CN103497160B - A kind of Chiral amine functional ionic liquid and preparation thereof - Google Patents

A kind of Chiral amine functional ionic liquid and preparation thereof Download PDF

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CN103497160B
CN103497160B CN201310439053.9A CN201310439053A CN103497160B CN 103497160 B CN103497160 B CN 103497160B CN 201310439053 A CN201310439053 A CN 201310439053A CN 103497160 B CN103497160 B CN 103497160B
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ionic liquid
aliphatic chain
chirality
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应安国
杨建国
胡华南
李嵘嵘
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Liu Zheng
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Taizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
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Abstract

The present invention relates to new chemical material and preparing technical field thereof, provide a kind of generation condensation reaction by chirality cyclohexanediamine and imidazoles SULPHURYL CHLORIDE, condensation product is by being obtained by reacting chiral ionic liquid and preparation method thereof with halogenated alkane, described ionic liquid has following structural formula I, wherein, R 1for the aliphatic chain of C1 ~ C4, R 2for the aliphatic chain of C1 ~ C5, X --for Br --, BF 4 --, PF 6 --, NTf 2 --, OAc --deng.Such chiral ionic liquid preparation technology is simple, has dual chirality spatiall induction catalytic performance, can be used as a kind of efficient chirality catalyst application in organic synthesis.

Description

A kind of Chiral amine functional ionic liquid and preparation thereof
Technical field:
The present invention relates to new chemical material and preparing technical field, specifically, relate to a kind of chiral ionic liquid and preparation method thereof.
Background technology:
In the past few decades, ionic liquid has a very wide range of applications in organic synthesis and separation and purification field as reaction medium and catalyzer.As everyone knows, ionic liquid is made up of organic cation and inorganic or organic anion, is the salt of liquid state under room temperature or near room temperature.Ionic liquid has the advantages such as low volatility, low melting point, structure designability, broadening window, good conductivity and good solubility energy, makes it all be widely used in every field.Chinese patent CN101148392, CN1563008, CN1810757, CN1712093 etc. have set forth the application of ionic liquid in extracting and separating.Ionic liquid is successfully applied to field of nanometer technology by Chinese patent CN101177252, CN11600429, CN101177299 etc.Chinese patent CN101164122, CN101248495 etc. report the applicable cases that ionic liquid is prepared at electro-conductive material and conducting film.Along with the requirement of the optical purity to new drug newly developed improves day by day, the exploitation of chiral catalyst more and more pay attention to by chemists.Therefore the chirality function ionic liquid of development of new becomes when the very critical task of last item.Because sulfonamides material is a kind of outstanding hydrogen bond donor, the chiral ionic liquid that the combination of it and proline(Pro) is prepared demonstrates good catalytic activity (Org.Lett.2009,11,1037.) in asymmetric Michael reaction.But as far as we know, the chirality function ionic liquid that sulfonamides material and the condensation of chirality cyclohexanediamine produce is reported there are no people.Consider the three-dimensional inducibility that chirality cyclohexanediamine is outstanding, we are necessary to prepare the chirality function ionic liquid that sulfonamides material and the condensation of chirality cyclohexanediamine produce.
Summary of the invention
The object of the invention there are provided a kind of generation condensation reaction by chirality cyclohexanediamine and imidazoles SULPHURYL CHLORIDE, and condensation product by being obtained by reacting chiral ionic liquid with halogenated alkane, and provides the preparation method of this kind of ionic liquid.
According to an aspect of the present invention, the invention provides a kind of with (1R, 2R)-2-aminocyclohexyl t-butyl carbamate and the chirality function ionic liquid with the condensation product basis of imidazoles SULPHURYL CHLORIDE, described chirality function ionic liquid has following structural formula I:
Wherein, R 1for the aliphatic chain of C1 ~ C4, R 2for the aliphatic chain of C1 ~ C5, X --for Br --, BF 4 --, PF 6 --, NTf 2 -, OAc -.
Wherein, described R 1the aliphatic chain of C1 ~ C4 be CH 3, CH 3cH 2, CH 3cH 2cH 2, and CH 3cH 2cH 2cH 2.
