CN107686452B - 6-bromoisovanillin long-chain organic amine Schiff base and preparation method thereof - Google Patents
6-bromoisovanillin long-chain organic amine Schiff base and preparation method thereof Download PDFInfo
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Abstract
A6-bromoisovanillin long-chain organic amine Schiff base and a preparation method thereof are disclosed: dissolving 6-bromoisovanillin in an anhydrous methanol-acetonitrile mixed solvent, and dissolving long-chain organic amine in ethanol to prepare a solution, wherein the long-chain organic amine is selected from n-hexylamine, n-heptylamine or n-dodecylamine; adding the long-chain organic amine ethanol solution into 6-bromoisovanillin in a dropwise manner for condensation reaction, wherein the mass ratio of the 6-bromoisovanillin to the long-chain organic amine is 1: 1.1-1.5, and the reaction temperature is 75-85 ℃; heating and refluxing; naturally cooling to room temperature, and separating out crystal form solid to obtain the target product 6-bromoisovanillin long-chain organic amine Schiff base. The novel 6-bromoisovanillin Schiff base compound is synthesized by taking 6-bromoisovanillin and long-chain organic amine as raw materials and adopting a mixed solvent method and controlling experimental conditions. The reaction condition is mild, the product yield is high, the solvent can be recycled, and no three-waste pollution is generated.
Description
Technical Field
The invention relates to the field of novel functional compounds and preparation thereof, in particular to novel 6-bromoisovanillin long-chain organic amine Schiff base and a preparation method thereof.
Background
Since the discovery of Schiff base for the first time in 1864, the Schiff base has been extensively and deeply studied due to a series of excellent properties including sterilization, antivirus, anticancer, reversible binding of oxygen, nonlinear optics, photochromism, thermochromism, fluorescence, magnetism, enzyme-like catalysis, etc. At present, Schiff base compounds and complexes thereof have important application in the fields of medicine, catalysis, analytical chemistry, corrosion and photochromism.
In recent years, the development of Schiff base compounds has been promoted particularly with the development of functional complexes and bio-inorganic chemistry. The Schiff base compound is researched, not only is the selection of functional raw materials studied and the deep research is carried out from the aspects of the formation mechanism, the spectral property and the like, but also the functionality and the broad spectrum property after the complex is formed are comprehensively considered. The research on the synthesis, structure and interaction between the metal ions and the Schiff base ligand plays an important role in deeply investigating the action mechanism, structure, stability and the like of the physiological and pharmacological activities of the Schiff base ligand. Due to the broad spectrum of action of schiff base complexes, research on such compounds has been a hotspot in the field of bioinorganics for nearly half a century.
The structure of the 6-bromoisovanillin contains active groups such as hydroxyl, aldehyde group and the like, and the 6-bromoisovanillin is mainly used in the industries of medicine, spice, pesticide chemistry and organic synthesis, and is particularly used as an intermediate of galanthamine. At present, the use of 6-bromoisovanillin is still basically in the initial stage, and the 6-bromoisovanillin is only used as an intermediate for various syntheses, and the development of derivatives of the 6-bromoisovanillin, particularly the development and research of Schiff bases of the 6-bromoisovanillin are less.
The Schiff base has unique structure and property, and has wide application in aspects of biological enzyme simulation, pharmaceutical chemistry, functional materials and the like, so that the research of the compound becomes a hotspot and has great research value. The synthesis of Schiff base compounds currently adopts a solvent method and a hydrothermal method. The solvent method can select different synthesis methods according to different properties of raw materials. The 6-bromoisovanillin contains aldehyde group, has stronger activity ratio and is easy to generate oxidation-reduction reaction; in the structure, the existence of hydroxyl on a benzene ring leads to the activation of the benzene ring and easy substitution; the long-chain organic amine is not easy to be condensed with aldehyde group due to steric hindrance, so that the 6-bromoisovanillin and the long-chain organic amine Schiff base are difficult to generate.
