CN105669389B - A kind of BINOL derivatives and its preparation method and application - Google Patents

A kind of BINOL derivatives and its preparation method and application Download PDF

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CN105669389B
CN105669389B CN201610137620.9A CN201610137620A CN105669389B CN 105669389 B CN105669389 B CN 105669389B CN 201610137620 A CN201610137620 A CN 201610137620A CN 105669389 B CN105669389 B CN 105669389B
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binol
solution
amino alcohol
derivatives
standard solution
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CN105669389A (en
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王力
王钦
韦思平
尤强
刘大亮
彭瑞光
杜曦
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Southwest Medical University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation

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Abstract

The present invention relates to a kind of BINOL derivatives, the BINOL derivatives have R the or S configurations of compound representated by below formula：Wherein, R1, R2It is each independently alkyl or containing fluorophenyl, works as R1、R2Identical and be methyl, ethyl or 3, during 5 two (trifluoromethyl) phenyl, BINOL derivatives have good chiral Recognition effect.The BINOL derivatives of the application can real-time be analyzed, determine chiral amino alcohol absolute configuration, and this method is few using sample size, analysis is quick and precisely, to sample structure not damaged, configuration is determined without complicated chemical reaction, and have the characteristics that with amino alcohol concentration to be measured to increase and Fluorescence Increasing, recognition effect are good.

Description

A kind of BINOL derivatives and its preparation method and application
Technical field
The invention belongs to technical field of chemistry, more particularly to a kind of BINOL derivatives and its preparation method and application.
Background technology
Enantioselectivity fluorescence identification technique can be that the definite offer of chiral organic compound absolute configuration is real-time Analysis detection, to determine the absolute configuration of chiral amino alcohol.This method is few using sample size, analyzes quick and precisely, to sample Structure not damaged.With photoactive 1,1 '-union -2-naphthol derivative has very strong chiral induction effect, and in suitable structure Hyperfluorescence can be produced under base group modification, can be used as fluorescence chemical sensor and Chiral Amine, amino alcohol, amino acid, alpha-hydroxy carboxylic acid compounds, The chiral organic compound such as chiral alcohol and monose acts on, in different recognition site Receiued object molecules so that chemical sensor is glimmering Light strengthens the change with decrease or launch wavelength.Usually used 1,1 '-union -2-naphthol derivative is C2 axial symmetry aromatics Thing, and the effect to amino alcohol shows as fluorescent quenching, and, slope relatively low to the recognition capability of corresponding D- types and L-type amino alcohol Ratio difference is smaller.
The content of the invention
The present invention first purpose be to provide a kind of BINOL derivatives, have the R of compound representated by below formula or S configurations：
Wherein, R1, R2It is each independently C1-10Alkyl or containing fluorophenyl.
Preferably, R1、R2Identical, at this time, BINOL derivatives have good chiral Recognition effect.
Alkyl of the present invention is C1-4Alkyl or C1-6Alkyl or C1-8Alkyl, be preferably C1-4Alkyl, into One step is preferably methyl or ethyl.
The phenyl of the phenyl directly substituted for fluorine atom containing fluorophenyl or the fluoric ether substitution, the fluoric ether are The group that one or more hydrogen on alkyl are replaced by fluorine atoms, of the present invention containing fluorophenyl is preferably 4- (trifluoromethyl) One kind in phenyl, 3- (trifluoromethyl) phenyl, 4- fluorophenyls, 3,5- bis- (trifluoromethyl) phenyl.
There is BINOL (dinaphthol) very strong chiral induction to act on, it is modified using the technological means of the application After can produce hyperfluorescence, when passing through interaction of hydrogen bond with chiral amino alcohol, can in different recognition site Receiued object molecules, Cause the change of its fluorescence intensity by Photo-induced electron transfer (PET) and electron exchange energy transfer (EET) etc., so that very well The chiral Recognition for amino alcohol.
Second object of the present invention is to provide the preparation method of the BINOL derivatives, and the preparation method is：It is right Hydroxyl in BINOL is protected, and gained protection product is reacted with letones, and products therefrom is deprotected to obtain the final product.
Wherein, hydroxyl protection can use technological means commonly used in the art, and present invention preferably employs dimethyl cellosolve group pair Hydroxyl is protected, and dimethyl cellosolve group can be provided by chloromethyl methyl ether.
