68386-90-3Relevant academic research and scientific papers
A Broad-Spectrum Synthesis of Tetravinylethylenes
Horvath, Kelsey L.,Newton, Christopher G.,Roper, Kimberley A.,Ward, Jas S.,Sherburn, Michael S.
, p. 4072 - 4076 (2019/03/22)
The first general synthesis of compounds of the tetravinylethylene (TVE) family is reported. Ramirez-type dibromo-olefination of readily accessible penta-1,4-dien-3-ones generates 3,3-dibromo[3]dendralenes, which undergo twofold Negishi, Suzuki–Miyaura or Mizoroki–Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically substituted tetravinylethylenes with up to three different alkenyl substituents attached to the central C=C bond. The extensive scope of the approach is demonstrated by the preparation of the first higher order oligo-alkenic through-conjugated/cross-conjugated hybrid compounds. An unsymmetrically substituted TVE is shown to undergo a domino electrocyclization–cycloaddition with high site-selectivity and diastereoselectivity, thereby demonstrating the substantial synthetic potential of substituted TVEs for controlled, rapid structural complexity generation.
Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
, p. 872 - 875 (2019/05/16)
The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.
Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
, p. 1027 - 1031 (2015/02/19)
In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
Syntheses of 4H-thiopyran-4-one 1,1-dioxides as precursors to sulfone-containing analogues of tetracyanoquinodimethane
Rule,Detty,Kaeding,Sinicropi
, p. 1665 - 1673 (2007/10/02)
Synthetic routes to the unsubstituted 4H-thiopynan-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation of 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.
Equilibrium acidities of some α,ω-diphenylpolyenes
Thiele, Georg,Streitwieser, Andrew
, p. 446 - 454 (2007/10/02)
Cesium ion pair acidities were measured in THF for a series of diphenylmethane vinylogues that form α,ω-diphenylpolyenyl anions with linearly conjugated chains of 3-9 carbon atoms. The dissociation constants of the diphenylpolyenyls in THF were determined by UV-vis spectroscopy and are rationalized with an electrostatic model. Acidity and dissociation data were combined with measurements of stereoisomer equilibria to estimate the differences in delocalization energy among the diphenylpolyenyl ions. The experimental differences in acidity correlate well with AMI and molecular mechanics (MMPI) calculations.
