کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5216864 1383279 2014 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and olfactory properties of unnatural derivatives of lilac aldehydes
ترجمه فارسی عنوان
سنتز و خواص بویایی مشتقات غیر طبیعی از آلدئیدها سیلان
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared and evaluated two sets of their unnatural racemic analogues as pure diastereomers. While the synthesis of gem-dimethyl homologues starts from geranyl acetate, the preparation of methylene derivatives commences from linalyl acetate. The key Lewis and/or Brønsted acid catalysed cyclisation furnishes easily separable cis-/trans-tetrahydrofuranyl esters as common advanced intermediates. The subsequent functional group transformations lead to target aldehydes, alcohols, nitriles and olefins. Unlike the homologues possessing similar herbal scents, methylene derivatives exhibit woody and/or flowery odours. In the latter case, the sensory evaluation suggests the importance of relative stereochemistry and/or type of functional group on the odour character of respective compounds.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 70, Issue 37, 16 September 2014, Pages 6420-6427
نویسندگان
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