CN108191793A - Fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- and its preparation method and application - Google Patents
Fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- and its preparation method and application Download PDFInfo
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- CN108191793A CN108191793A CN201810053597.4A CN201810053597A CN108191793A CN 108191793 A CN108191793 A CN 108191793A CN 201810053597 A CN201810053597 A CN 201810053597A CN 108191793 A CN108191793 A CN 108191793A
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- salicylidene
- fluoro
- schiff bases
- new compound
- morpholinyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- 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
Abstract
The invention discloses a kind of 3 fluorine of new compound salicylidene, 4 morpholinyl phenylamine schiff bases and its preparation method and application, its structural formula is as follows：, mole mass ratio 1.1 is pressed by salicylide and 3 fluorine, 4 morpholinyl phenylamine:1 in ethanol solution back flow reaction 1h obtain crude product, crude product is washed to obtain 3 fluorine of salicylidene, 4 morpholinyl phenylamine schiff bases with ethyl alcohol, and crystal structure is as follows：；The schiff bases of the present invention has certain antioxidant activity, there is potential application value in terms of antioxidant, prepares simply, and the reaction time is short, and purity is high, is easy to industrialize.
Description
Technical field
The present invention relates to a kind of fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- and preparation method thereof and
Using.
Background technology
Schiff bases is a kind of organic compound containing C=N groups, is generally contracted by amine and carbonyls aldehydes or ketones
Conjunction is reacted.Pass through the transformation of amine groups and the transformation of carbonyls group, it is possible to which combinatorial compound structure-rich is more
The schiff bases of change.Have the characteristics that synthesis is relatively easy, yield is high, by-product is few.In recent years, schiff bases has good anti-
Bacterium, anticancer, inoxidizability and the extensive bioactivity such as antiviral and pharmaceutical activity, imitative enzymatic, photoelectric property, fluorescence
Matter, thus increasingly paid attention to by researcher.
Morpholine ring is a kind of hexa-member heterocycle containing nitrogen, oxygen, is a kind of important Organic Chemicals.Beautiful jade and its derivative
Object is associated with and is widely studied with close with clinical practices with many biologies due to it.Due to the design feature of itself,
Beautiful jade and its derivative have various bioactivity, and purposes is very extensive, and one of important use therein is exactly as antioxygen
Agent.N, N- thiobis morpholine and N- tertiary butyls morpholine can be as the antioxidants of lubricating oil.A small amount of morpholine and ascorbic acid
Compound may be used as the collaboration antioxidant of oil and fat product.The alkylbenzyldimethylasaltsum saltsum of gallic acid is the antioxidant and dimension of glyceride
The stabilizer of raw element A and carrotene.
Invention content
The purpose of the present invention is：A kind of fluoro- 4- morpholinyl phenylamines schiff bases chemical combination of new compound salicylidene 3- is provided
Object and its preparation method and application, schiff bases purity of the invention is high, and preparation method is simple, and the reaction time is short, is easy to industrialize,
With certain antioxidant activity, there is potential application value in terms of antioxidant.
The present invention technical solution be：The fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3-
Structural formula is as follows：
Wherein, its structure warp1H nuclear magnetic resoance spectrums,13C nuclear magnetic resoance spectrums, mass spectral analysis, it is as a result as follows:1H NMR
(400Hz,CDCl3,δ/ppm):13.15 (s, 1H, OH), 8.57 (s, 1H, CH=N), 6.91-7.38 (m, 7H, H on
benzenes),3.88(t,3JH-H=4Hz, 2H, CH2O),3.10(t,3JH-H=4Hz, 2H, CH2N)；13C NMR(100Hz,
CDCl3,δ/ppm):161.41,161.04,157.04,154.57,143.05,142.96,139.00,133.10,132.20,
119.15,118.92,117.68,109.13,66.94,50.90；Mass spectrometric data：MS (m/z), 301.3, [M+1]+。
Wherein, its crystal structure is as follows：
Wherein, its crystallographic data is as follows:Monoclinic system, space group P21/c, a=16.0034 (19) A, b=
4.3093 (6) A, c=21.685 (2) A, α=90 °, β=103.609 (4) °, γ=90 °.Z=4, V=1453.5 (3) A3,Dc
=1.372gcm3, m (MoKa)=0.100mm-1, F (000)=632.
Wherein, its fusing point is 138-139 DEG C.
Wherein, mole mass ratio 1.1 is pressed by salicylide and the fluoro- 4- morpholinyl phenylamines of 3-:1 in alcohol solvent back flow reaction
1h obtains crude product, and crude product cooling, filtering are washed to obtain salicylidene 3- fluorine 4- morpholinyl phenylamine schiff bases with ethyl alcohol.