At present, the Schiff base derivatives of 6-bromoisovanillin are rarely researched, the application of the Schiff base derivatives is not widely excavated and applied, and due to the special biological performance of the Schiff base compounds, the 6-bromoisovanillin Schiff base compounds are researched, and the 6-bromoisovanillin derivatives with special biological activity are screened, so that the method has a certain significance.
Disclosure of Invention
The invention aims to solve the technical problem of providing a novel 6-bromoisovanillin long-chain organic amine Schiff base which is easier to synthesize, mild in reaction conditions and high in product yield, aiming at the defects of the prior art.
The invention also provides a preparation method of the 6-bromoisovanillin reduced long-chain organic amine Schiff base.
The technical problem to be solved by the present invention is achieved by the following technical means. The invention relates to a 6-bromoisovanillin long-chain organic amine Schiff base which is characterized by having the following general formula:
（I）
in formula (I): x is 4, 5 or 10.
The preparation method of the 6-bromoisovanillin long-chain organic amine Schiff base comprises the following steps: firstly, 6-bromoisovanillin is dissolved in an anhydrous methanol-acetonitrile mixed solvent, wherein the methanol accounts for 65-85% of the volume percentage of the mixed solvent, and then long-chain organic amine is dissolved in 85-98% ethanol to prepare a solution with the concentration of 0.1-0.5 mmol/L, wherein the long-chain organic amine is selected from n-hexylamine, n-heptylamine or n-dodecylamine; adding the long-chain organic amine ethanol solution into 6-bromoisovanillin in a dropwise manner for condensation reaction, wherein the dropwise adding flow is 1.0-1.5 mL/min; the mass ratio of the 6-bromoisovanillin to the long-chain organic amine is 1: 1.1-1.5, and the reaction temperature is 75-85 ℃; heating and refluxing; reacting for 6-7 hours; naturally cooling to room temperature, and separating out crystal form solid to obtain the target product 6-bromoisovanillin long-chain organic amine Schiff base.
Condensation of 6-bromoisovanillin and long-chain organic amines (n-hexylamine, n-heptylamine and n-dodecylamine) is difficult to synthesize due to steric hindrance; therefore, the choice of solvent and the optimization of the reaction conditions in the synthesis of the present invention are particularly important.
The invention relates to a preparation method of 6-bromoisovanillin reduced long-chain organic amine Schiff base, which further adopts the preferable technical scheme that: then dissolving the long-chain organic amine in 95% ethanol to prepare a solution of 0.2mmol/L-0.3 mmol/L.
The invention relates to a preparation method of 6-bromoisovanillin reduced long-chain organic amine Schiff base, which further adopts the preferable technical scheme that: the reaction temperature was 80 ℃.
The invention relates to a preparation method of 6-bromoisovanillin reduced long-chain organic amine Schiff base, which further adopts the preferable technical scheme that: the volume percentage of the methanol in the anhydrous methanol-acetonitrile mixed solvent is 75-80%.
The invention relates to a preparation method of 6-bromoisovanillin reduced long-chain organic amine Schiff base, which further adopts the preferable technical scheme that: the mass ratio of the 6-bromoisovanillin to the long-chain organic amine is 1: 1.1-1.2.
Compared with the prior art, the novel 6-bromoisovanillin Schiff base compound is synthesized by taking 6-bromoisovanillin and long-chain organic amine as raw materials and adopting a mixed solvent method and controlling experimental conditions. The synthesis method has the advantages of mild reaction conditions, high product yield, recyclable solvent and no three-waste pollution.
Drawings
FIG. 1 is an infrared spectrum of 6-bromoisovanillin n-hexylamine Schiff base;
FIG. 2 is an infrared spectrum of 6-bromoisovanillin n-heptylamine Schiff base;
FIG. 3 is an infrared spectrum of 6-bromoisovanillin shrinkage n-dodecylamine Schiff base.
Detailed Description
The following further describes particular embodiments of the present invention to facilitate further understanding of the present invention by those skilled in the art, and does not constitute a limitation to the right thereof.
