Unlock instant, AI-driven research and patent intelligence for your innovation.

(1R,2R) or (1S,2S)-1-(4'-substitute-1'8'-naphthoyl imdo group)-2-amino cyclohexane, preparation and application

A technology based on aminocyclohexane and naphthalimide, which is applied in the direction of organic chemistry methods, chemical instruments and methods, and organic racemization, can solve the problems of small inequalities in chemical shifts and application limitations, and achieve easy operation, Inexpensive and easy to synthesize effects

Inactive Publication Date: 2007-01-24
WUHAN UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But sometimes its application is limited due to the small chemical shift inequality (ΔΔδ) of the analyte

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • (1R,2R) or (1S,2S)-1-(4'-substitute-1'8'-naphthoyl imdo group)-2-amino cyclohexane, preparation and application
  • (1R,2R) or (1S,2S)-1-(4'-substitute-1'8'-naphthoyl imdo group)-2-amino cyclohexane, preparation and application
  • (1R,2R) or (1S,2S)-1-(4'-substitute-1'8'-naphthoyl imdo group)-2-amino cyclohexane, preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of (1R, 2R)-1-(1', 8'-naphthoimide)-2-aminocyclohexane 1

[0024] Add 240ml of cyclohexanediamine into 400ml of distilled water, heat to 75°C, and then control the temperature at 80-90°C while stirring, first add 150g (1mol) of (+)-tartaric acid in batches, and divide Add 100ml (1.7mol) of glacial acetic acid in batches to adjust the pH value to approximately equal to 6. Continue to stir, cool in an ice bath for 2 hours, filter with suction, wash with 80ml of ice water, then wash with 250×4ml of methanol, and dry in air to obtain white crystal {(-)chxnH 2}{(+)tart}144g, [α] D 20 =12.6° (c=2, H 2 O) [Document Value: [α] D 20 =12.2° (c=1, H 2 O) (Acta Chem. Scand. 1972, 26, 3605-3611)].

[0025] Heat the above mother liquor to 80°C, add 375g (2.5mol) of (+)-tartaric acid under stirring, stir overnight at room temperature, precipitate precipitate, filter, wash with 40ml of ice water, wash with 250×4ml of methanol, and dry in air to obtain whi...

Embodiment 2

[0028] Example 2: Preparation of (1R, 2R)-1-(4'-bromo-1', 8'-naphthalimide)-2-aminocyclohexane 2 Resolution of optically pure cyclohexanediamine Ditto.

[0029] Add the solution of 2.77g (0.01mol) 4-bromo-1,8-naphthalene dicarboxylic anhydride and 90mlDMF / ethanol (2: 1) in a 250ml three-neck round-bottomed flask, under nitrogen protection conditions, heating under reflux makes 4 -Bromo-1,8-naphthalene dicarboxylic anhydride was dissolved, and then 1.37g (0.012mol) (1R,2R)-cyclohexanediamine in 30ml DMF / ethanol (2:1 volume ratio) solution was added, and the solution was refluxed for half an hour. It becomes clear, then reflux for 4-5 hours, pour it into 1000ml of ice water while it is hot, and a large amount of solids precipitate out, filter with suction, wash with water, dry in a vacuum oven, and recrystallize twice with ethanol or acetonitrile to obtain a light yellow solid , is the target compound 2, yield: 95.0%; m.p.: 211-214°C; [α] D 20 =-12.8° (c=0.0625, CHCl 3 ); 1...

Embodiment 3

[0030] Example 3: Preparation of (1R, 2R)-1-(4'-(N, N-dimethylamino)-1', 8'-naphthalimide)-2-aminocyclohexane 3

[0031] The resolution of optically pure cyclohexanediamine is the same as above.

[0032] Add 1.2g (0.005mol) 4-(N,N-dimethylamino)-1,8-naphthalene dicarboxylic anhydride and 100ml ethanol solution in a 250ml three-necked round-bottomed flask, under nitrogen protection conditions, heat to reflux to make 4-(N,N-dimethylamino)-1,8-naphthalene dicarboxylic anhydride was dissolved, and then 0.68g (0.006mol) (1R,2R)-cyclohexanediamine in 30ml ethanol solution was added, and the solution was refluxed for half an hour. It becomes clear, then reflux for 4-5 hours, pour it into 500ml of ice water while it is hot, and a large amount of solids precipitate out, filter with suction, wash with water, dry in a vacuum oven, and recrystallize twice with ethanol or acetonitrile to obtain bright yellow needles. like crystals, the target compound 3, yield: 92.5%; m.p.: 183-184°C; [α]...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A chiral solvent (1R,2R) or (1S,2S)-1-(4'-substituent-1',8'-naphthalene imido)-2-aminocyclohexane with high antimer recognizing effet is prepared through discomposing the dl-cyclohexyldiamine to obtain optical-purity anti (1R, 2R) or (1S, 2S)-cyclohexyldiamines, reflux reaction on 4-substituent-1,8-naphthalene diformic anhydride in solvent under protection of N2, discharging resultant in ice water, educing out solid, and recrystallizing.

Description

technical field [0001] The invention discloses a novel chiral dissolving agent (1R, 2R)- or (1S, 2S)-1-(4'-substituted-1', 8'-naphthalimide)-2-amino ring The invention relates to hexane and a preparation method thereof, which belong to the technical field of preparation of chiral dissolving agents. The chiral dissolving agents are used for enantiomeric purity measurement of chiral compounds, and relate to the field of separation and analysis of enantiomers of chiral compounds. Background technique [0002] As far as the physical and chemical properties of chiral drugs are concerned, the only difference between enantiomers is optical activity, and there is no difference in other aspects. In many cases, there are significant differences between a pair of enantiomers of chiral compounds in terms of pharmacological activity, metabolic process, metabolic rate and toxicity in vivo. Therefore, in order to accurately understand the drug efficacy and safe drug use, it is urgent to d...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D221/06C07B57/00
Inventor 杨雪梅傅恩琴
Owner WUHAN UNIV