CN109096067A - A kind of method of the alpha-brominated cyclopentenone of synthesizing new - Google Patents
A kind of method of the alpha-brominated cyclopentenone of synthesizing new Download PDFInfo
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- CN109096067A CN109096067A CN201811127378.2A CN201811127378A CN109096067A CN 109096067 A CN109096067 A CN 109096067A CN 201811127378 A CN201811127378 A CN 201811127378A CN 109096067 A CN109096067 A CN 109096067A
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- alpha
- brominated
- cyclopentenone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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Abstract
The invention discloses a kind of new methods of alpha-brominated cyclopentene ketone compounds, it includes, 1 is added in t-butyl methyl ether solution, 3- eneyne ester, (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid are golden (I), confirm that raw material has reacted by thin-layer chromatography after stirring 1 hour and adds N- bromo-succinimide, entire reaction carries out at normal temperatures and pressures, mild condition, and energy consumption is cheap.Entire reaction is carried out using " one pot of two-step method ", and easy to operate efficient, yield is high, and product purity is 99% or more.Reaction substrate range is wide, is not only applicable to 1,3- eneyne ester type compound, and the complex compound containing natural products group is equally applicable.Alpha-brominated cyclopentene ketone compounds reactivity with higher obtained is researched and developed, is synthesis of natural product and the potential important intermediate of bioactive molecule.
Description
Technical field
The invention belongs to chemosynthesis technical fields, and in particular to a kind of method of the alpha-brominated cyclopentenone of synthesizing new.
Background technique
α-halogenatedketone such as alpha-chloro ketone, alpha-brominated ketone, alpha-iodine are that organic synthesis and complicated natural products synthesis are compared for ketone
Important intermediate.Cyclopentenone is widely present in biologically active natural products and pharmaceutical molecules.Currently, bromo ring
The research of ketene compounds is less, how in the precursor from acyclic organic matter efficiently, regioselectivity to introduce bromine atom
It is still a major challenge.
Summary of the invention
Regarding the issue above, the present invention provides a kind ofIt is mild, simple with wide application range of substrates, reaction condition Just efficientThe method of the alpha-brominated cyclopentenone of synthesizing new.
In order to solve the above technical problems, the present invention provides the following technical scheme that a kind of synthesizing new α-bromine of the invention
For the method for cyclopentenone, include the following steps: that methyl tertiary butyl ether(MTBE), 1,3- eneyne ester, (acetonitrile) [(2- biphenyl) two uncles is added
Butyl phosphine] hexafluoro-antimonic acid gold (I), N- bromo-succinimide, are reacted to obtain the alpha-brominated cyclopentenone；Reaction equation
Are as follows:
In formula, R1、R2For group independent, and carbon number is 1~16；
R1For substituent group, including any one in phenyl, naphthalene, halogenophenyl, chain alkylene, naphthenic base；
R2For substituent group, including methyl, chain alkylene, naphthenic base, carbonyl, ester group, benzenesulfonyl, phenyl, nitrogen-containing heterocycle
One of group is several.
Further, methyl tertiary butyl ether(MTBE), 1,3- eneyne ester, (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] are first sequentially added
Hexafluoro-antimonic acid gold (I) confirms that raw material has reacted by thin-layer chromatography after stirring 1 hour and adds N- bromo-succinimide, often
It is stirred 2 hours under normal temperature and pressure, then by reaction solution concentrated by rotary evaporation, and the alpha-brominated ring penta of target product is obtained by silica gel column chromatography
Ketenes.
Further, the reaction temperature is room temperature.
Further, concentration of 1, the 3- eneyne ester in methyl tertiary butyl ether(MTBE) is 0.05~0.1mol/L.
Further, 1, the 3- eneyne ester and (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid golden (I)
Molar ratio is 1: 0.01~1: 0.1.
Further, the molar ratio of 1, the 3- eneyne ester and N- bromo-succinimide is 1: 1.2~1: 2.
Further, the revolving, revolving speed are 150~300rpm, and temperature is 35~45 DEG C, vacuum degree 0.05
~0.09Mpa, processing time are 5~15min.
