CN103450229A - Application of chiral copper complex - Google Patents
Application of chiral copper complex Download PDFInfo
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- CN103450229A CN103450229A CN2013103225271A CN201310322527A CN103450229A CN 103450229 A CN103450229 A CN 103450229A CN 2013103225271 A CN2013103225271 A CN 2013103225271A CN 201310322527 A CN201310322527 A CN 201310322527A CN 103450229 A CN103450229 A CN 103450229A
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- nitroethylene base
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- 150000004699 copper complex Chemical class 0.000 title claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims abstract description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 abstract description 8
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract description 5
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract description 3
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 abstract description 2
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 abstract description 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003935 benzaldehydes Chemical class 0.000 abstract description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 abstract 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 abstract 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 abstract 2
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 abstract 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- -1 nitro ketenes Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000006842 Henry reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- YMNZDCGZFNOZDK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-nitroethanol Chemical compound [O-][N+](=O)CC(O)C1=CC=C(Br)C=C1 YMNZDCGZFNOZDK-UHFFFAOYSA-N 0.000 description 1
- VHQOMTRRZXGIFH-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-nitroethanol Chemical compound [O-][N+](=O)CC(O)C1=CC=C(F)C=C1 VHQOMTRRZXGIFH-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- IBGLUMJSLYZZRX-UHFFFAOYSA-N 2-nitro-1-(4-nitrophenyl)ethanol Chemical compound [O-][N+](=O)CC(O)C1=CC=C([N+]([O-])=O)C=C1 IBGLUMJSLYZZRX-UHFFFAOYSA-N 0.000 description 1
- 241000209121 Cenchrus setiger Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 238000006987 Nef reaction Methods 0.000 description 1
- SBPLLYNEUACCFM-FVGYRXGTSA-N [Cu].N[C@@H](CC1=CC=CC=C1)CO Chemical compound [Cu].N[C@@H](CC1=CC=CC=C1)CO SBPLLYNEUACCFM-FVGYRXGTSA-N 0.000 description 1
- ZFSMTXZEQODWPW-UHFFFAOYSA-N [N+](=O)([O-])CC(O)C1=C(C=CC=C1)CN Chemical compound [N+](=O)([O-])CC(O)C1=C(C=CC=C1)CN ZFSMTXZEQODWPW-UHFFFAOYSA-N 0.000 description 1
- YJKNJLRYEDVRFD-UHFFFAOYSA-N [N+](=O)([O-])CC(O)C1=CC=C(C=C1)CN Chemical compound [N+](=O)([O-])CC(O)C1=CC=C(C=C1)CN YJKNJLRYEDVRFD-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- NQFNBCXYXGZSPI-UHFFFAOYSA-L copper;diacetate;dihydrate Chemical compound O.O.[Cu+2].CC([O-])=O.CC([O-])=O NQFNBCXYXGZSPI-UHFFFAOYSA-L 0.000 description 1
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical compound [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000005648 named reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses an application of a chiral tri[(S)-phenylalaninol] copper chloride complex. The complex is used as a catalyst when a target product is prepared from aromatic aldehyde and nitromethane, wherein the aromatic aldehyde comprises benzaldehyde or substituted benzaldehyde, such as 4-methylbenzaldehyde, 4-methoxybenzaldehyde, 4-fluorobenzaldehyde, 4-bromobenzaldehyde, 4-nitrobenzaldehyde, 2-methoxybenzaldehyde, 2-bromobenzaldehyde, 2-methylbenzaldehyde and 2-fluorobenzaldehyde.
Description
One, technical field
The present invention relates to the purposes of a kind of organometallic complex (title complex), particularly the purposes of nitrogenous a metal-organic complex, be exactly the purposes of a kind of three [(S)-phenylalaninol] cupric chloride title complex.
