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Method for preparing 4-L(4-hydroxyphenyl) azo] benzoic cholestenone

A technology of benzoic acid and hydroxybenzene, which is applied in the field of preparing 4-[azo] benzoic acid cholesteryl ester, can solve problems such as unreported synthetic methods of compounds, and achieves less harsh reaction conditions, simple operation and easy operation. effect of operation

Inactive Publication Date: 2004-09-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 4-[(4-hydroxyphenyl)azo]benzoic acid cholesteryl ester is one of the compounds that meet the above conditions, has a liquid crystal phase and color rendering properties, and can be used as a liquid crystal display material (EP 896048, 1999), However, the synthesis method of this compound has not been reported

Method used

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  • Method for preparing 4-L(4-hydroxyphenyl) azo] benzoic cholestenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 10mmol of compound 1 was added to 100ml of benzene, then 50ml of benzene solution containing 10mmol of compound 2 was added dropwise, reacted at room temperature for 8h, the organic phase was spin-dried, and separated by flash column chromatography to obtain compound 3 (80%). C 34 h 49 NO 4

[0019] 1 H NMR (300MHz, CDCl 3 , ppm): 8.30-8.19 (4H, m), 5.45-5.43 (1H, m), 4.95-4.85 (1H, m), 2.50-0.70 (43H, m).

[0020] MS (MALDI): 535.5.

[0021] IR: 2945, 1721, 1527, 1467, 1348, 1272.

Embodiment 2

[0023] Add 7 mmol of compound 3 to 100 ml of absolute ethanol, then add 35 mmol of SnCl 2 , refluxed for 3 hours, neutralized by adding lye, extracted with dichloromethane, spin-dried the organic phase, and separated by flash column chromatography to obtain compound 4 (90%).

[0024] C 34 h 51 NO 2

[0025] 1 H NMR (300MHz, CDCl 3 , ppm): 7.87-7.84 (2H, dd, J=9Hz), 6.65-6.62 (2H, d, J=9Hz), 5.41-5.39 (1H, m), 4.85-4.75 (1H, m), 2.45- 0.69(43H, m).

[0026] MS (MALDI): 505.5.

[0027] IR: 3339, 2941, 1697, 1602, 1467, 1274, 1172, 1117.

Embodiment 3

[0029] 5mmol compound 4 was dissolved in acetone-water solution containing 3ml concentrated hydrochloric acid, cooled to 0°C, and then 20ml containing 6mmol NaNO was added dropwise 2 After reacting for 1 h at 0°C, this solution was added to 80 ml of alkaline aqueous solution containing 6 mmol of phenol. After reacting at 0°C for 4 hours, hydrochloric acid was added to adjust the pH to weak acidity, filtered, and separated by flash column chromatography to obtain compound 5 (75%).

[0030] C 40 h 54 N 2 o 3

[0031] 1 H NMR (300MHz, CDCl 3 , ppm): 8.19-8.16 (2H, d, J = 9Hz), 7.93-7.88 (4H, dd, J = 6Hz), 6.99-6.96 (2H, d, J = 9Hz), 5.45-5.43 (1H, m ), 4.95-4.85 (1H, m), 2.51-0.69 (43H, m).

[0032] MS (MALDI): 610.6.

[0033] IR: 3446, 3169, 2951, 1693, 1596, 1470, 1441, 1282, 1137.

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Abstract

The invention relates to a method to prepare 4-[(4-hydroxybenzene) azo] cholesteryl benzoate. Further speaking, it is a method to generate 4-[(4-hydroxybenzene) azo] cholesteryl benzoate by esterification, electronation and coupling reactions beginning with cholesterin. It begins with cheap raw material, the reaction is not rigorous and easy to operate, and it is applied to industrialized production.

Description

technical field [0001] The invention relates to a method for preparing cholesteryl 4-[(4-hydroxyphenyl)azo]benzoate. Further speaking, it is a method of generating 4-[(4-hydroxyphenyl)azo]benzyl acid cholesteryl ester through esterification, reduction, and coupling reactions starting from cholesterol. technical background [0002] Cholesterol is one of the important components of biofilm. The main function of cholesterol is to regulate the fluidity of biofilm. Below the phase transition temperature, cholesterol increases the fluidity of biofilm; above the phase transition temperature, cholesterol reduces the fluidity of biofilm. Mobility (R. Lewis, R.N. McElhaney. In: P.L. Yegle, editor. The structure of biological membranes. Boca Raton (FL, USA): CRC Press, 73-156, 1992; R.A. Demel, B.de Kruij. Biochim. Biophys . Acta 457(2), 109-32, 1976). Cholesterol also has the function (P.L.Yeagle.Biochim Biophys Acta 822(3-4), 267-87,1985) of increasing the mechanical strength of bi...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 王瑾晔刘新铭
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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