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4-arylmethylidene-2-hydroxy-3-pinone derivative as well as preparation method and application thereof

A technology for aryl methylene and derivatives, which is applied in the field of 4-aryl methylene-2-hydroxy-3-pinone derivatives and its preparation, can solve the problems of low yield and achieve short synthetic routes, The effect of good reaction selectivity and high yield

Inactive Publication Date: 2012-12-19
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0028] In 2008, Ognyan Petrov and others at Sofia University in Bulgaria reported the use of SOCl 2 / EtOH as a catalyst to synthesize chalcone, although the purity of the product is relatively high, but the yield is not high

Method used

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  • 4-arylmethylidene-2-hydroxy-3-pinone derivative as well as preparation method and application thereof
  • 4-arylmethylidene-2-hydroxy-3-pinone derivative as well as preparation method and application thereof
  • 4-arylmethylidene-2-hydroxy-3-pinone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The preparation of 2-hydroxy-3-pinone, the reaction formula is as follows:

[0062]

[0063] Specific process: In a 500mL three-necked flask equipped with a stirrer, a thermometer and an addition funnel, add 13.60g (0.1mol) of α-pinene, 110mL of acetone and 12mL of deionized water in sequence, and cool to about 0~5°C in an ice bath. Add 31.61g (0.2mol) of fully ground potassium permanganate in batches (the addition is completed within 1.5~2h, the temperature of the reaction system is controlled to prevent the temperature from being too high). Continue to react at room temperature for 6h (GC tracking monitoring). After the reaction, filter with a sand core funnel, and then wash the solid residue with acetone (3×10 mL). Use a rotary concentrator to recover acetone, add 30mL of ethyl acetate to the residue, wash with saturated brine until neutral, dry over anhydrous sodium sulfate, filter, concentrate, then rectify under reduced pressure, collect 120~122℃ / 2.66 The kPa...

Embodiment 2

[0069] Preparation of 4-arylmethylene-2-hydroxyl-3-pinone ultraviolet absorber: under the catalysis of alkalis such as sodium hydroxide or sodium ethoxide, take the 2-hydroxyl-3-pinone prepared in Example 1 , carry out aldol condensation reaction with benzaldehyde, p-tolualdehyde, p-methoxybenzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, p-nitrobenzaldehyde and furfural respectively to obtain 4-benzylidene -2-Hydroxy-3-pinone (1), 4-(4′-methylbenzylidene)-2-hydroxy-3-pinone (2), 4-(4′-methoxybenzylidene Methyl)-2-hydroxy-3-pinone (3), 4-(4′-hydroxybenzylidene)-2-hydroxy-3-pinone (4), 4-(4′-chlorobenzylidene Methyl)-2-hydroxy-3-pinone (5), 4-(4′-nitrobenzylidene)-2-hydroxy-3-pinone (6), 4-(furan-2′- methylene)-2-hydroxy-3-pinone (7). The reaction formula is:

[0070]

[0071] The compound formula structure of synthesis is as follows:

[0072]

[0073] 1. Preparation of 4-benzylidene-2-hydroxyl-3-pinone (1)

[0074] In a 50mL three-neck flask equipped with a...

Embodiment 3

[0126] Determination of light-absorbing ability of 4-arylmethylene-2-hydroxyl-3-pinone derivatives: 7 compounds synthesized in Example 2 were dissolved in 55% ethanol aqueous solution respectively, and the mass fraction was 0.0015 % sample solution, conduct a full scan in the range of 200-600nm, measure the ultraviolet absorption range of each compound, and determine the maximum absorption wavelength. And calculate their molar absorptivity ε according to the following formula, and the test results are shown in Table 2.

[0127] ε=A / CL

[0128] A—absorbance;

[0129] ε—molar absorptivity, L / mol cm;

[0130] C—sample concentration, mol / L;

[0131] L—the length of the optical path, cm.

[0132] Table 2 The UV absorption range and maximum absorption wavelength of 4-arymethylene-2-hydroxy-3-pinone derivatives

[0133] compound

[0134] As can be seen from Table 2, when the auxochromic group (such as -OH, -OCH 3 , -Cl) or chromophores (such as -NO 2 ) is directly co...

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Abstract

The invention discloses a 4-arylmethylidene-2-hydroxy-3-pinone derivative as well as a preparation method and an application thereof. The derivative comprises the following components of: 4-benzylidene-2-hydroxy-3-pinone, 4-(4'-methylbenzylidene)-2-hydroxy-3-pinone, 4-(4'-methoxybenzylidene)-2-hydroxy-3-pinone, 4-(4'-hydoxybenzylidene)-2-hydroxy-3-pinone, 4-(4'-chlorobenzylidene)-2-hydroxy-3-pinone, 4-(4'-nitrobenzylidene)-2-hydroxy-3-pinone and 4-(furan-2'-methylene)-2-hydroxy-3-pinone. The preparation method comprises the steps of: carrying out selective oxidation on alpha-pinene as a raw material through using potassium permanganate to obtain 2-hydroxy-3-pinone; carrying out aldol reaction on 2-hydroxy-3-pinone and aromatic aldehyde to prepare the derivative. The derivative has the characteristics of good ultraviolet absorption effect, wide ultraviolet spectrum absorption range, good photostability, broad application prospect in ultraviolet ray absorption, and short in synthetic route, simple and convenient and economic to operate, good in reaction selectivity, high in yield and little in pollution.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to an ultraviolet absorber compound and its preparation method and application, in particular to a 4-arymethylene-2-hydroxyl-3-pinone derivative and its preparation method and application. Background technique [0002] In recent years, with the continuous destruction of the atmospheric ozone layer, increased ultraviolet radiation has had a serious impact on human health. 320~400nm long-wave ultraviolet UVA, its energy can reach the dermis of the skin, bringing slow changes to the elastic fibers in the blood vessel wall or combined tissue, causing browning of the skin, decreased skin elasticity, and promoting the occurrence of wrinkles. Can promote erythema reaction and even cause phototoxicity or photosensitivity reaction. The 280~320nm medium-wavelength ultraviolet rays UVB can cause erythema or blisters on the skin, promote the formation of melanin, cause skin pigmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/747C07C49/753C07C45/74C07C205/45C07C201/12C07D307/46A61K8/49A61K8/40A61K8/35A61Q17/04
Inventor 王石发魏柏松杨益琴徐徐谷文
Owner NANJING FORESTRY UNIV
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