Two, background technology
Chirality nitrogen a metal-organic complex has some good catalytic performances, closely related with subjects such as Materials science, organic synthesis, life sciences, significant at polymer and organic synthesis asymmetric catalysis field containing the chiral amino alcohol a metal-organic complex of Cu-N key.Become one of focus of domestic and international research, a large amount of bibliographical informations has been arranged.（1-2）
1.Heterogeneous?Chiral?Copper?Complexes?of?Amino?Alcohol?for?Asymmetric?Nitroaldol?Reaction，Mayani,Vishal?J.;Abdi,Sayed?H.R.;Kureshy,Rukhsana?I.;Khan,Noor-ul?H.;Das,Anjan;Bajaj,Hari?C.Journal?of?Organic?Chemistry(2010),75(18),6191-6195.
2.Chiral?binuclear?copper(II)catalyzed?nitroaldol?reaction:scope?and?mechanism，Jammi,Suribabu;Saha,Prasenjit;Sanyashi,Sridhar;Sakthivel,Sekarpandi;Punniyamurthy,Tharmalingam，Tetrahedron(2008),64(51),11724-11731.
Three, summary of the invention
The present invention is intended to prepare target product for the addition reaction of aromatic aldehyde and Nitromethane 99Min., and technical problem to be solved is to provide effective catalyst.
The alleged chirality copper complex of the present invention be by copper acetate dihydrate and L-phenylalaninol, prepared by the compound shown in following chemical formula:
（I）。
Chemical name: four [(S)-phenylalaninol] cupric chloride title complex, be called for short title complex (I).
Described synthetic (S)-phenylalaninol is reacted with the ratio of mol ratio 3:1 with Copper dichloride dihydrate, take (S)-phenylalaninol 2.265g (0.015mol) and Copper dichloride dihydrate 0.8524g (0.005mol) with electronic balance, join in the round-bottomed flask of 100ml, then the dehydrated alcohol that adds about 35ml is made solvent, heating, stirring and refluxing 48h, filtered while hot, be spin-dried for ， Change solvent by filtrate and be made into saturated solution, standing, volatilization voluntarily, the same processing of filter residue.After for some time, separate out the light blue crystal that is suitable for the test of X-single crystal diffraction.
With sherwood oil, fully rinse 3-4 time, vacuum-drying 30min, obtain purer target product.
Building-up reactions is as follows:
This synthetic method one step obtains target product, and technique is simple, easy to operate.
The Henry reaction is one of classical organic name reaction.This reaction refers to normally aromatic aldehyde and the condensation reaction between the nitro-compound of α-hydrogen is arranged of carbonyl compound, and the result of reaction is that the alpha-carbon atom of nitro adds on carbonyl, forms the compound of the bifunctional with hydroxyl, nitro.The product of Henry reaction can be converted into the compound that important use is arranged of all kinds easily, as beta-alkamine, nitroolefin, nitroketone, nitro ketenes or carry out the Nef reaction.Therefore the Henry reaction is one of very practical reaction in organic synthesis.Expand the range of application of this reaction, synthetic have a more more complicated compound on polyfunctional group, structure, is a significant job.
The present invention has found the Henle reaction dewatered product in experimentation, alleged purposes is to prepare 1-R-2-[(1E in the aromatic series aldehydes Henle reaction replaced at ortho para)-2-nitroethylene base] purposes of benzene, described aromatic aldehyde comprises phenyl aldehyde or substituted benzaldehyde, as 4-tolyl aldehyde, 4-methoxybenzaldehyde, 4-fluorobenzaldehyde, the 4-bromobenzaldehyde, 2-tolyl aldehyde, Benzaldehyde,2-methoxy, 2-bromobenzaldehyde and 1-naphthaldehyde.
Four, accompanying drawing explanation
Fig. 1 is the single crystal diffraction figure of title complex (I).
