CN106008566A - 5-chlorosalicylaldehyde-alanine Schiff base zinc complex and preparation method thereof - Google Patents
5-chlorosalicylaldehyde-alanine Schiff base zinc complex and preparation method thereof Download PDFInfo
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- CN106008566A CN106008566A CN201610473927.6A CN201610473927A CN106008566A CN 106008566 A CN106008566 A CN 106008566A CN 201610473927 A CN201610473927 A CN 201610473927A CN 106008566 A CN106008566 A CN 106008566A
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- 239000011701 zinc Substances 0.000 title claims abstract description 31
- 239000002262 Schiff base Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 14
- 150000004753 Schiff bases Chemical class 0.000 title claims abstract description 11
- ZSSQOLNIAJAJSK-WNQIDUERSA-N N[C@@H](C)C(=O)O.ClC1=CC=C(C(C=O)=C1)O Chemical compound N[C@@H](C)C(=O)O.ClC1=CC=C(C(C=O)=C1)O ZSSQOLNIAJAJSK-WNQIDUERSA-N 0.000 title 1
- 238000010668 complexation reaction Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 41
- -1 deprotonated 5-chlorosalicylaldehyde-alanine Schiff base anion Chemical class 0.000 claims abstract description 18
- 239000003446 ligand Substances 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229960003767 alanine Drugs 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- ZSSQOLNIAJAJSK-UHFFFAOYSA-N NC(C)C(=O)O.ClC1=CC=C(C(C=O)=C1)O Chemical compound NC(C)C(=O)O.ClC1=CC=C(C(C=O)=C1)O ZSSQOLNIAJAJSK-UHFFFAOYSA-N 0.000 abstract 2
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- 235000001014 amino acid Nutrition 0.000 description 11
- 239000013078 crystal Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910000474 mercury oxide Inorganic materials 0.000 description 3
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention provides a 5-chlorosalicylaldehyde-D,L-alanine Schiff base zinc complex and a preparation method thereof. The chemical formula of the zinc complex is [ZnL(H2O)2], and L is deprotonated 5-chlorosalicylaldehyde-alanine Schiff base anion. The complex is of a one-dimensional chain structure. The preparation method comprises the steps that firstly, D,L-alanine, KOH and 5-chlorosalicylaldehyde are dissolved in small amount of methanol solution, and 5-chlorosalicylaldehyde-D,L-alanine Schiff base ligand is synthesized under the ultrasonic wave effect. The ligand and equal mass of Zn(NO3)2.6H2O are in reaction in a methanol or ethanol solution, and then the solution is filtered, stood at the normal temperature and volatilized to obtain the target complex. According to the 5-chlorosalicylaldehyde-D,L-alanine Schiff base zinc complex and the preparation method thereof, amino acid Schiff base ligand is synthesized with an ultrasonic method, not only is the reaction time shortened greatly, but also the product purity and the yield are high.
Description
Technical field
The present invention relates to transient metal complex Material Field, be specifically related to a kind of containing 5-chloro-salicyloyl al- D ,L-the third
Propylhomoserin Schiff base zinc coordination compound and preparation method thereof.
Background technology
Amino-acid schiff base is by aminoacid and the organic compound of aldehyde radical (ketone group) compound condensation.This quasi-molecule
Inside usually contain O atom and the atom N of multiple strong electronegativity, therefore there is stronger coordination ability and various coordination mode, can
Stable metal complex is formed with transition metal.Both at home and abroad Vittal, Nakahara, Casella, Hodnett, Su Lingling and
Wang Zhong et al. has successively synthesized many amino-acid schiff base parts and coordination compound, finds that these compounds great majority have good
Optical, electrical, magnetic material property and significantly biological activity, so that the research in this field causes the extensive concern of people.
