CN106749116B - A kind of preparation method of 3- amino methyls tetrahydrofuran - Google Patents
A kind of preparation method of 3- amino methyls tetrahydrofuran Download PDFInfo
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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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Abstract
The present invention relates to a kind of preparation methods of 3 amino methyl tetrahydrofuran.The method for preparing 3 amino methyl tetrahydrofurans in particular to 3 cyano tetrahydrofurans of reduction.The present invention uses a kind of new synthesis process, i.e., with gamma butyrolactone and halogen simple substance X23 X gamma butyrolactones are prepared for raw material, 3 X gamma butyrolactones are then restored using reducing agent and obtain 2 X 1,4 butanediols, then 3 X tetrahydrofurans are obtained under the action of dehydrating agent, and 3 cyano tetrahydrofurans are obtained under the action of cyaniding catalyst, 3 amino methyl tetrahydrochysene furans are finally obtained under the action of hydrogenation catalyst.This synthesis technology raw material is easy to get, and experimental implementation is simple, and reaction condition is mild, and products collection efficiency and purity are higher, and environmental pollution is small, and production cost is relatively low, is suitble to industrialization expanding production, application prospect very wide.
Description
Technical field
The invention belongs to compound synthesis technical fields, are related to a kind of preparation method of 3- amino methyls tetrahydrofuran, tool
Body is related to a kind of method preparing 3- amino methyl tetrahydrofurans using reduction method.
Background technology
3- amino methyl tetrahydrofurans are the common intermediates such as medical pesticide, in the prior art for preparation method
Disclose less, reason is simply derive 2 upper tetrahydrochysene furans with substituent group by the substitution reaction of furan nucleus
It mutters compound, in contrast, it is very difficult to synthesize 3 upper tetrahydrofuran-compounds with substituent group；Currently, only disclosing
Following 3 kinds of methods.
(1), one of the preparation method as 3- amino methyl tetrahydrofurans, it is known to which in ammonia spirit, hydrogen exists
Under, using tetrahydrofuran -3- formaldehyde as the method for raw material progress reductive amination.But in this method, it is used as raw material in order to obtain
Tetrahydrofuran -3- formaldehyde, it has to use very expensive raw material, so not being advantageous method industrially.
(2), as another preparation method, using 3- hydroxymethyls tetrahydrofuran as raw material, 3- (tetrahydrofurans are derived as
Base) halide or 3- (tetrahydrofuran base) methylmesylate, so that it is reacted with potassium phthalimide, is hydrolyzed or hydrazine
Solution.But in this method, the by-product for largely coming from phthalimide is generated, or using dangerous high hydrazine etc., be not
Industrial advantageous approach.
(3), a kind of preparation method prepares 2- hydroxyls-Isosorbide-5-Nitrae-fourth by high-pressure hydrogenation using malic acid as raw material
Glycol, and be cyclized and obtain 3- hydroxyl tetrahydrofurans, further it is derived as 3- (tetrahydrofuran base) alkyl halides or 3- (tetrahydrofurans
Base) methylmesylate, 3- cyano tetrahydrofurans are prepared by being reacted with Cymag, and be reduced to 3- amino methyl tetrahydrochysenes
Furans.But this method step is longer, and using expensive ruthenium catalyst, is unfavorable for industrial production.
Invention content
Goal of the invention：Present invention aims in view of the deficiencies of the prior art, providing, a kind of raw material is cheap, production process peace
Entirely, the preparation method of efficient 3- amino methyls tetrahydrofuran.
Technical solution：The preparation method of a kind of formula (I) compound of the present invention, with gamma-butyrolacton and halogen simple substance X2
Formula (II) compound 3-X- gamma-butyrolactons are prepared for raw material, formula is then obtained using reducing agent reduction formula (II) compound
(III) then compound 2-X-1,4- butanediol formula (III) compound dehydration condensation are obtained by the reaction under the action of dehydrating agent
Formula (IV) compound 3-X tetrahydrofurans, and formula (IV) compound cyaniding is obtained into formula (V) chemical combination under the action of cyaniding catalyst
Object 3- cyano tetrahydrofurans finally restore formula (V) compound under the action of hydrogenation catalyst to obtain formula (I) compound 3- ammonia
Ylmethyl tetrahydrofuran；Specific equation is as follows：
As the preferred embodiment of the present invention, the gamma-butyrolacton and halogen simple substance X2Molar ratio be 1:1~2, wherein described
Halogen simple substance X2For Cl2。
As the preferred embodiment of the present invention, the reducing agent is sodium borohydride or Lithium Aluminium Hydride.