Five, embodiment
1. the preparation of chirality L-phenylalaninol copper complex:
(S)-phenylalaninol is reacted with the ratio of mol ratio 3:1 with Copper dichloride dihydrate, take (S)-phenylalaninol 2.265g (0.015mol) and Copper dichloride dihydrate 0.8524g (0.005mol) with electronic balance, join in the round-bottomed flask of 100ml, the dehydrated alcohol that adds again about 35ml is made solvent, heating, stirring and refluxing 48h, filtered while hot, filtrate is spin-dried for to Change solvent and is made into saturated solution, standing, volatilization voluntarily, the same processing of filter residue.After for some time, separate out the light blue crystal that is suitable for the test of X-single crystal diffraction; With sherwood oil, fully rinse 3-4 time, vacuum-drying 30min, obtain purer target product, and fusing point is 132-134 ℃.α=-110.76 ° (c0.0632, CH
3oH), ultimate analysis (C
36h
50cl
2cu
2n
4o
4) theoretical value: C:53.994%; N:6.996%; H:6.293%; Measured value: C:53.83%; N:7.04%; H:6.37%; IR (cm-1), 3340,3123,2923,1571,1488,1446,1054,745,513.
2. Henle reaction application
(1) 2-nitro-1-phenylethyl alcohol
Catalyst I (0.148mmol), phenyl aldehyde 0.10mL (0.986mmol) and Nitromethane 99Min. (0.50mL, 9.255mmol) at room temperature stir 6h, with nuclear-magnetism monitoring, transformation efficiency: 91%
(2) 2-nitro-1-(2-aminomethyl phenyl) ethanol
Reactions steps same (1), transformation efficiency: 99%
(3) 2-nitro-1-(2-p-methoxy-phenyl) ethanol
Reactions steps same (1), transformation efficiency: 99%
(4) 2-nitro-1-(4-aminomethyl phenyl) ethanol
Reactions steps is with (1), transformation efficiency: 52%
(5) 2-nitro-1-(4-nitrophenyl) ethanol
Reactions steps is with (1), transformation efficiency: 48%
(6) 2-nitro-1-(4-p-methoxy-phenyl) ethanol
Reactions steps is with (1), transformation efficiency: 52%
(7) 2-nitro-1-(4-fluorophenyl) ethanol
Reactions steps is with (1), transformation efficiency: 35%
(8) 2-nitro-1-(4-bromophenyl) ethanol
Reactions steps is with (1), transformation efficiency: 91%
(9) (1E)-2-nitroethylene base benzene
Reactions steps is with (1), transformation efficiency: 91%
(10) 1-methyl-2-[(1E)-2-nitroethylene base] benzene
Reactions steps same (1), transformation efficiency: 99%
(11) 1-methoxyl group-2-[(1E)-2-nitroethylene base] benzene
Reactions steps same (1), transformation efficiency: 99%
(12) the fluoro-2-[(1E of 1-)-2-nitroethylene base] benzene
Reactions steps is with (1), transformation efficiency: 49%
(13) the fluoro-4-[(1E of 1-)-2-nitroethylene base] benzene
Reactions steps is with (1), transformation efficiency: 35%
(14) the bromo-2-[(1E of 1-)-2-nitroethylene base] benzene
Reactions steps is with (1), transformation efficiency: 44%
(15) 1-methoxyl group-4-[(1E)-2-nitroethylene base] benzene
Reactions steps is with (1), transformation efficiency: 52%
(16) the bromo-4-[(1E of 1-)-2-nitroethylene base] benzene
Reactions steps is with (1), transformation efficiency: 52%.
Claims (9)
1. the purposes by the chirality copper complex shown in following chemical formula, is characterized in that preparing target product 1-R-2-[(1E at the Henle reaction of aromatic aldehyde)-2-nitroethylene base] during benzene as catalyzer
Purposes according to claim 1, is characterized in that preparing target product 1-methyl-2-[(1E at the Henle reaction of 2-tolyl aldehyde)-2-nitroethylene base] during benzene as catalyzer.
2. purposes according to claim 1, is characterized in that preparing target product 1-methoxyl group-2-[(1E at the Henle reaction of Benzaldehyde,2-methoxy)-2-nitroethylene base] during benzene as chiral catalyst.
