71711-98-3

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

• 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 
• 1097202-60-2 ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(diethoxyphosphoryl)-3-(4-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

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.).

Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with para-Quinone Methides

An interesting remote I-C 1,6-Addition and an isomerization cascade reaction for phosphine-catalyzed activated alkynes have been disclosed. The products featuring a functional diene and a 1,1-diaryl methyl motif have been obtained in moderate to good yields (30-86%) by applying para-quinone methides (p-QMs) and I-substituted alkynoate with tributylphosphine (PnBu3) catalysis, along with high regioselectivity and stereoselectivity (dr > 20:1). The wide scope of compatible substrates (35 examples), such as indolyl, oxindolyl, ester, and cinnamyl, expand the utility of this methodology. A plausible mechanism and some applications of it have also been 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.

Iron-Catalyzed Ring Opening of Cyclopropanols and Their 1,6-Conjugate Addition to p-Quinone Methides

A novel iron-catalyzed ring opening of cyclopropanols and their 1,6-conjugate addition to p-quinone methides for accessing substituted phenols is disclosed. In this protocol, various cyclopropanols are converted to alkyl radicals and undergo 1,6-conjugate addition to p-quinone methides toward C–C bond formation. The salient features of this methodology include operationally simple and mild reaction conditions, environmentally benign protocol, high efficiency, inexpensive catalyst, good to excellent yield, and a wide range of substrate scope.

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.

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.]

TBAB-catalyzed 1,6-conjugate sulfonylation of paraquinone methides: A highly efficient approach to unsymmetrical gem-diarylmethyl sulfones in water ?

A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

Visible-light-promoted radical cross-coupling of: Para-quinone methides with N-substituted anilines: An efficient approach to 2,2-diarylethylamines

An efficient protocol to access 2,2-diarylethylamines via visible-light-promoted radical reactions of para-quinone methides (p-QMs) with N-alkyl anilines has been disclosed. These reactions feature metal-free, redox-neutral, and mild reaction conditions with wide functional group compatibility.

The strategic use of: Para-quinone methides to access synthetically challenging and chemoselective α,α-diarylmethyl N-glycosides from unprotected carbohydrate amines

Reported herein is a practical route to access synthetically challenging and chemoselective α,α-diarylmethyl N-glycosides via Sc(OTf)3-catalyzed 1,6-conjugate addition of amino sugars with para-quinone methides (p-QMs). The reactions proceed smoothly without a base and under mild reaction conditions with a broad substrate scope and moderate to good yields.

An Efficient One-Pot Protocol for Direct Access to Diarylmethyl Thioglycosides with para -Quinone Methides via S -Glycosyl Isothiouronium Salts

An efficient one-pot protocol has been developed for the direct preparation of diarylmethyl thioglycosides starting from per-O-acetylated sugars via glycosyl isothiouronium salts. The one-pot reaction conditions involve rapid conversion of the per-O-acetylated sugar with thiourea in the presence of boron trifluoride etherate as catalyst to give the corresponding glycosyl isothiouronium salt, which is subsequently treated with a para -quinone methide in the presence of a base to give the a diarylmethyl thioglycoside in excellent yield.