75091-79-1Relevant academic research and scientific papers
NMR studies on [2+3] cycloaddition of nitrile oxides to cyclohexene derivatives
Gucma, Miros?aw,Go??biewski, W. Marek,Michalczyk, Alicja K.
, p. 223 - 232 (2014/02/14)
Site selectivity, regioselectivity and stereoselectivity of [2+3] cycloaddition of 4-trifluoromethylbenzonitrile oxide to cyclohexene carboxylates substituted with alkenyl functions were examined. Site selectivity was correlated with electron charges of alkenyl carbon atoms. Structure of the products has been established by an extensive application of 2D 1H and 13C NMR spectroscopy and electrospray ionization mass spectrometry.
Key structural features of cis-cinnamic acid as an allelochemical
Abe, Masato,Nishikawa, Keisuke,Okuda, Katsuhiro,Shindo, Mitsuru,Fukuda, Hiroshi,Nakanishi, Kazunari,Tazawa, Yuta,Taniguchi, Tomoya,Park, So-Young,Hiradate, Syuntaro,Fujii, Yoshiharu
, p. 56 - 67,12 (2012/12/12)
1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.
Isomerisation de dienes-1,5 fonctionnalises par le fer pentacarbonyle
Rodriguez, J.,Brun, P.,Waegell, B.
, p. 343 - 370 (2007/10/02)
A series of various, functionnalized 4-vinylcyclohexene derivatives, substituted with electron-withdrawing or -donating groups on the exocyclic double bond, have been isomerized by pentacarbonyliron, under thermodynamic control with heating, into a mixture of conjugated cyclohexadiene tricarbonyliron complexes, of which the 2-substituted derivative is the predominant.When ferrous chloride is used as the co-catalyst, the isomerisation proceeds under kinetic control to give the 1-substituted cyclohexadienetricarbonyliron complex as the major derivative.Reaction mechanisms, have been proposed for these isomerisation processes, which provide a new selective route to such derivatives.The formation of η4-1,4-cyclohexadienetricarbonyl complexes as intermediates has been excluded, and it is shown that the thermal isomerisation proceeds via η2-complexes that are formed by successive 1,3-hydrogen shifts.
SYNTHESIS OF CYCLOHEXENYL-SUBSTITUTED ACRYLIC AND 3-HYDROXYPROPIONIC ACIDS AND THEIR HOMOLOGS
Gramenitskaya, V. N.,Inozemtseva, L. V.,Koz'mina, E. A.,Vul'fson, N. S.
, p. 2260 - 2267 (2007/10/02)
The corresponding 3-cyclohexenyl-substituted Z- and E-acrylic and 3-hydroxypropionic acids were synthesized from 3-cyclohexene-1-carbaldehyde and its methyl derivatives.Dehydration of the products under various conditions leads to the formation of the E isomers of the substituted acrylic acid and also isomerization, aromatization, and cyclization products.