As the more preferably scheme of the present invention, the reducing agent is sodium borohydride, in reduction reaction, 3-X- γ-Ding Nei
The molar ratio of ester and sodium borohydride is 1:0.5~1,3-X- gamma-butyrolactons are dissolved in methanol in reaction process and form 3-X- γ-
Then the methanol solution of butyrolactone is added sodium borohydride, and is stirred to react 3~6h at 20~30 DEG C, obtain formula (III) chemical combination
Object.
As the more preferably scheme of the present invention, the reducing agent is Lithium Aluminium Hydride, in reduction reaction, 3-X- γ-Ding Nei
The molar ratio of ester and Lithium Aluminium Hydride is 1:0.5~1,3-X- gamma-butyrolactons are dissolved in tetrahydrofuran in reaction process and form 3-
Then the tetrahydrofuran solution of X- gamma-butyrolactons is added Lithium Aluminium Hydride, and is stirred to react 3~6h at 20~30 DEG C, obtain formula
(III) compound.
As the preferred embodiment of the present invention, the dehydrating agent is butyl tin trichloride or the concentrated sulfuric acid.
As the present invention more preferably scheme, the dehydrating agent be butyl tin trichloride, wherein 2-X-1,4- butanediols and
The molar ratio of butyl tin trichloride is 1:0.05~0.1, to 2-X-1 in reaction, butyl tin trichloride is added in 4- butanediols, so
After be warming up to 130~160 DEG C reaction 6~10h after rectification under vacuum, obtain formula (IV) compound 3-X tetrahydrofurans.
As the more preferably scheme of the present invention, the dehydrating agent is the concentrated sulfuric acid, wherein 2-X-1,4- butanediols and the concentrated sulfuric acid
Molar ratio be 1:0.05~0.1, to 2-X-1 in reaction, in 4- butanediols, the concentrated sulfuric acid is added, then heats to 130~160
DEG C reaction 6~10h after rectification under vacuum, obtain formula (IV) compound 3-X tetrahydrofurans.
As the more preferably scheme of the present invention, the cyaniding catalyst is Cymag, wherein 3-X tetrahydrofurans and Cymag
Molar ratio be 1:1~2, in reaction into the DMSO solution of 3- chlorine tetrahydrofurans, Cymag is added, then heat to 130~
Rectification under vacuum after 160 DEG C of 6~10h of reaction, obtains formula (V) chemical compound 3-cyano tetrahydrofuran.
As the more preferably scheme of the present invention, the hydrogenation catalyst is Raney's nickel, wherein 3- cyano tetrahydrofuran and thunder
The molar ratio of Buddhist nun's nickel is 1:0.05~0.1, in reaction into the mixture of 3- cyano tetrahydrofuran and ammonium hydroxide, Raney's nickel is added,
It then passes to high-purity hydrogen and reacts 3~6h, rear rectification under vacuum obtains formula (I) compound 3- amino methyl tetrahydrofurans.
Advantageous effect：(1) the present invention provides the method for a newer synthesis 3- amino methyl tetrahydrofuran, this method
It is had the following advantages that relative to existing synthesis technology：(1) raw material is easy to get, and experimental implementation is simple；(2) reaction condition is mild, former
Expect that utilization rate is high, products collection efficiency and purity are higher, and environmental pollution is small；(3) production cost is relatively low, and industrialization is suitble to expand life
Production.
Description of the drawings
Fig. 1 is the gas-chromatography spectrogram of 3- amino methyl tetrahydrofurans in the embodiment of the present invention 1；
Fig. 2 is 3- amino methyl tetrahydrofuran reference substance gas-chromatography spectrograms.
Specific implementation mode
Technical solution of the present invention is described in detail below by specific embodiment, but protection scope of the present invention is not
It is confined to the embodiment.