Wherein, described R 2the aliphatic chain of C1 ~ C5 be CH 3, CH 3cH 2, CH 3cH 2cH 2, CH 3cH 2cH 2cH 2and CH 3cH 2cH 2cH 2cH 2.
Preferably, described chirality function ionic liquid is:
According to an aspect of the present invention; the invention provides a kind of preparation method of chirality function ionic liquid; wherein; (1R; 2R)-2-aminocyclohexyl t-butyl carbamate with at temperature of reaction is 0 ~ 30 DEG C, carry out condensation reaction with imidazoles SULPHURYL CHLORIDE; the condensation product obtained and halogenated alkane react, ion exchange reaction and deprotection reaction obtain described chirality function ionic liquid, and its reaction equation is as follows:
Wherein, R 1for the aliphatic chain of C1 ~ C4, R 2for the aliphatic chain of C1 ~ C5, X --for Br --, BF 4 --, PF 6 --, NTf 2 -, OAc -.
Wherein, described R 1the aliphatic chain of C1 ~ C4 be CH 3, CH 3cH 2, CH 3cH 2cH 2, and CH 3cH 2cH 2cH 2.
Wherein, described R 2the aliphatic chain of C1 ~ C5 be CH 3, CH 3cH 2, CH 3cH 2cH 2, CH 3cH 2cH 2cH 2and CH 3cH 2cH 2cH 2cH 2.
The intermediate of preparation and chiral ionic liquid are used 1hNMR, 13cNMR structural confirmation.
Novel ion liquid provided by the invention and preparation method thereof, compared to the prior art, has following unusual effect:
(1) the present invention is to provide a kind of novel ion liquid, develop the new variety of ionic liquid;
(2) new function ionic liquid provided by the invention has chiral configuration, possesses outstanding dual stereoselectivity catalytic activity, can be used as from now in a kind of chiral catalyst application asymmetry catalysis.
Embodiment
Below with reference to embodiment, the present invention will be further described, and embodiments of the invention are only for illustration of technical scheme of the present invention, and non-limiting the present invention.
Embodiment 1
(1R is added in 250 milliliters of there-necked flasks, 2R)-2-aminocyclohexyl t-butyl carbamate 1 (7.1g, 33mmol), triethylamine (3.6g, 36mmol) with methylene dichloride (50mL), about 0 DEG C starts the dichloromethane solution (30mL) dripping 1-methyl-2-SULPHURYL CHLORIDE imidazoles 2 (6g, 33mmol).After dropping terminates, room temperature reaction 2 hours, TLC point plate reacts completely, washing, then use dichloromethane extraction, merge organic phase, with anhydrous sodium sulfate drying, filter, remove solvent under reduced pressure, column chromatography for separation obtains white solid 3 (11.3g), yield 96%.Reaction formula is:
1HNMR(400MHz,CDCl 3)(ppm):1.05-1.31(m,4H),1.43(s,9H),1.55-1.63(m,2H),1.76-1.83(m,2H),2.28-2.37(m,1H),2.95-3.01(m,1H),3.83(s,3H),6.96(s,1H),7.33(s,1H); 13CNMR(100MHz,CDCl 3)(ppm):156.9,126.3,123.9,119.5,79.2,56.8,54.9,35.8,32.7,28.1,24.7,24.3.
In 250 milliliters of there-necked flasks, add condensation product 3 (3.58g, 10mmol), methyl iodide (1.86mL, 30mmol) and toluene (40mL), reflux 6 hours, TLC detects, and reaction completes.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 4 (4.35g), yield 87%.Reaction formula is:
1HNMR(400MHz,CDCl 3)(ppm):1.12-1.44(m,4H),1.42(s,9H),1.45-1.58(m,2H),1.78-1.83(m,2H),2.23-2.38(m,1H),3.01-3.08(m,1H),3.89(s,3H),3.95(s,3H),7.05(s,1H),7.41(s,1H); 13CNMR(100MHz,D 2O)(ppm):157.1,125.9,125.1,120.5,80.3,56.9,53.8,35.8,34.7,33.4,29.5,25.3,24.2.
