38651-65-9Relevant articles and documents
Synthesis and antibacterial activity of pinanyl-2-amino pyrimidines
Wu, Jun,Wang, Peng-Na,Xu, Xu,Yang, Yi-Qin,Wang, Shi-Fa
, p. 7769 - 7775 (2014)
A new series of pinene-2-alkyl amino pyrimidines were synthesized from (-)-β-pinene. (+)-No-pinone was obtained from (-)-β-pinene by selective oxidation with potassium permanganate and it was reacted with aromatic aldehydes including benzaldehyde, p-methylbenzaldehyde, p-methoxylbenzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, p-nitrobenzaldehyde, p-fluorobenzaldehyde, o-chlorobenzaldehyde, m-nitrobenzaldehyde, o-vanillin and furfural catalyzed with alkali catalysts to get optically active 3-arylidenenopinones 2a-2l. Then in the alkali catalytic conditions, they were used to synthesize pinanyl-2-amino pyrimidines (3a-3l) with guanidine hydrochloride. The structures of the synthesized compounds were identified by 1H NMR, 13 C NMR, FT-IR, GC-MS and elemental analysis. The antimicrobial activity of the newly synthesized pinanyl-2-amino pyrimidines (3a-3l) was done against C. albicans, A. niger, G. tropicalis, E. coli, S. aureus, B. Subtilis and P. fluorescens. It has been observed that compounds 3a and 3g have strong inhibition effect against Candida albicans, 3g has strong inhibition effect against Aspergillus niger, while 3g also has strong inhibition effect against Candida tropicalis.
Sustainable terpene-based polyamides: Via anionic polymerization of a pinene-derived lactam
Winnacker, Malte,Sag, Jacob
, p. 841 - 844 (2018)
A sustainable lactam, which is derived from the renewable terpene β-pinene, is converted to polyamides via a convenient anionic ring-opening polymerization (ROP), which can be easily handled without the use of a costly catalyst. The resulting polyamides have prosperous thermal properties, which enable their future use as high-performance polymers.
Synthesis and study of the antimalarial cardamom peroxide
Hu, Xirui,Lim, Pharath,Fairhurst, Rick M.,Maimone, Thomas J.
, p. 3358 - 3369 (2018)
A full account of our previously disclosed synthesis of the monoterpene dimer cardamom peroxide is reported. Inspired by hypotheses regarding the potential biosynthetic origins of this natural product, several unproductive routes are also reported. The ch
(1R,5S)-(+)-nopinone of high enantiomeric purity
Kozmina, Natasha,Paquette, Leo A.
, p. 2027 - 2030 (1996)
Commercial β-pinene of 87% ee can be upgraded to the 98+% ee level by simple treatment with silver perchlorate. A solid complex is obtained whose formation is more rapid when two like enantiomers are involved. Simple dissolution of this precipitate in water releases the enantio-enriched hydrocarbon from which (+)-nopinone of high enantiomeric purity is obtained via ozonolysis.
Synthesis and oxidative transformations of new chiral pinane-type γ-ketothiols: Stereochemical features of reactions
Frolova, Larisa L.,Lezina, Olga M.,Rubtsova, Svetlana A.,Subbotina, Svetlana N.,Sudarikov, Denis V.
, (2021/09/06)
Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)2 catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed.
Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene
Kmieciak, Anna,Krzemiński, Marek P.
, p. 2493 - 2499 (2019/12/11)
New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1R,2R,4S,5R)-3-methyleneneoisoverbanol and (1R,2R,3R,5R)-4-methyleneneoisopinocampheol, to allylphosphine oxides. Hydroxy groups were introduced stereoselectively through a hydroboration–oxidation reaction proceeding from the less hindered site providing a trans relationship between the hydroxy and the phosphine substituents.
