アクリルアルデヒド-ジエチルアセタールを原料とするγ-オキソアルデヒド及び関連化合物の合成

• 司 英隆

  豊玉香料株式会社

書誌事項

タイトル別名

• Synthesis of γ-Oxoaldehydes and Their Related Compounds from Acrylaldehyde Diethyl Acetal
• アクリルアルデヒド ジエチルアセタール オ ゲンリョウ ト スル ガンマ オキ

抄録

This paper describes the synthesis of pheromones and jasmonoids from acrylaldehyde diethyl acetal (1). The synthetic route is shown in Scheme-1. <BR>The radical addition reaction of aldehyde with (1) was carried out with benzoyl peroxide as the initiator in N₂ atomosphere. γ-Oxoaldehyde acetal [(6), (7), (8), (9)] was obtained as the major product by this reaction. <BR>cis-12-Nonadecen-9-one (14) was synthesized from 1, 1-diethoxy-4-oxododecanal (11) prepared from (7), by Wittig reaction in 62% yield. Similarly, cis-13-icosen-1O-one (15) and cis-5-undecen-2-one (16) were prepared from γ-oxoaldehyde in 6062% yield. <BR>Methyl jasmonate (18) and cis-jasmone (19) were synthesized from 2- (cis-2-pentenyl) -2-cyclopentenone (17) prepared from 4-oxo-cis-7-decenal (10), according to the published method. γ-Jasmolactone (21) was prepared from 1, 1-diethoxy-cis-7-decen-4-ol (20) by Jones oxidation in 88% yield.

収録刊行物

• 油化学

  油化学 36 (5), 362-365, 1987

  公益社団法人 日本油化学会

詳細情報

• CRID: 1390001205336023168
• NII論文ID: 130001020088
• NII書誌ID: AN00245435
• ISSN: 0513398X
• ISSN: 18842003
• DOI: 10.5650/jos1956.36.362
• NDL書誌ID: 3132666
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I3132666
• Web Site: https://www.jstage.jst.go.jp/article/jos1956/36/5/36_5_362/_pdf
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