4 (5.0g, 10mmol) are added, NaBF in 100 milliliters of there-necked flasks 4(1.09g, 10mmol) and dehydrated alcohol (50mL), reflux 12 hours.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 5 (4.71g), yield 91%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.15-1.41(m,4H),1.45(s,9H),1.43-1.69(m,4H),2.32-2.39(m,1H),2.95-3.06(m,1H),3.93(s,3H),4.01(s,3H),7.11(s,1H),7.38(s,1H); 13CNMR(100MHz,D 2O)(ppm):158.3,125.6,125.5,118.3,82.1,56.6,52.2,36.8,33.2,31.4,28.8,26.3,25.6.
5 (2.3g, 5mmol), the 4M hydrochloric acid dioxane aqueous solution (20 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 6 (1.67g), yield 93%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.01-1.23(m,4H),1.53-1.64(m,4H),1.75(d,1H,J=12.8Hz),1.78(d,1H,J=12.8Hz),2.36-2.38(m,1H),2.70-2.75(m,1H),3.92(s,3H),3.96(s,3H),6.99(s,1H),7.36(s,1H); 13CNMR(100MHz,D 2O)(ppm):127.6,124.3,119.2,68.8,67.0,66.5,31.2,29.7,24.9,24.6.
Embodiment 2
4 (5.0g, 10mmol) are added, LiNTf in 100 milliliters of there-necked flasks 2(2.87g, 10mmol) and dehydrated alcohol (50mL), reflux 12 hours.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C,
5 hours) obtain yellow oily liquid 7 (6.06g), yield 93%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.12-1.38(m,4H),1.38(s,9H),1.49-1.73(m,4H),2.35-2.41(m,1H),2.83-2.92(m,1H),3.91(s,3H),3.98(s,3H),7.02(s,1H),7.28(s,1H); 13CNMR(100MHz,D 2O)(ppm):161.3,126.2,125.9,118.1,84.2,55.8,50.9,36.2,35.8,29.6,28.2,26.7,23.5.
7 (0.6g, 1mmol), the 4M hydrochloric acid dioxane aqueous solution (4 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 8 (0.48g), yield 88%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.15-1.29(m,4H),1.56-1.68(m,4H),1.68(d,1H,J=12.8Hz),1.73(d,1H,J=12.8Hz),2.28-2.33(m,1H),2.68-2.78(m,1H),3.95(s,3H),3.98(s,3H),7.13(s,1H),7.39(s,1H); 13CNMR(100MHz,D 2O)(ppm):129.2,125.8,118.7,66.5,67.1,66.3,33.8,29.3,25.4,23.2.
Embodiment 3
In 100 milliliters of there-necked flasks, add 4 (2.5g, 5mmol), NaOAc (0.41g, 5mmol) and dehydrated alcohol (25mL), reflux 12 hours.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 9 (2.05g), yield 96%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.06-1.27(m,4H),1.32(s,9H),1.38-1.59(m,4H),1.85(s,3H),2.31-2.36(m,1H),2.71-2.83(m,1H),3.96(s,3H),4.08(s,3H),7.11(s,1H),7.34(s,1H); 13CNMR(100MHz,D 2O)(ppm):165.1,125.9,119.6,86.3,53.3,49.6,38.1,35.7,29.6,28.2,26.8,26.3,22.8.
9 (0.6g, 1mmol), the 4M hydrochloric acid dioxane aqueous solution (4 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 10 (0.48g), yield 88%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.21-1.28(m,4H),1.55-1.70(m,4H),1.63(d,1H,J=12.4Hz),1.69(d,1H,J=12.4Hz),1.86(s,3H),2.23-2.31(m,1H),2.68-2.76(m,1H),3.95(s,3H),3.98(s,3H),7.13(s,1H),7.39(s,1H); 13CNMR(100MHz,D 2O)(ppm):130.5,125.6,120.9,68.1,67.5,64.8,34.6,31.3,29.4,25.9,23.9.
