1995 Fiscal Year Final Research Report Summary
Fluorination of terpenoid carbonyl compounds used in perfumery
| Project/Area Number |
06650977
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Chiba University |
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Principal Investigator |
WATANABE Shoji Chiba University, Faculty of Engineering, Prof., 工学部, 教授 (60009222)
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| Co-Investigator(Kenkyū-buntansha) |
SAKAMOTO Masami Chiba University, Faculty of Engineering,, 工学部, 助教授 (00178576)
FUJITA Tsutomu Chiba University, Faculty of Engineering,, 工学部, 助教授 (70009538)
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| Project Period (FY) |
1994 – 1995
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| Keywords | Reformatsky reaction / Trifluromethylation / Olah reagent / Terpenic aldehyde / Swern oxidation / Trifluoroacetaldehyde / Antimicrobial test |
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| Research Abstract |
Reformatsky reaction of trifluoroacetaldehyde with lower bromoesters gave their corresponding adducts. The reaction of trifluoroacetaldehyde with methyl 2-(bromomethyl)acrylate gave gamma-trifluoromethyl-alpha-methylene-gamma-butyrolactone. Reformatsky reaction of terpenic aldehydes with difluoromonobromo acetate gave their corresponding adducts. The reaction of citronellal with difluoromonobromo acetate gave ethyl 2,2-difluoro-5,9-dimethyl-3-hydroxy-8-decenoate. Swern oxidation of these hydroxyesters gave their corresponding alpha, alpha-difluoro-beta-ketoesters.
The reaction of trifluoromethyltrimethylsilane with a variety of terpenoid carbonyl compounds and other carbonyl compounds used in perfumery gave the corresponding trifluoromethylated derivatives. Pentafluoroethylated compounds were similarlly obtained from the reaction of pentafluoroethyltrimethylsilane with various substrate.(-)-2-Trifluoro-1-furyl ethanol has been obtained with high optical purity by enzymatic hydrolysis of 2-trifluoro-1-furyl ethyl acetate.
We had expected that trifluoromethylated and pentafluoroethylated compounds derived from terpenoid compounds would have biological activity. However, our biological tests showed no antimicrobial activity agatint Gram positive and Gram negative bacteria, mycelial fungi and yeasts.
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