Synthesis of 1,2-diarylethene compound

A technology of diarylethenes and aromatic compounds, applied in 1 field, can solve the problems of toxic organic solvents, long reaction time, high price and the like, and achieve the effects of easy purification, short reaction time and low cost

Inactive Publication Date: 2010-06-09
SHAANXI NORMAL UNIV +1
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AI Technical Summary

Problems solved by technology

The common disadvantage of these methods is that organic solvents are required as reaction media, and even some reactions require toxic and expensive catalysts.
Patent CN200310111885 discloses a method for preparing pterostilbene, which first uses 3,5-dimethoxybenzaldehyde and p-nitrotoluene as raw materials, and refluxes them in methanol for more than 40 hours in the presence of sodium methoxide to obtain 3 , 5-dimethoxy-4'-nitrostilbene, and then the target product is obtained through subsequent reactions. This method of building a 1,2-diarylethene skeleton needs to be carried out under anhydrous conditions. The reaction time long and requires large amounts of toxic organic solvents

Method used

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  • Synthesis of 1,2-diarylethene compound
  • Synthesis of 1,2-diarylethene compound
  • Synthesis of 1,2-diarylethene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of (E)-3,4,5-trimethoxy-4'-nitrostilbene

[0020]

[0021] Take 1.96g (10.00mmol) 3,4,5-trimethoxybenzaldehyde, 1.37g (10.00mmol) p-nitrotoluene, 2.76g (20.00mmol) anhydrous potassium carbonate, 1.0mL PEG-400, add to In a 50mL reaction flask, react at 100°C for 3.0 hours under electromagnetic stirring, stop heating, cool to room temperature, add water and filter with suction to obtain 2.40g of the target product as a brown-yellow solid, yield: 85%. Melting point: 192~194℃;

[0022] 1 HNMR (300MHz, CDCl 3 )δ: 3.89 (s, 3H, OCH 3 ), 3.93(s, 6H, 2OCH 3 ), 6.77 (s, 2H, 2, 6-Ar-H), 7.07 (d, 1H, J=16.2Hz, -CH=CH-), 7.17 (d, 1H, J=16.2Hz, -CH=CH -), 7.64(d, 2H, 2', 6'-Ar-H), 8.24(d, 2H, 3', 5'-Ar-H);

[0023] 13 CNMR (75MHz, CDCl 3 )δ: 56.2, 60.9, 104.4, 124.1, 125.7, 126.7, 131.8, 133.3, 139.2, 143.8, 146.7, 153.6;

[0024] IRv KBr max cm -1 : 3066, 2928, 2831, 1633, 1587, 1503, 1454, 1329, 1236, 1122, 980;

[0025] Elemental analysis (%): C 17 h 17...

Embodiment 2

[0027] Synthesis of (E)-3,4-dimethoxy-4'-nitrostilbene

[0028]

[0029] Get 1.66g (10.00mmol) 3,4-dimethoxybenzaldehyde, 1.37g (10.00mmol) p-nitrotoluene, 2.76g (20.00mmol) anhydrous potassium carbonate, join in the reaction flask of 50mL, add 1.0mL PEG-400, reacted at 100°C for 3.0 hours under electromagnetic stirring, stopped heating, cooled to room temperature, added water and filtered with suction to obtain 2.60g of the target product as a brown-yellow solid, yield: 81%; melting point: 131.3~132.5°C;

[0030] 1 HNMR (300MHz, CDCl 3 )δ: 3.3.92 (s, 3H, -OCH 3 ), 3.96 (s, 3H, -OCH 3 ), 6.90 (d, 1H, J=8.5Hz, 5-Ar-H), 7.03 (d, 1H, J=16.2Hz, -CH=CH-), 7.09 (d, 1H, 6-Ar-H) , 7.09 (s, 1H, 2-Ar-H), 7.24 (d, 1H, J=16.2Hz, -CH=CH-), 7.61 (d, 2H, J=8.7Hz, 2′, 6′-Ar -H), 8.22(d, 2H, 3', 5'-Ar-H);

[0031] 13 CNMR (75MHz, CDCl 3 )δ: 56.0, 109.2, 111.4, 120.9, 124.1, 124.3, 126.5, 129.4, 133.2, 144.2, 149.4, 150.1;

[0032] IR(KBr)vmax / cm -1 : 1508, 1462, 1259, 1633, 1587,...

Embodiment 3

[0035] Synthesis of (E)-4-methoxy-4'-nitrostilbene

[0036]

[0037] Take 1.36g (10.00mmol) p-methoxybenzaldehyde, 1.37g (10.00mmol) p-nitrotoluene, 2.76g (20.0mmol) anhydrous potassium carbonate, join in 50mL reaction flask, then add 1.0mL PEG- 400, react at 70°C for 1 hour under electromagnetic stirring, then adjust to 100°C, react for 3 hours, stop heating, cool to room temperature, add water and filter with suction to obtain a yellow solid crude product, wash the solid with methanol to obtain 0.76g of the target product, the yield : 30%; Melting point: 130.0~131.8℃;

[0038] 1 HNMR (300MHz, CDCl 3 )δ: 3.85(s, 3H, OCH 3 ), 6.93 (d, 2H, 3, 5-Ar-H), 7.00 (d, 1H, J=16.6Hz, -CH=CH-), 7.20 (d, 1H, J=16.6Hz, -CH=CH -), 7.49 (d, 2H, 2, 6-Ar-H), 7.84 (d, 2H, 2', 6'-Ar-H), 8.20 (d, 2H, 3', 5'-Ar-H );

[0039] 13 CNMR (75MHz, CDCl 3 )δ: 54.3, 113.3, 123.1, 125.4, 127.3, 127.9, 131.9, 143.2, 145.4, 159.2;

[0040] IRv KBr max cm -1 : 3436, 2919, 1586, 1507, 1333 (NO 2 ...

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Abstract

The invention provides a synthesis method of 1,2-diarylethene compound, in particular to a diarylethene compound which is prepared by taking polyethylene glycol with small molecular weight as a catalyst under the existence of anhydrous alkaline matters and through the condensation reaction between aryl aldehyde and aromatic compounds containing active methyl. The synthesis method has simple reaction process and posttreatment and less environmental pollution and is suitable for mass preparation of the compound.

Description

technical field [0001] The invention belongs to the technical field of diarylethene compounds, and in particular relates to a synthesis method of 1,2-diarylethene compounds. technical background [0002] 1,2-Diarylethene compounds have important application value, and these compounds are mostly used as liquid crystal materials, fluorescent materials and medical drugs. For example, resveratrol (3,4',5-trihydroxystilbene), pterostilbene (3,5-dimethoxy-4'-hydroxystilbene) because of their good anti-tumor, antibacterial and anti-inflammatory properties, etc. The drug activity is applied clinically. Such compounds are generally obtained in two ways, one is to extract and isolate from natural plants; the other is to obtain by chemical synthesis. Because natural resources are limited and the separation process of extracts is complicated, it is of great significance to synthesize such compounds by efficient and green chemical methods. [0003] The chemical synthesis methods of su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/37C07C201/12C07C211/52C07D307/52C07D209/60C07D209/10B01J31/06
Inventor 李宝林王丽张喜全郭健顾红梅王伟
Owner SHAANXI NORMAL UNIV
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