23925-16-8

Upstream product

• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 108-95-2 phenol 
• 21040-45-9 Cinnamyl acetate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 888-12-0 (E)-2'-hydroxy-chalcone 
• 1616917-76-0 (E)-2-(2-(cinnamyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 4392-24-9 Cinnamyl bromide 
• 269409-97-4 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 

Downstream Products

• 13524-66-8 2-benzyldihydrobenzofuran 
• 494-12-2 flavan 
• 1155867-61-0 (E)-1-phenyl-3-[2-(tert-butyldimethylsilyloxy)phenyl]propene 
• 55539-36-1 (2R,3S)-2-phenyl-3-(phenylthio)chromane 
• 93514-42-2 2-phenylchromene 

Relevant academic research and scientific papers

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols

The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans and benzoxepins. The reaction is catalyzed by a BINAM-based phosphoramide Lewis base c

Hydrazone-palladium-catalyzed allylic arylation of cinnamyloxyphenylboronic acid pinacol esters

Allylic arylation of cinnamyloxyphenylboronic acid pinacol esters 3, which have arylboronic acid moiety and allylic ether moiety, using a hydrazone 1d-Pd(OAc)2 system proceeded and gave the corresponding 1,3-diarylpropene derivatives 4 with a phenolic hydroxyl group via a selective coupling reaction of the π-allyl intermediate to the boron-substituted position of the leaving group.

Deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction

An efficient protocol for deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction is described. The reaction shows very good selectivity and tolerates a wide range of functionalities on α,β-unsaturated acylphenols, giving corresponding 2-allylphenols in good to excellent yields.

Enantioselective synthesis of flavan-3-ols using a mitsunobu cyclization

The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC. Georg Thieme Verlag Stuttgart New York.

Allylic alcohols as substrate for ruthenium-catalyzed C-C coupling allylation reactions: Preliminary communication

Allylic alcohols, rather than halides, acetates, or carbonates can be used directly in the Friedel-Crafts-type coupling with various phenols. The use of a RuIV, rather than a RuII, precursor promotes the formation of one H per cycle

Bronsted acid-catalyzed nucleophilic substitution of alcohols

Simple Bronsted acids such as p-toluene-sulfonic acid monohydrate (PTS) or polymer-bound p-toluenesulfonic acid efficiently catalyze the direct nucleophilic substitution of the hydroxy group of allylic and benzylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reaction conditions are mild, the process is conducted under an atmosphere of air without the need for dried solvents, and water is the only side product of the reaction.

High-yield ruthenium-catalyzed Friedel-Crafts-type allylation reactions using dicationic RuIV catalysts

(Chemical Equation Presented) Unexpected linkage: The use of dicationic RuIV complexes in the Friedel-Crafts-type allylation of aromatic alcohols leads unexpectedly to the formation of a new C-C bond and not to the phenolation product (see sche

A convenient and improved montmorillonite K-10 catalysed Friedel-Crafts benzylation and allylation with activated esters

Benzyl benzoate and cinnamyl acetate has been effectively used respectively as alkylating and allylating substrates in Friedel-Crafts reaction catalysed by montmorillonite K-10 clay.

Methods in synthesis of flavonoids. Part 3: Molybdenum(IV)-catalyzed coupling of cinnamyl alcohols to phenol derivatives

This paper deals with the formal total synthesis of flavonoids bearing the hydroxylation pattern of the catechin series based on an access to the fully functionalized skeleton via the alkylation of phloroglucinol tribenzyl ether by 3,4-dibenzyloxycinnamyl alcohol. This reaction was revealed to be most successful when catalyzed by the Mo(acac)2(SbF6)2 complex. In addition, the underlying concepts to the different ways that can be used in this C6-C3+C6 strategy are discussed.