62429-57-6Relevant articles and documents
Syntheses of perillene and natural congeners via Li2CuCl4-catalyzed cross-coupling reaction of allylic carbonates
Sun, Ya-Nan,Wang, Qi,He, Ling,Wang, Xi,Li, Wei-Dong Z.
, (2022/01/24)
Perillene is an essential ingredient in a Chinese patent drug and features some fascinating biological activities. We present herein an efficient pathway to perillene that hangs on the cross-coupling reaction of allylic carbonates with furfuryl Grignard r
A novel recyclable sulfur monoxide transfer reagent
Grainger, Richard S.,Procopio, Alberto,Steed, Jonathan W.
, p. 3565 - 3568 (2007/10/03)
(matrix presented) Trisulfide 2-oxide 11 has been prepared from disulfide 9 via reduction to the corresponding dithiol and subsequent trapping with thionyl chloride. Heating trisulfide oxide 11 in the presence of dienes results in transfer of sulfur monoxide to form cyclic unsaturated sulfoxides 13 in good to excellent yields, along with recovery of disulfide 9. A Pummerer reaction can be used to convert the cyclic sulfoxides into thiophenes.
Structure-Odor Correlation, XXI. Olfactory Properties and Convenient Synthesis of Furans and Thiophenes Related to Rose Furan and Perillene and Their Isomers
Weyerstahl, Peter,Schenk, Anja,Marschall, Helga
, p. 1849 - 1854 (2007/10/03)
Starting from 3-bromofuran (1) or 3-bromothiophene (2) via alkylation in 2-position (-> 3-8) followed by the corresponding second alkylation in 3-position, we obtained rose furan (9), rose thiophene (10), and their analogs 11-16.From the α,β-unsaturated esters 17-20 by hydrogenation (-> 21-24), DIBAH reduction (-> 25-28), and Wittig reaction, perillene (29), thioperillene (30), and their analogs 29-36 were obtained.Olfactory evaluation showed that the difference between the furans and thiophene derivatives is remarkably small, particularly for perillene (29) compared with thioperillene (30), and their analogs.Also the influence of position and structure of the side chain is lower than expected within the compared compounds 9-36. - Keywords: Rose furan / Perillene / Furans / Thiophenes / Structure-odor correlation / Odoriferous substances