183666-79-7

Usage

Molecular Structure

The compound has a complex molecular structure that consists of a cyclohexadienone ring with tert-butyl substituents at the 2 and 6 positions and a dimethylamino-benzylidene group at the 4 position.

Reactivity

The presence of both aromatic and alkyl functional groups in its structure gives it a range of reactivity, making it a useful reactant in organic synthesis.

Potential Applications

2,6-ditert-butyl-4-[4-(dimethylamino)benzylidene]-2,5-cyclohexadien-1-one has potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Biological Activities

The compound has been studied for its potential biological activities, which could lead to the development of new and useful chemical products.

Complex Molecular Structure

The compound's complex molecular structure makes it a promising candidate for a range of applications in various industries.

Upstream product

• 619-60-3 4-(N,N-dimethylamino)phenol 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 128-39-2 2,6-di-tert-butylphenol 

Downstream Products

• 1093168-97-8 4-(1-cyano-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(4-(dimethylamino)phenyl)ethyl)-benzonitrile 
• 1093168-95-6 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(4-(dimethylamino)phenyl)-2-(4-(trifluoromethyl)-phenyl)propionitrile 
• 1097202-69-1 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(diethoxyphosphoryl)-3-(4-dimethylaminophenyl)propiononitrile 
• 1097202-61-3 ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(diethoxyphosphoryl)-3-(4-dimethylaminophenyl)propanoate 
• 1057717-25-5 4-[1-benzenesulfonyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(4-dimethylaminophenyl)ethyl]benzonitrile 
• 1057717-21-1 4-[2-benzenesulfonyl-1-(4-dimethylaminophenyl)-2-(4-trifluoromethylphenyl)ethyl]-2,6-di-tert-butylphenol 

Relevant academic research and scientific papers

Lipase-Catalyzed Highly Efficient 1,6-Conjugated Addition for Synthesis of Triarylmethanes

Lipase from porcine pancreas (PPL) is first reported to catalyze direct 1,6-conjugated addition for synthesis of triarylmethanes using p-quinonemethides (p-QMs) and 2-naphthols. The catalytic activity of PPL was evaluated through investigating the solvent, the ratio of substrates, the enzyme loading and the temperature of the enzyme-catalyzed reactions. The present method proves to be environmentally friendly and efficient in terms of high yield, green catalyst and simple synthesis method. GraphicAbstract: [Figure not available: see fulltext.]

Thiourea catalyzed 1,6-conjugate addition of indoles to para-quinone methides

An efficient thiourea catalyzed 1,6-conjugate addition of indoles to para-quinone methides (p-QMs) was developed. p-QMs was activated by a weak hydrogen-bond effect. The reaction is featured mild reaction conditions and wide substrate scope. A series of C-3 bisaryl methine substituted indoles are prepared in high yield.

Silver-Catalyzed Cascade 1,6-Addition/Cyclization of para-Quinone Methides with Propargyl Malonates: An Approach to Spiro[4.5]deca-6,9-dien-8-ones

An unprecedented silver-catalyzed cascade 1,6-addition/5-exo-dig cyclization reaction between para-quinone methides and propargyl malonates under mild reaction conditions has been described. This reaction provides an efficient method to construct versatile spiro[4.5]cyclohexadienones in moderate to excellent yields with high atom economy and scalability.

Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides

The use of Cinchona alkaloid-based chiral ammonium ylides allows for the first highly enantioselective and broadly applicable spirocyclopropanation reactions of para-quinone methides. This strategy provides a straightforward protocol toward the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, which is a frequently found structural motif in important biologically active molecules.

Copper-Catalyzed 1,6-Hydrodifluoroacetylation of para-Quinone Methides at Ambient Temperature with Bis(pinacolato)diboron as Reductant

An original and efficient copper-catalyzed 1,6-hydrodifluoroacetylation of para-quinone methides with difluoroalkyl bromides has been described with bis(pinacolato)diboron (B2pin2) as reductant. In this reaction, a new C(sp3)–CF2bond is constructed under smart conditions. A broad substrate scope of para-quinone methides (p-QMs) make this protocol very practical and attractive. Preliminary mechanistic studies manifested that a difluoroalkyl radical pathway was involved in this reaction. Also the presence of the diboron reagent was an essential requisite in this transformation. (Figure presented.).

1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes

A 1,6-addition arylation reaction of para-quinone methides with α-isocyanoacetamides and electron-rich aromatic compounds under metal-free conditions has been developed. BF3·Et2O plays two roles in the reaction: catalyzing the cyclization of α-isocyanoacetamides to give oxazoles, and activating the para-quinone methides to achieve the 1,6-addition arylation process. The reaction shows good functional group tolerance, scalability, and regioselectivity. It is a consice protocol for the synthesis of diverse unsymmetrical triarylmethanes. Further transformation of the resulting triarylmethanes provides an efficient route to some functionalized molecules.

Electrophilicity parameters for benzylidenemalononitriles

Kinetics of the reactions of stabilized carbanions (derived from nitroethane, diethyl malonate, ethyl cyanoacetate, ethyl acetoacetate, acetyl acetone) with benzylidenemalononitriles have been determined in dimethyl sulfoxide solution at 20 °C. The second-order rate constants are employed to determine the electrophilicity parameters E of the benzylidenemalononitriles according to the correlation equation log k (20 °C) = s(E + N). Comparison with literature data shows that this equation allows the semiquantitative prediction of the reactivities of benzylidenemalononitriles toward a wide variety of nucleophiles, including carbanions, enamines, amines, water, and hydroxide.

Inhibition of unsaturated monomers with 7-aryl quinone methides

Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-aryl quinone methide compound.

7-substituted quinone methides as inhibitors for unsaturated monomers

Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.

A new one-pot process for the preparation of 7-aryl-2,6-disubstituted quinone methides

The instant invention pertains to a new one-pot process for the facile preparation of 7-aryl-2,6-disubstituted quinone methides of formula I where R1and R2are independently alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or phenylalkyl of 7 to 15 carbon atoms, and R3is 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-pyrryl, 2- or 3-furyl, aryl of 6 to 10 carbon atoms, or said aryl substituted by one to three alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkylthio of 1 to 8 carbon atoms, alkylamino of 1 to 8 carbon atoms, dialkylamino of 2 to 8 carbon atoms, alkoxycarbonyl of 2 to 8 carbon atoms, hydroxy, nitro, amino, cyano, carboxy, aminocarbonyl, chloro or mixtures of said substituents,which are useful as polymerization inhibitors for vinyl aromatic and acrylic monomers.