CN104529887A - Pyridine hydrazone compound and preparation method and application thereof - Google Patents
Pyridine hydrazone compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN104529887A CN104529887A CN201410730378.7A CN201410730378A CN104529887A CN 104529887 A CN104529887 A CN 104529887A CN 201410730378 A CN201410730378 A CN 201410730378A CN 104529887 A CN104529887 A CN 104529887A
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- Prior art keywords
- pyridine
- almond oil
- bitter almond
- oil camphor
- ethanol solution
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Plasma & Fusion (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a pyridine hydrazone compound and a preparation method and an application thereof. A chemical structural formula of the pyridine hydrazone compound is as shown in the specification. The pyridine hydrazone compound can be used for selective colorimetric recognition of copper ions. A synthetic method of the pyridine hydrazone compound is simple, has low equipment requirements, and is convenient to operate. In addition, the pyridine hydrazone compound is used as a new approach to selective colorimetric recognition of copper ions. Lower limit of copper ions detected by naked eyes by the use of the compound can reach 2 micro mole, lower than the lower limit 20 micro mole of copper ions in drinking water.
Description
Technical field
The present invention relates to technical field of chemistry and chemical engineering, particularly relate to a kind of pyridine hydrazone compounds and its production and use.
Background technology
In recent years, transition metal ion plays an important role in environment and life science, in numerous transition metal ion and heavy metal ion, cupric ion and our life closely bound up.Copper is trace heavy metal element required in a kind of animal and plant body, and nearly twenties kinds of effects need the participation of cupric ion, as Terminal oxidase, superoxide dismutase and tyrosine oxidase etc.If but content of copper ion is too high in body, then can makes cell damage and necrosis, cause organ function injury.Cupric ion is also one of heavy metal ion of contaminate environment.For these reasons, the detection of cupric ion attracts attention, and constantly inquires into its detection method.Wherein particularly noticeable by the chemical sensitisation method of colorimetric or fluorescence molecule.So far, people design and synthesis some can with Cu
2+the compound of selective binding, as rhodamine B hydrazides, rhodamine B hydrazides oxalamide, dansyl and triazole Schiff etc.But it is possible to the single colorimetric detection Cu of selectivity
2+acceptor at present still rarely seen report.
Summary of the invention
The invention provides a kind of pyridine hydrazone compounds and its production and use.
The present invention adopts following technical scheme:
The chemical structural formula of pyridine hydrazone compounds of the present invention is as follows:
The concrete steps of the legal manner of pyridine hydrazone compounds of the present invention are as follows:
Add bitter almond oil camphor and ethanol solution in the reactor, the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:10-30mmol/ml, then under reflux, slowly drip the ethanol solution being dissolved with 2-hydrazino pyridine, the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 0.5-2:1,2-hydrazino pyridine is 0.005-0.02:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it, drip off rear continuation back flow reaction 2-4 hour, removal of solvent under reduced pressure ethanol, crude product dehydrated alcohol recrystallization obtains pure target compound.
Preferred: the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:20mmol/ml.
Preferred: the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 1:1.
Preferred: 2-hydrazino pyridine is 0.01:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it.
Preferred: to drip off rear continuation back flow reaction 3 hours.
Pyridine hydrazone compounds of the present invention may be used for the selectivity ratios colour discrimination to cupric ion.
Positively effect of the present invention is as follows:
Pyridine hydrazone compounds synthetic method of the present invention is simple, low to matching requirements, convenient operation, and pyridine hydrazone compounds of the present invention is as a kind of selectivity ratios colour discrimination of new cupric ion, the cupric ion lower limit that its naked eyes detect can reach 2 μMs, lower than the lower limit 20 μMs of copper in drinking water ion.
Embodiment
The following examples describe in further detail of the present invention.
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Material used in following embodiment, reagent etc., if no special instructions, all can obtain from open commercial sources.
Embodiment 1
The concrete steps of the legal manner of pyridine hydrazone compounds of the present invention are as follows:
Add bitter almond oil camphor and ethanol solution in the reactor, the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:10mmol/ml, then under reflux, slowly drip the ethanol solution being dissolved with 2-hydrazino pyridine, the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 0.5:1,2-hydrazino pyridine is 0.005:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it, drip off rear continuation back flow reaction 2 hours, removal of solvent under reduced pressure ethanol, crude product dehydrated alcohol recrystallization obtains pure target compound.
Embodiment 2
The concrete steps of the legal manner of pyridine hydrazone compounds of the present invention are as follows:
Add bitter almond oil camphor and ethanol solution in the reactor, the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:30mmol/ml, then under reflux, slowly drip the ethanol solution being dissolved with 2-hydrazino pyridine, the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 2:1,2-hydrazino pyridine is 0.02:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it, drip off rear continuation back flow reaction 4 hours, removal of solvent under reduced pressure ethanol, crude product dehydrated alcohol recrystallization obtains pure target compound.
