Preparation method and application of anthraquinone ester-based fragrance-fixing slow-release agent

An anthraquinone and alkyl technology, applied in the field of ester compounds based on anthraquinone structure and its preparation

Active Publication Date: 2022-04-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, no ester compound based on anthraquinone structure with fluorescent properties and hydrolysis slow-release fragrance has been reported

Method used

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  • Preparation method and application of anthraquinone ester-based fragrance-fixing slow-release agent
  • Preparation method and application of anthraquinone ester-based fragrance-fixing slow-release agent
  • Preparation method and application of anthraquinone ester-based fragrance-fixing slow-release agent

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Compound I-1

[0040]

[0041] (1) Preparation of Intermediate 6-1

[0042] 1-phenylethyl alcohol compound 5-1 (3.66 g, 30 mmol) and pyridine (2.37 g, 30 mmol) were added to 15 ml of dichloromethane, and the bromine bromide 4 (6.03 g, 30 mmol) was added dropwise at 0 ° C. 1H, gradually increased to room temperature, end the reaction after 2 h after 2 hours of room temperature, and extracted three times with dichloromethane, adding silica gel powder in the filtrate, and the column chromatography obtained -1 (eluent is petroleum ether: ethyl acetate = 20: 1).

[0043] The NMR of the intermediate 6-1 is as follows: 1 H NMR (400 MHz, ChlorOform-D) δ 7.28-7.11 (m, 5H), 5.85-5.75 (m, 1H), 3.67 (S, 2H), 1.45 (D, J = 6.6 Hz, 3H). 13 C NMR (101 MHz, Chloroform-D) δ166.46, 140.76, 128.66, 127.38, 126.20, 74.47, 26.35, 20.80.

[0044] (2) Preparation of Compound I-1

[0045]

[0046] 1,4-dihydroxy hydrazine compound 1 (0.6 g, 2.5 mmol) was added to 20 mL of acetonitrile, then cesi...

Embodiment 2

[0049] Compound I-2

[0050]

[0051] (1) Preparation of Intermediate 6-2

[0052]Dimethylbenylylbenyl alcohol compounds 5-2 (4.5 g, 30 mmol) and pyridine (2.37 g, 30 mmol) were added to 15 ml of dichloromethane, and the bromine bromide 4 (6.03) was added dropwise to 0 ° C. g, 30 mmol), reaction 1H, gradually increased to room temperature, end the reaction after 2 h at room temperature, dissolved the white solid, extracted three times with dichloromethane, adding silica gel powder in the filtrate, obtained by column chromatography Intermediate 6-2 (eluent is petroleum ether: ethyl acetate = 20: 1).

[0053] The NMR of Compound 6-2 is as follows: 1 H NMR (400 MHz, ChlorOform-D) δ 7.20-6.99 (m, 5H), 3.58 (S, 2H), 2.35 (S, 2H), 1.35 (S, 6H). 13 C NMR (101 MHz, Chloroform-D) δ166.29, 136.76, 130.68 (Q, J = 2.9 Hz), 128.41-127.87 (M), 126.73, 84.59, 46.50, 27.73, 25.68.

[0054] (2) Preparation of Compound I-2

[0055]

[0056] 1,4-dihydroxy hydrazine compound 1 (0.6 g, 2.5 mmol) w...

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Abstract

The invention discloses an ester compound based on an anthraquinone structure, the structure is shown as a formula I, R is selected from-OR1, R1 is selected from C1-C12 branched chain or straight chain alkyl, and C1-C12 branched chain or straight chain alkyl containing double bonds, the ester compound based on the anthraquinone structure is based on common anthraquinone, and the structural formula is shown in the description. The molecules with fluorescence and fragrance release functions can be obtained only through one-step reaction, the preparation method is simple, synthesis steps are few, raw material cost is low, raw materials are easy to obtain, consumed time is short, the yield is high, and purification is easy. The method can be used in the fields of organic fluorescent dyes and flavors and fragrances.

Description

Technical field [0001] The present invention belongs to the field of chemical synthesis, and in particular, to a ester compound based on an anthraquinone structure and a preparation method thereof. Background technique [0002] Anthraquinones is a class of compounds in a variety of natural quinone compounds. For a long time, anthraquinone is used as natural dyes, 1,4-dihydroxy hydrazine is one of the anthraquinone compound, and is contained in its chemical structure containing two hydroxyl groups, the two hydroxyl groups formed in a strong molecule in a strong molecule within a strong molecule The entire molecule is formed to form a quasi-aromatic ring structure, and while increasing its molecular structure, it is greatly improved its fluorescent properties, and is an organic fluorescent dye. [0003] Organic fluorescent dyes, initially due to its special function of luminescence, the visual effect of people is far exceeded in other traditional materials, and is widely used as co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/712C07C67/31C07C67/14C07C69/63C09K11/06C11B9/00
CPCY02E10/549
Inventor 李旭扬王利民邹佩琨吴晨茜周忻宇张蒙徐佳宇李俊肖倩李兴璋马璋琳唐璐韩建伟
Owner EAST CHINA UNIV OF SCI & TECH
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