A compound for recognizing chiral amino alcohol, a fluorescent probe and a preparation method and application thereof

Abstract

This invention provides a compound for recognizing chiral amino alcohols, a fluorescent probe, its preparation method, and its application. Naphthol and sodium hydride are weighed and dissolved separately in ultra-dry tetrahydrofuran, mixed, and then reacted with bromomethyl methyl ether. The mixture is extracted with ethyl acetate, and the organic phases are combined to obtain product (R)-1. This product is dissolved in ultra-dry tetrahydrofuran, and n-butyllithium is added. The reaction system changes from colorless to brown, and the reaction is allowed to return to room temperature. Ultra-dry N,N-dimethylformamide solution is then added, and the reaction is quenched by adding saturated ammonium chloride solution under ice-water bath conditions. The product is then extracted with ethyl acetate to obtain product (R)-2. Product (R)-2 is dissolved in a mixed solvent of tetrahydrofuran and anhydrous methanol, and sodium triacetoxyborohydride is added. The product is then extracted with ethyl acetate to obtain reduced product (R)-3. Product (R)-3 is dissolved in a mixed solvent of dichloromethane and anhydrous ethanol, and concentrated hydrochloric acid is added. After the reaction is complete, the reaction is quenched with sodium bicarbonate, and then extracted with dichloromethane to finally obtain compound (R)-4, which recognizes chiral amino alcohols.

Description

Technical Field

[0001] This invention relates to the field of chemical technology, and in particular to a compound for recognizing chiral amino alcohols, a fluorescent probe, its preparation method, and its application. Background Technology

[0002] Chiral amino alcohols are a class of optically active chiral amine compounds with excellent coordination abilities; their nitrogen and oxygen atoms can form complexes with various elements. Therefore, chiral amino alcohols are widely used as chiral catalysts or ligands, and as important chiral sources for certain chiral compounds. They have wide applications in fine chemicals, materials science, medicine, biology, and asymmetric catalysis in organic synthesis. Particularly in the pharmaceutical field, chiral amino alcohols are important precursors for the synthesis of many chiral drugs. For example, valine is an important intermediate in the synthesis of drugs such as salmeterol; threonine, alanine, and phenylalanine are widely used in the synthesis of polypeptide and quinolone chiral drugs. It is a key intermediate for antidepressants such as atomoxetine and fluoxetine. Different chiral configurations of drugs exhibit different physiological functions in vivo, some even being diametrically opposed, the most famous example being the thalidomide tragedy. Therefore, the chiral recognition of amino alcohols is of great significance. Fluorescent recognition methods offer high sensitivity and real-time analysis capabilities; constructing highly enantioselective chiral fluorescent probes facilitates rapid analysis and quantitative detection of asymmetric catalytic reactions.

[0003] Currently, the main methods for detecting chiral amino alcohols include high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis. These methods offer advantages such as good separation and accurate quantification, but also have some drawbacks. For example, these methods require complex pretreatment steps, making sample preparation and separation operations cumbersome, time-consuming, and expensive. In contrast, fluorescence spectroscopy offers advantages such as simple operation, high sensitivity, low cost, short detection time, low detection limit, and the ability to perform high-throughput analysis. Therefore, establishing a fluorescence spectroscopy method for the enantioselective fluorescence recognition of chiral amino alcohols is a very meaningful endeavor. Summary of the Invention

[0004] The purpose of this invention is to provide a compound for recognizing chiral amino alcohols, a fluorescent probe, a method for preparing the same, and its applications, in order to solve the problems mentioned in the background art.

[0005] According to one objective of the present invention, the present invention provides a compound for recognizing chiral amino alcohols, the chemical structural formula of which is as follows: .

