71711-98-3

Basic information

• Product Name: 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one
• CAS NO: 71711-98-3
• Molecular Formula: C₂₂H₂₈O₂
• Molecular Weight: 324.4565
• Mol File: 71711-98-3.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 468.1°C at 760 mmHg
• Flash Point: 187.4°C
• Density: 1.047g/cm³
• Vapor Pressure: 6.16E-09mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one(71711-98-3)
• EPA Substance Registry System: 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one(71711-98-3)

Safety Data

• Hazardous Substances Data: 71711-98-3(Hazardous Substances Data)

Usage

Physical form

Yellow crystalline compound

Uses in industry and research

+ Flavoring agent in the food industry
+ Fragrance ingredient in perfumes and cosmetics
+ Potential antioxidant and anticancer properties (pharmaceutical research)
+ Potential in electronic and optical applications (due to unique photophysical properties)

Upstream product

• 75393-95-2 2,6-Di-tert-butyl-4-[(4-methoxy-phenyl)-piperidin-1-yl-methyl]-phenol 
• 128-39-2 2,6-di-tert-butylphenol 
• 123-11-5 4-methoxy-benzaldehyde 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 75393-95-2 2,6-Di-tert-butyl-4-[(4-methoxy-phenyl)-piperidin-1-yl-methyl]-phenol 
• 75393-94-1 2,6-di-tert-butyl-4-<α-(p-methoxyphenyl)morpholinomethyl>phenol 
• 75401-65-9 2,6-di-tert-butyl-4-((1H-imidazol-1-yl)(4-methoxyphenyl)methyl)phenol 
• 75393-96-3 2,6-Di-tert-butyl-4-[(4-methoxy-phenyl)-(pyridin-2-ylamino)-methyl]-phenol 
• 75393-93-0 2,6-bis(1,1-dimethylethyl)-4-<(4-methoxyphenyl)methoxymethyl>phenol 
• 1097202-77-1 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(diphenylphosphoryl)-3-(4-methoxyphenyl)propiononitrile 
• 1097202-71-5 ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(diphenylphosphoryl)-3-(4-methoxyphenyl)propanoate 

Relevant articles and documents

Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives

Herein, we report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol exhibits good functional group tolerance and provides a straightforward method to access spiro-imidazolidinone-cyclohexadienones. In follow-up chemistry, we have shown the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas. (Figure presented.).

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.

Organocatalytic Enantioselective 1,6-aza-Michael Addition of Isoxazolin-5-ones to p-Quinone Methides

A thiourea-Br?nsted base bifunctional catalyst allowed the enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides to give isoxazolin-5-ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses. To the best of our knowledge this reaction represents the first example of enantioselective N-alkylation of isoxazolin-5-ones as well as the first example of enantioselective 1,6-aza-Michael reaction involving p-quinone methides.