100017-26-3

Basic information

• Product Name: 3-Buten-2-ol, 4-phenyl-, acetate, (2R,3Z)-
• CAS NO: 100017-26-3
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol File: 100017-26-3.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 3-Buten-2-ol, 4-phenyl-, acetate, (2R,3Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-2-ol, 4-phenyl-, acetate, (2R,3Z)-(100017-26-3)
• EPA Substance Registry System: 3-Buten-2-ol, 4-phenyl-, acetate, (2R,3Z)-(100017-26-3)

Safety Data

• Hazardous Substances Data: 100017-26-3(Hazardous Substances Data)

Upstream product

• 87246-95-5 (R)-(-)-α-Phenyl-γ-methylallyl alcohol 
• 87246-94-4 (R)-(-)-α-Phenyl-γ-methylallyl acetate 
• 92075-81-5 trans-(S)-1-Phenyl-2-buten-1-ol 
• 108-24-7 acetic anhydride 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 108-05-4 vinyl acetate 
• 61550-03-6 2-trimethylsilyloxy-3-methylfurane 
• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 61423-03-8 (1R)-acetic acid 1-methyl-3-phenylprop-2-ynyl ester 
• 211996-17-7 4-phenyl-1-buten-3-yn-2-yl acetate 
• 1896-62-4 (E)-benzalacetone 

Downstream Products

• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 867266-93-1 (E)-(2S,3S)-2-(Benzhydrylidene-amino)-3-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 1391742-83-8 (R)-2-(4-phenylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 112528-98-0 (E)-(±)-2-methyl-4-phenylbut-3-enenitrile 
• 88083-20-9 [(C₂H₄(P(C₆H₅)2)2)Pd(CH₃CHCHCHC₆H₅)]⁽¹⁺⁾*BF₄^(1-)=[(C₂H₄(P(C₆H₅)2)2)Pd(CH₃CHCHCHC₆H₅)]BF₄ 
• 114968-90-0 (E)-3-Phenyl-hex-4-enoic acid methyl ester 
• 90383-11-2 methyl <1-((E)-styryl)ethyl>acetate 
• 102882-04-2 3-phenylhexanoic methyl ester 
• 99903-37-4 methyl <1-phenyl-2-(E)-butenyl>acetate 
• 100-52-7 benzaldehyde 
• 873653-83-9 (E)-(2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 120990-36-5 (S)-(E)-4-phenyl-3-buten-2-yl azide 
• 200191-40-8 (E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate 

Relevant articles and documents

Palladium-catalyzed asymmetric synthesis of allylic alcohols from unsymmetrical and symmetrical racemic allylic carbonates featuring C-O-bond formation and dynamic kinetic resolution

Described is the asymmetric synthesis of the allylic alcohols 11 (85% ee), 15 (99% ee), 17 (93% ee), 19 (61% ee), and 21 (69% ee) through a Pd-catalyzed reaction of the unsymmetrical carbonates rac-10, rac-12, rac-14, rac-16, rac-18, and rac-20, respectively, with KHCO3 and H2O in the presence of bisphosphane 6. Similarly the allylic alcohols 23 (99% ee) and 25 (97% ee) have been obtained from the symmetrical carbonates rac-22 and rac-24, respectively. Reaction of the meso-biscarbonate 26 with H2O and Pd(0)/6 afforded alcohol 27 (96% ee), which was converted to the PG building block 32. The unsaturated bisphosphane 33 showed in the synthesis of alcohols 36, 37, and 39 a similar high selectivity as 6. The formation of alcohols 11, 15, and 17 involves an efficient dynamic kinetic resolution.

Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol

The enzymatic kinetic resolution of (RS)-trans-4-phenyl-3-butene-2-ol was investigated by screening a range of lipases both for enantioselective transesterification and for enantioselective hydrolysis of its acetate. The lipase from Pseudomonas cepacia immobilized on diatomaceous earth (PSL-D)-catalyzed asymmetric transesterification was performed on gram scale using isopropenyl acetate as an innocuous acyl donor in organic media affording the (S)-alcohol in high enantiomeric excess (>99% ee) and enantiomeric ratio E >150. The lipase (Candida antarctica B, CAL-B)-catalyzed asymmetric hydrolysis of the racemic acetate was performed on gram scale in phosphate buffer affording the (R)-alcohol in high enantiomeric excess (>99% ee) and enantiomeric ratio E >150. The investigation demonstrates that the transesterification of the racemic alcohol in organic solvent was faster than the hydrolysis of the corresponding acetate in phosphate buffer. A GC method was developed to achieve an effective analytical separation of the enantiomers of both substrate and product in one analysis using the chiral stationary phase heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin.

Highly enantioselective synthesis of 3-substituted furanones by palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates

Resolving the issue: A near-perfect Pd-catalyzed kinetic resolution of 1,3-disubstituted unsymmetrical allylic acetates uses silyl enol ethers as nucleophiles to access the important 3-substituted-furanone scaffold (see scheme; DACH=diaminocyclohexyl, dba=dibenzylideneacetone). The reaction proceeds under mild conditions and provides the desired products with excellent chemo-, regio-, and enantioselectivity. Copyright

Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens

A new asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens has been found. Although alcohols are not the natural substrates for this enzyme, a high R enantioselectivity was observed. Stereochemical studies showed that variations in substrate structure lead to strong variations in enantioselectivity. The highest enantioselectivities are obtained when the β-carbon of the secondary alcohol is tertiary or quaternary.