Embodiment 1：(1) halogenation
500g (5.8mol) gamma-butyrolactons are weighed in 1000ml four-hole bottles, equipment condensation and device for absorbing tail gas, stirring
And 120 DEG C are heated to, start to be passed through chlorine, temperature gradually rises up to 140 DEG C, maintains temperature at 140~160 DEG C, is continually fed into
Chlorine 494g (6.96mol), used time 12h recycle unreacted gamma-butyrolacton, then then by the direct rectification under vacuum of reaction solution
Stablize and collect the chloro- gamma-butyrolactons of 3-, is colorless oil, the chloro- gamma-butyrolactons of as 3-；Purity 95%, yield 70%.
(2) reduction reaction
It weighs the chloro- gamma-butyrolactons of 120g (1.0mol) 3- to be placed in 1000ml four-hole bottles, it is molten that 500ml absolute methanols is added
Solution, is added portionwise sodium borohydride 22.68g (0.6mol), and 4~6h is stirred to react at 25 DEG C, vapor detection is extremely at 25 DEG C
The reaction was complete, removes methanol under reduced pressure, 200ml ethyl acetate is added into residue, and under stiring, be slowly added to 200ml water,
It is used in combination concentrated hydrochloric acid to adjust PH=2~3；Continuation stirs 1h at 25 DEG C；Organic phase, water phase is gone to continue to use ethyl acetate after liquid separation
100ml is extracted 2 times, merges organic phase.
Ethyl acetate is removed under reduced pressure to organic phase, obtains faint yellow to yellow oil, the chloro- 1,4-butanediol of as 2-,
Purity 95%, yield 90%.Without being further purified, it is directly used in and reacts in next step.
(3) dehydration
It weighs the chloro- 1,4-butanediol of 124g (1.0mol) 2- to be placed in 500ml four-hole bottles, concentrated sulfuric acid 5g is added at 25 DEG C
(0.05mol), and 150 DEG C are warming up to, react 8h；It then begins to be evaporated under reduced pressure, the azeotropic mixture of 3- chlorine tetrahydrofuran and water is same
When steam, obtain colourless muddy grease, after product of distillation is further removed water, obtain clear colorless oil, as 3- chlorine
Tetrahydrofuran, purity 99%, yield 85%.
(4) cyanogenation
It weighs 106g (1.0mol) 3- chlorine tetrahydrofurans to be placed in 1000ml four-hole bottles, dimethyl sulfoxide (DMSO) is added at 25 DEG C
250ml dissolves, and under stiring, Cymag 73.5g (1.5mol) is added, and be warming up to 150 DEG C, reacts 8h.
25 DEG C are then cooled to, 250ml water and the extraction of 250ml toluene is added, toluene mutually uses 50ml water washings 2 times, collects
Toluene phase simultaneously carries out rectification under vacuum, obtains clear colorless oil, as 3- cyano tetrahydrofuran, purity 99%, yield 70%.
(5) hydrogenation reaction
It weighs 97g (1.0mol) 3- cyano tetrahydrofurans to be placed in 1000ml autoclave pressures, the dense ammonia of 200ml is added at 25 DEG C
It is water-dispersed, and under stiring, 5g Raney's nickels are added, confining pressure kettle is passed through hydrogen to 1MPa and is warming up to 100 DEG C, reaction 4h；
It is cooled to 25 DEG C after reaction, reaction solution is subjected to rectification under vacuum after exhaust, obtains clear colorless oil, as 3- amino
Methyltetrahydrofuran, purity 99%, yield 85%.
It is the chromatography of gases spectrogram of the 3- amino methyl tetrahydrofurans obtained in the present embodiment, shown in Fig. 2 if Fig. 1 shows
3- amino methyl tetrahydrofuran reference substance gas-chromatography spectrogram comparative analyses known to retention time it is completely the same, thus prove this
What is obtained in embodiment is 3- amino methyl tetrahydrofurans.