[0006] According to another objective of the present invention, the present invention provides a method for preparing the above-mentioned compound that identifies chiral amino alcohols, comprising the following steps:

[0007] Step 1: Synthesis of 2,2'-bis(methoxymethoxy)-1,1'-binaphthyl (R)- 1

[0008] Naphthol and sodium hydride were weighed and dissolved separately in an appropriate amount of ultra-dry tetrahydrofuran. The two solutions were mixed thoroughly under suitable temperature conditions, and then the mixture was allowed to return to room temperature for reaction. After a certain period, the reaction system was cooled to a suitable temperature, and bromomethyl methyl ether was added dropwise. The mixture was then allowed to return to room temperature and reacted overnight. The reaction was quenched with ultrapure water under ice-water bath conditions, and then extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and evaporated by rotary evaporation. The product was then purified by recrystallization from n-hexane to obtain a white solid product. (R)- 1;

[0009] Step 2: Synthesis of 2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]-3,3'-dicarboxaldehyde (R)- 2

[0010] Weigh out the white solid product (R)- 1. Dissolve an appropriate amount of ultra-dry tetrahydrofuran. Under suitable temperature conditions, add n-butyllithium dropwise. The reaction system changes from colorless to brown. Return to room temperature and continue the reaction. After a certain period of time, cool the reaction system to a suitable temperature, and then gradually add ultra-dry N,N-dimethylformamide. The reaction system turns into a grayish-white turbid liquid. Return to room temperature and continue the reaction. After a certain period of time, quench the reaction with saturated ammonium chloride solution under ice-water bath conditions. Extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, filter, and rotary evaporate to obtain a yellow solid product. Purify by column chromatography and dry under vacuum to obtain the final product. (R)- 2;

[0011] Step 3: Synthesis of 3'-(hydroxymethyl)-2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]-3-carboxaldehyde (R)- 3

[0012] Products (R)- 2. Dissolved in a mixed solvent of methanol and tetrahydrofuran, sodium triacetoxyborohydride was added in portions, and the mixture was heated to a suitable temperature and reacted for a certain period of time. The reaction was quenched with ultrapure water under ice-water bath conditions, and then extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and rotary evaporated to obtain a yellow solid. The solid was purified by column chromatography and dried under vacuum to obtain the product. (R)- 3.

[0013] Step 4: Synthesis of 2,2'-dihydroxy-3'-(hydroxymethyl)-[1,1'-binaphthyl]-3-carboxaldehyde (R)- 4

[0014] Products (R)-3. Dissolve in a suitable amount of a mixed solvent of dichloromethane and anhydrous ethanol, and add concentrated hydrochloric acid dropwise; after a certain time, quench the reaction with sodium bicarbonate, then extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, filter, and rotary evaporate to obtain the target product as a yellow solid. (R)- 4. The product (R)- 4 refers to compounds that identify chiral amino alcohols.

[0015] Further, in the method described above, in step 1, the suitable temperature is -5 to 5°C; the certain time is... The recrystallization temperature is set to -20 to 0°C; the binaphthol is... or The molar ratio of binaphthol: sodium hydride: bromomethyl methyl ether is 1:6:3.

[0016] Further, in the method described above, in step 2, the suitable temperature is -5 to 5°C; the reaction time is [time missing] during which the reaction system changes from colorless to brown and returns to room temperature. The reaction system was allowed to turn into a grayish-white turbid liquid and then return to room temperature for 2.5–3.5 hours.

[0017] The volume ratio of the eluent phase for column chromatography purification is petroleum ether: ethyl acetate = 10:1;

[0018] The molar ratio of n-butyllithium to N,N-dimethylformamide is 1:2.5:2.4.

[0019] Furthermore, in the method described above, in step 3, the suitable temperature is 60°C; the certain time is overnight; and the volume ratio of tetrahydrofuran to methanol is 2:1.

[0020] The volume ratio of the eluent phase for column chromatography purification is petroleum ether: ethyl acetate = 2:1.

[0021] Furthermore, in the method described above, in step 4, the certain time is overnight; the volume ratio of dichloromethane to anhydrous ethanol is 1:1.

[0022] According to a third objective of the present invention, the present invention provides a fluorescent probe for recognizing chiral amino alcohols, comprising the compounds for recognizing chiral amino alcohols as described above.

[0023] According to a fourth objective of the present invention, the present invention also provides an application of a fluorescent probe for recognizing chiral amino alcohols, for highly enantioselective fluorescent recognition of chiral amino alcohols in an aqueous phase.

