28357-10-0Relevant academic research and scientific papers
Reduction by a Model of NAD(P)H. 32. Stereoselective Reduction of Camphoroquinone by a Chiral NAD(P)H Model
Ohno, Atsuyoshi,Goto, Takehiko,Nakai, Jun-ichi,Oka, Shinzaburo
, p. 3478 - 3481 (1981)
(+)-, (-)-, and racemic camphoroquinones (CQ) were reduced by each of four NAD(P)H-models such as N-(α-methylbenzyl)-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide (Me2PNPH) in the presence of magnesium ion in acetonitrile with a view to elucidating the intermolecular arrangement in the transition state for asymmetric reduction.Partial rate factors for each attacking mode were calculated.Electronegative substituents in the substrate prefer to facing the carbamoyl group in Me2PNPH, which is the most important factor determining the stereochemical course of the reduction. 1-Methyl group in CQ has a tendency to interfere with the dihydropyridine moiety in Me2PNPH approaching the C2-carbonyl group in CQ.This interference is more important for the selectivity than the intrinsic exo/endo reactivity difference.
Biotransformation of (+)- and (-)-camphorquinones by plant cultured cells
Chai, Wen,Hamada, Hiroki,Suhara, Jumpei,Akira Horiuchi
, p. 669 - 673 (2007/10/03)
Biotransformation of (+)- and (-)-camphorquinones with suspension plant cultured cells of Nicotiana tabacum and Catharanthus roseus was investigated. It was found that the plant cultured cells of N. tabacum and C. roseus reduce stereoselectively the carbonyl group of (+)- and (-)-camphorquinones to the corresponding α-keto alcohols.
Minor Products in Photoreactions of α-Diketones with Arenes. Abstraction of Hydroxylic Hydrogen by Triplet Carbonyl
Rubin, Mordecai B.,Gutman, Arie L.
, p. 2511 - 2515 (2007/10/02)
Photochemical reactions of cyclic saturated α-diketones in toluene or p-xylene produce 1:1 adducts as major products and smaller amounts of reduced diketone and bibenzyls, as expected from previous work.In addition, reaction of BOD gave 2percent of the decarbonylation product, p-methylbenzyl cyclohexyl ketone; reaction of camphorquinone gave a mixture of decarbonylation products (10percent total) including saturated and unsaturated monoketones.These compounds were secondary products arising from reaction of photoexcited diketone with the initially formed adducts; quenching andsensitization studies showed that triplet states of α-diketones were involved in both primary and secondary reactions.The decarbonylation products were also formed by reaction of benzophenone triplets or of tert-butoxy radicals with adducts.Deuterium labeling of the adducts was employed to demonstrate that the decarbonylation process involves abstraction of hydroxylic hydrogen.
