60168-64-1

Upstream product

• 96-09-3 styrene oxide 
• 107-18-6 allyl alcohol 
• 100-52-7 benzaldehyde 
• 3970-20-5 allyl chloromethyl ether 
• 93-56-1 phenylethane 1,2-diol 
• 70122-89-3 tert-butyl allyl carbonate 
• 106-95-6 allyl bromide 

Downstream Products

• 1071506-54-1 2-(oxirane-2-ylmethoxy)-1-phenylethanol 
• 55668-32-1 2-ethyl-4-phenyl-1,3-dioxolane 
• 746647-93-8 1-[2-(allyloxy)-1-phenylethyl]-7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine 
• 507481-72-3 7-[2-(allyloxy)-1-phenylethyl]-2-aminopurin-6-one 
• 507481-66-5 7-(2-allyloxy-1-phenylethyl)-2-amino-6-chloropurine 
• 880081-92-5 O⁶-[2-(allyloxy)-1-phenylethyl]guanine 
• 507481-64-3 allyl(2-bromo-2-phenylethyl) ether 
• 65755-81-9 1-phenyl-2-(2-propenyloxy)ethanone 
• 60168-71-0 Methanesulfonic acid (S)-1-phenyl-2-[((E)-propenyl)oxy]-ethyl ester 
• 60168-72-1 (R)-2-Propenyloxy-1-phenyl-1-deuterioethan 

Relevant academic research and scientific papers

Well-defined epoxide-containing styrenic polymers and their functionalization with alcohols

Polymers containing electrophilic moieties, such as activated esters, epoxides, and alkyl halides, can be readily modified with a variety of nucleophiles to produce useful functional materials. The modification of epoxide-containing polymers with amines and other strong nucleophiles is well-documented, but there are no reports on the modification of such polymers with alcohols. Using phenyloxirane and glycidyl butyrate as low molecular weight model compounds, it was determined that the acid-catalyzed ring-opening of aryl-substituted epoxides by alcohols to form β-hydroxy ether products was significantly more efficient than that of alkyl-substituted epoxides. An aryl epoxide-type styrenic monomer, 4-vinylphenyloxirane (4VPO), was synthesized in high yield using an improved procedure and then polymerized in a controlled manner under reversible addition-fragmentation chain-transfer (RAFT) polymerization conditions. A successful chain extension with styrene proved the high degree of chain-end functionalization of the poly4VPO-based macro chain transfer agent. Poly4VPO was modified with a library of alcohols and phenols, some of which contained reactive functionalities, e.g., azide, alkyne, allyl, etc., using either CBr4 (in PhCN at 90°C for 2-3 days) or BF3 (in CH2Cl2 at ambient temperature over 30 min) as the catalyst. The resulting β-hydroxy ether-functionalized homopolymers were characterized using size exclusion chromatography, 1H NMR and IR spectroscopy, and thermal gravimetric analysis.

Regioselective mono and multiple alkylation of diols and polyols catalyzed by organotin and its applications on the synthesis of value-added carbohydrate intermediates

A catalytic amount of dibutyltin dichloride was used to develop regioselective alkylation of diols and multiple alkylation of polyols. Alkyl groups, including allyl, alkynyl and long-chain alkyl groups, were successfully introduced to one or two hydroxyl

Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Bronsted acid-catalyzed isomerization/cyclization of allylic ethers

A ruthenium hydride/Bronsted acid-catalyzed tandem sequence is reported for the synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to enol ethers (Ru catalysis), then to oxocarbenium ions (Bronsted acid catalysis) amenable to endo cyclization with tethered nucleophiles. This methodology provides not only an attractive alternative to the traditional oxa-Pictet-Spengler reaction for the synthesis of THPIs, but also convenient access to THPI congeners and other important oxacycles such as acetals.

A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions

The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.

Hydrophobic amplification of noncovalent organocatalysis

The effects of hydrogen-bonding organocatalysts and water for the acceleration of epoxide openings with a variety of nucleophiles are additive and lead to excellent yields of the catalyzed reactions in water. The Royal Society of Chemistry 2006.

General method for the palladium-catalyzed allylation of aliphatic alcohols

A palladium catalysis-mediated approach to coupling aliphatic alcohols with allyl carbonates has been developed. The method allows for the allylation of primary, secondary, and tertiary alcohols efficiently under mild conditions. Limitations were explored as well as the asymmetric application of the chemistry. Regiochemical and olefin geometry was controlled in the coupling of unsymmetrical allylating agents. Transient allyl carbonates were observed in the coupling, which comprised the trans-carboxylation of the allyl-carbonate with the requisite alcohol.

FUMARATE DERIVATIVE, METHOD FOR PRODUCING THE SAME

This invention is to provide a polymerizable composition having excellent curability and surface hardness, and a cured product thereof. A novel fumarate derivative having two or more fumarate groups within one molecule and ensuring high copolymerizability with the terminal alkenyloxy group, a method for producing the derivative, a polymerizable composition containing the derivative, and a cured product thereof are provided.

Stereoselective Synthesis of (1R,2S)-2-Amino-1,3-diols from (R)-Cyanohydrins

Vinyl substituted (1R,2S)-amino alcohols 5 were obtained by addition of vinyl magnesium bromide to the corresponding cyanohydrin O-trimethylsilyl ethers (R)-2.The O- and N-protected vinyl amino alcohols 6 were ozonized at -78 deg C in methanol yielding (1R,2S)-2-amino-1,3-diols 7 in high enantiomeric and diastereomeric excesses.For purification, compounds 7 in some cases were acetylated to give the derivatives (1R,2S)-8.Racemic 6a was converted by oxidative ozonolysis at -78 deg C in methanolic NaOH solution to the corresponding methyl N-acetyl-β-hydroxy propanoate 9a.The configuration of (1R,2S)-8a was confirmed by x-ray crystallographic analysis.

HIGHLY REGIOSELECTIVE RING OPENING OF EPOXIDES WITH ALCOHOLS CATALYZED BY ORGANOTIN PHOSPHATE CONDENSATES

Organotin phosphate condensates proved to catalyze the ring opening reaction of epoxides with alcohols in a highly regioselective manner.