The present invention provides a kind of preferable preparation method, its reaction mechanism mechanism of reaction is：
Concrete operations are：
(1) under condition of ice bath, first BINOL and NaH is reacted, chloromethyl methyl ether is then added drop-wise to the reaction system, room The lower reaction of temperature, is quenched reaction, extraction, concentrates up to protection product after the reaction was complete；
(2) under -5 DEG C -0 DEG C, anaerobic anhydrous condition, highly basic is added into the solution for dissolving the protection product, then Ketone is added into reaction system, and in reacting under room temperature, reaction, extraction, concentration, column chromatography are quenched after the reaction was complete up to first The intermediate of base methyl ether protection；
(3) after the intermediate is dissolved, acid solution is added, stirring at room temperature is reacted up to BINOL derivatives.
In above-mentioned preparation method, in step (1), BINOL, NaH, the molar ratio of chloromethyl methyl ether are：1：(1.2-2)：(1- 1.3)。。
In step (2), protection product, highly basic, the molar ratio of ketone are 1：(1-1.5)：(1-1.3).
The highly basic can use material commonly used in the art, and present invention preferably employs metal alkyl lithium, specifically may be selected from just One or more in butyl lithium, tert-butyl lithium, lithium amide, phenyl lithium, highly basic can capture the Hydrogen Proton of BINOL 3, shape Viability reaction intermediate.
The letones make choice according to the structure of BINOL derivatives.
Quenching reaction can use this area conventional technology, present invention preferably employs saturated aqueous ammonium chloride, water, One or more quenching reactions in saturated sodium bicarbonate aqueous solution.
The extraction can use solvent well known in the art to carry out, and present invention preferably employs ethyl acetate, dichloromethane, two One or more in chloroethanes, chloroform, ether are as extractant.
The condition of the column chromatography is preferably：Stationary phase is silica gel, and mobile phase is：Ethyl acetate/n-hexane, preferably elutes Gradient is 1:20-1:5, concretely：According to 1:20、1:15、1:10、1:5 carry out gradient elution.
In step (3), acid used is deprotected as concentrated hydrochloric acid, BF3, acetic acid, the one or more in trifluoroacetic acid, preferably For concentrated hydrochloric acid.Depending on the dosage of concentrated hydrochloric acid is according to the amount of BINOL, concretely：Corresponded to per 1mmolBINOL and add 0.5-1.5mL Concentrated hydrochloric acid.
Third object of the present invention is to provide application of the BINOL derivatives in amino alcohol chiral Recognition.
The amino alcohol is preferably one kind in valerian ammonia alcohol, leucinol, phenylalaninol, Propanolamine, benzene glycinol.
Fourth object of the present invention is to provide a kind of side using BINOL derivatives identification chiral beta-alkamine material Method, it is characterised in that include the following steps：
(1) amino alcohol standard solution is prepared：Weigh equivalent D- amino alcohols and L- amino alcohols are dissolved in equivalent solvent respectively, match somebody with somebody D- amino alcohols standard solution and L- amino alcohol standard solution is made；
(2) BINOL derivative standard solution is prepared：The BINOL derivatives for weighing S or R configurations are dissolved in solvent, are configured to BINOL derivative standard solution；
(3) testing sample solution is prepared：Weigh single unknown configuration amino alcohol to be dissolved in solvent, it is molten to be configured to sample to be tested Liquid；
(4) standard solution is measured, obtains regression equation：By the BINOL derivatives standard solution respectively and not The L- amino alcohols standard solution of same amount is uniformly mixed, the fluorescence intensity I and unmixed L- of test mixing solution after standing The fluorescence intensity I of the BINOL derivative standard solution of amino alcohol0；Finally, with the concentration of L- amino alcohols in the mixed solution ([Q]) is abscissa, I0The ratio of/I draws curve for ordinate, obtains regression equation, and calculate its slope K-L；
The method of repeat step (4) is measured D- amino alcohol standard solution, obtains regression equation, calculates its binding constant K-D；
(5) testing sample solution is measured, judges the amino alcohol configuration of sample to be tested：By the BINOL derivatives Standard solution is uniformly mixed with the different amounts of testing sample solution respectively, the fluorescence intensity I of test mixing solution after standing, And the fluorescence intensity I of the BINOL derivative solutions of unmixed testing sample solution0, with the concentration ([Q]) of testing sample solution For abscissa, I0The ratio of/I draws curve for ordinate, obtains regression equation, slope calculations, slope then judges to be measured close to K-L Sample configuration amino alcohol configuration corresponding with K-L is identical, and slope then judges sample to be tested configuration ammonia corresponding with K-D close to K-D Base alcohol configuration is identical.
