98184-95-3

Basic information

• Product Name: (E)-4-phenylbut-3-ene-1,2-diol
• Synonyms: (E)-4-phenylbut-3-ene-1,2-diol
• CAS NO: 98184-95-3
• Molecular Weight: 164.204
• Mol File: 98184-95-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (E)-4-phenylbut-3-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-phenylbut-3-ene-1,2-diol(98184-95-3)
• EPA Substance Registry System: (E)-4-phenylbut-3-ene-1,2-diol(98184-95-3)

Safety Data

• Hazardous Substances Data: 98184-95-3(Hazardous Substances Data)

Upstream product

• 93-59-4 Perbenzoic acid 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 107969-78-8 methyl benzylidenepyruvate 
• 20047-19-2 (Z)-4-phenylbut-3-en-1-ol 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 869111-33-1 (E)-4-phenylbut-3-enyl hydroxycarbamate 
• 273212-42-3 (E)-2-[(1-Benzenesulfonyl-cyclopropyl)-dimethyl-silanyl]-4-phenyl-but-3-enoic acid ethyl ester 
• 126580-12-9 (E)-ethyl 2-diazo-4-phenylbut-3-enoate 
• 105885-67-4 (+/-)-(3E)-1-chloro-4-phenyl-but-3-en-2-ol 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 17451-20-6 (E)-ethyl-2-oxo-4-phenylbut-3-enoate 

Downstream Products

• 505085-76-7 (2R,3E)-2-amino-4-phenylbut-3-en-1-ol 
• 20296-07-5 1-hydroxy-4-phenyl-2-butanone 
• 112698-74-5 (E)-1-hydroxy-4-phenylbut-3-en-2-one 
• 229648-88-8 (2S,3E)-4-phenylbut-3-ene-1,2-diol 
• 206257-91-2 (S)-1-benzoyloxy-4-phenyl-E-3-butene-2-ol 
• 206257-90-1 Benzoic acid (E)-(S)-2-acetoxy-4-phenyl-but-3-enyl ester 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 55177-35-0 4-phenylbut-2-enal 
• 206257-87-6 1-benzoyloxy-4-phenyl-E-3-butene-2-ol 

Relevant articles and documents

Solid-phase synthesis of dihydropyrans by Eu(fod)3-catalysed [4+2] heterocycloaddition of vinyl ethers with benzylidenepyruvic acid esters. Comparison with conventional homogeneous liquid phase conditions

The OH groups of Wang resin were esterified with benzylidenepyruvic acid (1) to give the immobilized 1-oxabutadiene 2. The latter reacted with vinyl ethers 3a-h (dienophiles) in the presence of Eu(fod)3, and the resulting adducts 4a-h underwent reductive cleavage with LiAlH4 to afford the dihydropyrans 5a-h in high (62 to 100%) overall yields. A similar sequence carried out under conventional homogeneous liquid phase conditions led to significantly lower yields. The endo/exo selectivity of the cycloaddition reaction was the same in both cases.

Copper-catalyzed oxyvinylation of diazo compounds

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such as an aryl iodide, an ester, and an allylic leaving group, enabling further modification.

The phenylthiocyclopropylsilyl group: A useful latent hydroxy group

The α-dimethyl(1-phenylthio)cyclopropylsilyl group was used as a new masked hydroxy group. Three procedures have been devised to allow the oxidation of this silicon group in the presence of various functionalities. The desired alcohols are obtained in high yields with retention of configuration at the carbon centre. (C) 2000 Elsevier Science Ltd.