Embodiment 4
In 250 milliliters of there-necked flasks, add condensation product 3 (3.58g, 10mmol), N-PROPYLE BROMIDE (0.91mL, 10mmol) and toluene (30mL), reflux 8 hours, TLC detects, and reaction completes.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 11 (4.08g), yield 85%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):1.12-1.44(m,4H),1.42(s,9H),1.45-1.58(m,2H),1.78-1.83(m,2H),2.23-2.38(m,1H),3.01-3.08(m,1H),3.89(s,3H),3.95(s,3H),7.05(s,1H),7.41(s,1H); 13CNMR(100MHz,D 2O)(ppm):157.1,125.9,125.1,16.5.120.5,80.3,56.9,53.8,35.8,34.7,33.4,29.5,25.3,24.2.
11 (2.4g, 5mmol), the 4M hydrochloric acid dioxane aqueous solution (4 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 12 (1.75g), yield 92%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.99(t,3H,J=7.2Hz),1.13-1.72(m,6H),1.47-1.62(m,4H),1.58(d,1H,J=12.4Hz),1.65(d,1H,J=12.4Hz),2.09-2.14(m,1H),2.51-2.63(m,1H),3.83(t,2H,J=7.2Hz),3.93(s,3H),7.08(s,1H),7.32(s,1H); 13CNMR(100MHz,D 2O)(ppm):131.2,124.8,121.5,67.91,67.1,64.6,35.2,34.4,32.5,30.9,29.6,24.8,23.5.
Embodiment 5
11 (4.8g, 5mmol) are added, NaBF in 100 milliliters of there-necked flasks 4(1.1g, 10mmol) and dehydrated alcohol (50mL), reflux 12 hours.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 13 (2.2g), yield 90%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.92(t,3H,J=7.2Hz),1.21-1.45(m,6H),1.48(s,9H),1.51-1.72(m,4H),2.35-2.41(m,1H),2.89-3.01(m,1H),3.93(t,3H,J=7.2Hz),4.03(s,3H),7.08(s,1H),7.31(s,1H); 13CNMR(100MHz,D 2O)(ppm):157.9,125.3,125.1,119.2,82.3,55.8,53.1,36.3,33.5,30.8,29.1,26.2,24.7.
13 (2.44g, 5mmol), the 4M hydrochloric acid dioxane aqueous solution (20 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 14 (1.69g), yield 87%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.91(t,3H,J=7.2Hz),1.03-1.18(m,4H),1.48-1.58(m,6H),1.69(d,1H,J=12.8Hz),1.75(d,1H,J=12.8Hz),2.28-2.35(m,1H),2.71-2.75(m,1H),3.86(t,2H,J=7.2Hz),3.91(s,3H),7.08(s,1H),7.31(s,1H); 13CNMR(100MHz,D 2O)(ppm):128.3,124.6,120.3,69.2,66.4,66.1,32.7,31.6,29.5,25.3,24.8.
Embodiment 6
11 (4.8g, 10mmol) are added, LiNTf in 100 milliliters of there-necked flasks 2(2.87g, 10mmol) and dehydrated alcohol (50mL), reflux 12 hours.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 15 (5.39g), yield 86%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.88(t,3H,J=7.2Hz),1.15-1.36(m,6H),1.45(s,9H),1.53-1.68(m,4H),2.28-2.43(m,1H),3.02-3.09(m,1H),3.96(t,3H,J=7.2Hz),4.08(s,3H),7.11(s,1H),7.31(s,1H); 13CNMR(100MHz,D 2O)(ppm):158.2,125.5,124.8,120.6,83.5,56.4,53.5,38.2,33.5,31.2,29.5,25.8,25.3.
15 (0.6g, 1mmol), the 4M hydrochloric acid dioxane aqueous solution (5 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains brown oil liquid 16 (0.49g), yield 91%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.93(t,3H,J=7.2Hz),1.05-1.19(m,4H),1.39-1.61(m,6H),1.61(d,1H,J=12.8Hz),1.73(d,1H,J=12.8Hz),2.31-2.36(m,1H),2.63-2.71(m,1H),3.88(t,2H,J=7.2Hz),3.91(s,3H),7.13(s,1H),7.32(s,1H); 13CNMR(100MHz,D 2O)(ppm):129.1,125.2,120.1,68.6,66.5,64.2,32.9,30.9,28.2,24.3,22.9.