Example 1, a method for preparing a 6-bromoisovanillin long-chain organic amine schiff base, the general formula of the 6-bromoisovanillin long-chain organic amine schiff base is as follows:
（I）
in formula (I): x is 4, 5 or 10;
the preparation method comprises the following steps: firstly, 6-bromoisovanillin is dissolved in an anhydrous methanol-acetonitrile mixed solvent, wherein the methanol accounts for 65% of the volume of the mixed solvent, and then long-chain organic amine is dissolved in 85% ethanol to prepare a solution with the concentration of 0.1mmol/L, wherein the long-chain organic amine is selected from n-hexylamine, n-heptylamine or n-dodecylamine; adding the long-chain organic amine ethanol solution into 6-bromoisovanillin in a dropwise manner for condensation reaction, wherein the dropwise adding flow is 1.0 mL/min; the mass ratio of 6-bromoisovanillin to long-chain organic amine is 1:1.1, and the reaction temperature is 75 ℃; heating and refluxing; reacting for 6 hours; naturally cooling to room temperature, and separating out crystal form solid to obtain the target product 6-bromoisovanillin long-chain organic amine Schiff base.
Example 2, a method for preparing a 6-bromoisovanillin long-chain organic amine schiff base, the general formula of the 6-bromoisovanillin long-chain organic amine schiff base is as follows:
（I）
in formula (I): x is 4, 5 or 10;
the preparation method comprises the following steps: firstly, 6-bromoisovanillin is dissolved in an anhydrous methanol-acetonitrile mixed solvent, wherein the methanol accounts for 85 percent of the volume of the mixed solvent, and then long-chain organic amine is dissolved in 98 percent ethanol to prepare a solution of 0.5mmol/L, wherein the long-chain organic amine is selected from n-hexylamine, n-heptylamine or n-dodecylamine; adding the long-chain organic amine ethanol solution into 6-bromoisovanillin in a dropwise manner for condensation reaction, wherein the dropwise adding flow is 1.5 mL/min; the mass ratio of 6-bromoisovanillin to long-chain organic amine is 1:1.5, and the reaction temperature is 85 ℃; heating and refluxing; reacting for 7 hours; naturally cooling to room temperature, and separating out crystal form solid to obtain the target product 6-bromoisovanillin long-chain organic amine Schiff base.
Example 3, a method for preparing a 6-bromoisovanillin long-chain organic amine schiff base, the general formula of the 6-bromoisovanillin long-chain organic amine schiff base is as follows:
（I）
in formula (I): x is 4, 5 or 10;
the preparation method comprises the following steps: firstly, 6-bromoisovanillin is dissolved in an anhydrous methanol-acetonitrile mixed solvent, wherein the methanol accounts for 75% of the volume of the mixed solvent, and then long-chain organic amine is dissolved in 85% ethanol to prepare a solution of 0.3mmol/L, wherein the long-chain organic amine is selected from n-hexylamine, n-heptylamine or n-dodecylamine; adding the long-chain organic amine ethanol solution into 6-bromoisovanillin in a dropwise manner for condensation reaction, wherein the dropwise adding flow is 1.2 mL/min; the mass ratio of 6-bromoisovanillin to long-chain organic amine is 1:1.3, and the reaction temperature is 80 ℃; heating and refluxing; reacting for 6 hours; naturally cooling to room temperature, and separating out crystal form solid to obtain the target product 6-bromoisovanillin long-chain organic amine Schiff base.
Example 4 preparation of 6, 6-bromoisovanillin n-hexylamine schiff base:
the synthetic route is as follows:
the synthesis method comprises the following steps: A1L multifunctional reactor with a four-neck flask is characterized in that four necks are respectively connected with a dropping funnel, a thermometer, a condensing tube and a stirrer. Adding a certain amount of acetonitrile-methanol mixed solvent into a reactor, and adding a certain amount of 6-bromoisovanillin. Starting the stirring device, stirring at the rotating speed of 100r/min for about 20 minutes until the 6-bromoisovanillin is completely dissolved. Heating to about 50 ℃, dropwise adding a proper amount of prepared 0.1mol/L n-hexylamine ethanol solution, controlling the flow rate to be 1.0-1.5 mL/min, and controlling the reaction temperature to be about 80 ℃. After the dropwise addition is finished, reacting for 6-7 hours at the temperature; the solution changed from colorless to yellow-brown and the condensation was complete.