Wherein, the solvent is absolute ethyl alcohol, and the fluoro- 4- morpholinyl phenylamines of every mM of 3- need to use 4 milliliters of absolute ethyl alcohols.
Wherein, its application in terms of inoxidizability is tested using DPPH methods.
It is an advantage of the invention that：The yield of the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3- is 92%；Using stable
E formula structures, less than 138 DEG C crystal structures are stablized.
Description of the drawings
Fig. 1 is the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3-1H NMR spectras.
Fig. 2 is the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3-13C NMR spectras.
Fig. 3 is the MS spectrograms of the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3-.
Fig. 4 is the crystal structure figure of the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3-.
Fig. 5 is the free radical scavenging activity curve of the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3-.
Specific embodiment
The present invention is described in further detail with reference to embodiment.
Embodiment:The preparation of the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3-
1.34g (11mo1) salicylides and the 1.96g (l being dissolved in 40mL absolute ethyl alcohols are added in 100mL three-neck flasks
0mmo 1) the fluoro- 4- morpholinyl phenylamines of 3-, heating, back flow reaction, TLC monitoring reactions, 1h, which reacts, to be finished；Solid is precipitated in cooling,
Filtering, is washed with ethyl alcohol, dry, obtains golden transparent solid 2.76g, the fluoro- 4- morpholinyl phenylamines Schiffs of as salicylidene 3-
Alkali.Yield：92%；Fusing point：138-139℃.
As shown in Figure 1, 2, 3,1H NMR(400Hz,CDCl3,δ/ppm):13.15 (s, 1H, OH), 8.57 (s, 1H, CH=
N),6.91-7.38(m,7H,Honbenzenes),3.88(t,3JH-H=4Hz, 2H, CH2O),3.10(t,3JH-H=4Hz, 2H,
CH2N)；13C NMR(100Hz,CDCl3,δ/ppm):161.41,161.04,157.04,154.57,143.05,142.96,
139.00,133.10,132.20,119.15,118.92,117.68,109.13,66.94,50.90；Mass spectrometric data：MS(m/
Z), 301.3, [M+1]+。
As shown in figure 4, it is in VEthyl alcohol：VEther=1:Crystal is cultivated to obtain in 1 solution, crystal structure is as follows：
Its crystallographic data is as follows:Monoclinic system, space group P21/c, a=16.0034 (19) A, b=4.3093 (6)
A, c=21.685 (2) A, α=90 °, β=103.609 (4) °, γ=90 °.Z=4, V=1453.5 (3) A3, Dc=
1.372g·cm3, m (MoKa)=0.100mm-1, F (000)=632.
Test example：The antioxidant activity for realizing the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3- by DPPH methods is surveyed
It is fixed
DPPH methods：DPP H are a kind of very stable free radicals centered on nitrogen, and ethanol solution has at 517nm
Maximum absorption band, if schiff bases can remove it, illustrating that schiff bases has reduces the free radicals such as hydroxyl and interrupts lipid peroxidation
The effect of chain reaction；DPP H methods are had been widely used in the screening operation of free radical scavenger at present.
Experimental method is：By the sample solution of 0.2mL various concentrations respectively with 3.8mL concentration 6.35x10-6The DPP of mol/L
H ethanol solutions are uniformly mixed, and 30min is reacted in placement in the dark, and using absolute ethyl alcohol as reference, its absorbance, meter are surveyed at 517nm
It calculates it and removes the clearance rate K of DPP H,
K=[(A0-As)/A0] * 100%,
In formula:A.For absorbance of the DPP H ethanol solutions at 517nm, AsIt is anti-for various concentration sample and DPP H solution
The absorbance at 517nm after 30min is answered, is mapped with clearance rate to solution concentration, obtains schiff bases to DPPH free radical scavenging activities
Curve, as a result such as attached drawing 5.From attached drawing 5 it is found that the fluoro- 4- morpholinyl phenylamines schiff bases of salicylidene 3- of the present invention is different dense
A degree of elimination effect is respectively provided with when spending to hydroxyl radical free radical, shows good antioxidant activity, is led in antioxidant
Domain has potential application value.
It these are only the preferred embodiment of the present invention and test example, be not intended to restrict the invention, it is clear that the skill of this field
Art personnel can carry out the present invention various changes, modification without departing from the spirit and scope of the present invention.If to the present invention's
These modifications and variations belong within the scope of the claims in the present invention and its equivalent technologies, belong to the protection model of the present invention
It encloses.
