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bce ›› 2018, Vol. 52 ›› Issue (3): 23-28.doi: 10.3969/j.issn.1673-5854.2018.03.004

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One-step Catalytic Synthesis and Herbicidal Activity of (1S,4R)-4,7,7-Trimethyl-6-oxabicyclo[3.2.1] octane-1,4-diol

XIE Zhipeng, HUANG Daozhan, HUANG Yanpei, HUANG Yanni   

  1. College of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530008, China
  • Received:2017-09-22 Online:2018-05-30 Published:2018-05-31

Abstract: (1S,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-1,4-diol(2) was synthesized from terpinolene by using hexadecyl pyridinium peroxo heteropolyoxomolybdotungstate(HPP) as redox-acid bifunctional catalyst and 30%(mass fraction) H2O2 as oxidant. The optimal conditions for the reaction were terpinolene 4 mmol, HPP catalyst 7.35%(calculated by the mass of terpinolene), solvent chloroform 0.8 mL, the reaction material ratio(molar ratio of H2O2 and terpinolene) 3, reaction temperature 35℃, reaction time 6 h. Under these conditions, the conversion rate of terpinolene reached 100% and the yield of compound 2 reached 29%. The molecular structure was identified by means of IR, NMR and single crystal X-ray diffraction. The preliminary herbicidal activity assay indicated that compound 2 showed excellent inhibitory effect against the root growth and shoot elongation of ryegrass(Lolium rigidum); the inhibition rates against the root growth and shoot elongation were up to 91.8% and 80.7%, respectively, at the concentration of 120 mmol/L. Compared with the reported 1, 8-cineole, compound 2 had better inhibitory effect on ryegrass.

Key words: monoterpene oxabicyclodiol, one-step catalytic synthesis, terpinolene, peroxypolyoxometalate, herbicidal activity

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