The present invention relates to abscissa be sample to be tested or the concentration of L- amino alcohols or D- amino alcohols, wherein described " dense The unit of degree " is mol/L.
Preferably, the range of linearity of the regression equation is 0-0.0035.
In addition, the slope ratio of two kinds of configuration amino alcohols can be calculated, the slope ratio for having the sensor of chiral Recognition effect It should be greater than 1 or less than 1, and ratio more deviates 1, recognition effect is better.
Wherein, amino alcohol standard solution is identical with the solvent of testing sample solution, is preferably dichloroethanes, methanol, isopropyl One kind in alcohol, dichloromethane, chloroform, it is preferred to use dichloromethane.
The BINOL derivatives of the application can real-time be analyzed compared with other reagents, determine that chiral amino alcohol is absolute Configuration, and this method is few using sample size, quick and precisely, to sample structure not damaged, configuration is determined without complicated change for analysis Learn reaction, and have the characteristics that with amino alcohol concentration to be measured increase and Fluorescence Increasing, recognition effect are good.
Brief description of the drawings
Fig. 1 is the curve of embodiment 7.
Fig. 2 is the curve of embodiment 8.
Fig. 3 is the curve of embodiment 9.
Fig. 4 is the curve of embodiment 10.
Embodiment
Following embodiments are used to illustrate the present invention, but are not limited to the scope of the present invention.Arrived involved in following embodiments Medicine commercially available acquisition unless otherwise specified, the operation being related to is this area routine operation unless otherwise specified.Its In, the S configurations BINOL of chloromethyl methyl ether protection is prepared via a method which to obtain：Under condition of ice bath, by (S)-BINOL THF solution instill NaH THF suspensions in, chloromethyl methyl ether is then added drop-wise to the reaction system, is reacted at room temperature, instead Should completely afterwards plus water quenching go out reaction, extraction, concentrate to obtain the final product.Similarly, the R configurations BINOL of chloromethyl methyl ether protection is using identical Method prepare, its differ only in raw material use R configurations BINOL.
In addition, the BINOL derivatives of R configurations can also use the method described in embodiment 4-6 to be prepared, by S configurations BINOL replaces with the BINOL of R configurations.
Embodiment 1：Sensor 1 with following structures
((S)-3-(2-hydroxypropan-2-yl)-1,1'-binaphthyl-2,2'-diol)
Embodiment 2：Sensor 2 with following structures
((S)-3-(3-hydroxypentan-3-yl)-1,1'-binaphthyl-2,2'-diol)
Embodiment 3：Sensor 3 with following structures
((S)-3-(hydroxydiphenylmethyl)-1,1'-binaphthyl-2,2'-diol)
Embodiment 4：
The embodiment provides the synthesis of sensor 1 described in embodiment 1, is specially：0 DEG C, under nitrogen protection, toward chloromethyl first In (S)-BINOL tetrahydrofuran solutions of ether protection n-butyllithium solution (14.4mmol) is added in (12mmol, THF 120mL) And be stirred at room temperature 5 it is small when.Anhydrous propanone is added to reaction system and is warming up to room temperature reaction overnight.Reaction is through saturated ammonium chloride Aqueous solution is quenched and is extracted with ethyl acetate, and merges organic phase, it is molten that removing is evaporated under reduced pressure after being dried with anhydrous magnesium sulfate in organic phase Agent, through column chromatography for separation, (eluant, eluent is ethyl acetate/n-hexane to residue, v/v=1:20-1:5) dimethyl cellosolve protection is obtained Intermediate.Intermediate is dissolved in tetrahydrofuran and adds 10mL concentrated hydrochloric acids and is stirred at room temperature, it is symmetrically glimmering to obtain BINOL derivatives C1 Optical sensor 1.Yield 48%.1H NMR(400MHz/CDCl3)δ1.83(s,6H),3.28(s,1H),5.17(s,1H),7.12 (d, J=8.00Hz, 2H), 7.24-7.27 (m, 2H), 7.31-7.38 (m, 3H), 7.83-7.86 (m, 3H), 7.91 (d, J= 12.00Hz,1H),8.33(s,1H).13C NMR(100MHz,CDCl3)δ29.9,30.0,74.9,113.7,113.7,117.7, 123.4,124.0,124.2,124.6,126.0,126.7,127.1,128.2,128.3,128.5,129.2,130.3, 133.2,133.5,134.1,151.7,152.1.HRMS(ESI)m/z:calcd.for C23H19O3[M-H]-: 343.1334.Found 343.1299.
