Novel Synthesis, Crystal Structure, and Plant-growth Regulation Activity of (1S,4R)-4,7,7-Trimethyl-6-oxabicyclo[3.2.1]octane-1,4-diol

作者：Huang Dao-Zhan^*; Xie Zhi-Peng; Lan Hong-Yun

来源：Chinese Journal of Structural Chemistry, 2018, 37(5): 741-746.

DOI：10.14102/j.cnki.0254-5861.2011-1876

• monoterpene oxabicyclodiol
• one-step catalytic synthesis
• crystal structure
• plant-growth regulation activity
• terpinolene

The title compound, (1S,4R)-4,7,7-trimethyl-6-oxabicyclo [3.2.1] octane-1,4-diol (C10H18O3), has been synthesized from terpinolene via one-step catalytic synthetic method and structurally characterized by means of HRMS, IR, H-1-NMR, C-13-NMR and single-crystal X-ray diffraction. The compound crystallizes in trigonal, space group R-3, with a = 27.892(9), b = 27.892(9), c = 6.720(2) angstrom, gamma = 120 degrees, Z = 18, V = 4527(3) angstrom(3), D-c = 1.230 g/cm(3), M-r = 186.24, lambda(MoK alpha) = 0.71073 angstrom, mu = 0.09 mm(-1), F(000) = 1836, the final R = 0.051 and wR = 0.161. The title compound molecule contained a 6-oxabicyclo[3.2.1]octane skeleton and two hydroxyl groups, which were connected through intermolecular O-H...O hydrogen bonds to generate a two-dimensional network. Especially, the preliminary bioassay showed that the title compound can promote the root growth and shoot elongation of rape (Brassica campestris) at low concentration (0.625 similar to 70 mmol.L-1) and inhibit them at high concentration (> 70 mmol.L-1).

• 出版日期2018-5-8
• 单位广西民族大学