[0024] The present invention provides a fluorescent probe for chiral amino alcohols, its preparation method, and its applications. This probe offers advantages such as simple synthesis, low cost, favorable reaction conditions, convenient post-processing, and environmental friendliness. The aldehyde-hydroxyl bifunctional fluorescent probe prepared by this invention, with binaphthol as its backbone, achieves highly enantioselective fluorescence recognition of valine in aqueous solution in just 5 minutes. Substrate expansion revealed that the fluorescent probe (R)-4 exhibits similar enantioselectivity for various chiral amino alcohols, with weaker fluorescence observed in S-configuration amino alcohols, while R-configuration amino alcohols significantly enhance the fluorescence of (R)-4. The fluorescence intensity at a specific location was measured. This method achieves highly enantioselective fluorescence recognition of chiral amino alcohols in aqueous phase, providing a novel approach for identifying the enantiomeric structures of various chiral amino alcohols and possessing the potential for high-throughput analysis. The detection method features a short response time and high sensitivity, meeting the need for rapid detection of chiral amino alcohols and holding significant application value in many fields. Attached Figure Description

[0025] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0026] Figure 1 The chemical structural formulas of two chiral valine alcohols are shown.

[0027] Figure 2 Compounds that identify chiral valine (R)- 4. Synthesis route diagram;

[0028] Figure 3 For compounds (R)- 4. 1H NMR spectrum;

[0029] Figure 4 For compounds (R)- The carbon NMR spectrum of 4;

[0030] Figure 5 fluorescent probe (R)- 4. Schematic diagram of the principle of D / L-valine recognition;

[0031] Figure 6 fluorescent probe (R)- 4 after reaction with 18 chiral amino alcohols A histogram of fluorescence intensity at the location.

[0032] Figure 7 For the reaction time of the fluorescent probe (R)-Figure 4 shows the results of the test on the effect of enantioselective recognition of valine. Figure 7 (a) is a fluorescent probe (R)- 4. Fluorescence spectra of D-valine at different reaction times; Figure 7 (b) is a fluorescent probe (R)- Fluorescence spectra of 4- and L-valine at different reaction times; Figure 7 (c) is a fluorescent probe (R)- 4. A graph showing the trend of fluorescence intensity changes of D / L-valine at different reaction times;

[0033] Figure 8 The figure shows the results of the test study on the effect of D / L valine concentration on the enantioselective recognition of valine. Figure 8 (a) is a fluorescent probe (R)- 4. Fluorescence spectra after reaction with different equivalents of D-valine; Figure 8 (b) is a fluorescent probe (R)- Fluorescence spectra of 4 pairs of L-valine after reaction with different equivalents; and Figure 8 (c) is a fluorescent probe (R)- 4. A graph showing the trend of fluorescence intensity of D / L-valine at different valine concentrations;

[0034] Figure 9 for Figure showing the results of the test on the effect of concentration on the enantioselective recognition of valine; Figure 9 (a) is a fluorescent probe (R)- 4. D-Valine in different Fluorescence spectra after reaction at certain concentrations; Figure 9 (b) is a fluorescent probe (R)- 4 pairs of L-valine in different Fluorescence spectra after reaction at the specified concentration; Figure 9 (c) is a fluorescent probe (R)- 4. Identify the fluorescence intensity of D / L-valine at different levels Concentration trend graph;

[0035] Figure 10 fluorescent probe (R)- 4 in The hydrogen NMR spectra of L-valine or D-valine at different reaction times in the presence of [the substance]. Detailed Implementation

[0036] The technical solution of the present invention will be clearly and completely described below with reference to the embodiments. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0037] Chiral compounds exist in two configurations: S and R. This invention aims to identify chiral valine alcohols, which exist in two configurations: D and L. Figure 1 These are the chemical structural formulas of two chiral valine alcohols. (Example:) Figure 1 As shown, chiral valine includes: and Two types. Example

[0038] Figure 2 The synthetic route for preparing compounds that recognize chiral valine in embodiments of the present invention is shown below. Figure 2 As shown, it includes the following steps:

[0039] Step 1. Synthesis of 2,2'-bis(methoxymethoxy)-1,1'-binaphthyl (R)- 1 Weigh Sodium hydride Dissolved in In ultra-dry tetrahydrofuran, the two solutions were mixed thoroughly at 0°C, and then the mixture was allowed to return to room temperature for further reaction. Then, the reaction system was cooled to 0°C, and bromomethyl methyl ether was added dropwise. The reaction was then allowed to proceed overnight at room temperature. The reaction was quenched with ultrapure water in an ice-water bath, followed by extraction with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and purified by rotary evaporation and recrystallization from n-hexane to obtain the final product. White solid product (R)- 1. Yield was 91.9%.

[0040] Step 2. Synthesis Weigh out the white solid product Dissolve In ultra-dry tetrahydrofuran, n-butyllithium was added dropwise at 0°C. The reaction system changed from colorless to brown, and the reaction was allowed to proceed at room temperature. The reaction system was then cooled to 0°C, and ultra-dry N,N-dimethylformamide was added dropwise. The reaction system turned into a grayish-white turbid liquid, and the reaction was allowed to return to room temperature. After the reaction is complete, add [the following ingredients] under ice-water bath conditions. The reaction was quenched with saturated ammonium chloride solution. Extraction was then performed with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give a yellow solid product. Purification was achieved by column chromatography with a petroleum ether:ethyl acetate volume ratio of 10:1, followed by vacuum drying to obtain... product (R)- 2. Yield was 67.0%.

[0041] Step 3. Synthesis of 3'-(hydroxymethyl)-2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]-3-carboxaldehyde (R)- 3 Products Dissolve Methanol and Sodium triacetoxyborohydride was added in batches to an ultra-dry tetrahydrofuran mixed solvent. Heat to 60°C and react overnight; add [the following ingredients] under ice-water bath conditions. The reaction was quenched with ultrapure water, followed by extraction with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and rotary evaporated to give a yellow solid. The solid was purified by column chromatography with a petroleum ether:ethyl acetate volume ratio of 2:1. After vacuum drying, the solid was obtained. yellow solid product (R)- 3. Yield was 49.7%.

[0042] Step 4. Synthesis of 2,2'-dihydroxy-3'-(hydroxymethyl)-[1,1'-binaphthyl]-3-carboxaldehyde (R)- 4

[0043] Products Dissolve dichloromethane and Add dropwise to anhydrous ethanol mixed solvent Concentrated hydrochloric acid; after a certain time, sodium bicarbonate is added to quench the reaction, followed by extraction with dichloromethane. The organic phases are combined, dried over anhydrous sodium sulfate, filtered, and then rotary evaporated to obtain the final product. Yellow solid target product (R)- 4. The yield is 99%. The product... (R)- 4 refers to compounds that recognize chiral amino alcohols. Their structural formulas are as follows: .

[0044] The compound prepared using this example (R)- For the 1H and 1C NMR spectra of 4, please refer to [link / reference needed]. Figure 3 , Figure 4 .

[0045] The preparation method provided in this invention is simple, low-cost, and has mild reaction conditions. Example

[0046] The difference between this embodiment and Embodiment 1 is that... Replace with The final product was obtained (S)- 4. Example

[0047] The method for detecting chiral amino alcohols in an aqueous phase using the compound prepared in Example 1 includes:

[0048] Preparation of probe solution: (R)- 4 is dissolved in an appropriate amount of chromatographic grade dimethyl sulfoxide to obtain Probe solution;

[0049] Preparation of amino alcohol solution: The amino alcohol is dissolved in ultrapure water to prepare the solution. Amino alcohol solution;

[0050] Preparation of zinc acetate solution: Zinc acetate is dissolved in ultrapure water to prepare... Zinc acetate solution;

[0051] Then add 50g to the centrifuge tubes sequentially. probe solution, 50 Amino alcohol solution, 50 Zinc acetate solution, reaction Then add Ultrapure water to a final volume After shaking well, perform fluorescence testing. The fluorescence testing parameters are as follows: excitation slit width is... The light-emitting slit is The excitation wavelength is . Example

[0052] The difference between this embodiment and Example 3 is that the compound prepared in Example 1 is used instead. (R)- 4. Detection of chiral amino alcohols in aqueous phase.