Embodiment 2：
(1) halogenation
500g (5.8mol) gamma-butyrolactons are weighed in 1000ml four-hole bottles, equipment condensation and device for absorbing tail gas, stirring
And 120 DEG C are heated to, start to be passed through chlorine, temperature gradually rises up to 140 DEG C, maintains temperature at 140~160 DEG C, is continually fed into
Chlorine 494g (6.96mol), used time 12h recycle unreacted gamma-butyrolacton, then then by the direct rectification under vacuum of reaction solution
Stablize and collect the chloro- gamma-butyrolactons of 3-, is colorless oil, the chloro- gamma-butyrolactons of as 3-；Purity 95%, yield 70%.
(2) reduction reaction
It weighs the chloro- gamma-butyrolactons of 120g (1.0mol) 3- to be placed in 1000ml four-hole bottles, the anhydrous tetrahydrochysene furans of 500ml is added
It mutters dissolving, Lithium Aluminium Hydride 37.95g (1.0mol) is added portionwise at 20 DEG C, and be stirred to react 3h at 20 DEG C, vapor detection is extremely
The reaction was complete, is cooled to 0 DEG C, and under stiring, is slowly added to 200ml water, and concentrated hydrochloric acid is used in combination to adjust PH=2~3；It removes under reduced pressure
Tetrahydrofuran, 200ml ethyl acetate is added into residue, and continuation stirs 1h at 25 DEG C；Go organic phase after liquid separation, water phase after
It is continuous to be extracted 2 times with ethyl acetate 100ml, merge organic phase.
Ethyl acetate is removed under reduced pressure to organic phase, obtains faint yellow to yellow oil, the chloro- 1,4-butanediol of as 2-,
Purity 96%, yield 87%.Without being further purified, it is directly used in and reacts in next step.
(3) dehydration
It weighs the chloro- 1,4-butanediol of 124g (1.0mol) 2- to be placed in 500ml four-hole bottles, concentrated sulfuric acid 5g is added at 25 DEG C
(0.05mol), and 130 DEG C are warming up to, react 10h；It then begins to be evaporated under reduced pressure, the azeotropic mixture of 3- chlorine tetrahydrofuran and water is same
When steam, obtain colourless muddy grease, after product of distillation is further removed water, obtain clear colorless oil, as 3- chlorine
Tetrahydrofuran, purity 99%, yield 85%.
(4) cyanogenation
It weighs 106g (1.0mol) 3- chlorine tetrahydrofurans to be placed in 1000ml four-hole bottles, dimethyl sulfoxide (DMSO) is added at 25 DEG C
250ml dissolves, and under stiring, Cymag 73.5g (1.5mol) is added, and be warming up to 130 DEG C, reacts 10h.
25 DEG C are then cooled to, 250ml water and the extraction of 250ml toluene is added, toluene mutually uses 50ml water washings 2 times, collects
Toluene phase simultaneously carries out rectification under vacuum, obtains clear colorless oil, as 3- cyano tetrahydrofuran, purity 99%, yield 70%.
(5) hydrogenation reaction
It weighs 97g (1.0mol) 3- cyano tetrahydrofurans to be placed in 1000ml autoclave pressures, the dense ammonia of 200ml is added at 25 DEG C
It is water-dispersed, and under stiring, 5g Raney's nickels are added, confining pressure kettle is passed through hydrogen to 1MPa and is warming up to 100 DEG C, reaction 4h；
It is cooled to 25 DEG C after reaction, reaction solution is subjected to rectification under vacuum after exhaust, obtains clear colorless oil, as 3- amino
Methyltetrahydrofuran, purity 99%, yield 85%.
Embodiment 3：
(1) halogenation
500g (5.8mol) gamma-butyrolactons are weighed in 1000ml four-hole bottles, equipment condensation and device for absorbing tail gas, stirring
And 120 DEG C are heated to, start to be passed through chlorine, temperature gradually rises up to 140 DEG C, maintains temperature at 140~160 DEG C, is continually fed into
Chlorine 494g (6.96mol), used time 12h recycle unreacted gamma-butyrolacton, then then by the direct rectification under vacuum of reaction solution
Stablize and collect the chloro- gamma-butyrolactons of 3-, is colorless oil, the chloro- gamma-butyrolactons of as 3-；Purity 95%, yield 70%.