It is known that zinc is important life metallic element, the coordination compound of zinc has less toxic and side effects, by zinc from
Son is combined with the amino-acid schiff base part with good biological activity, and design synthesizes the amino-acid schiff base zinc of novel structure
Coordination compound, antitumor drug antibacterial for R and D has important scientific meaning and using value.The present invention uses
" ultrasonic irradiation " successfully synthesizes 5-chloro-salicyloyl al alanine schiff base ligand, and is combined with zinc ion further and obtains
Corresponding amino-acid schiff base Zn complex, at home and abroad there is not been reported for the structure of this coordination compound.
Summary of the invention
It is an object of the invention to provide a kind of 5-chloro-salicyloyl al- D ,L-alanine Schiff base zinc coordination compound and system thereof
Preparation Method.
The chemical formula of the Zn complex that the present invention provides is [ZnL (H2O)2], wherein L is the 5-chloro-salicylic aldehyde of deprotonation
Contracting- D ,L-alanine schiff base ligand, structural formula is as follows:
。
A kind of 5-chloro-salicyloyl al that the present invention provides- D ,LThe preparation method of-alanine Schiff base zinc coordination compound, main
Following two to be related to is reacted.
(1) 5-chloro-salicyloyl al- D,LThe preparation method of-alanine schiff base ligand: add solid in methanol solution
BodyD,L-alanine and KOH, after mix homogeneously, be placed in ultrasonic about 20min in ultrasonic cleaner, after solid is completely dissolved,
In mixed solution, add the methanol solution of 5-chloro-salicylic aldehyde, then reaction vessel is placed in ultrasonic cleaner, be then warming up to
40 DEG C, after Ultrasonic Radiation 30-45min, generate a large amount of yellow mercury oxide, wash through filtration, absolute ether and be dried to obtain 5-chlorine
Salicylidene- D ,L-alanine schiff base ligand yellow powder.Its synthetic route such as following formula:
。
(2) preparation method of amino-acid schiff base Zn complex: in the methanol solution dissolved with amino-acid schiff base part,
Zn (the NO of the amount of the materials such as dropping3)2Methanol solution, stir under room temperature after 30-40 min and filter, filtrate is the slowest
Volatilization, separating out yellow bulk crystals after 5-7 days is [ZnL (H2O)2]。
Reactant in described reaction (1)D ,L -Alanine, the ratio of amount of KOH and 5-chloro-salicylic aldehyde's material are 1:1:1；
Methanol solution described in reaction (1) and reaction (2) can substitute with dehydrated alcohol.
The amino-acid schiff base part synthetic method that the present invention provides is simple, and the response time is short, and productivity is high.
The Zn complex preparation method of the present invention is simple, and repeatability is strong, and crystal is easy to get.
Accompanying drawing explanation
Fig. 1 coordination compound [ZnL (H2O)2] crystal structure figure.
The one-dimensional catenary structure figure of Fig. 2 coordination compound.
Detailed description of the invention
In order to be better understood from the present invention, illustrate technical scheme below by specific embodiment.
Embodiment 1:5-chloro-salicyloyl al-D ,LThe preparation of-alanine schiff base ligand.
Solid is added in 20 mL methanol solutionsD,L-alanine (10mmol, 0.891g) and KOH (10mmol,
0.561g), after mix homogeneously, it is placed in ultrasonic about 20 min in ultrasonic cleaner, after solid is completely dissolved, to mixed solution
The methanol solution of middle addition 20 mL 5-chloro-salicylic aldehyde (10mmol, 1.566g), then reaction vessel is placed in ultrasonic cleaner
In, then it is warming up to 40 DEG C, after Ultrasonic Radiation 30 min, generates a large amount of yellow mercury oxide, wash and dry through filtration, absolute ether
Dry obtain 5-chloro-salicyloyl al-D ,L-alanine schiff base ligand yellow powder (productivity 90%).
Embodiment 2:5-chloro-salicyloyl al-D,LThe preparation of-alanine schiff base ligand.
