80434-33-9Relevant academic research and scientific papers
Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids
Singh, Bara,Bankar, Siddheshwar K.,Ramasastry
supporting information, p. 1043 - 1048 (2022/02/05)
We describe the palladium-catalyzed Nazarov-type cyclization of easily accessible (hetero)arylallyl acetates to pentannulated (hetero)arenes. This method provides ready access to various types of bi-, tri-, tetra-, and pentacyclic cyclopentanoids under ne
Effect of methoxyl groups on the NMR spectra: configuration and conformation of natural and synthetic indanic and tetralinic structures
Lanta?o, Beatriz,Aguirre, José M.,Drago, Eleonora V.,de la Faba, Diego J.,Pomilio, Nicolás,Mufato, Jorge D.
, p. 619 - 633 (2017/06/08)
Here, we studied the influence of the methoxyl groups attached at C-7 and C-2′ of natural and synthetic 1-arylindanes on the chemical shift of the signal of bibenzylic hydrogen and carbon atoms and J1,2 coupling constants. This influence was also analysed in natural 1-aryltetralins and related compounds that possess methoxyl and/or hydroxyl groups bound at C-8 and C-2′. The methoxyl groups attached at C-7 in indanes or at C-8 in tetralins produce a deshielding signal at H-1 and shield at C-1 and a strong decrease in the value of J1,2 due to the pseudoequatorial location adopted by the aryl group bound at C-1, avoiding an ‘A1,3 strain’. Furthermore, compounds with hydroxyl or methoxyl groups in C-2′, in the absence of substituents of C-7 or C-8, present a strong deshielding signal at H-1, strong shield of the C-1 signal and a decrease in the value of J1,2. This is attributed to the stereoelectronic effects of the methoxyl or hydroxyl groups, which we have called ‘Asarone effect’. NOESY experiments were conducted to confirm the configuration and conformation of some of the compounds included in this work. This study shows that both effects, A1,3 strain and Asarone effect, must be taken into account when the structure of natural indanes and tetralins is analysed by using 1H-NMR and 13C-NMR spectra. Copyright
Gold-Catalyzed Dimeric Cyclization of Isoeugenol and Related 1-Phenylpropenes in Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of 1,2,3-Trisubstituted 2,3-Dihydro-1 H -indenes
Morita, Nobuyoshi,Mashiko, Rie,Hakuta, Dai,Eguchi, Daisuke,Ban, Shintaro,Hashimoto, Yoshimitsu,Okamoto, Iwao,Tamura, Osamu
, p. 1927 - 1933 (2016/07/06)
Gold-catalyzed dimerization of isoeugenol and related 1-phenylpropenes in ionic liquid enabled environmentally friendly, stereoaselective synthesis of 1,2,3-trisubstituted 2,3-dihydro-1H-indenes. Dimerization of isoeugenol or isohomogenol afforded diisoeu
Scope of the formal [3+2] cycloaddition for the synthesis of substituted 3-arylindanes and related compounds
Lanta?o, Beatriz,Aguirre, José Manuel,Ugliarolo, Esteban Ariel,Benegas, María Laura,Moltrasio, Graciela Yolanda
, p. 4090 - 4102 (2008/09/20)
We report the single step synthesis of several 3-arylindanes and related compounds via a formal [3+2] cycloaddition. A study of the influence of the aromatic ring substitution pattern on the reaction was carried out.