(2) reduction reaction
It weighs the chloro- gamma-butyrolactons of 120g (1.0mol) 3- to be placed in 1000ml four-hole bottles, it is molten that 500ml absolute methanols is added
Solution, is added portionwise sodium borohydride 22.68g (0.6mol), and 6h is stirred to react at 25 DEG C at 25 DEG C, vapor detection to reaction
Completely, it removes methanol under reduced pressure, 200ml ethyl acetate is added into residue, and under stiring, be slowly added to 200ml water, be used in combination
Concentrated hydrochloric acid adjusts PH=2~3；Continuation stirs 1h at 25 DEG C；Organic phase, water phase is gone to continue to use ethyl acetate 100ml after liquid separation
Extraction 2 times merges organic phase.
Ethyl acetate is removed under reduced pressure to organic phase, obtains faint yellow to yellow oil, the chloro- 1,4-butanediol of as 2-,
Purity 95%, yield 90%.Without being further purified, it is directly used in and reacts in next step.
(3) dehydration
It weighs the chloro- 1,4-butanediol of 124g (1.0mol) 2- to be placed in 500ml four-hole bottles, butyl trichlorine is added at 25 DEG C
Change tin 14.1g (0.05mol), and be warming up to 160 DEG C, reacts 6h；It then begins to be evaporated under reduced pressure, by 3- chlorine tetrahydrofuran and water
Azeotropic mixture steams simultaneously, obtains colourless muddy grease and obtains clear colorless oil after further removing water product of distillation,
As 3- chlorine tetrahydrofuran, purity 99%, yield 88%.
(4) cyanogenation
It weighs 106g (1.0mol) 3- chlorine tetrahydrofurans to be placed in 1000ml four-hole bottles, dimethyl sulfoxide (DMSO) is added at 25 DEG C
250ml dissolves, and under stiring, Cymag 73.5g (1.5mol) is added, and be warming up to 160 DEG C, reacts 6h.
25 DEG C are then cooled to, 250ml water and the extraction of 250ml toluene is added, toluene mutually uses 50ml water washings 2 times, collects
Toluene phase simultaneously carries out rectification under vacuum, obtains clear colorless oil, as 3- cyano tetrahydrofuran, purity 99%, yield 70%.
(5) hydrogenation reaction
It weighs 97g (1.0mol) 3- cyano tetrahydrofurans to be placed in 1000ml autoclave pressures, the dense ammonia of 200ml is added at 25 DEG C
It is water-dispersed, and under stiring, 5g Raney's nickels are added, confining pressure kettle is passed through hydrogen to 1MPa and is warming up to 100 DEG C, reaction 4h；
It is cooled to 25 DEG C after reaction, reaction solution is subjected to rectification under vacuum after exhaust, obtains clear colorless oil, as 3- amino
Methyltetrahydrofuran, purity 99%, yield 85%.
As described above, although the present invention has been indicated and described with reference to specific preferred embodiment, must not explain
For the limitation to invention itself.It without prejudice to the spirit and scope of the invention as defined in the appended claims, can be right
Various changes can be made in the form and details for it.
Claims (8)
1. a kind of preparation method of formula (I) compound, it is characterised in that：With gamma-butyrolacton and halogen simple substance X2It is prepared for raw material
Formula (II) compound 3-X- gamma-butyrolactons then obtain formula (III) compound 2-X- using reducing agent reduction formula (II) compound
Then under the action of dehydrating agent formula (IV) compound 3-X is obtained by the reaction in formula (III) compound dehydration condensation by 1,4-butanediol
Tetrahydrofuran, and formula (IV) compound cyaniding is obtained into formula (V) chemical compound 3-cyano tetrahydrochysene furan under the action of cyaniding catalyst
It mutters, finally restores formula (V) compound under the action of hydrogenation catalyst to obtain formula (I) compound 3- amino methyl tetrahydrochysene furans
It mutters；Specific equation is as follows：
The reducing agent is sodium borohydride or Lithium Aluminium Hydride；The dehydrating agent is butyl tin trichloride or the concentrated sulfuric acid；The cyaniding
Catalyst is Cymag.
