36065-09-5Relevant academic research and scientific papers
Synthesis and structural characterization of novel camphor-derived amines
Groselj, Uros,Sevsek, Alen,Ricko, Sebastijan,Golobic, Amalija,Svete, Jurij,Stanovnik, Branko
, p. 778 - 788,11 (2020/08/20)
Two novel 4-substituted camphidine derivatives 10a,b have been prepared from (+)-camphor (1) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b, formed as a side product during the hydrogenation of arylidene ketone 3b, under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12. (1S)-(+)-Camphorquinone (13) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17, an N-heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X-ray analysis. Copyright
Synthesis and structural elucidation of novel camphor-derived thioureas
Groselj, Uros,Golobic, Amalija,Stare, Katarina,Svete, Jurij,Stanovnik, Branko
scheme or table, p. 307 - 317 (2012/06/18)
Nine novel (+)-camphor-derived thioureas have been prepared. 3-((Dimethylamino)methylene)camphor (2) served as the common precursor for the preparation of both, 2-thiourea 15-20 and 3-thiourea functionalized camphor derivatives 6, 7/7′, respectively. Starting from 2, the latter were prepared in two or three steps whereas the former in five steps, respectively. Configuration of all novel compounds has been meticulously determined using NMR techniques and/or single crystal X-ray crystallography. Copyright
Synthesis of the first C2-asymmetric phosphinine and its pyrylium precursor
Bell, Jason R.,Franken, Andreas,Garner, Charles M.
body text, p. 9368 - 9372 (2009/12/28)
The synthesis of the first C2 chiral phosphinine (phosphabenzene) and its pyrylium salt precursor is reported. The chiral phosphinine is derived from (+)-camphor, is a crystalline air-stable solid and is shown to effectively form complexes with metals. A preliminary result using the phosphinine as a ligand for asymmetric catalysis is reported and rationalized structurally.
Simple and effective protocol for Claisen-Schmidt condensation of hindered cyclic ketones with aromatic aldehydes
Vashchenko, Valeriy,Kutulya, Lidiya,Krivoshey, Alexander
, p. 2125 - 2134 (2008/03/28)
A simple and effective methodology for Claisen-Schmidt condensation of (-)-menthone and other hindered cyclic ketones with aromatic aldehydes under highly basic conditions using a polar aprotic solvent and a strong base (alkali metal hydroxide or an alkoxide) is described and discussed. Georg Thieme Verlag Stuttgart.
RuCl2(DMSO)4 catalyzes the β-alkylation of secondary alcohols with primary alcohols through a hydrogen autotransfer process
Martínez, Ricardo,Ramón, Diego J.,Yus, Miguel
, p. 8982 - 8987 (2007/10/03)
The electrophilic β-alkylation of secondary alcohols with primary alcohols is accomplished by a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4. The reaction can produce either simple alkylated secondary alcohols or α,β-unsaturated ketones with good to excellent results just by choosing the appropriate starting secondary alcohol (methyl or longer chain secondary alcohol, respectively), as well as quinolines (by using 2-aminobenzyl alcohol).
Stereoselective additions to the exocyclic C{double bond, long}C bond of some α-alkylidene-(+)-camphor derivatives
Groselj, Uros,Bevk, David,Jakse, Renata,Meden, Anton,Stanovnik, Branko,Svete, Jurij
, p. 1217 - 1237 (2007/10/03)
Stereoselective additions to the exocyclic C{double bond, long}C double bond of some (1R,3E,4S)-3-alkylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and (1R,4E,5S)-4-alkylidene-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones were studied. All additions took place predominantly from the less hindered endo-face of the methylidene compounds to give the corresponding exo-adducts as the major isomers. Thus, catalytic hydrogenations afforded the α-alkylated (1R,3R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and (1R,4R,5R)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones in 28-100% de. Similarly, 1,3-dipolar cycloadditions of 2,4,6-trisubstituted benzonitrile oxides gave the corresponding spiro cycloadducts in 66-100% de. The structures were determined by 2D NMR techniques, NOESY spectroscopy and X-ray diffraction.
A class II aldolase mimic
Hedin-Dahlstroem, Jimmy,Rosengren-Holmberg, Jenny P.,Legrand, Sacha,Wikman, Susanne,Nicholls, Ian A.
, p. 4845 - 4853 (2007/10/03)
A class II aldolase-mimicking synthetic polymer was prepared by the molecular imprinting of a complex of cobalt (II) ion and either (1S,3S,4S)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4a) or (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4b) in a 4-vinylpyridine-styrene-divinylbenzene copolymer. Evidence for the formation of interactions between the functional monomer and the template was obtained from NMR and VIS titration studies. The polymers imprinted with the template demonstrated enantioselective recognition of the corresponding template structure, and induced a 55-fold enhancement of the rate of reaction of camphor (1) with benzaldehyde (2), relative to the solution reactions, and were also compared to reactions with a series of reference polymers. Substrate chirality was observed to influence reaction rate, and the reaction could be competitively inhibited by dibenzoylmethane (6). Collectively, the results presented provide the first example of the use of enantioselective molecularly imprinted polymers for the catalysis of carbon-carbon bond formation.
Synthesis and properties of benzylidene derivatives of terpenoid ketones
Chuiko,Vinarskaya,Izotova,Tychinskaya
, p. 196 - 199 (2007/10/03)
Optically active benzylidene derivatives of camphor and menthone were obtained in preparative yields by condensation of the ketones with aromatic aldehydes in DMSO in the presence of t-BuOLi. The synthesized α,β-unsaturated ketones show high specific rotation and thus are suitable to bedoping component to liquid-crystalline compositions.
THE OCTANT RULE XXIII. ANTIOCTANT EFFECTS IN γ,δ-UNSATURATED KETONES
Toan, Vien Van,Lightner, David A.
, p. 5769 - 5774 (2007/10/02)
The exo and endo α-benzyl derivatives (1 and 2. respectively) of (+)-camphor have been synthesized and are found to exert a strong influence on the circular dichroism n?* Cotton effects: 1: Δε301max -0.36 (n-heptane) and 2: Δε302max +3.22, relative to camphor: Δε304max + 1.8 (n-heptane).Evidence for electric dipole transition moment coupling in these γ,δ-unsaturated systems is found in the n?* UV: 1: ε291max 84 (n-heptane) and 2: ε285max 303, relative to camphor: ε290max 25.
