157952-84-6

Upstream product

• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 

Downstream Products

• 142672-76-2 2-(3,3-dimethyl-but-1-ynyl)-5,5-dimethylcyclohex-2-enone 
• 271572-53-3 5,5-dimethyl-2-ethynylcyclohex-2-enone 
• 329933-25-7 2-benzyl-5,5-dimethyl-2-cyclohexenone 
• 1123311-91-0 5,5-dimethyl-2-(3-methylbut-3-en-1-ynyl)cyclohex-2-enone 
• 776295-17-1 3,3,5,8-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol 
• 776295-17-1 3,3,5,8-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol 
• 181276-74-4 5,5-Dimethyl-2-trimethylsilanylethynyl-cyclohex-2-enone 

Relevant academic research and scientific papers

Concerning the proposed structure of (+)-laurobtusol: Spectral discrepancies with synthetic, racemic stereoisomers

Laurobtusol, a minor metabolite from Laurencia obtusa, had been assigned constitution 1 and relative stereochemistry, 2. However, several stereoisomers of this novel, cyclopropane-containing system 1 have now been synthesized and spectral correspondence b

Strictly regiocontrolled α-monosubstitution of cyclic carbonyl compounds with alkynyl and alkyl groups via Pd-catalyzed coupling of cyclic α-iodoenones with organozincs

The conditions for the Pd-catalyzed cross coupling of cyclic α-iodoenones, such as 2-iodo-2-cyclohexenone, with alkynylzincs have been optimized. The use of tris(o-furyl)phosphine (TFP) as a ligand and DMF as a solvent has led to the formation of α-alkynylenones in excellent yields. This optimized procedure has been applied to the synthesis of (±)-harveynone and (±)-tricholomenyn A in high yields. Investigation of related α-alkylation reactions using alkylzincs has revealed the following. Methylzinc and primary alkylzinc derivatives readily undergo Pd-catalyzed cross coupling with α-iodoenones. Although (s-Bu)2Zn also undergoes Pd-catalyzed cross coupling, only the n-Bu-substituted products were obtained, α-Benzylation and α-homobenzylation can proceed satisfactorily, whereas allylzinc and propargylzinc derivatives undergo only addition to the carbonyl group. Although some promising results have been obtained in α-homoallylation and α-homopropargylation, these reactions need to be further improved. (C) 2000 Elsevier Science Ltd.

Furans from novel [3+2] photocycloaddition of alkenes to 2-(1-alkynyl)cyclohexenones

Photocycloaddition of 2-alkynyl-substituted cyclohexenones 8c-11c with isobutylene (2) and tetramethylethylene (3a) leads to tricyclic furans 15a-18a and 15b-17b, respectively, in gas chromatographic yields of ~90%. A suggested mechanism for this novel pr