94348-71-7

Upstream product

• 930-68-7 cyclohexenone 
• 100-52-7 benzaldehyde 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 

Downstream Products

• 94348-81-9 2-(acetoxyphenylmethyl)-cyclohex-2-enone 
• 5682-83-7 (E)-2-benzylidenecyclohexanone 
• 1044744-82-2 2-({4-hydroxy-3,5-dimethylphenyl}(phenyl)methyl)cyclohex-2-enone 
• 1156004-31-7 2-[(p-toluidino)(phenyl)methyl]cyclohex-2-enone 
• 1156004-30-6 2-[(phenylamino)(phenyl)methyl]cyclohex-2-enone 
• 1156004-32-8 2-[(4-fluorophenylamino)(phenyl)methyl]cyclohex-2-enone 
• 81039-06-7 2-benzoylcyclohex-2-en-1-one 
• 1204473-86-8 (E)-2-benzylidene-3-(4-methylphenyl)cyclohexanone 
• 1204473-85-7 (E)-2-benzylidene-3-(4-methoxyphenyl)cyclohexanone 
• 1204473-87-9 (E)-2-benzylidene-3-(3,5-dimethylphenyl)cyclohexanone 
• 1204512-34-4 (E)-2-benzylidene-3-phenylcyclohexanone 
• 1198078-55-5 2-((but-3-enyloxy)(phenyl)methyl)cyclohex-2-enone 
• 133381-91-6 2-(ethoxy(phenyl)methyl)cyclohex-2-enone 
• 1198078-43-1 ethyl 2-benzoyl-3-(6-oxocyclohex-1-enyl)-3-phenylpropanoate 

Relevant academic research and scientific papers

Rhodium(II)-Catalyzed Reaction of 1-Tosyl-1,2,3-triazoles with Morita–Baylis–Hillman Adducts: Synthesis of 3,4-Fused Pyrroles

A cascade reaction of rhodium azavinylcarbenes with Morita–Baylis–Hillman (MBH) adducts enables a novel synthetic approach to 3,4-fused pyrroles. The cascade reaction begins with the insertion of O?H bond into rhodium azavinylcarbenes, subsquent sigmatropic rearrangement provides substituted α,β-unsaturated cyclic ketone intermediates. Then the intramolecular aza Michael addition/oxidative aromatization sequence give rise to a wide range of 3,4-fused pyrroles in good yields, and with excellent functional group compatibility.

The effect of chiral: N-substituents with methyl or trifluoromethyl groups on the catalytic performance of mono-and bifunctional thioureas

We evaluated thiourea organocatalysts that incorporate a chiral group which includes a trifluoromethyl moiety and contrasted their performance with non-fluorinated analogs. The comparison between such systems allows the direct study of the NH acidity of a thiourea bonded to an aliphatic substituent. In principle,-CF3 systems feature an enhanced hydrogen bond (HB) donor capacity that is undoubtedly beneficial for HB-catalysis applied to the Baylis-Hillman reaction. We found that the thiourea substituted on both nitrogens with this group accelerates this reaction like Schreiner's thiourea. On the other hand, we observed a different behavior in reactions promoted by bifunctional catalysts (thiourea-primary amine). In the Michael addition of isobutyraldehyde to methyl benzylidenepyruvate, the-CF3 containing catalysts were better than the-CH3 systems, whereas the conjugate addition to N-phenylmaleimide showed the opposite behavior. Theoretical calculations of the transition states indicated that the phenylethyl group in fluorinated and non-fluorinated compounds have different kinds of interactions with the electrophile. These interactions are responsible for a different arrangement of the electrophile and thereby the selectivity of the catalyst. Therefore, it cannot be generalized that in all cases NH acidity correlates with the performance of the catalyst, particularly, with aliphatic substituents that unlike the aromatic ones possess groups that are outside the plane of the thiourea.

Substituted (E)-2-methylene-3,4-cyclohexenones through direct and convenient synthesis from cyclohexenone-MBH alcohol in the presence of DMAP

An unexpected and effective DMAP catalyzed one-step construction of 3,4-cyclohexenone skeleton from simple and easily available cyclohexenone-MBH alcohol has been disclosed. A series of substituted (E)-2-methylene-3,4-cyclo-hexenones have been effectively prepared in excellent yields (up to 93 %) under convenient reaction conditions. Succesful scale-up preparation and synthetic transformations have demonstrated the potentials of this new protocol.

Ionic Thiourea Organocatalysis of the Morita-Baylis-Hillman Reaction

An ionic thiourea based organocatalyst has been shown to promote a 1,4-diazabicyclo[2.2.2]octane, (DABCO) catalysed Morita-Baylis-Hillman reaction between benzaldehyde and cyclohex-2-en-1-one. The ionic thiourea catalyst was easily prepared from a pyrroli

Efficient catalysis of aqueous Morita-Baylis-Hillman reactions of cyclic enones by a bicyclic imidazolyl alcohol

In this paper a new phosphorus-free catalyst for the Morita-Baylis-Hillman reaction is disclosed. A bicyclic imidazolyl alcohol having a Lewis basic center associated with a hydrogen-bond donor group was used as catalyst for the reaction. Aliphatic cycloalkanones such as 2-cyclopentenone and 2-cyclohexanone and aliphatic and aromatic aldehydes were used successfully, and the reaction was found to work nicely using water as solvent in the presence of a phase-transfer additive. Copyright

Click mechanochemistry: Quantitative synthesis of "ready to use" chiral organocatalysts by efficient two-fold thiourea coupling to vicinal diamines

Mechanochemical methods of neat grinding and liquid-assisted grinding have been applied to the synthesis of mono- and bis(thiourea)s by using the click coupling of aromatic and aliphatic diamines with aromatic isothiocyanates. The ability to modify the re

Switching the reactivity of dihydrothiopyran-4-one with aldehydes by aqueous organocatalysis: Baylis-Hillman, aldol, or aldol condensation reactions

An aqueous medium containing catalytic amounts of a tertiary amine was employed to direct the chemoselectivity of the reaction of aldehydes with 1a. With DBU, 2 was formed at room temperature as a rare exemplary of Baylis-Hillman reactions in heterocyclic

Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts

A related series of bisamides have been evaluated for rational correlation between anion complexation and organocatalysis: remarkable enhancement of hydrogen bonding to anions was observed along with significant increases in catalytic activity in the Bayl

Highly chemoselective Baylis - Hillman and aldol reactions of 2 H-thiopyran-4(3H)-one using tertiary amine catalysts in aqueous media

For the first time, the Baylis - Hillman (BH) reaction of 2H-thiopyran-4(3H)-one is investigated, and surprisingly, the reaction of 2H-thiopyran-4(3H)-one with aldehydes in the presence of different tertiary amines shows excellent chemo- and regioselectiv

Acceleration of the Morita-Baylis-Hillman reaction by a simple mixed catalyst system

(Chemical Equation Presented) By using a catalytic amount of 4-dimethylaminopyridine (DMAP) as a nucleophile in the presence of an equal amount of tetramethylethylenediamine (TMEDA) and MgI2, Morita-Baylis-Hillman adducts can be obtained in good to excellent yields from various aromatic and aliphatic aldehydes and cyclic enones/enoates at room temperature after convenient reaction times.