A convenient synthesis of 4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-enone, an alcohol moiety of a synthetic pyrethroid having strong killing and knockdown activity.

MATSUO N; FUJITA F; MAGARA O; YAMAZAKI H; AKETA K; NISHIOKA T; ITAYA N

Art

J-GLOBAL ID：200902084174201634 Reference number：82A0431434

A convenient synthesis of 4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-enone, an alcohol moiety of a synthetic pyrethroid having strong killing and knockdown activity.

強い殺虫力とノックダウン活性を持つ合成ピレトロイドのアルコール側鎖である,4-ヒドロキシ-3-メチル-2-(2-プロピニル)-シクロペント-2-エノンの簡易合成

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Author (7)： , , , , , ,
Material：
Volume： 46 Issue： 7 Page： 1911-1912 Publication year： Jul. 1982
JST Material Number： G0021A ISSN： 0002-1369 CODEN： ABCHA6 Document type： Article
Article type：短報 Country of issue： Japan (JPN) Language： ENGLISH (EN)

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Pesticides to insect pest

Reference (6)：

1) W. A. Gersdorff and P. G. Piquett, 7. Econ. Entomol, 54, 1250 (1961).
2) M. Hirano et al., unpublished results.
3) a) M. S. Schechter and F. B. LaForge, US Patent 2574500 (1951) [C.A., 46, 5078h (1952)] and 2661374 (1953) [C.A., 49, 1788e (1955)]. The claims in these patents include the synthesis of the alcohol (II) from 5-hexyn-2-one, but no example was disclosed. Our experiments proved that the total yield of II from ethyl acetoacetate via 5-hexyn-2-one was below 5% in 5 steps.
b) R. W. Kierstead and R. A. Lemahieu, US Patent 3715400 (1973); [C.A., 78, 147438t (1973)].
c) M. Matsui, J. Katsube, H. Shimomura and S. Kitamura, Japanese Patent Kokai 7705736 (1977) [C.A., 87, 5495 (1977)].

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