Embodiment 7
(1R is added in 250 milliliters of there-necked flasks, 2R)-2-aminocyclohexyl t-butyl carbamate 1 (7.1g, 33mmol), N, N-diisopropylethylamine (3.9g, 33mmol) with chloroform (80mL), about 0 DEG C starts the dichloromethane solution (30mL) dripping 1-n-propyl-2-SULPHURYL CHLORIDE imidazoles 17 (6g, 33mmol).After dropping terminates, room temperature reaction 3 hours, TLC point plate reacts completely, washing, then use dichloromethane extraction, merge organic phase, with anhydrous sodium sulfate drying, filter, remove solvent under reduced pressure, column chromatography for separation obtains white solid 18 (10.0g), yield 85%.Reaction formula is:
1HNMR(400MHz,CDCl 3)(ppm):0.88(s,3H,J=7.2Hz),1.05-1.36(m,6H),1.43(s,9H),1.54-1.63(m,2H),1.74-1.80(m,2H),2.29-2.37(m,1H),2.98-3.05(m,1H),3.79(t,3H,J=7.2Hz),7.08(s,1H),7.31(s,1H); 13CNMR(100MHz,CDCl 3)(ppm):157.6,129.2,123.5,119.1,78.8,57.5,55.3,35.8,33.9,28.6,25.7,23.9.
In 250 milliliters of there-necked flasks, add condensation product 18 (3.58g, 10mmol), bromo pentane silane (1.86mL, 30mmol) and toluene (40mL), reflux 8 hours, TLC detects, and reaction completes.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 19 (4.27g), yield 84%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.93(t,3H,J=7.2Hz),0.96(t,3H,J=7.2Hz),1.08-1.48(m,8H),1.38(s,9H),1.52-1.59(m,2H),1.79-1.82(m,2H),2.33-2.39(m,1H),2.91-3.03(m,1H),3.82-3.88(m,6H),7.12(s,1H),7.29(s,1H); 13CNMR(100MHz,D 2O)(ppm):157.3,130.2,123.5,118.6,79.2,59.3,56.8,37.9,35.8,35.6,33.6,28.1,26.1,24.3,23.8.
19 (2.54g, 5mmol), the 4M hydrochloric acid dioxane aqueous solution (30 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 20 (1.88g), yield 92%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.89(t,3H,J=7.2Hz),0.92(t,3H,J=7.2Hz),1.08-1.45(m,8H),1.52-1.66(m,6H),1.78(d,1H,J=12.4Hz),1.83(d,1H,J=12.4Hz),2.33-2.41(m,1H),2.71-2.75(m,1H),3.86-3.92(m,4H),7.05(s,1H),7.32(s,1H); 13CNMR(100MHz,D 2O)(ppm):131.6,125.2,121.2,69.3,68.2,66.5,63.9,35.4,33.7,31.4,29.8,27.5,25.8,24.6,22.1.
Embodiment 8
19 (5.08g, 10mmol) are added, KBF in 100 milliliters of there-necked flasks 6(1.26g, 10mmol) and dehydrated alcohol (60mL), reflux 12 hours.Remove solvent under reduced pressure, with anhydrous diethyl ether washing, vacuum drying (60 DEG C, 5 hours) obtains yellow oily liquid 21 (4.20g), yield 82%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.89(t,3H,J=6.4Hz),0.93(t,3H,J=6.4Hz),1.03-1.48(m,8H),1.42(s,9H),1.53-1.62(m,2H),1.82-1.87(m,2H),2.35-2.45(m,1H),2.95-2.99(m,1H),3.79-3.86(m,6H),7.10(s,1H),7.31(s,1H); 13CNMR(100MHz,D 2O)(ppm):156.9,131.2,123.8,119.8,78.6,60.3,56.3,38.4,35.5,35.1,32.9,29.3,27.6,25.5,23.9,21.6.
