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Chemistry and Industry of Forest Products ›› 2016, Vol. 36 ›› Issue (5): 30-36.doi: 10.3969/j.issn.0253-2417.2016.05.005

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Synthesis of α-Brominated Isolongifolenone with Chirality

DING Zhi-bin1, SUN Nan1, ZHANG Qi1, CAO Xiao-qin1, XU Xu1,2,3, WANG Shi-fa1,2,3   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    2. Jiangsu Co-innovation Center of Efficient Process and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China;
    3. Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, Nanjing 210037, China
  • Received:2015-10-14 Online:2016-10-25 Published:2016-11-05

Abstract: The bromo-reaction of (2R, 4aS)-isolongifolenone to α-brominated isolongifolenone was investigated. Isolongifolenone was reacted with copper bromide in ethyl acetate, and the two isomerides, (2R,4aR,6R)-(+)-6-Br-isolongifolenone ([α]D25+81°) and (2R,4aR,6S)-(-)-6-Br-isolongifolenone ([α] D25-58°), were obtained by purification with preparative liquid chromatography. The structures of the two compounds were characterized by 1H NMR,FT-IR,GC-MS, specific rotation, and singal crystal X-ray diffraction. Furthermore, the effects of preparing conditions on the products were also explored. It was shown that (2R,4aR,6S)-(-)-6-Br-isolongifolenone could be obtained through a selective bromination of isolongifolenone by using ethanol as solvent and copper bromide as the reaction reagent. The optimum conditions of preparing (2R,4aR,6S)-(-)-6-Br-isolongifolenone were the molar ratio of copper bromide/isolongifolenone 3:1, ethanol dosage 60 mL, reaction time 3 h and reaction temperature 78℃. Under the foresaid conditions, the reaction selectivity and the yield of (2R,4aR,6S)-(-)-6-brominated isolongifolenone were 93% and 88%, respectively.

Key words: isolongifolenone, α-bromination, (2R,4aR,6R)-(+)-6-Br-isolongifolenone, (2R,4aR,6S)-(-)-6-Br-isolongifolenone

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