Embodiment 5：
The embodiment provides the synthesis of sensor 2 described in embodiment 2, and with embodiment 1, it is differed only in its synthetic method The ketone of use is different, and the present embodiment uses anhydrous propione, yield 51%.1H NMR(400MHz,CDCl3)δ0.95-0.98 (m,6H),2.00-2.05(m,2H),2.14-2.22(m,2H),2.61(s,1H),5.09(s,1H),7.10-7.12(m,2H), 7.23-7.30 (m, 2H), 7.32-7.38 (m, 2H), 7.73 (s, 1H), 7.82-7.87 (q, J=8.00Hz, 2H), 7.93 (d, J =12.00Hz, 1H), 8.96 (s, 1H)13C NMR(100MHz,CDCl3)δ8.1,8.1,33.3,33.6,81.5,113.3, 114.3,117.4,123.4,123.8,124.2,124.6,126.6,127.0,128.0,128.2(2C),128.3,129.3, 130.1,133.3,133.5,151.5,153.4.HRMS(ESI)m/z:calcd.for C25H23O3[M-H]-: 371.1647.Found 371.1607.
Embodiment 6：
The embodiment provides the synthesis of sensor 3 described in embodiment 3, its synthetic method only exists with embodiment 1, its difference Different in the ketone of use, the present embodiment uses anhydrous 3,3', 5,5'-tetra- (trifluoromethyl) benzophenone, yield 37%.1H NMR(400MHz,CDCl3) δ 5.05 (s, 1H), 5.34 (s, 1H), 5.54 (s, 1H), 7.02-7.05 (m, 2H), 7.21 (d, J= 8.00Hz, 1H), 7.31-7.46 (m, 5H), 7.74 (d, J=8.00Hz, 1H), 7.86-7.89 (m, 6H), 7.98-8.00 (m, 2H).13C NMR(100MHz,CDCl3)δ52.87,149.25,148.01,146.49,133.31,133.02,132.25, 131.97,131.91,131.58,131.33,131.25,130.60,129.37,129.17,128.66,128.51,128.38, 127.89,127.86,127.26,127.22,125.36,124.47,124.34,124.10,123.31,122.21,122.17, 122.13,122.09,121.76,117.86,114.48,110.11,109.31,80.84.HRMS(ESI)m/z:calcd.for C37H19F12O3[M-H]-:739.1143.Found 739.1046.
Embodiment 7：Chiral Recognition of the sensor 1 to valerian ammonia alcohol
(1) amino alcohol standard solution is prepared：Take fluorescent optical sensor 1 to be dissolved in dichloromethane, be configured to concentration as 5 × 10-3μ 1 standard solution of sensor of mol/mL；
(2) BINOL derivative standard solution is prepared：The L- valerian ammonia alcohols and D- valerian ammonia alcohols for taking equivalent are dissolved in equivalent dichloro respectively In methane solvent, it is 0.1 μm of ol/ μ l L- valerian ammonia alcohols standard solution and D- valerian ammonia alcohol standard solution to be configured to concentration；
(3) testing sample solution is prepared：The amino alcohol of single unknown configuration is taken to be dissolved in dichloromethane, being configured to concentration is The testing sample solution of 0.1 μm of ol/ μ l；
(4) standard solution is detected, obtains regression equation：Take 1 standard solution 3ml of sensor respectively with 0 μ l, 20 μ L, 40 μ l, 60 μ l, 80 μ l, 100 μ l L- valerian ammonia alcohol standard solution mix and stand 30 minutes, then test each mixed solution The fluorescence intensity I of 1 standard solution of fluorescence intensity I and sensor of sample0, each sample is parallel to be done 3 times, and fluorescence intensity is made even Average.
With I0The ratio of/I is ordinate, and the concentration of L- valerian ammonia alcohols maps for abscissa and carries out Linear Quasi in mixed solution Close, obtain regression equation, and record slope K-L；The regression equation for obtaining D- valerian ammonia alcohols in a like fashion is adopted, and is recorded with reference to normal Number K-D, regression equation are shown in attached drawing 1；
(5) amino alcohol of unknown configuration is detected：Take 0 μ, 20 μ l, 40 μ l, 60 μ l, 80 μ l, 100 μ l testing sample solutions, and Add 1 standard solution of 3ml sensors thereto respectively, the fluorescence for being uniformly mixed and each sample being tested after standing 30 minutes is strong Degree, and the fluorescence intensity of 1 standard solution of sensor, each sample is parallel to be done 3 times, and fluorescence intensity is averaged.
