Synthesis and Ultraviolet Absorption Characteristics of 4-Arylidene-2-hydroxy-3-pinanones

doi:10.6023/cjoc201207039

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2287-2293.DOI: 10.6023/cjoc201207039 Previous Articles Next Articles

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4-芳亚甲基-2-羟基-3-蒎酮类化合物的合成及其紫外吸收特征研究

魏柏松^a, 徐徐^a,b, 杨益琴^c, 曹晓琴^a, 王石发^a,b

a 南京林业大学化学工程学院南京 210037;
b 江苏省生物质绿色燃料与化学品重点实验室南京 210037;
c 南京林业大学轻工科学与工程学院南京210037

收稿日期:2012-07-26 修回日期:2012-08-23 发布日期:2012-09-04
通讯作者: 王石发 E-mail:wangshifa65@yahoo.com.cn
基金资助:
国家自然科学基金(No. 31170538)资助项目.

Synthesis and Ultraviolet Absorption Characteristics of 4-Arylidene-2-hydroxy-3-pinanones

Wei Baisong^a, Xu Xu^a,b, Yang Yiqin^c, Cao Xiaoqin^a, Wang Shifa^a,b

a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037;
c College of Light Industry and Engineering, Nanjing Forestry University, Nanjing 210037

Received:2012-07-26 Revised:2012-08-23 Published:2012-09-04
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31170538).

A new series of 4-arylidene-2-hydroxy-3-pinanones were synthesized from (-)-α-pinene. (+)-2-Hydroxy- 3-pinanone was obtained from (-)-α-pinene by selective oxidation with potassium permanganate, and it was reacted with aromatic aldehydes including benzaldehyde, p-methylbenzaldehyde, p-methoxybenzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, p-nitrobenzaldehyde, and furfural catalyzed with alkali catalysts to get optical activity 4-arylidene-2-hydroxy-3-pinanones a～g. The structures of a～g were identified by means of ¹H NMR, ¹³C NMR, GC-MS and FT-IR techniques, and their ultraviolet absorption characteristics and light stabilities were also investigated. The results showed that compounds a, b and e exhibit good absorbency as the UV-B-type absorbents, and compounds c, d, f and g had both functions as long-wave ultraviolet (UVA) and medium-wave ultraviolet (UVB) absorbents. The light stability sequence of these compounds was d>c>e>f>b>a>g.

Key words: (-)-α-pinene, (+)-2-hydroxy-3-pinanone, 4-arylidene-2-hydroxy-3-pinanones, ultraviolet absorption

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Wei Baisong, Xu Xu, Yang Yiqin, Cao Xiaoqin, Wang Shifa. Synthesis and Ultraviolet Absorption Characteristics of 4-Arylidene-2-hydroxy-3-pinanones[J]. Chin. J. Org. Chem., 2012, 32(12): 2287-2293.

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4-芳亚甲基-2-羟基-3-蒎酮类化合物的合成及其紫外吸收特征研究

Synthesis and Ultraviolet Absorption Characteristics of 4-Arylidene-2-hydroxy-3-pinanones

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