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A kind of chiral amine functional ionic liquid and its preparation

A functional ionic liquid and chiral technology, which is applied in the field of chiral ionic liquid and its preparation, can solve the problems of chiral functional ionic liquid that no one has reported, and achieve the effect of excellent dual stereoselective catalytic activity

Active Publication Date: 2016-03-30
柳政
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as far as we know, no chiral functional ionic liquids produced by the condensation of sulfonamides and chiral cyclohexanediamine have been reported.

Method used

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  • A kind of chiral amine functional ionic liquid and its preparation
  • A kind of chiral amine functional ionic liquid and its preparation
  • A kind of chiral amine functional ionic liquid and its preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add (1R,2R)-tert-butyl 2-aminocyclohexylcarbamate 1 (7.1g, 33mmol), triethylamine (3.6g, 36mmol) and dichloromethane (50mL) into a 250ml three-necked flask, 0°C A solution of 1-methyl-2-sulfonylchloroimidazole 2 (6 g, 33 mmol) in dichloromethane (30 mL) was added dropwise around the start. After the dropwise addition, react at room temperature for 2 hours, TLC spot plate reaction is complete, wash with water, then extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure, and separate by column chromatography to obtain white Solid 3 (11.3 g), yield 96%. The reaction formula is:

[0023]

[0024] 1 HNMR (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); 13 CNMR (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.

[0025] Add conden...

Embodiment 2

[0035] Add 4 (5.0g, 10mmol) to the 100ml three-necked flask, LiNTf 2 (2.87g, 10mmol) and absolute ethanol (50mL), refluxed for 12 hours. The solvent was evaporated under reduced pressure, washed with anhydrous ether, and dried in vacuum (60°C,

[0036] 5 hours) to obtain yellow oily liquid 7 (6.06g), yield 93%. The reaction formula is:

[0037]

[0038] 1 HNMR (400MHz,D 2 O)(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); 13 CNMR (100MHz,D 2 O) (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.

[0039] Add 7 (0.6g, 1mmol), 4M dioxane hydrochloride aqueous solution (4ml) into a 100ml three-necked flask, and stir at room temperature for 12 hours. The solvent was distilled off under reduced pressure, followed by basic alumina column chromatography and eluting with anhydrous methanol to obtain a light yellow oily liquid 8 (0.48 g), with a yield of 88%. T...

Embodiment 3

[0043] Add 4 (2.5g, 5mmol), NaOAc (0.41g, 5mmol) and absolute ethanol (25mL) into a 100ml three-necked flask, and reflux for 12 hours. The solvent was evaporated under reduced pressure, washed with anhydrous ether, and dried under vacuum (60°C, 5 hours) to obtain yellow oily liquid 9 (2.05g), yield 96%. The reaction formula is:

[0044]

[0045] 1 HNMR (400MHz,D 2 O)(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); 13 CNMR (100MHz,D 2 O) (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.

[0046] Add 9 (0.6g, 1mmol), 4M dioxane hydrochloride aqueous solution (4ml) into a 100ml three-necked flask, and stir at room temperature for 12 hours. The solvent was evaporated under reduced pressure, followed by basic alumina column chromatography and eluting with anhydrous methanol to obtain 10 (0.48 g) as a light yellow oily liquid with a yield of 88%. T...

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Abstract

The invention relates to the fields of a novel chemical material and a preparation technology thereof, and provides a chiral amine functional ionic liquid which is obtained by carrying out a condensation reaction on chiral hexamethylene diamine and imidazole sulfonyl chloride and then reacting a condensation product with halogenated hydrocarbon, and a preparation method thereof. The ionic liquid has the structural formula I as shown in the specification, in the formula, R1 is an aliphatic chain of C1-C4, R2 is the aliphatic chain of C1-C5, X<-> is Br<->, BF4<->, PF6<->, NTf2<->, OAc<->, and the like. The chiral ionic liquid is simple is simple in a preparation process, has double chiral spatial induction catalytic performance, and can be used in organic synthesis as an efficient chiral catalyst.

Description

Technical field: [0001] The invention relates to the technical field of novel chemical materials and preparation, in particular to a chiral ionic liquid and a preparation method thereof. Background technique: [0002] In the past few decades, ionic liquids have been widely used as reaction media and catalysts in the fields of organic synthesis and separation and purification. As we all know, ionic liquids are composed of organic cations and inorganic or organic anions, and are salts in a liquid state at or near room temperature. The advantages of ionic liquids such as low volatility, low melting point, structural designability, wide chemical window, good electrical conductivity and good solubility make them widely used in various fields. Chinese patents CN101148392, CN1563008, CN1810757, CN1712093, etc. describe the application of ionic liquids in extraction and separation. Chinese patents CN101177252, CN11600429, and CN101177299 have successfully applied ionic liquids to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/84
CPCC07D233/84
Inventor 应安国杨建国胡华南李嵘嵘
Owner 柳政