93302-57-9Relevant academic research and scientific papers
FRAGRANCES WITH NOTE OF LILY OF THE VALLEY
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Paragraph 0274; 0275; 0276, (2013/04/13)
A compound of formula (I) is described and use thereof as fragrance, especially as lily-of-the-valley fragrance and/or as an agent for increasing the substantivity and/or the retention of a fragrance preparation and/or as a fixative.
Synthesis of the Alleged Natural Monoterpenoid α-Santolinenone
Guella, Graziano,Cavazza, Marino,Guerriero, Antonio,Pietra, Francesco
, p. 1248 - 1253 (2007/10/02)
Authentic α-santolinenone ( = (+)-(4R)-1(7)-p-menthen-2-one; (+)-1) is made available for the first time in 30 percent overall yield from (+)-(4R)-p-menthene ((+)-2) via the diastereomeric allylic alcohols (+)-4a/(+)-4b, which are oxidized to (+)-1 with Ag2CO3/Celite.Yields are good, except for the last stage; indeed, only alcohol (+)-4a, with equatorial OH-group, undergoes oxidation, and (+)-1 is partly substracted via a hetero Diels-Alder dimerization giving a mixture of the diastereomeric dihydropyrans (+)-5a/(+)-5b.When Cr(VI) reagents are used, (+)-4a/(+)-4b mainly give phelandral (6) and carvotanacetone (7).MnO2 reacts too sluggishly with (+)-4a/(+)-4b.A camphor pyrolyzate, previously thought to be 1 must be a different compound, probably 7.
Stereoselective Synthesis of Alcohols, IV Conformational Factors Determining the Stereochemistry of the Allyl Sulfoxide/ Allyl Sulfenate-Rearrangement
Hoffmann, Reinhard W.,Gerlach, Rainer,Goldmann, Siegfried
, p. 856 - 863 (2007/10/02)
The stereochemistry of the sigmatropic rearrangement of the conformationally rigid allyl sulfoxides 5 revealed a 6.2 fold preference for axial formation of the new C-O-bond.This preference dominates the 3.1 fold preference for an exo-versus endo-tran
