25172-06-9

Usage

InChI:InChI=1/C8H12O/c1-3-4-5-6-7-8(2)9/h3,6-7H,1,4-5H2,2H3/b7-6-

Upstream product

• 2100-17-6 4-pentenal 
• 30935-85-4 (2-oxopropyl) diethyl phosphate 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 821-09-0 n-Pent-4-enyl alcohol 
• 3664-60-6 7-octene-2-one 
• 4643-20-3 (E)-4-chloro-3-buten-2-one 
• 51049-54-8 Di-3-butenyl-cadmium 
• 5162-44-7 1-bromo-4-butene 
• 1809-59-2 4-(diethylamino)-3-butene-2-one 
• 1809-59-2 1-diethylamino-1-buten-3-one 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 1235-21-8 acetonyltriphenylphosphonium chloride 

Downstream Products

• 863603-64-9 (4E,8E)-10-Hydroxy-1-phenyl-undeca-4,8-dien-3-one 
• 863603-62-7 (2E,6E)-8-Hydroxy-1-phenyl-nona-2,6-dien-1-one 

Relevant academic research and scientific papers

Tertiary Amine Promoted Aziridination: Preparation of NH-Aziridines from Aliphatic α,β-Unsaturated Ketones

trans-NH-Aziridines were prepared from aliphatic α,β-unsaturated ketones using a tertiary amine promoted reaction via in situ generated N,N-ylides. Through use of modified conditions the reaction proved to be applicable for the diastereoselective aziridination of a range of enolisable aliphatic α,β-unsaturated ketones of varying substitution patterns.

NOVEL SPIROOXINDOLE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

Disclosed is a compound of formula I: wherein R?1?, R?2?, R?3?, R?4?, R?5?, n and m are defined herein. The compound of formula I is prepared by a concise, catalytic enantioselective formal hetero-Diels-Alder (hDA) reactions of enones with isatins and is useful for making pharmaceutical composition for the treatment of proliferative diseases.

Catalytic enantioselective formal Hetero-Diels-Alder reactions of enones with isatins to give spirooxindole tetrahydropyranones

Organocatalytic formal hetero-Diels-Alder reactions of enones with isatins, which gave highly enantiomerically enriched functionalized spirooxindole tetrahydropyranones via an enamine-based mechanism, were developed. The catalyst systems were identified by a screen of combinations of amines, acids, and additives. With the identified catalyst systems, various spirooxindole tetrahydropyranones were synthesized in high yields with high diastereo- and enantioselectivities (see scheme). Copyright

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Organomediated Morita-Baylis-Hillman cyclization reactions

We have developed the Morita-Baylis-Hillman reaction to include, for the first time in a completely organomediated process, intramolecular examples bearing allylic leaving groups as the electrophilic partner providing a facile, high yielding, straightforw

Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes

o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form α, β-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.

Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.

[reaction: see text] With this communication we extend the methodology of proline-catalyzed direct asymmetric aldol reactions to include alpha-unsubstituted aldehydes as acceptors. This important aldehyde class gives the corresponding aldols in 22-77% yield and up to 95% ee when the reactions are performed in pure acetone or in ketone/chloroform mixtures. On the basis of these results we have developed a concise new synthesis of (S)-ipsenol.

The Cycloaddition of the 1,3-Butadiene Radical Cation with Acrolein and Methyl Vinyl Ketone

The 1,3-butadiene radical cation reacts with acrolein and methyl vinyl ketone to produce 'stable' adducts.The nature of the reaction and the structures of the adducts were investigated by collisional activation decomposition (CAD) combined with tandem mas

THERMOLYSE ET PHOTOLYSE DE CETONES NON SATUREES XXVII. SYNTHESE DE COMPOSES BICYCLIQUES PAR DOUBLE THERMOCYCLISATION DE DIENONES ET DE DIENEDIONES

The thermal isomerisation of some dienones and dienediones is explored as a route to bi- and polycyclic compounds.A dicyclopentylketone (6, from 3), two 3a-acetyl-cis-perhydropentalenes (32 and 33, from 29) and two spirononane-1,6 diones (27 and 28,