84519-63-1

Basic information

• Product Name: (R,E)-4-phenyl-3-buten-2-yl acetate
• Synonyms: (R,E)-4-phenyl-3-buten-2-yl acetate
• CAS NO: 84519-63-1
• Molecular Weight: 190.242
• Mol File: 84519-63-1.mol
• Article Data: 40

Chemical Properties

• CAS DataBase Reference: (R,E)-4-phenyl-3-buten-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (R,E)-4-phenyl-3-buten-2-yl acetate(84519-63-1)
• EPA Substance Registry System: (R,E)-4-phenyl-3-buten-2-yl acetate(84519-63-1)

Safety Data

• Hazardous Substances Data: 84519-63-1(Hazardous Substances Data)

Upstream product

• 108-22-5 Isopropenyl acetate 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 108-05-4 vinyl acetate 
• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 1896-62-4 (E)-benzalacetone 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 61550-03-6 2-trimethylsilyloxy-3-methylfurane 
• 108-24-7 acetic anhydride 
• 581-55-5 benzylidene 1,1-diacetate 
• 100-58-3 phenylmagnesium bromide 
• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 876-27-7 4-chlorophenyl acetate 
• 211996-14-4 acetic acid (E)-1-methylene-3-phenyl-allyl ester 

Downstream Products

• 120990-36-5 (S)-(E)-4-phenyl-3-buten-2-yl azide 
• 635317-41-8 (E)-(2S,3R)-2-Acetyl-2,3-dimethyl-5-phenyl-pent-4-enoic acid methyl ester 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 102680-24-0 (R)-(-)-3-methyl-1-phenyl-1-heptene 
• 96391-85-4 4-phenyl-2-octene 
• 1248350-27-7 (S)-(-)-1-phenyl-3-(6-methoxy-2-naphthyl)-1-butene 
• 1248350-25-5 (S)-(-)-1-phenyl-3-((3-fluoro-4-phenyl)phenyl)-1-butene 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 1391742-83-8 (R)-2-(4-phenylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 112528-98-0 (E)-(±)-2-methyl-4-phenylbut-3-enenitrile 

Relevant articles and documents

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols

Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.

Continuous-Flow Dynamic Kinetic Resolution of Racemic Alcohols by Lipase–Oxovanadium Cocatalysis

A continuous-flow dynamic kinetic resolution of racemic secondary alcohols was carried out using a single column reactor packed with a mixture of immobilized lipase and an immobilized oxovanadium species, VMPS4. As a result, optically pure esters were produced in 88–92 % yields. Problems encountered in this study were overcome by using fillers that efficiently maintained the initial distribution of the catalysts in the reactor and by using a packing method in which the mixing ratio of the two catalysts was varied in a stepwise fashion. The flow process led to an increased turnover number of each catalyst compared to those of batch reactions.

Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation

N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.