With I0/ I ratios are ordinate, and unknown configuration valerian ammonia alcohol concentration is gone forward side by side line for abscissa mapping in mixed solution Fitting, obtains regression equation, and it is -3.891 to record slope K, is approached with K-L, judge this valerian ammonia alcohol is configured as L-type.
Binding constant ratio K-D/K-L=13.32, it is a kind of good chiral Recognition material to illustrate sensor 1；Using this The common specific rotatory power method in field contrasts the valerian ammonia alcohol and standard sample of unknown configuration in step (5), after testing its structure Type is really L-type, illustrates that sensor 1 can accurately be used for the chiral Recognition of valerian ammonia alcohol.
Embodiment 8：Chiral Recognition of the sensor 1 to leucinol
The embodiment is identical with the operating procedure of embodiment 7 to the chiral Recognition method of leucinol, its differ only in by L- valerian ammonia alcohols replace with L- leucinols, and D- valerian ammonia alcohols are replaced with D- leucinols.Obtained curve and regression equation is shown in attached drawing 2, The slope ratio K-D/K-L=3.28 of the two, it is a kind of good chiral Recognition material to illustrate it.To the leucinol of unknown configuration When being identified, the slope of obtained regression equation is -40.092, is approached with K-D, judge this leucinol is configured as D types.
The leucinol of unknown configuration is measured using specific rotatory power method commonly used in the art, its configuration is certain after testing For D types, illustrate that sensor 1 can accurately be used for the chiral Recognition of leucinol.
Test example 9：Chiral Recognition of the sensor 2 to valerian ammonia alcohol
The embodiment is identical with the operating procedure of embodiment 7 to the chiral Recognition method of valerian ammonia alcohol, its differ only in by Sensor 1 replaces with sensor 2 and carries out chiral Recognition, and obtained curve and regression equation is shown in attached drawing 3, the slope ratio K- of the two D/K-L=7.92, it is a kind of good chiral Recognition material to illustrate it.When the valerian ammonia alcohol of unknown configuration is identified, obtain The slope of regression equation is -23.453, is approached with K-L, judge this valerian ammonia alcohol is configured as L-configuration.
The valerian ammonia alcohol and standard sample of unknown configuration are contrasted using specific rotatory power method commonly used in the art, after testing Its configuration is really L-type, illustrates that sensor 2 can be used in the chiral Recognition of valerian ammonia alcohol.
Test example 10：Chiral Recognition of the sensor 3 to phenylalaninol
The embodiment is identical with the operating procedure of embodiment 1 to the chiral Recognition method of phenylalaninol, it is differed only in Sensor 1 is replaced with into sensor 3, valerian ammonia alcohol is replaced with into phenylalaninol, obtained curve and regression equation is shown in attached drawing 4, two The slope ratio K-L/K-D=2.29 of person, it is a kind of good chiral Recognition material to illustrate it.To the phenylalaninol of unknown configuration When being identified, the slope of obtained regression equation is -77.039, is approached with D types, judge this phenylalaninol is configured as D types.
The phenylalaninol and standard sample of unknown configuration are contrasted using specific rotatory power method commonly used in the art, through inspection It is really D types to survey its configuration, illustrates that sensor 3 can accurately be used for the chiral Recognition of phenylalaninol.
Although above the present invention is made to retouch in detail with general explanation, embodiment and experiment State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art 's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed Scope.

Claims (16)

1. a kind of BINOL derivatives, have R the or S configurations of compound representated by below formula：
Wherein, R1, R2It is all C1-10Alkyl or containing fluorophenyl.
2. BINOL derivatives according to claim 1, it is characterised in that：The alkyl is C1-8Alkyl；It is described fluorine-containing Phenyl is selected from one in 4- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 4- fluorophenyls, 3,5- bis- (trifluoromethyl) phenyl Kind.