2. the preparation method of formula (I) compound according to claim 1, it is characterised in that：The gamma-butyrolacton and halogen list
Matter X2Molar ratio be 1:1~2, wherein the halogen simple substance X2For Cl2。
3. the preparation method of formula (I) compound according to claim 1, it is characterised in that：The reducing agent is boron hydrogen
Change sodium, in reduction reaction, the molar ratio of 3-X- gamma-butyrolactons and sodium borohydride is 1:0.5~1, by 3-X- γ-in reaction process
Butyrolactone is dissolved in the methanol solution that 3-X- gamma-butyrolactons are formed in methanol, sodium borohydride is then added, and stirred at 20~30 DEG C
3~6h of reaction is mixed, formula (III) compound is obtained.
4. the preparation method of formula (I) compound according to claim 1, it is characterised in that：The reducing agent is tetrahydrochysene
Aluminium lithium, in reduction reaction, the molar ratio of 3-X- gamma-butyrolactons and Lithium Aluminium Hydride is 1:0.5~1, by 3-X- γ-in reaction process
Butyrolactone is dissolved in the tetrahydrofuran solution that 3-X- gamma-butyrolactons are formed in tetrahydrofuran, is then added Lithium Aluminium Hydride, and 20~
It is stirred to react 3~6h at 30 DEG C, obtains formula (III) compound.
5. the preparation method of formula (I) compound according to claim 1, it is characterised in that：The dehydrating agent is butyl three
The molar ratio of stannic chloride, wherein 2-X-1,4- butanediols and butyl tin trichloride is 1:0.05~0.1, to 2-X-1,4- in reaction
Butyl tin trichloride is added in butanediol, then heats to rectification under vacuum after 130~160 DEG C of 6~10h of reaction, obtains formula (IV)
Compound 3-X tetrahydrofurans.
6. the preparation method of formula (I) compound according to claim 1, it is characterised in that：The dehydrating agent is the concentrated sulfuric acid,
Wherein the molar ratio of 2-X-1,4- butanediols and the concentrated sulfuric acid is 1:0.05~0.1, to 2-X-1 in reaction, in 4- butanediols, it is added
The concentrated sulfuric acid then heats to rectification under vacuum after 130~160 DEG C of 6~10h of reaction, obtains formula (IV) compound 3-X tetrahydrofurans.
7. the preparation method of formula (I) compound according to claim 1, it is characterised in that：Wherein 3-X tetrahydrofurans and cyanogen
The molar ratio for changing sodium is 1:1~2, in reaction into the DMSO solution of 3- chlorine tetrahydrofurans, Cymag is added, then heats to
Rectification under vacuum after 130~160 DEG C of 6~10h of reaction, obtains formula (V) chemical compound 3-cyano tetrahydrofuran.
8. the preparation method of formula (I) compound according to claim 1, it is characterised in that：The hydrogenation catalyst is thunder
Buddhist nun's nickel, the wherein molar ratio of 3- cyano tetrahydrofuran and Raney's nickel are 1:0.05~0.1, in reaction to 3- cyano tetrahydrofuran and
In the mixture of ammonium hydroxide, Raney's nickel is added, then passes to high-purity hydrogen and reacts 3~6h, rear rectification under vacuum obtains formula (I) compound
3- amino methyl tetrahydrofurans.
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| EP1486479A1 (en) * | 2003-06-12 | 2004-12-15 | Mitsui Chemicals, Inc. | Method for producing organic compounds by substituting halogen atoms |
| CN1968941A (en) * | 2004-06-14 | 2007-05-23 | 三井化学株式会社 | Method for producing 3-aminomethyltetrahydrofuran derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1486479A1 (en) * | 2003-06-12 | 2004-12-15 | Mitsui Chemicals, Inc. | Method for producing organic compounds by substituting halogen atoms |
| CN1968941A (en) * | 2004-06-14 | 2007-05-23 | 三井化学株式会社 | Method for producing 3-aminomethyltetrahydrofuran derivative |
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| Synthesis and catalytic performance of ruthenium complexes ligated with rigid o-(diphenylphosphino)aniline for chemoselective hydrogenation of dimethyl oxalate;Xiaolong Fang 等;《RSC Advances》;20160504;第6卷;45512-45518 * |
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