3. purposes according to claim 1, is characterized in that preparing the bromo-2-[(1E of target product 1-at the Henle reaction of 2-bromobenzaldehyde)-2-nitroethylene base] during benzene as chiral catalyst.
4. purposes according to claim 1, is characterized in that preparing the fluoro-2-[(1E of target product 1-at the Henle reaction of 2-fluorobenzaldehyde)-2-nitroethylene base] during benzene as chiral catalyst.
5. purposes according to claim 1, is characterized in that preparing target product 1-nitro-4-[(1E at the Henle reaction of 4-nitrobenzaldehyde)-2-nitroethylene base] during benzene as chiral catalyst.
6. purposes according to claim 1, is characterized in that preparing the fluoro-4-[(1E of target product 1-at the Henle reaction of 4-fluorobenzaldehyde)-2-nitroethylene base] during benzene as chiral catalyst.
7. purposes according to claim 1, is characterized in that preparing target product 1-methyl-4-[(1E at the Henle reaction of 4-tolyl aldehyde)-2-nitroethylene base] during benzene as catalyzer.
8. purposes according to claim 1, is characterized in that preparing target product 1-methoxyl group-4-[(1E at the Henle reaction of 4-methoxybenzaldehyde)-2-nitroethylene base] during benzene as catalyzer.
9. purposes according to claim 1, is characterized in that preparing the bromo-4-[(1E of target product 1-at the Henle reaction of 4-bromobenzaldehyde)-2-nitroethylene base] during benzene as catalyzer.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103819493A (en) * | 2014-03-01 | 2014-05-28 | 合肥工业大学 | A copper nitrogen complex |
| CN104292062A (en) * | 2014-08-25 | 2015-01-21 | 荆楚理工学院 | Method for catalyzing and synthesizing optically pure beta-nitramine derivative |
| CN104592257A (en) * | 2015-03-10 | 2015-05-06 | 合肥工业大学 | Copper-nitrogen complex |
| CN105566357A (en) * | 2016-03-15 | 2016-05-11 | 合肥祥晨化工有限公司 | Preparation and synthesis method of chiral L-valine copper complex |
| CN105817264A (en) * | 2016-04-18 | 2016-08-03 | 合肥祥晨化工有限公司 | Use of copper complex |
| CN106008611A (en) * | 2016-06-03 | 2016-10-12 | 合肥工业大学 | Chiral cobalt complex |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102731539A (en) * | 2012-07-12 | 2012-10-17 | 罗梅 | Preparation and synthesizing method of chiral compound |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102731539A (en) * | 2012-07-12 | 2012-10-17 | 罗梅 | Preparation and synthesizing method of chiral compound |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103819493A (en) * | 2014-03-01 | 2014-05-28 | 合肥工业大学 | A copper nitrogen complex |
| CN103819493B (en) * | 2014-03-01 | 2015-12-09 | 合肥工业大学 | A kind of copper-nitrogen compound |
| CN104292062A (en) * | 2014-08-25 | 2015-01-21 | 荆楚理工学院 | Method for catalyzing and synthesizing optically pure beta-nitramine derivative |
| CN104592257A (en) * | 2015-03-10 | 2015-05-06 | 合肥工业大学 | Copper-nitrogen complex |
| CN104592257B (en) * | 2015-03-10 | 2017-06-27 | 合肥工业大学 | A kind of copper-nitrogen compound |
| CN105566357A (en) * | 2016-03-15 | 2016-05-11 | 合肥祥晨化工有限公司 | Preparation and synthesis method of chiral L-valine copper complex |
| CN105817264A (en) * | 2016-04-18 | 2016-08-03 | 合肥祥晨化工有限公司 | Use of copper complex |
| CN106008611A (en) * | 2016-06-03 | 2016-10-12 | 合肥工业大学 | Chiral cobalt complex |
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