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2-(2-alkoxy phenyl)-4, 5-diphenyl imidazole compound as well as synthesis method and application thereof

A technology of diphenylimidazole and alkoxyphenyl, applied in the field of 2--4,5-diphenylimidazole compounds and their synthesis

Inactive Publication Date: 2020-04-03
GUANGDONG RES INSTITITUTE OF PETROCHEM & FINE CHEM ENG
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still few reports on the practical application of these compounds.

Method used

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  • 2-(2-alkoxy phenyl)-4, 5-diphenyl imidazole compound as well as synthesis method and application thereof
  • 2-(2-alkoxy phenyl)-4, 5-diphenyl imidazole compound as well as synthesis method and application thereof
  • 2-(2-alkoxy phenyl)-4, 5-diphenyl imidazole compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Synthesis of 2-(4-butoxy-4'-(tert-butyl)-[1,1'-biphenyl]-3-yl)phenanthrene[9,10-d]imidazole (compound 1).

[0064]

[0065] Synthesis of 5-bromo-2-alkoxybenzaldehyde from 5-bromo-2-hydroxybenzaldehyde was accomplished according to the conventional method reported in the literature. References: Liu Jingzi, Wang Yuliang, Chen Shuhua, Journal of Southwest Normal University (Natural Science Edition), 2005, 30(2): 301-303; Li Jie, Tang Hongye, Xu Suoping, Jiangsu Normal University Journal (Natural Science Edition), 2012 , 30(3):43-46). Here, the reaction of 2-hydroxybenzaldehyde and 1-bromobutane is taken as an example. 20mmol (4.01g) of 5-bromo-2-hydroxybenzaldehyde, 40mmol (1.60g) of sodium hydroxide and 30mmol (4.11g) of bromobutane were added to 50mL of N,N-dimethylformamide. After stirring at room temperature for 5 hours, it was poured into 500 mL of water with stirring, the mixture was extracted with dichloromethane (50 mL×3 times), and the obtained organic layer ...

Embodiment 2

[0070] Synthesis of 2-(1-(2-butoxynaphthyl))-4,5-diphenylimidazole (compound 2).

[0071]

[0072]With reference to the reaction conditions of 5-bromo-2-hydroxybenzaldehyde and bromobutane in Example 1, 2-hydroxyl-1-naphthaldehyde and 1-bromobutane react to obtain 2-butoxyl-1-naphthaldehyde; With reference to the reaction conditions of 2-butoxyl-5-(4-tert-butyl)phenylbenzaldehyde and 9,10-phenanthrenequinone and ammonium acetate in Example 1 to synthesize imidazoles, the 2-butoxyl- The target compound 2 was synthesized from 1-naphthaldehyde, 1,2-diphenylethanedione and ammonium acetate, and the yield was 81% based on 2-butoxy-1-naphthaldehyde.

[0073] The NMR detection results of compound 2 are as follows: 1 H NMR (300MHz, CDCl 3 )δ: 9.35(d, J=8.7Hz, 1H), 8.70(d, J=7.8Hz, 2H), 7.81-7.74(m, 3H), 7.66-7.52(m, 7H), 7.42-7.39(m ,1H),7.23-7.19(m,2H),4.07(t,J=6.6Hz,2H),1.79-1.69(m,2H),1.48-1.38(m,2H),0.87(t,J=7.2 Hz, 3H). 13 C NMR (75MHz, CDCl3) δ: 155.0, 146.0, 132.9, 131....

Embodiment 3

[0075] Synthesis of 2-(1-(2-butoxynaphthyl))-phenanthrene[9,10-d]-imidazole (compound 3).

[0076]

[0077] Referring to Example 2, the target compound 3 was synthesized from 2-butoxy-1-naphthaldehyde, 9,10-phenanthrenequinone and ammonium acetate, and the yield was 86% based on 2-butoxy-1-naphthaldehyde.

[0078] The NMR detection results of compound 3 are as follows: 1 H NMR (300MHz, CDCl 3 )δ: 9.48(d, J=8.7Hz, 1H), 7.78(J=9.0Hz, 2H), 7.64-7.53(m, 4H), 7.41-7.22(m, 7H), 4.15(t, J=6.6 Hz, 2H), 1.82-1.75 (m, 2H), 1.49-1.42 (m, 2H), 0.91 (t, J=7.5Hz, 3H). 13 C NMR (75MHz, CDCl3) δ: 154.4, 142.8, 132.6, 130.7, 129.7, 128.6, 127.9, 127.5, 127.2, 127.0, 124.2, 114.2, 112.7, 69.9, 31.7, 19.5, 13.8. ESI-MS, m / z 417.2[M+H] + .

[0079] Performance Testing

[0080] The absorption properties of 2-(2-alkoxyphenyl)-4,5-diphenylimidazoles to ultraviolet light and blue light were detected.

[0081] Compound 1, compound 2 and compound 3 were dissolved in ethyl acetate and 1,2-dich...

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Abstract

The invention discloses a 2-(2-alkoxy phenyl)-4, 5-diphenyl imidazole compound as well as a synthesis method and application thereof. The structural formula of the 2-(2-alkoxy phenyl)-4, 5-diphenyl imidazole compound is shown in the specification, wherein, R1 is selected from a hydrogen, alkyl, alkoxy, halogen or aryl group, R2 is selected from an alkyl group. The 2-(2-alkoxy phenyl)-4, 5-diphenylimidazole compound provided by the invention has the effect of absorbing ultraviolet rays and blue light, the compound can be used as an ultraviolet and blue light absorber to be applied to eye-viewoptical protection products in the fields of glasses, mobile phones, televisions, computer displays, game machines and the like, high-energy ultraviolet light and part of short-wavelength blue light of electronic display screens are absorbed, and the application prospect is wide.

Description

technical field [0001] The invention relates to the technical field of organic materials, in particular to 2-(2-alkoxyphenyl)-4,5-diphenylimidazole compounds and their synthesis method and application. Background technique [0002] The 2015 Digital Eye Fatigue Report of the American Vision Council pointed out that almost all digital products and light-emitting devices and equipment emit blue light. To a certain extent, it can lead to changes in the retina, which can cause problems with visual health, such as age-related macular degeneration and cataracts. [0003] Compared with UV-A, UV-B, and UV-C, the proportion of high-energy short-wave blue light reaching the retina is relatively large, and it is not only UV-A ultraviolet light in sunlight that causes phototoxic damage to the retina, but more It is blue light in visible light. After light exposure, polyunsaturated fatty acids lead to oxidation of the outer segment of photoreceptor cells, causing them to fall off, retin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K3/00C08L25/06C08L45/00C08K5/3447C08K5/3445
CPCC07D235/02C08L25/06C08L2201/08C09K3/00C08L45/00C08K5/3447C08K5/3445
Inventor 宋森川麦裕良史华红
Owner GUANGDONG RES INSTITITUTE OF PETROCHEM & FINE CHEM ENG
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