Solid is added in 20 mL ethanol solutionsD,L-alanine (10mmol, 0.891g) and KOH
(10mmol, 0.561g), after mix homogeneously, is placed in ultrasonic 20-30 about min in ultrasonic cleaner, treats that solid is completely dissolved
After, in mixed solution, add the ethanol solution of 20 mL 5-chloro-salicylic aldehyde (10mmol, 1.566g), then reaction vessel is put
In ultrasonic cleaner, then it is warming up to 50 DEG C, after Ultrasonic Radiation 30-45 min, produces a large amount of yellow mercury oxide, through filtering,
Absolute ether washing and be dried to obtain 5-chloro-salicyloyl al-D ,L-alanine schiff base ligand yellow powder (productivity 84%).
Embodiment 3: the preparation of Zn complex.
Weigh prepared amino-acid schiff base part (0.2mmol, 0.053g) to be dissolved in 15 mL methanol solutions, dropwise add
Enter 10 mL Zn (NO3)2·6H2The methanol solution of O (0.2mmol, 0.059g), filters after stirring 30-40 min under room temperature,
Filtrate is the most slowly volatilized, and separates out yellow bulk crystals (productivity 75%) after 5-7 days.C10H12ClNO5Zn elementary analysis (%)
Theoretical value: C 36.72, H 3.70, N4.28；Actual value: C 36.60, H 3.79, N 4.17. IR(KBr, cm-1)
3448(ms), 3380(s), 3036(s), 2970(m), 1789(m), 1650(vs), 1556(s), 1510(m),
1436(s), 1397(s), 1251(m), 1006(m), 850(m), 683(m)。
Embodiment 4: the preparation of Zn complex.
Weigh prepared amino-acid schiff base part (0.1mmol, 0.027g) to be dissolved in 10 mL ethanol solution, dropwise add
Enter 10 mL Zn (NO3)2·6H2The ethanol solution of O (0.1mmol, 0.030g), filters after stirring 30-40 min under room temperature,
Filtrate is the most slowly volatilized, and separates out yellow bulk crystals (productivity 68%) after 7-9 days.C10H12ClNO5Zn elementary analysis (%)
Theoretical value: C 36.72, H 3.70, N4.28；Actual value: C 36.60, H 3.79, N 4.17.IR(KBr, cm-1)
3448(ms), 3380(s), 3036(s), 2970(m), 1789(m), 1650(vs), 1556(s), 1510(m),
1436(s), 1397(s), 1251(m), 1006(m), 850(m), 683(m)。
Embodiment 5: the structural characterization of Zn complex.
Choose the Zn complex monocrystalline of embodiment 3 synthesis, with Oxford Diffraction Gemini R CCD diffractometer
It is collected, when temperature is 293K, uses graphite monochromator Mo KαRay is radiation source (λ=0.71073).Crystal is tied
Structure resolves (Sheldrick, 1997) by SHELXS-97 program with direct method, uses SHELXL-97 software kit, and uses complete
Matrix method of least squareF 2Refine.Non-hydrogen atom anisotropic temperature factor correction.Except the hydrogen atom on hydrone is by poor
Value Fourier figure determines outside position, and other all of hydrogen atom coordinate is determined by Theoretical Calculation.Coordination compound [ZnL (H2O)2]
Crystallographic data is shown in Table 1, and crystal structure figure is shown in accompanying drawing 1.
Coordination compound belongs to monoclinic system, and space group isP 21/ c, zinc ion is hexa-coordinate, and coordination environment is deformation octahedral
Body. L2-Anion both formed a five-membered ring and six membered ring, again a conduct respectively as tridentate chelating ligand and zinc ion
Two tooth bridge ligands connect zinc ion and form one-dimensional sawtooth chain structure (see accompanying drawing 2).
Table 1 coordination compound [ZnL (H2O)2] crystallographic data and structure refinement data.