And (3) filtering and drying a product: and cooling the reactor, taking out the reactant, filtering and drying to obtain the 6-bromoisovanillin long-chain organic amine Schiff base.
And (3) solvent recovery: evaporating part of the solvent, continuously separating out part of the target product dissolved in the solvent, filtering, drying and collecting the target product.
The target product was a light yellow crystalline solid with melting point 140-.
The reaction raw materials are proportioned, and the mass ratio of 6-bromoisovanillin to n-hexylamine is 1: 1.1; a slight excess of n-hexylamine ensured complete conversion of 6-bromoisovanillin.
Example 5 preparation of 6, 6-Bromoiso-iso-vanillin n-heptylamine Schiff base:
the synthetic route is as follows:
the synthesis method comprises the following steps: A1L multifunctional reactor with a four-neck flask is characterized in that four necks are respectively connected with a dropping funnel, a thermometer, a condensing tube and a stirrer. Adding a certain amount of acetonitrile-methanol mixed solvent into a reactor, and adding a certain amount of 6-bromoisovanillin. Starting the stirring device, stirring at the rotating speed of 100r/min for about 20 minutes until the 6-bromoisovanillin is completely dissolved. Heating to about 50 ℃, dropwise adding a proper amount of prepared 0.1mol/L n-heptylamine ethanol solution, controlling the flow rate to be 1.0-1.5 mL/min, and controlling the reaction temperature to be 75-85 ℃. After the dropwise addition is finished, reacting for 6-7 hours at the temperature; the solution changed from colorless to yellow-brown and the condensation was complete.
And (3) filtering and drying a product: and cooling the reactor, taking out the reactant, filtering and drying to obtain the 6-bromoisovanillin long-chain organic amine Schiff base.
And (3) solvent recovery: evaporating part of the solvent, continuously separating out part of the target product dissolved in the solvent, filtering, drying and collecting the target product.
The desired product is a pale yellow crystalline solid with a melting point of 120.5-121 ℃.
The ratio of the reaction raw materials is 1:1.1, wherein the mass ratio of the 6-bromoisovanillin to the n-heptylamine is 1; a slight excess of n-heptylamine ensured complete conversion of 6-bromoisovanillin.
Example 6 preparation of 6, 6-Bromoiso Isovanillin n-dodecylamine Schiff base
The synthetic route is as follows:
the synthesis method comprises the following steps: A1L multifunctional reactor with a four-neck flask is characterized in that four necks are respectively connected with a dropping funnel, a thermometer, a condensing tube and a stirrer. Adding a certain amount of acetonitrile-methanol mixed solvent into a reactor, and adding a certain amount of 6-bromoisovanillin. Starting the stirring device, stirring at the rotating speed of 100r/min for about 20 minutes until the 6-bromoisovanillin is completely dissolved. Heating to about 50 ℃, dropwise adding a proper amount of prepared 0.1mol/L n-dodecylamine ethanol solution, controlling the flow rate to be 1.0-1.5 mL/min, and controlling the reaction temperature to be 75-85 ℃. After the dropwise addition, the reaction was carried out at this temperature for 7 hours; the solution changed from colorless to yellow-brown and the condensation was complete.
And (3) filtering and drying a product: and cooling the reactor, taking out the reactant, filtering and drying to obtain the 6-bromoisovanillin long-chain organic amine Schiff base.
And (3) solvent recovery: evaporating part of the solvent, continuously separating out part of the target product dissolved in the solvent, filtering, drying and collecting the target product.
The target product was a light yellow crystalline solid with melting point 103-105 ℃.
Note: the proportion of reaction raw materials is that the mass ratio of 6-bromoisovanillin to n-dodecylamine is 1: 1.1; a slight excess of n-dodecylamine ensures complete conversion of 6-bromoisovanillin.