Embodiment 3
The concrete steps of the legal manner of pyridine hydrazone compounds of the present invention are as follows:
Add bitter almond oil camphor and ethanol solution in the reactor, the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:20mmol/ml, then under reflux, slowly drip the ethanol solution being dissolved with 2-hydrazino pyridine, the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 1:1,2-hydrazino pyridine is 0.01:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it, drip off rear continuation back flow reaction 3 hours, removal of solvent under reduced pressure ethanol, crude product dehydrated alcohol recrystallization obtains pure target compound.
Pyridine hydrazone compounds of the present invention is at THF/water (9:1, v/v) HEPESbuffer (10mM is comprised, pH=7.0) in buffered soln, utilize ultraviolet-visible pectrophotometer, the solution of this compound 1 (10 μMs) can be used for the selective determination of cupric ion, and under natural light, add this solution of cupric ion can directly observe colour-change from colourless to peach, as a kind of selectivity ratios colour discrimination of new cupric ion, the cupric ion lower limit that its naked eyes detect can reach 2 μMs, lower than the lower limit 20 μMs of copper in drinking water ion.
Although illustrate and describe embodiments of the invention, for the ordinary skill in the art, be appreciated that and can carry out multiple change, amendment, replacement and modification to these embodiments without departing from the principles and spirit of the present invention, scope of the present invention is by claims and equivalents thereof.
Claims (7)
1. a pyridine hydrazone compounds, is characterized in that: the chemical structural formula of described pyridine hydrazone compounds is as follows:
2. synthesize a method for pyridine hydrazone compounds as claimed in claim 1, it is characterized in that: the concrete steps of described method are as follows:
Add bitter almond oil camphor and ethanol solution in the reactor, the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:10-30mmol/ml, then under reflux, slowly drip the ethanol solution being dissolved with 2-hydrazino pyridine, the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 0.5-2:1,2-hydrazino pyridine is 0.005-0.02:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it, drip off rear continuation back flow reaction 2-4 hour, removal of solvent under reduced pressure ethanol, crude product dehydrated alcohol recrystallization obtains pure target compound.
3. synthetic method as claimed in claim 2, is characterized in that: the molecular volume of bitter almond oil camphor and dehydrated alcohol is than being 0.01:20mmol/ml.
4. synthetic method as claimed in claim 2, is characterized in that: the mol ratio of 2-hydrazino pyridine and bitter almond oil camphor is 1:1.
5. synthetic method as claimed in claim 2, is characterized in that: 2-hydrazino pyridine is 0.01:20mmol/ml with the molecular volume ratio of the ethanol solution dissolving it.
6. synthetic method as claimed in claim 2, is characterized in that: drip off rear continuation back flow reaction 3 hours.
7. pyridine hydrazone compounds as claimed in claim 1 is used for the purposes to the selectivity ratios colour discrimination aspect of cupric ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410730378.7A CN104529887A (en) | 2014-12-04 | 2014-12-04 | Pyridine hydrazone compound and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410730378.7A CN104529887A (en) | 2014-12-04 | 2014-12-04 | Pyridine hydrazone compound and preparation method and application thereof |
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| Publication Number | Publication Date |
|---|---|
| CN104529887A true CN104529887A (en) | 2015-04-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410730378.7A Pending CN104529887A (en) | 2014-12-04 | 2014-12-04 | Pyridine hydrazone compound and preparation method and application thereof |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2327986A1 (en) * | 1973-06-01 | 1975-01-02 | Henkel & Cie Gmbh | Dyeing keratin fibres, pref. hair - with nickel or cobalt complex cpds. opt. formed in situ |
-
2014
- 2014-12-04 CN CN201410730378.7A patent/CN104529887A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2327986A1 (en) * | 1973-06-01 | 1975-01-02 | Henkel & Cie Gmbh | Dyeing keratin fibres, pref. hair - with nickel or cobalt complex cpds. opt. formed in situ |
Non-Patent Citations (4)
| Title |
|---|
| MOHAMED M. H.: "FAAS determination of palladium after its selective recovery by silica modified with hydrazone derivative", 《MICROCHIM ACTA》 * |
| RONALD T.ET AL.: "Spectrophotometric Determination of Cobalt with Benzil Mono- (2-Pyridyl) Hydrazone", 《ANALYTICAL CHEMISTRY》 * |
| SELMAN A.B.: "The Solvent Extraction of Cu(II),Ni(II),and Co(II)with Benzil-mono-(2-pyridylhydrazone)", 《MIKROCHIMICA ACTA》 * |
| 马世昌 主编: "《化学物质词典》", 30 April 1999 * |
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| CB02 | Change of applicant information |
Address after: 435002 Huangshi, Huangshi port, magnetic Lake Road, No. 11, No. Applicant after: Hubei Normal University Address before: 435002 Huangshi, Hubei magnetic Lake Road, No. 11 Applicant before: Hubei Normal College |
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| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150422 |