Abstract: The long-chain terminal olefin compounds 1-decene(CM1) and methyl 9-decenoate(CM2) were prepared through olefin cross-metathesis of methyl oleate(MO) with low olefin substrate. The second-generation Hoveyda-Grubbs catalyst was screened out from 4 typical ruthenium-catalyst through the self-metathesis of methyl oleate. The catalytic mechanism was discussed with 4 substrates, then the proposed mechanism was verified by 6 substrates. The results suggested that the short-chain substrates containing electron-rich and bulk-large group like styrene, eugenol and allyl trimethylsilane were beneficial for the preparation of terminal olefin products, since the property of aromatic group, which could chelate with central metal and formed the key ring intermediate, so that it changed the route of reaction and prepared the highly-selectivity of the aim product yield.