3. BINOL derivatives according to claim 2, it is characterised in that：The alkyl is C1-6Alkyl.
4. BINOL derivatives according to claim 3, it is characterised in that：The alkyl is C1-4Alkyl.
5. BINOL derivatives according to claim 2, it is characterised in that：The alkyl is methyl or ethyl.
6. the preparation method of any one of the claim 1-5 BINOL derivatives, it is characterised in that：To the hydroxyl in BINOL into Row protection, gained protection product react with letones, products therefrom are deprotected to obtain the final product.
7. the preparation method of BINOL derivatives according to claim 6, it is characterised in that：Using dimethyl cellosolve base to described Hydroxyl is protected.
8. the preparation method according to claim 6 or 7, it is characterised in that：The reaction mechanism mechanism of reaction of the preparation method is：
Include the following steps：
(1) under condition of ice bath, first BINOL and NaH is reacted, chloromethyl methyl ether is then added drop-wise to the reaction system, at room temperature Reaction, is quenched reaction, extraction, concentrates up to protection product after the reaction was complete；
(2) under -5 DEG C -0 DEG C, anaerobic anhydrous condition, highly basic is added into the solution for dissolving the protection product, then by ketone Reaction system is added, and in reacting under room temperature, reaction, extraction, concentration, column chromatography are quenched after the reaction was complete up to methyl first The intermediate of ether protection；
(3) after the intermediate is dissolved, acid solution is added, stirring at room temperature is reacted up to BINOL derivatives.
9. preparation method according to claim 8, it is characterised in that：The highly basic is metal alkyl lithium class compound, ammonia Base lithium or phenyl lithium；
And/or the protection product, highly basic, the molar ratio of ketone are 1：(1-1.5)：(1-1.3).
10. preparation method according to claim 9, it is characterised in that：The highly basic is n-BuLi, the one of tert-butyl lithium Kind is a variety of.
11. application of the claim 1-5 any one of them BINOL derivatives in amino alcohol chiral Recognition.
12. application according to claim 11, it is characterised in that：The amino alcohol is valerian ammonia alcohol, leucinol, phenylpropyl alcohol ammonia One kind in alcohol, Propanolamine, benzene glycinol.
13. a kind of method that usage right requires any one of the 1-5 BINOL derivatives identification chiral beta-alkamine materials, its It is characterized in that, includes the following steps：
(1) amino alcohol standard solution is prepared：The D- amino alcohols and L- amino alcohols for weighing equivalent are dissolved in equivalent solvent respectively, are prepared Into D- amino alcohols standard solution and L- amino alcohol standard solution；
(2) BINOL derivative standard solution is prepared：The BINOL derivatives for weighing S or R configurations are dissolved in solvent, are configured to BINOL derivative standard solution；
(3) testing sample solution is prepared：Weigh single unknown configuration amino alcohol to be dissolved in solvent, be configured to testing sample solution；
(4) standard solution is measured, obtains regression equation：The respectively and not same amount by the BINOL derivatives standard solution The L- amino alcohols standard solution be uniformly mixed, fluorescence intensity I and BINOL the derivative mark of test mixing solution after standing The fluorescence intensity I of quasi- solution0；Finally, using the concentration of L- amino alcohols in the mixed solution as abscissa, I0The ratio of/I is vertical Coordinate draws curve, obtains regression equation, and calculate its slope K-L；
The method of repeat step (4) is measured D- amino alcohol standard solution, obtains regression equation, calculates its binding constant K-D；
(5) testing sample solution is measured, judges the amino alcohol configuration of sample to be tested：By the BINOL derivatives standard Solution is uniformly mixed with the different amounts of testing sample solution respectively, the fluorescence intensity I of test mixing solution after standing, and The fluorescence intensity I of BINOL derivative solutions0, using the concentration of testing sample solution in mixed solution as abscissa, I0The ratio of/I Curve is drawn for ordinate, obtains regression equation, slope calculations, slope then judges that sample to be tested configuration is corresponding with K-L close to K-L Amino alcohol configuration is identical, and slope then judges that sample to be tested configuration amino alcohol configuration corresponding with K-D is identical close to K-D.
14. according to the method for claim 13, it is characterised in that：The range of linearity of the regression equation is 0-0.0035.
15. the method according to claim 13 or 14, it is characterised in that：The solvent for dissolving amino alcohol and sample to be tested is two One or more in chloroethanes, dichloromethane, methanol, isopropanol, chloroform.
16. according to the method for claim 15, it is characterised in that：The solvent for dissolving amino alcohol and sample to be tested is dichloromethane Alkane.
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