FIGS. 1-3 are infrared spectra IR; as can be seen from the infrared map 1-3, the 6-bromoisovanillin condensed long-chain organic amine has similar structure and 3300 cm-1The absorption peak is attributed to the stretching vibration of the phenolic hydroxyl; at 3300 and 3350 cm-1The symmetrical and antisymmetric peaks of nearby NH2 disappeared, indicating that the Schiff base condensation reaction has proceeded completely; 2943 cm-1 to 2835 cm-1The nearby strong absorption peak is attributed to stretching vibration of CH2 in the long-chain organic amine; at 1400-1600 cm-1The absorption peak is caused by the stretching vibration of the benzene ring skeleton, the stretching vibration of the C = N double bond is also in the section and is overlapped with the absorption peak of the benzene ring skeleton, and the absorption peak is 1650--1The nearby C = O absorption peak disappeared,c = N stretching vibration of aldehyde Schiff base compounds is generally 1630 cm-1Nearby, and as can be seen from the infrared data, the C = N stretching vibration peak of the paeonol Schiff base compound is red-shifted to 1600 cm-1Nearby.
Meanwhile, the inventor also makes a relevant ultraviolet spectrogram, and as can be seen from the ultraviolet spectrogram of 6-bromoisovanillin, three absorption peaks exist at 238nm, 279nm and 326 nm. The ultraviolet spectrum structures of the 6-bromoisovanillin n-hexylamine Schiff base, the 6-bromoisovanillin n-heptylamine Schiff base and the 6-bromoisovanillin n-dodecylamine Schiff base in the embodiments 1 to 3 are very similar to those of the Schiff base, and four absorption peaks are formed at the positions of 220 nm, 235nm, 272nm and 314nm, so that the situation that after the Schiff base is formed by the 6-bromoisovanillin and the long-chain organic amine, the fine structure of a benzene ring B band disappears, and an R band generates very obvious red shift, which indicates that a larger conjugated system is formed in a compound molecule is shown. Meanwhile, the structure of Schiff base formed by the three kinds of 6-bromoisovanillin and the long-chain organic amine is verified by a nuclear magnetic resonance spectrum.
The invention adopts an agar diffusion method to research the biological activity of the 6-bromoisovanillin Schiff base.
The method is characterized in that the agar diffusion bacteriostasis method is to observe the inhibition degree of the toxicant on the indicator bacteria by utilizing the horizontal diffusion characteristic of agar, and the inhibition degree of the toxicant on the indicator bacteria is represented according to the size of an inhibition zone, wherein the larger the inhibition zone is, the stronger the inhibition of the sample on the microbes is, and the stronger the toxicity is.
In the experiment, staphylococcus aureus [ CMCC (B) 26003 ], bacillus pumilus [ CMCC (B) 63202], salmonella [ CMCC (B) 50094] and three bacteria are used as indicator organisms, and an agar diffusion method is adopted to carry out bacteriostatic activity research on the three synthesized Schiff base compounds.
Test method
Adding 1L distilled water into 40g agar culture medium, heating to dissolve, subpackaging, and autoclaving at 120 deg.C for 30 min. 20 mL of culture medium liquid is taken while the culture medium liquid is hot and evenly spread on the bottom layer of a glass plate, and the culture medium liquid is cooled and solidified. Then 20 mL of culture medium liquid is added into 0.5 mL of cultured (cultured at 37 ℃ for 24 h) bacterial liquid by aseptic technique, and after uniform mixing, the mixture is immediately poured into a glass plate with a culture substrate layer. After cooling into flat plates, the oxford cups were placed vertically, four in each plate.
Taking N, N-dimethylformamide as a solvent, and respectively preparing 6-bromoisovanillin and three Schiff base compound solutions with certain concentrations. Quantitatively injecting a sample to be detected with a certain concentration (0.04 mL) into an Oxford cup by using a micro-sampler, covering a plate by using a porcelain cover, and culturing in a constant-temperature incubator at 37 ℃ for 24 hours. The transparent zone of inhibition (mm) produced around each oxford cup was removed and measured. Blank experiments show that the N, N-dimethylformamide does not have an inhibiting effect on the tested strains. All samples were tested in triplicate and the average was taken as the final test result.
