloxy,
Aryl；
The aryl is the aromatic ring for replacing or not replacing, or the heteroaromatic for replacing or not replacing；
The aromatic ring is phenyl ring, naphthalene nucleus, anthracene nucleus, phenanthrene ring, quinoline ring, isoquinolin ring, pyrrole ring, pyridine ring, pyrimidine ring, furans
Ring, thiphene ring；Substituent group is halogen, methyl, trifluoromethyl, hydroxyl, nitro, amino, substituted amino, carboxyl, ester group, alcoxyl
Base, alkanoyloxy or cyano.
2. the preparation method of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative according to claim 1, feature exist
In steps are as follows：By benzaldehyde, malononitrile and 3- benzofuranones potassium carbonate is catalyst, dichloromethane is solvent, temperature
It is reacted 1-72 hours under conditions of being 20-80 DEG C, polysubstituted 3- benzofuranones loop coil hexene, which is made, through column chromatography for separation derives
Object.
3. the preparation method of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative according to claim 2, feature exist
In：The ratio between amount of substance of the benzaldehyde, malononitrile and 3- benzofuranones is 2:2:1~3:3:1.
4. the preparation method of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative according to claim 2, feature exist
In：On the basis of the amount of the substance of 3- benzofuranones, the amount of the substance of potassium carbonate is the amount of 3- benzofuranone substances
10%-80%.
5. the preparation method of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative according to claim 2, feature exist
In：The reaction temperature is 30-60 DEG C.
6. the preparation method of polysubstituted 3- benzofuranones spiral shell cyclohexene derivative according to claim 2, feature exist
In：The eluent petroleum ether and ethyl acetate of the column chromatography, the petroleum ether with and ethyl acetate volume ratio be 15:1 to 1:
1。
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| CN113307786A (en) * | 2021-05-28 | 2021-08-27 | 河南大学 | Spiro dihydrofluorene derivative and preparation method thereof |
| CN116283868A (en) * | 2023-02-03 | 2023-06-23 | 三峡大学 | Synthesis method of spiro [ benzofuran-cyclohexene ] compound |
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Cited By (2)
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