21 (5.13g, 10mmol), the 4M hydrochloric acid dioxane aqueous solution (50 milliliters) is added, stirring at room temperature 12 hours in 100 milliliters of there-necked flasks.Remove solvent under reduced pressure, use alkali alumina column chromatography, anhydrous methanol wash-out obtains pale yellow oily liquid body 22 (3.72g), yield 90%.Reaction formula is:
1HNMR(400MHz,D 2O)(ppm):0.91(t,3H,J=6.4Hz),0.95(t,3H,J=6.4Hz),1.11-1.48(m,8H),1.55-1.68(m,6H),1.82(d,1H,J=12.4Hz),1.85(d,1H,J=12.4Hz),2.33-2.43(m,1H),2.69-2.73(m,1H),3.79-3.88(m,4H),7.03(s,1H),7.33(s,1H); 13CNMR(100MHz,D 2O)(ppm):130.8,126.3,121.8,70.4,68.1,66.3,62.8,36.4,33.8,31.9,30.5,27.8,24.8,23.7,21.6.
It should be noted that, foregoing invention content and embodiment are intended to the practical application proving technical scheme provided by the present invention, should not be construed as limiting the scope of the present invention.Those skilled in the art in spirit of the present invention and principle, when doing various amendment, equivalent replace or improve.Protection scope of the present invention is as the criterion with appended claims.

Claims (8)

1. the chirality function ionic liquid based on the condensation product of chirality cyclohexanediamine and imidazoles SULPHURYL CHLORIDE, it is characterized in that, described chirality function ionic liquid has following structural formula I:
Wherein, R 1for the aliphatic chain of C1 ~ C4, R 2for the aliphatic chain of C1 ~ C5, X --for Br --, BF 4 --, PF 6 --, NTf 2 --, OAc --.
2. chirality function ionic liquid as claimed in claim 1, is characterized in that, described R 1the aliphatic chain of C1 ~ C4 be CH 3, CH 3cH 2, CH 3cH 2cH 2and CH 3cH 2cH 2cH 2.
3. chirality function ionic liquid as claimed in claim 1, is characterized in that, described R 2the aliphatic chain of C1 ~ C5 be CH 3, CH 3cH 2, CH 3cH 2cH 2, CH 3cH 2cH 2cH 2and CH 3cH 2cH 2cH 2cH 2.
4. the preparation method of a chirality function ionic liquid; it is characterized in that; (1R; 2R)-2-aminocyclohexyl t-butyl carbamate with at temperature of reaction is 0 ~ 30 DEG C, carry out condensation reaction with imidazoles SULPHURYL CHLORIDE; the condensation product obtained and halogenated alkane react, ion exchange reaction and deprotection reaction obtain described chirality function ionic liquid, and its reaction equation is as follows:
Wherein, A is chlorine, bromine and iodine; R 1for the aliphatic chain of C1 ~ C4, R 2for the aliphatic chain of C1 ~ C5, X -for Br --, BF 4 --, PF 6 --, NTf 2 --and OAc --.
5. preparation method as claimed in claim 4, is characterized in that, described R 1the aliphatic chain of C1 ~ C4 be CH 3, CH 3cH 2, CH 3cH 2cH 2and CH 3cH 2cH 2cH 2.
6. preparation method as claimed in claim 4, is characterized in that, described R 2the aliphatic chain of C1 ~ C5 be CH 3, CH 3cH 2, CH 3cH 2cH 2, CH 3cH 2cH 2cH 2and CH 3cH 2cH 2cH 2cH 2.
7. preparation method as claimed in claim 4, is characterized in that, the solvent used in the condensation reaction is methylene dichloride, toluene, ethyl acetate, tetrahydrofuran (THF), chloroform and dimethyl sulfoxide (DMSO).
8. preparation method as claimed in claim 4, is characterized in that, the alkali used in the condensation reaction is triethylamine, DIPEA and pyridine.
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