[0053] In the aqueous phase (R)- 4 itself does not exhibit obvious fluorescence, when (R)- 4 and Valine and During the reaction of zinc acetate, at A strong fluorescence enhancement is produced at the location; when (R)- 4 and When valine and 1 eq zinc acetate react, in A weaker fluorescence enhancement occurs at this location. This results in... (R)- The reason for the difference in fluorescence intensity between D-valine and L-valine is due to... (R)- 4 reacts with D-valine and then with Coordination occurred, forming a ring structure, which enhanced structural rigidity and thus increased fluorescence intensity; while(R)- 4. After reacting with L-valine, no further reaction occurred. It undergoes coordination, therefore its fluorescence intensity is much lower than that of D-valine, such as Figure 5 As shown. Under the same conditions, (S)- 4 showed strong fluorescence enhancement for L-valine and weak fluorescence enhancement for D-valine. (R)- 4 and (S)- 4. The fluorescence response of chiral valine is mirror-image, indicating that the fluorescent probe has a chiral recognition effect on the two enantiomers of valine.

[0054] Expanding the discovery of 17 additional substrates, fluorescent probes (R)- Four pairs of chiral amino alcohols exhibited similar enantioselectivity, with S-configuration amino alcohols producing weaker fluorescence, while R-configuration amino alcohols showed significantly enhanced fluorescence. (R)- 4 in The fluorescence intensity at that location. For example... Figure 6 As shown, the chiral amino alcohols exhibiting high enantioselectivity and enhanced fluorescence include 3-amino-3-phenylpropanol, 3-amino-1,2-propanediol, 2-amino-1-propanol, and 3-amino-1,2-propanediol. Among the remaining chiral amino alcohols, 6 amino alcohols show enhanced fluorescence but lack chemoselectivity, while the remaining 7 chiral amino alcohols show virtually no enhanced fluorescence.

[0055] Therefore, this invention achieves highly enantioselective fluorescence recognition of chiral amino alcohols in an aqueous phase, providing a new method for rapid detection of enantiomeric structures of chiral amino alcohols and has the potential for high-throughput analysis.

[0056] Example 5: This invention explores the influencing factors and principles of fluorescent probe recognition of chiral amino alcohols.

[0057] A test study on the effect of reaction time on the enantioselective recognition of valine.

[0058] from (R)- Take 50 μL of the stock solution from the standard sample 4 and transfer it to a clean container. In centrifuge tubes. Then, aspirate... Or transfer the D-valine sample to a centrifuge tube. Simultaneously, quickly aspirate... Transfer zinc acetate solution to centrifuge tubes. After gentle shaking to mix, react at room temperature for 1 min, 5 min, 10 min, 20 min, 30 min, and 40 min, respectively. After the reaction is complete, add The reaction solution was brought to a final volume with ultrapure water. Immediately after dilution, transfer the solution to a cuvette for fluorescence spectroscopy analysis. Results are referenced below. Figure 7 , Figure 7(a) reflects the fluorescent probe (R)- The recognition effect of D-valine at different time points. Figure 7 (b) reflects the fluorescent probe (R)- The recognition effect of L-valine at different time points. Figure 7 (c) shows the trend of fluorescence intensity of D / L-valine recognition by the fluorescent probe at different reaction times. As can be seen from the figure, the fluorescence intensity increases significantly with increasing reaction time, and... The reaction reached a plateau at a certain point, and the fluorescence intensity remained generally stable thereafter. Therefore, the reaction time was determined to be... .

