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

Articles

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   

  1. 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 Baisonga, Xu Xua,b, Yang Yiqinc, Cao Xiaoqina, Wang Shifaa,b   

  1. 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 ag. The structures of ag 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