Claims (8)
1. the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3-, it is characterized in that：Its structural formula is as follows：
2. the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as described in claim 1, it is characterized in that：Its
Structure passes through1H nuclear magnetic resoance spectrums,13C nuclear magnetic resoance spectrums, mass spectral analysis, it is as a result as follows:1H NMR(400Hz,CDCl3,δ/ppm):
13.15 (s, 1H, OH), 8.57 (s, 1H, CH=N), 6.91-7.38 (m, 7H, H on benzenes), 3.88 (t,3JH-H=
4Hz,2H,CH2O),3.10(t,3JH-H=4Hz, 2H, CH2N)；13C NMR(100Hz,CDCl3,δ/ppm):161.41,
161.04,157.04,154.57,143.05,142.96,139.00,133.10,132.20,119.15,118.92,117.68,
109.13 66.94,50.90；Mass spectrometric data：MS (m/z), 301.3, [M+1]+。
3. the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as described in claim 1, it is characterized in that it
Crystal structure is as follows：
4. the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as claimed in claim 3, it is characterized in that it is brilliant
Body data are as follows:Monoclinic system, space group P21/c, a=16.0034 (19) A, b=4.3093 (6) A, c=21.685 (2)
A, α=90 °, β=103.609 (4) °, γ=90 °.Z=4, V=1453.5 (3) A3, Dc=1.372gcm3, m (MoKa)=
0.100mm-1, F (000)=632.
5. the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as described in claim 1, it is characterized in that：It
Fusing point be 138-139 DEG C.
6. the preparation method of the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as described in claim 1,
It is characterized in：Mole mass ratio 1.1 is pressed by salicylide and the fluoro- 4- morpholinyl phenylamines of 3-:1 in alcohol solvent back flow reaction 1h obtain slightly
Product, crude product cooling, filtering, is washed to obtain salicylidene 3- fluorine 4- morpholinyl phenylamine schiff bases with ethyl alcohol.
7. the preparation method of the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as claimed in claim 6,
It is characterized in：The solvent is absolute ethyl alcohol, and the fluoro- 4- morpholinyl phenylamines of every mM of 3- need to use 4 milliliters of absolute ethyl alcohols.
8. the application of the fluoro- 4- morpholinyl phenylamines schiff bases of new compound salicylidene 3- as described in claim 1, feature
It is：Its application in terms of inoxidizability is tested using DPPH methods.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105433A (en) * | 2021-04-07 | 2021-07-13 | 淮阴师范学院 | Heterocyclic compound containing pyrazole ring and quinoline ring, preparation method and application thereof |
| CN113912566A (en) * | 2021-09-23 | 2022-01-11 | 淮阴师范学院 | 1-pyrene formaldehyde morpholinyl aniline Schiff base compound and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1925643A1 (en) * | 2006-11-13 | 2008-05-28 | Clariant International Ltd. | Nitro schiff base metal complex dyes and their use in optical layers for optical data recording |
-
2018
- 2018-01-19 CN CN201810053597.4A patent/CN108191793A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1925643A1 (en) * | 2006-11-13 | 2008-05-28 | Clariant International Ltd. | Nitro schiff base metal complex dyes and their use in optical layers for optical data recording |
Non-Patent Citations (5)
| Title |
|---|
| G. S. SENTHILKUMAR 等: "Synthesis, Spectral Characterization, DNA Interaction, Antioxidant, and Antimicrobial Studies of New Water Soluble Metal(II) Complexes of Morpholine Based Ligand", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》 * |
| ISMET KAYA 等: "Synthesis, characterization, conductivity and thermal degradation of oligo-2-[(4-morpholin-4-yl-phenyl)imino]methylphenol and its oligomer–metal complex compounds", 《SYNTHETIC METALS》 * |
| SERPIL DEMIRCI等: "Structure-based hybridization, conventional and microwave irradiated synthesis, biological evaculation and molecular docking studies of new compounds derived from thiomorpholin", 《LETTERS IN DRUG DESIGN & DISCOVERY》 * |
| 孙凤梅 等: "含吗啉基片段的水杨醛席夫碱化合物的合成及其抗氧化活性", 《化学试剂》 * |
| 孙凤梅 等: "含吗啉基片段的水杨醛席夫碱类化合物的合成及其淬灭1,1-二苯基-2-三硝基苯肼自由基性能", 《应用化学》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105433A (en) * | 2021-04-07 | 2021-07-13 | 淮阴师范学院 | Heterocyclic compound containing pyrazole ring and quinoline ring, preparation method and application thereof |
| CN113912566A (en) * | 2021-09-23 | 2022-01-11 | 淮阴师范学院 | 1-pyrene formaldehyde morpholinyl aniline Schiff base compound and preparation method and application thereof |
| CN113912566B (en) * | 2021-09-23 | 2023-09-19 | 淮阴师范学院 | 1-pyrene formaldehyde morpholinyl aniline Schiff base compound and preparation method and application thereof |
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