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(1R, 5R)-(-)-3-arylmethylene nopinone ultraviolet absorbent and preparation method thereof

A technology of arylmethylene nopinone and ultraviolet rays, which is applied in the field of ultraviolet absorbers and its preparation, can solve the problems of high price of natural camphor, great environmental pollution, long synthesis route, etc., and achieve good ultraviolet absorption effect and wide spectral range , the effect of less pollution

Inactive Publication Date: 2014-03-05
NANJING FORESTRY UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a terpene compound, synthetic camphor has disadvantages such as long synthetic route and great environmental pollution, while natural camphor has disadvantages such as high price and few sources.

Method used

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  • (1R, 5R)-(-)-3-arylmethylene nopinone ultraviolet absorbent and preparation method thereof
  • (1R, 5R)-(-)-3-arylmethylene nopinone ultraviolet absorbent and preparation method thereof
  • (1R, 5R)-(-)-3-arylmethylene nopinone ultraviolet absorbent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of Norpinene

[0023] For the preparation method of nopinene, please refer to the literature [Research on the selective oxidation of L-β-pinene to dextrononpine, Journal of Nanjing Forestry University: Natural Science Edition, 2010, 34(2), 89-94] Method to proceed. You can also use the following methods:

[0024] Add acetone, sulfuric acid and β-pinene into a 100mL four-necked flask equipped with a stirrer, thermometer, constant pressure addition funnel and reflux condenser, cool to about 15℃ in an ice bath, and add fully ground KMnO in batches 4 , Add it in 1~1.5h. Remove the ice bath and continue the reaction at room temperature for 5-6 hours. After the reaction, filter with sand core funnel to remove MnO 2 , And then wash the solid residue with acetone. Use a rotary concentrator to recover acetone, add cyclohexane to the remainder, wash with saturated brine to neutrality, and use anhydrous Na 2 SO 4 The organic layer was dried, and cyclohexane wa...

Embodiment 2

[0025] Example 2: Preparation of (1R, 5R)-(-)-3-arylmethylene norpinene ultraviolet absorber

[0026] Under alkali catalysis, the (1R,5S)-(+)-nopinene prepared in Example 1 was used for hydroxylation with p-hydroxybenzaldehyde, vanillin, o-vanillin, p-chlorobenzaldehyde, and furfural. Aldehyde condensation reaction and further dehydration to obtain (1R,5R)-(-)-3-(4′-hydroxybenzylidene)nopine (1), (1R,5R)-(-)-3-(4 '-Hydroxy-3'-Methoxybenzylidene) Nopinone (2), (1R,5R)-(-)-3-(2'-Hydroxy-3'-Methoxybenzylidene) Noll Pinone(3), (1R,5R)-(-)-3-(4′-chlorobenzylidene)norpineone(4), (1R,5R)-(-)-3-(furan-2 '-Methylene) Nopinene (5).

[0027] Preparation of (1R, 5R)-(-)-3-(4'-hydroxybenzylidene)norpinene (1):

[0028] Add 1.38g (0.01mol) of norpinone, 30ml of a 10% potassium tert-butoxide solution in tert-butanol and 1.83g (0.015mol) of p-hydroxybenzaldehyde into 100mL three ports equipped with a stirrer, thermometer and reflux condenser In the flask, the reaction was refluxed for 7-8 hours ...

Embodiment 3

[0041] Example 3 Determination of the light absorption ability of (1R, 5R)-(-)-3-arylmethylene norpinene derivatives

[0042] The five compounds synthesized in Example 2 were dissolved in 55% ethanol and prepared into a solution with a mass fraction of about 0.0015%, and a full ultraviolet scan was performed in the range of 200-700nm to determine the absorbance range and maximum absorption wavelength. The molar absorption coefficient ε of each compound was calculated according to the following formula, and the results are shown in Table 2.

[0043] ε=A / CL

[0044] A- Absorbance

[0045] ε-molar absorption coefficient, L / mol.cm

[0046] C-The concentration of the sample, mol / L,

[0047] L-length of light path, cm

[0048] Table 2 Ultraviolet absorption range and maximum absorption wavelength of (1R, 5R)-(-)-3-arylmethylene nopinene derivatives

[0049] Compound

[0050] It can be seen from Table 2: Compounds 1-5 have strong UV absorption. The UV absorption ranges of compounds 3 and 5 a...

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Abstract

The invention discloses a (1R, 5R)-(-)-3-arylmethylene nopinone ultraviolet absorbent and a preparation method thereof. The ultraviolet absorbent is (1R, 5R)-(-)-3-(4'-hydroxylbenzylidene) nopinone, (1R, 5R)-(-)-3-(4'-hydroxyl-3'-methoxylbenzylidene) nopinone, (1R, 5R)-(-)-3-(2'-hydroxyl-3'-methoxylbenzylidene) nopinone, (1R, 5R)-(-)-3-(4'-chlorobenzylidene) nopinone or (1R, 5R)-(-)-3-(furan-2'-ylbenzylidene) nopinone. The preparation method of the ultraviolet absorbent comprises the following steps: beta-pinene which is cheap and easy to get is taken as a raw material; nopinone with a bicyclic structure similar with that of camphor is obtained through selective oxidation; and the aldol condensation is carried out on the nopinone and aromatic aldehyde with a different structure so as to synthesize the ultraviolet absorbent. The preparation method has the advantages of simple synthetic route, simplicity and convenience, and economy for operating, high yield, little pollution and the like, and the defect that the camphor has long synthetic route, and high cost and the like is overcome. The synthesized ultraviolet absorbent has the advantages of good ultraviolet absorption effect, wide range of ultraviolet absorption spectrum and good stability and the like, and thus, the ultraviolet absorbent can have an excellent application prospect in ultraviolet absorption.

Description

Technical field [0001] The invention relates to an ultraviolet absorber and a preparation method thereof, in particular to a (1R, 5R)-(-)-3-arylmethylene norpineone ultraviolet absorber and a preparation method thereof. Background technique [0002] The amount of ultraviolet radiation is increasing with the destruction of the ozone layer, and its impact on humans has been recognized worldwide. The skin science community divides the ultraviolet rays contained in sunlight into short-wave ultraviolet (UVC) from 200 to 280 nm, medium-wave ultraviolet (UVB) from 280 to 320 nm and long-wave ultraviolet (UVA) from 320 to 400 nm. The ultraviolet rays below 280 nm are absorbed by the ozone layer. Absorb and cannot reach the ground. Ultraviolet rays that reach the ground will have various effects on people's skin. UVB can cause erythema or blisters on the skin, promote the formation of melanin, cause skin pigmentation, and cause the formation of brown spots. It is the main object of preve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/747C07C49/753C07C49/697C07C45/74C07D307/46A61K8/49A61K8/35A61Q17/04
Inventor 王石发兰蓝杨益琴黄敬怡徐徐鲍名凯赖杰
Owner NANJING FORESTRY UNIV
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