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
收稿日期: 2012-07-26
修回日期: 2012-08-23
网络出版日期: 2012-09-04
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
Received date: 2012-07-26
Revised date: 2012-08-23
Online published: 2012-09-04
Supported by
Project supported by the National Natural Science Foundation of China (No. 31170538).
以(-)-α-蒎烯为原料合成了系列新型4-芳亚甲基-2-羟基-3-蒎酮类化合物. (-)-α-蒎烯经选择性氧化得到(+)-2-羟基-3-蒎酮; 在碱催化作用下, (+)-2-羟基-3-蒎酮与苯甲醛、对甲基苯甲醛、对甲氧基苯甲醛、对羟基苯甲醛、对氯苯甲醛、对硝基苯甲醛和糠醛等芳香醛缩合, 得到系列光学活性4-芳亚甲基-2-羟基-3-蒎酮类化合物a～g. 采用1H NMR, 13C NMR, GC-MS和FT-IR等分析手段对合成所得4-芳亚甲基-2-羟基-3-蒎酮类化合物的结构进行了表征, 考察了它们的紫外吸收特性及光稳定性. 结果表明, 化合物a, b, e对UVB具有良好的吸收性能; 而化合物c, d, f, g兼具长波紫外线(UVA)和中波紫外线(UVB)的吸收性能. 化合物a～g的光稳定性顺序为d>c>e>f>b>a>g.
关键词： (-)-α-蒎烯; (+)-2-羟基-3-蒎酮; 4-芳亚甲基-2-羟基-3-蒎酮; 紫外吸收
魏柏松 , 徐徐 , 杨益琴 , 曹晓琴 , 王石发 . 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[J]. 有机化学, 2012 , 32(12) : 2287 -2293 . DOI: 10.6023/cjoc201207039
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.
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