Further, the silica gel column chromatography, using 200~300 mesh column chromatography silica gels, eluant, eluent volume ratio is acetic acid
Ethyl ester: petroleum ether=1~30: 100.
It is carried out at normal temperatures and pressures the utility model has the advantages that the present invention entirely reacts, mild condition, energy consumption is cheap.It is suitable with substrate
With range is wide, reaction condition is mild, simple and effective.Easy to operate, yield is high, and product purity is 99% or more.
Compared with prior art, the present invention has the advantage that
(1) reaction substrate range is wide, is applicable not only to simple 1,3- eneyne ester type compound, for containing natural products base
The complex compound of group is equally applicable.
(2) alpha-brominated cyclopentene ketone compounds reactivity with higher obtained is researched and developed, is synthesis of natural product
And the potential important intermediate of bioactive molecule.
(3) entire reaction is carried out using " one pot of two-step method ", and easy to operate efficiently yield is high, product purity 99% with
On.Reaction substrate range is wide, is not only applicable to 1,3- eneyne ester type compound, the complex compound containing natural products group
It is equally applicable.Research and develop alpha-brominated cyclopentene ketone compounds reactivity with higher obtained, be synthesis of natural product with
And the potential important intermediate of bioactive molecule.
Specific embodiment
The present invention is further illustrated combined with specific embodiments below.
Embodiment 1
1,3- eneyne ester 1a (0.5mmol) is added in round-bottomed flask, 5mL methyl tertiary butyl ether(MTBE) is then added as molten
Golden (I) catalyst of (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid is added in agent while stirring.Stirring passes through after 1 hour
Thin-layer chromatography confirmation raw material, which has reacted, adds N- bromo-succinimide, 2 hours end of reaction is stirred under normal temperature and pressure, then
By reaction solution concentrated by rotary evaporation, target product is separated using silica gel column chromatography, eluant, eluent volume ratio is ethyl acetate: petroleum
Ether=3: 100, target product 2a, yield 84% are obtained using vacuum distillation.
1H NMR (400MHz, CDCl3): δ 7.65-7.62 (m, 2H), 7.52-7.46 (m, 3H), 6.61 (t, 1H, J=
1.7Hz), 3.76 (dd, 1H, J=18.9,1.6Hz), 3.41 (dd, 1H, J=18.9,1.9Hz), 1.90 (s, 3H)；13C NMR
(100MHz, CDCl3): δ 203.0,168.5,132.9,132.1,129.1,127.1,122.7,57.3,48.5,27.6.
Embodiment 2
The present embodiment and the method for embodiment 1 are essentially identical, the difference is that: using 1,3- eneyne ester 1b as reaction
Substrate, other conditions are constant, handled to obtain target product 2b, yield 84%.
1H NMR (600MHz, CDCl3): δ 7.65-7.63 (m, 2H), 7.50-7.45 (m, 3H), 6.60 (t, 1H, J=
1.8Hz), 3.50 (dd, 1H, J=19.1,1.9Hz), 3.42 (dd, 1H, J=19.1,1.6Hz), 2.37-2.35 (m, 1H),
2.18-2.10 (m, 1H), 1.88 (t, 1H, J=2.0Hz), 1.70 (d, 2H, J=17.5Hz), 1.59 (d, 1H, J=
12.1Hz), 1.37-1.26 (m, 2H), 1.21-1.12 (m, 2H), 0.93-0.86 (m, 1H)
13C NMR (150MHz, CDCl3): δ 203.3,169.4,133.0,131.9,129.1,127.1,124.2,68.0,
44.9,42.7,28.8,27.8,26.2 (d, 1C, J=4.5Hz), 25.8.
Embodiment 3
The present embodiment and the method for embodiment 1 are essentially identical, the difference is that: using 1,3- eneyne ester 1c as reaction
Substrate, eluant, eluent volume ratio be ethyl acetate: petroleum ether=20: 100, other conditions are constant, handled to obtain target product 2c,
Yield is 85%.
1H NMR (600MHz, CDCl3): δ 7.82-7.79 (m, 2H), 7.70-7.68 (m, 2H), 7.60-7.59 (m, 2H),
7.50-7.43 (m, 3H), 6.57 (t, 1H, J=1.7Hz), 3.76-3.70 (m, 2H), 3.57 (dd, 1H, J=18.7,
1.5Hz), 3.42 (dd, 1H, J=18.9,2.0Hz), 2.23-2.18 (m, 1H), 2.06-2.01 (m, 1H), 1.91-1.79 (m,
2H).