| Chemical formula | C10H12ClNO5Zn |
| Molecular weight | 327.03 |
| Crystallographic system | Monocline |
| Space group | P 21/c |
| a [Å ] | 16.873(2) |
| b [Å ] | 8.1796(7) |
| c [Å ] | 9.0355(9) |
| α [ ˚ ] | 90 |
| β [ ˚ ] | 105.002(12) |
| γ [ ˚ ] | 90 |
| Volume [Å3 ] | 1204.5(2) |
| Z | 4 |
| Solid density (g/cm3) | 1.803 |
| GOF | 1.059 |
| R int | 0.0501 |
| R 1 [I>2σ(I)] | 0.0511 |
| w R 2 (all data) | 0.1450 |
Claims (3)
1. a 5-chloro-salicyloyl al- D ,L-alanine Schiff base zinc coordination compound, it is characterised in that structural formula is
。
5-chloro-salicyloyl al the most according to claim 1- D ,LThe preparation method of-alanine Schiff base zinc coordination compound,
It is characterized in that it comprises the steps: under Ultrasonic Radiation, withD ,L -Alanine, KOH and 5-chloro-salicylic aldehyde are reaction
Raw material, with methanol as solvent, reaction temperature is 40-50 DEG C, carry out condensation reaction obtain 5-chloro-salicyloyl al-D ,L-the third ammonia
Acid schiff base ligand, then by this part and equimolar Zn (NO3)2Effect, with methanol as reaction medium, obtains Zn complex.
Preparation method the most according to claim 2, it is characterised in that describedD,L -Alanine, KOH and 5-chloro-salicylic aldehyde
The ratio of the amount of material is 1:1:1；Reaction medium methanol can substitute with dehydrated alcohol.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107698460A (en) * | 2017-10-01 | 2018-02-16 | 桂林理工大学 | A kind of schiff bases sylvite and preparation method thereof |
| CN107960533A (en) * | 2016-10-20 | 2018-04-27 | 湖南晶天科技实业有限公司 | A kind of amino acid aldehyde schiff bases feed addictive and a kind of feed |
| CN114805116A (en) * | 2022-03-03 | 2022-07-29 | 北京理工大学 | Zn-based Schiff base complex, and preparation method and application thereof |
| CN115894262A (en) * | 2022-11-23 | 2023-04-04 | 辽宁大学 | N-methylated amantadine reduction Schiff base derivative and preparation method and application thereof |
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| CN1305490A (en) * | 1998-06-26 | 2001-07-25 | 辉瑞产品公司 | Improved processing for preparing schift base adducts of amines with i(o)-hydroxy aldehydes and compositions of matter based thereon |
| CN101811919A (en) * | 2010-04-27 | 2010-08-25 | 哈尔滨理工大学 | Method for preparing amino acid schiff base metal complexes without solvent |
| CN102391293A (en) * | 2011-08-16 | 2012-03-28 | 周口师范学院 | Method for quickly synthesizing Schiff base composition under assistance of microwaves and fluorescence property of Schiff base composition |
-
2016
- 2016-06-27 CN CN201610473927.6A patent/CN106008566A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305490A (en) * | 1998-06-26 | 2001-07-25 | 辉瑞产品公司 | Improved processing for preparing schift base adducts of amines with i(o)-hydroxy aldehydes and compositions of matter based thereon |
| CN101811919A (en) * | 2010-04-27 | 2010-08-25 | 哈尔滨理工大学 | Method for preparing amino acid schiff base metal complexes without solvent |
| CN102391293A (en) * | 2011-08-16 | 2012-03-28 | 周口师范学院 | Method for quickly synthesizing Schiff base composition under assistance of microwaves and fluorescence property of Schiff base composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107960533A (en) * | 2016-10-20 | 2018-04-27 | 湖南晶天科技实业有限公司 | A kind of amino acid aldehyde schiff bases feed addictive and a kind of feed |
| CN107698460A (en) * | 2017-10-01 | 2018-02-16 | 桂林理工大学 | A kind of schiff bases sylvite and preparation method thereof |
| CN114805116A (en) * | 2022-03-03 | 2022-07-29 | 北京理工大学 | Zn-based Schiff base complex, and preparation method and application thereof |
| CN114805116B (en) * | 2022-03-03 | 2023-03-24 | 北京理工大学 | Zn-based Schiff base complex, and preparation method and application thereof |
| CN115894262A (en) * | 2022-11-23 | 2023-04-04 | 辽宁大学 | N-methylated amantadine reduction Schiff base derivative and preparation method and application thereof |
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