[0059] A Study on the Effect of D / L Valine Concentration on Enantioselective Recognition of Valine

[0060] from (R)- Take 50 μL of the stock solution from the standard sample 4 and transfer it to a clean container. In centrifuge tubes. Then, aspirate separately... , Add 96 Mm L-valinol or D-valinol to a centrifuge tube. Simultaneously, quickly pipette 50 μL of zinc acetate solution into the centrifuge tube, gently vortex to mix, and allow the reaction to stand. After that, join The reaction solution was brought to a final volume with ultrapure water. Immediately after dilution, transfer the solution to a cuvette for fluorescence spectroscopy testing. The results are referenced in the original text. Figure 8 , Figure 8 (a) reflects the fluorescent probe (R)- The recognition effect of 4 pairs of different equivalents of D-valine. Figure 8 (b) reflects the fluorescent probe (R)- The recognition effect of 4 pairs of different equivalents of L-valine. Figure 8 (c) shows the fluorescent probe. (R)- 4. Identify the trend of fluorescence intensity changes of D / L-valine at different valine concentrations. As shown in the figure, the fluorescence intensity increases significantly with the increase of valine equivalent, and... The fluorescence intensity reaches its peak at a certain point, then decreases slightly before remaining constant. Therefore, the optimal equivalent of the amino alcohol is determined to be... .

[0061] Study on the effect of concentration on the enantioselective recognition of valine

[0062] from (R)- Take 50 μL of the stock solution from the standard sample 4 and transfer it to a clean container. In centrifuge tubes. Then, aspirate... (10 equivalents) L-valine or D-valine into a centrifuge tube. Simultaneously, rapidly aspirate... , , and Pour zinc acetate solution into centrifuge tubes. Gently vortex to mix, then let stand at room temperature. ,join in The reaction solution was brought to a final volume with ultrapure water. Immediately after dilution, transfer the solution to a cuvette for fluorescence spectroscopy analysis. Results are referenced below. Figure 9 , Figure 9 (a) reflects the fluorescent probe (R)- 4 pairs of D-valine in different Recognition performance at different concentrations. Figure 9 (b) reflects the fluorescent probe (R)- 4 pairs of L-valine in different Recognition performance at different concentrations. Figure 9 (c) shows the fluorescent probe. (R)- 4. Identify the fluorescence intensity of D / L-valine at different levels The trend of concentration changes can be seen from the figure. With increasing equivalent concentration, fluorescence intensity increased significantly, and in The fluorescence intensity reaches its peak at a certain point, and then remains essentially constant. Therefore, it is determined that... The best equivalent is .

[0063] (R)- Kinetic studies of 4 and L-valine or D-valine

[0064] Will (R)- 4 (2 mg, 0.0058 mmol) dissolved in Then, L-valine or D-valine (5.98 mg, 0.0580 mmol) and zinc acetate (1.27 mg, 0.0058 mmol) were dissolved in 0.2 mL of heavy water, respectively. The L-valine or D-valine and zinc acetate solution was added to... (R)- 4. In the solution. After mixing thoroughly, the solution was reacted for 5 min, 10 min, 30 min, 1 h, 2 h, 3 h, and 5 h, respectively. The reaction was then analyzed using 1H NMR spectroscopy. (R)- 4. Monitor the interaction process with D / L-valine to further study its reaction mechanism (e.g., Figure 10 ).

[0065] The principle behind the use of the fluorescent probe of this invention for highly enantioselective fluorescent recognition of chiral valine is as follows:

[0066] pass Figure 10A hydrogen nuclear magnetic resonance spectrum can detect that (R)- When 4 reacts with D / L-valine, it can be observed that... aldehyde group The signal completely disappeared within 5 minutes, while the new imine-C H =N-signal in The presence of these features directly demonstrates the formation of imine, thus indicating that the fluorescent probe... (R)- The aldehyde group on probe 4 underwent a condensation reaction with the amino group on D / L-valine, thereby enhancing the probe's strength. (R)- 4 in Fluorescence emission at that location. And causing... (R)- The reason for the difference in fluorescence intensity between D-valine and L-valine is due to... (R)- 4 and D-valine react with Coordination occurred, forming a rigid ring structure, thereby enhancing fluorescence intensity; and (R)- 4. After reacting with L-valine, no further reaction occurred. It has undergone coordination, therefore its fluorescence intensity is much lower than that of D-valine.