13C NMR (150MHz, CDCl3): δ 202.2,168.8,168.2,134.0,132.8,132.1 (d, 1C, J=
8.9Hz), 129.1,127.1,123.3 (d, 1C, J=6.8Hz), 61.7,46.0,37.5,36.5,25.3.
Embodiment 4
The present embodiment and the method for embodiment 1 are essentially identical, the difference is that: using 1,3- eneyne ester 1d as reaction
Substrate, eluant, eluent volume ratio be ethyl acetate: petroleum ether=6: 100, other conditions are constant, handled to obtain target product 2d,
Yield is 83%.
1H NMR (600MHz, CDCl3): δ 8.10-8.08 (m, 1H), 7.94-7.91 (m, 2H), 7.58-7.49 (m, 4H),
6.55 (t, 1H, J=1.7Hz), 3.82 (dd, 1H, J=19.2,1.5Hz), 3.49 (dd, 1H, J=19.2,2.1Hz), 1.97
(s, 3H)
13C NMR (150MHz, CDCl3): δ 202.8,169.7,133.9,132.8,130.9,130.1,128.9,
128.7,127.4,126.6,125.0,124.9,124.6,57.1,52.1,27.2.
Embodiment 5
The present embodiment and the method for embodiment 1 are essentially identical, the difference is that: using 1,3- eneyne ester 1e as reaction
Substrate, eluant, eluent volume ratio be ethyl acetate: petroleum ether=10: 100, other conditions are constant, handled to obtain target product 2e,
Yield is 82%.
1H NMR (600MHz, CDCl3): δ 7.63-7.62 (m, 2H), 7.51-7.44 (m, 3H), 6.60 (t, 1H, J=
1.7Hz), 4.11-4.08 (m, 2H), 3.61 (dd, 1H, J=18.9,1.5Hz), 3.42 (dd, 1H, J=18.9,2.0Hz),
2.23-2.18 (m, 1H), 2.02 (s, 3H), 1.99-1.88 (m, 2H), 1.79-1.72 (m, 1H)
13C NMR (150MHz, CDCl3): 8202.5,171.1,168.9,132.8,132.2,129.2,127.1,
123.2,63.7,61.8,46.0,35.8,25.4,21.0.
Embodiment 6
The present embodiment and the method for embodiment 1 are essentially identical, the difference is that: using 1,3- eneyne ester 1f as reaction
Substrate, other conditions are constant, handled to obtain target product 2f, yield 52%.
1H NMR (600MHz, C6D6): δ 5.70 (t, 1H, J=1.5Hz), 2.80 (dt, 1H, J=19.2,0.7Hz),
2.20 (dt, 1H, J=19.1,1.0Hz), 1.66 (t, 2H, J=7.4Hz), 1.59 (s, 3H), 1.22-1.17 (m, 2H),
1.11-1.05 (m, 4H), 1.03-1.00 (m, 2H), 0.88 (t, 3H, J=7.3Hz)；
13C NMR (150MHz, C6D6): δ 201.4,175.5,124.7,57.4,50.5,32.5,31.4,28.8,26.8,
26.2,22.5,13.9.
Embodiment 7
Using 1a as raw material, preparation method is screened: 1a being added in round-bottomed flask first, gold is added in a solvent
Catalyst confirms raw material end of reaction by thin-layer chromatography after stirring 1 hour, bromide reagent is then added.
The screening of 1 preparation method of table
Experimental data shows some other solvents, such as methylene chloride, tetrahydrofuran etc., yield and methyl tertiary butyl ether(MTBE) phase
Than yield is lower；And some other bromide reagents such as N- bromo imines (NBP), N-bromoacetamide (NBA), it shows to be lower than
The reactivity of N- bromo-succinimide (NBS)；And in Au catalyst, (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro antimony
Sour gold (I) (JohnPhosAu (MeCN) SbF6) catalyst shows superior yield and shortest reaction time, therefore, this hair
It is bright that solvent, (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid golden (I) are made as catalyst, N- bromine using methyl tertiary butyl ether(MTBE)
It is bromide reagent for succimide, as more excellent scheme of the invention.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, the present invention
Claimed range is delineated by the appended claims, the specification and equivalents thereof from the appended claims.
