56745-22-3

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 6267-39-6 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 109-72-8 n-butyllithium 
• 78998-88-6 5,5-dimethyl-3-(phenylseleno)-2-cyclohexen-1-one 
• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 693-04-9 butyl magnesium bromide 
• 126-81-8 dimedone 
• 4683-45-8 3-methoxy-5,5-dimethyl-cyclohex-2-enone 
• 80534-76-5 diethyl 5,5-dimethyl-3-oxocyclohex-1-enyl phosphate 
• 849595-89-7 3-(butyltellanyl)-5,5-dimethyl-cyclohex-2-enone 
• 140840-48-8 C₈H₁₁FO₄S 
• 10416-78-1 5,5-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one 
• 13271-49-3 3-bromo-5,5-dimethlycyclohex-2-en-1-one 

Downstream Products

• 133969-86-5 3-butyl-5,5-dimethyl-2-cyclohexenol 
• 77729-46-5 3-Butyl-5,5-dimethyl-cyclohex-2-enone oxime 
• 92859-97-7 1,1-Dimethyl-3-butyl-4-allyl-cyclohexen-⁽³⁾-on-⁽⁵⁾ 
• 118465-13-7 3-butyl-5,5-dimethyl-2-cyclohexenyl p-nitrobenzoate 
• 92790-71-1 1,1-Dimethyl-4-propyl-3-butyl-cyclohexen-⁽³⁾-on-⁽⁵⁾ 

Relevant academic research and scientific papers

Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides

A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.

ANTICONVULSANT COMPOUNDS

The present application relates to compounds and methods for reducing the severity of convulsant activity or epileptic seizures, or for the treatment of chronic or acute pain.

Iron thiolate complexes: Efficient catalysts for coupling alkenyl halides with alkyl grignard reagents

Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron-catalyzed cross-coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo- and stereoselective. With this new procedure, the use of N-methylpyrrolidone as a co-solvent is no longer required. Copyright

Diastereoselective synthesis of α,β-unsaturated systems

Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to α,β-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature.

Highly stereo and chemoselective iron-catalyzed alkenylation of organomagnesium compounds

In the presence of Fe(acac)3, Grignard reagents react readily with alkenyl halides (X = I, Br or Cl) in a THF/NMP mixture to give the cross-coupling products in high yields with an excellent stereoselectivity (≤99.5%). The scope of the reaction is very broad since a vast array of functional groups are tolerated (esters, nitriles, aromatic or aliphatic halides and even ketones). The procedure reported herein is an interesting alternative to the classical Pd- or Ni-catalyzed reactions, especially for preparative organic chemistry.

Cobalt-catalyzed alkenylation of organomagnesium reagents

Alkenyl iodides, bromides and chlorides react with organomagnesium reagents in THF, in the presence of Co(acac)2 and NMP (9 to 4 equiv.), to give the cross-coupling products in good yields. The reaction is chemoselective (aryl or alkyl bromides, esters and ketones) and stereoselective (≤ 99.5%).

Carbonyl transposition on organoselenium compounds

Carbonyl conjugated vinylic selenides undergo 1,3 and 1,5-carbonyl transposition sequences through organometallic reagents addition reactions followed by acid hydrolysis.

Higher order, mixed cyanocuprates derived from N-lithio-imidazole and pyrrole: New 'dummy' ligand alternatives in organocopper chemistry

Treatment of N-lithioimidazole or N-lithiopyrrole with CuCN followed by an organolithium leads to cuprates R(Imid)Cu(CN)Li2 and R(Pyrr)Cu(CN)Li2 which show 'higher order' reactivity relative to RCu(CN)Li.

Reaction of β-halo α,β-unsaturated ketons with cuprate reagents. Efficient syntheses of β,β-dialkyl ketones and β-alkyl α,β-unsaturated ketones. A synthesis of (Z)-jasmone

Treatment of the 3-halo-2-cyclohexen-1-ones 11-15 and 17 with an excess of lithium dimethylcuprate provided good to excellent yields of the corresponding 3,3-dimethylcyclohexanones 21-24.Similar reactions involving the β-bromo cyclopentenones 19 and 20 stopped at the monoaddition stage, producing the cyclopentenones 40 and 43.Reaction of the β-bromo cyclohexenones 12 and 15 with 1.1 equiv. of lithium dimethylcuprate did not effect clean conversion of these substrates into the corresponding 3-methyl-2-cyclohexen-1-ones.When a series of β-bromo enones 12, 14-19were allowed to react with the lithium (phenylthio)(alkyl)cuprates 44-47, the correspondig β-alkyl enones were, in general, produced cleanly and efficiently.However, reaction of 3-bromo-2-methyl-2-cyclopenten-1-one (19) with the cuprate reagent 44 gave mainly the β-phenylthio enone 49.This undesired result could be avoided by employing, in the place of 19, The β-iodo cyclopentenone 50, which reacted smoothly with 44 to give a high yield of 2,3-dimethyl-2-cyclopenten-1-one (40).Reaction of 3-bromo-2-cyclohexen-1-one (14) with 3 equiv. of the mixed vinylcuprate reagent 48 gave 3-(3-butenyl)-2-cyclohexen-1-one (32).Alkylation of 1,3-cyclopentanedione with (Z)-1-chloro-2-pentene afforded compound 51, which was converted into the β-bromo enone 52.Treatment of the latter substance with lithium dimethylcuprate provided (Z)-jasmone (53).