The test results are shown in Table 1.
TABLE 16 diameters of inhibition zones for bromoisovanillin and its three Schiff bases
Under the same substance quantity concentration, the three 6-bromoisovanillin Schiff base compounds and the 6-bromoisovanillin have certain bacteriostatic performance on tested microorganisms, and the diameter of a bacteriostatic zone is increased along with the increase of the sample concentration in a tested concentration range; the Schiff base compound formed by condensing 6-bromoisovanillin and different long-chain organic amines has obviously different inhibiting effects on different strains.
The inhibition effect of the three Schiff base compounds on the tested microorganism is obviously stronger than that of 6-bromoisovanillin, which indicates that the Schiff base is formed and has certain bioactivity. The results show that the inhibition effect of the three Schiff base compounds on the salmonella is obviously stronger than that of the other two strains.
The three Schiff base compounds have very similar structures, so that the inhibition effects on tested microorganisms are similar, and the inhibition effects of the three Schiff base compounds on three strains are not greatly different. However, the inhibition effect of the 6-bromoisovanillin hexedrine Schiff base is slightly stronger than that of the other two compounds, the specific mechanism is still to be further researched, and the structure of the compound and the compound are probably in great relation.
And (4) comprehensive conclusion: the antibacterial performance can be enhanced by the formation of the Schiff base, the lipophilicity of the substance is enhanced due to the introduction of the organic long chain, and the lipophilicity is required by the antitumor activity of the Schiff base; therefore, further research on the antibacterial performance of the 6-bromoisovanillin reduced-chain organic amine and expansion of experiments on different strains or research on in-vitro antitumor activity has certain significance.
Claims (5)
1. The preparation method of the 6-bromoisovanillin long-chain organic amine Schiff base is characterized in that the general formula of the 6-bromoisovanillin long-chain organic amine Schiff base is as follows:
（I）
in formula (I): x is 4, 5 or 10;
the preparation method comprises the following steps: firstly, 6-bromoisovanillin is dissolved in an anhydrous methanol-acetonitrile mixed solvent, wherein the methanol accounts for 65-85% of the volume percentage of the mixed solvent, and then long-chain organic amine is dissolved in ethanol with the mass concentration of 85-98% to prepare a solution with the mass concentration of 0.1-0.5 mmol/L, wherein the long-chain organic amine is selected from n-hexylamine, n-heptylamine or n-dodecylamine; adding the long-chain organic amine ethanol solution into 6-bromoisovanillin in a dropwise manner for condensation reaction, wherein the dropwise adding flow is 1.0-1.5 mL/min; the mass ratio of the 6-bromoisovanillin to the long-chain organic amine is 1: 1.1-1.5, and the reaction temperature is 75-85 ℃; heating and refluxing; reacting for 6-7 hours; naturally cooling to room temperature, and separating out crystal form solid to obtain the target product 6-bromoisovanillin long-chain organic amine Schiff base.
2. The method for preparing 6-bromoisovanillin reduced long-chain organic amine Schiff base as claimed in claim 1, wherein: then dissolving the long-chain organic amine in ethanol with the mass concentration of 95% to prepare a solution with the mass concentration of 0.2mmol/L-0.3 mmol/L.
3. The method for preparing 6-bromoisovanillin reduced long-chain organic amine Schiff base as claimed in claim 1, wherein: the reaction temperature was 80 ℃.
4. The method for preparing 6-bromoisovanillin reduced long-chain organic amine Schiff base as claimed in claim 1, wherein: the volume percentage of the methanol in the anhydrous methanol-acetonitrile mixed solvent is 75-80%.
5. The method for preparing 6-bromoisovanillin reduced long-chain organic amine Schiff base as claimed in claim 1, wherein: the mass ratio of the 6-bromoisovanillin to the long-chain organic amine is 1: 1.1-1.2.
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