Claims (8)
1. a kind of method of the alpha-brominated cyclopentenone of synthesizing new, it is characterised in that include the following steps: that methyl tertbutyl is added
Ether, 1,3- eneyne ester, (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid gold (I), N- bromo-succinimide are carried out anti-
It should obtain the alpha-brominated cyclopentenone；Reaction equation are as follows:
In formula, R1、R2For group independent, and carbon number is 1~16；
R1For substituent group, including any one in phenyl, naphthalene, halogenophenyl, chain alkylene, naphthenic base；
R2For in substituent group, including methyl, chain alkylene, naphthenic base, carbonyl, ester group, benzenesulfonyl, phenyl, nitrogen-containing heterocycle group
One or several kinds.
2. the method for the alpha-brominated cyclopentenone of synthesizing new described in claim 1, it is characterised in that: first sequentially add methyl- tert
Butyl ether, 1,3- eneyne ester, (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid are golden (I), and stirring passed through thin layer after 1 hour
Chromatography confirmation raw material, which has reacted, adds N- bromo-succinimide, stirs 2 hours under normal temperature and pressure, then rotates reaction solution
Concentration, and the alpha-brominated cyclopentenone of target product is obtained by silica gel column chromatography.
3. the method for the alpha-brominated cyclopentenone of synthesizing new as claimed in claim 1 or 2, it is characterised in that: the reaction
Temperature is room temperature.
4. the method for the alpha-brominated cyclopentenone of synthesizing new as claimed in claim 1 or 2, it is characterised in that: described 1,3-
Concentration of the eneyne ester in methyl tertiary butyl ether(MTBE) is 0.05~0.1mol/L.
5. the method for the alpha-brominated cyclopentenone of synthesizing new as claimed in claim 1 or 2, it is characterised in that: described 1,3-
The molar ratio of eneyne ester and (acetonitrile) [(2- biphenyl) di-t-butyl phosphine] hexafluoro-antimonic acid golden (I) is 1: 0.01~1: 0.1.
6. the method for the alpha-brominated cyclopentenone of synthesizing new as claimed in claim 1 or 2, it is characterised in that: described 1,3-
The molar ratio of eneyne ester and N- bromo-succinimide is 1: 1.2~1: 2.
7. the method for the alpha-brominated cyclopentenone of synthesizing new as claimed in claim 2, it is characterised in that: the revolving,
Revolving speed is 150~300rpm, and temperature is 35~45 DEG C, and vacuum degree is 0.05~0.09Mpa, and the processing time is 5~15min.
8. the method for the alpha-brominated cyclopentenone of synthesizing new as claimed in claim 2, it is characterised in that: the silica gel column layer
Analysis, using 200~300 mesh column chromatography silica gels, eluant, eluent volume ratio is ethyl acetate: petroleum ether=1~30: 100.
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| CN113999118A (en) * | 2021-11-23 | 2022-02-01 | 浙江师范大学 | Derivative containing 2-trifluoromethyl cyclopentenone and preparation method thereof |
| CN116354806A (en) * | 2023-01-13 | 2023-06-30 | 武汉理工大学 | Phosphine catalysis preparation method of full-carbon quaternary carbon cyclopentenone derivative |
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| CN110105318A (en) * | 2019-06-21 | 2019-08-09 | 南京林业大学 | A kind of green synthesis method of alpha-pyrone compound |
| CN110105318B (en) * | 2019-06-21 | 2021-04-09 | 南京林业大学 | Green synthesis method of alpha-pyrone compound |
| CN113999118A (en) * | 2021-11-23 | 2022-02-01 | 浙江师范大学 | Derivative containing 2-trifluoromethyl cyclopentenone and preparation method thereof |
| CN116354806A (en) * | 2023-01-13 | 2023-06-30 | 武汉理工大学 | Phosphine catalysis preparation method of full-carbon quaternary carbon cyclopentenone derivative |
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