[0067] It will be apparent to those skilled in the art that the present invention is not limited to the details of the exemplary embodiments described above, and that the invention can be implemented in other specific forms without departing from the spirit or essential characteristics of the invention. Therefore, the embodiments should be considered in all respects as exemplary and non-limiting, and the scope of the invention is defined by the appended claims rather than the foregoing description. Thus, it is intended that all variations falling within the meaning and scope of equivalents of the claims be included within the present invention.

Claims

1. Use of a fluorescent probe for the identification of chiral amino alcohols, characterized in that, The fluorescent probe has the following structural formula: ; The application of the fluorescent probe is used for highly enantioselective fluorescent recognition of one of chiral amino alcohols selected from the following: 3-amino-3-phenylpropanol, 3-amino-1,2-propanediol, 2-amino-1-propanol, valinol; The preparation method of the fluorescent probe comprises the following steps: Step 1, synthesis of 2,2'-bis(methoxymethoxy)-1,1'-binaphthyl (R)- 1 weighing R- The binaphthol and sodium hydride were dissolved in appropriate amount of super dry tetrahydrofuran respectively, the two solutions were mixed uniformly at appropriate temperature, and then restored to room temperature for reaction; after a certain time, the reaction system was cooled to appropriate temperature, and then bromomethyl methyl ether was added dropwise, followed by restoring to room temperature for overnight reaction; the reaction was quenched by adding ultrapure water under ice water bath condition, and then extracted with ethyl acetate, and the organic phases were combined, dried with anhydrous sodium sulfate, filtered, and then rotary evaporated, and then the product was purified by recrystallization with n-hexane to obtain white solid product (R)- 1; Step 2, synthesis of 2,2'-bis(methoxymethoxy)-[1,1 '-binaphthalenyl]-3,3'- dicarboxylic acid (R)- 2 The white solid product was weighed (R)- 1The white solid product was weighed (R)- 2; Step 3, synthesis of 3'-(hydroxymethyl)-2,2'-bis(methoxymethoxy)-[1,1'- binaphthalenyl]-3-carbaldehyde (R)- 3 Products (R)- 2. Dissolved in a mixed solvent of methanol and tetrahydrofuran, sodium triacetoxyborohydride was added in portions, and the mixture was heated to a suitable temperature and reacted for a certain period of time. The reaction was quenched with ultrapure water under ice-water bath conditions, and then extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and rotary evaporated to obtain a yellow solid. The solid was purified by column chromatography and dried under vacuum to obtain the product. (R)- 3; Step 4, synthesis of 2,2'-dihydroxy-3'-(hydroxymethyl)-[1,1'- binaphthalenyl]-3-carbaldehyde (R)- 4 The product (R)- 3 was dissolved in a mixture of dichloromethane and anhydrous ethanol, and concentrated hydrochloric acid was added dropwise; after a certain period of time, sodium bicarbonate was added to quench the reaction, and dichloromethane was used for extraction; the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain the target product as a yellow solid (R)- 4, the product (R)- 4 is a fluorescent probe for identifying chiral amino alcohols.

2. Use according to claim 1, characterized in that, In step 1, the suitable temperature is -5-5 DEG C; the certain time is 1.5-2.5 h; the recrystallization temperature is set to -20-0 DEG C; the molar ratio of R-coupled naphthol, sodium hydride and bromomethyl methyl ether is 1:6:

3.

3. Use according to claim 1, characterized in that, In step 2, the suitable temperature is -5-5 DEG C; When the reaction system changes from colorless to brown and returns to room temperature, the reaction time is 0.5-1.5 h; When the reaction system changes into grayish white turbid liquid and returns to room temperature, the reaction time is 2.5-3.5 h; The (R)- 1 : n-butyllithium: molar ratio 1 :2.5:2.4; The elution phase volume ratio of the column chromatography purification is petroleum ether: ethyl acetate = 10:

1.

4. Use according to claim 1, characterized in that, In step 3, the suitable temperature is 60 DEG C; the certain time is overnight; the volume ratio of tetrahydrofuran: methanol is 2:1; The elution phase volume ratio of the column chromatography purification is petroleum ether: ethyl acetate = 2:

1.

5. The use according to claim 1, characterized in that, In step 4, the certain time is overnight; The volume ratio of dichloromethane: anhydrous ethanol is 1:1.

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