Synthesis of Novel Fragrant Molecules 6-Methoxy-2,6-dimethyl Heptanol Derivatives

摘要

Methoxy elgenol as an important class of monomeric spices, has rich and pleasing aroma of sandalwood and flowers. We have synthesized a series of derivatives of methoxy elgenol, which have the similar structure of (CH3)2COCH3(CH2)3CHCH3CHROH, expecting sandalwood odor molecules. Actually, the novel compounds possess a wide odor range, different from methoxy elgenol, from typically melon odorants to derivatives with floral, marine, fruity, faint scent or even metallic aroma. This work describes the methoxylation of methyl heptenone and Darzens condensation to form 6-methoxy-2,6-dimethyl-heptanol (4), which is an important starting material for synthesizing the derivatives of 6-methoxy-2,6-dimethyl-heptanol (5), namely 8-mefhoxy-4,8-dimethylnoman-3-ol (5a), 9-methoxy-5,9-dimethyldecan-4-ol (5b), 8-methoxy-2,4,8-dimefhyl-decan-3-ol (5c), 10-methoxy-6,10-dimethylundecan-5-ol (5d), 9-meth-oxy-2,5,9-trimethyldecan-4-ol (5e), 10-methoxy-2,6,10-trimefhylundecan-5-ol (5f'), l-cyclopentyl-6-mefhoxy-2,6-dimethyl-heptan-1-ol (5g), 2-methoxy-2,6-dimethyltridecan-7-ol (5h), 1-cyclohexyl-6-methoxy-2,6-dimethylheptan-1-ol (5i), 9-methoxy-5,9-dimethyldec-1-en-4-ol (5j), pleasant smell emanating from 10-methoxy-2,6,10-trimethylundecan-5-ol (5f) with elegant melon and delicatesea breeze, 2-methoxy-2,6-dimethyltridecan-7-ol (5h) with faint scent, fruity and oce-an-like taste and 9-methoxy-5,9-dimethyldec-1-en-4-ol (5j) with melon and elegant floral.