39652-50-1

Basic information

• Product Name: 5-hydroxy-3-methyl-5-phenyl-pent-2-enoic acid methyl ester
• Synonyms: 5-hydroxy-3-methyl-5-phenyl-pent-2-enoic acid methyl ester
• CAS NO: 39652-50-1
• Molecular Weight: 220.268
• Mol File: 39652-50-1.mol

Chemical Properties

• CAS DataBase Reference: 5-hydroxy-3-methyl-5-phenyl-pent-2-enoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-3-methyl-5-phenyl-pent-2-enoic acid methyl ester(39652-50-1)
• EPA Substance Registry System: 5-hydroxy-3-methyl-5-phenyl-pent-2-enoic acid methyl ester(39652-50-1)

Safety Data

• Hazardous Substances Data: 39652-50-1(Hazardous Substances Data)

Upstream product

• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 100-52-7 benzaldehyde 
• 924-50-5 Methyl 3,3-dimethylacrylate 

Downstream Products

• 476688-17-2 (1R,3S)-3-methyl-1-phenylpentane-1,5-diol 
• 149713-23-5 (2S,2S)-4-methyl-2-phenyl-tetrahydro-2H-pyran 
• 149713-23-5 (2S,2R)-4-methyl-2-phenyl-tetrahydro-2H-pyran 
• 149713-23-5 (2R,2S)-4-methyl-2-phenyl-tetrahydro-2H-pyran 
• 149713-23-5 (2R,2R)-4-methyl-2-phenyl-tetrahydro-2H-pyran 
• 201145-41-7 (E)-5-hydroxy-3-methyl-5-phenyl-pent-2-enal 
• 89393-73-7 methyl (3R)-3-methyl-5-oxo-5-phenylpentanoate 
• 476687-78-2 (E)-3-methyl-5-phenyl-2-pentene-1,5-diol 

Relevant articles and documents

Molecular recognition of α,β-unsaturated carbonyl compounds using aluminum tris(2,6-diphenylphenoxide) (ATPH): Structural and conformational analysis of ATPH complexes and application to the selective vinylogous aldol reaction

Various α,β-unsaturated carbonyl compounds were coordinated with aluminum tris(2,6-diphenylphenoxide) (ATPH) to give the corresponding Lewis acid-base complexes in a distinctive coordination fashion (selective coordination). ATPH recognizes carbonyl substrates and subsequently orients itself as it forms a stable complex through selective coordination with the carbonyl oxygen. Selective coordination also confers a conformational preference to each carbonyl compound under the steric and electronic influence of ATPH, which enables the vinylogous aldol reaction of α,β-unsaturated carbonyl compounds to give the corresponding γ-aldol products with different regio- and stereoselectivities.

Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox)

The four stereoisomers of the rose oxide analogue Doremox were prepared in enantiomerically enriched form by enantiospecific bakers' yeast reduction of suitable derivatives and by lipase-mediated kinetic resolution of diol precursors.

Cadmium chloride mediated regiocontrol of dienolates and ketene thioacetals: γ condensation with aldehydes

The use of cadmium chloride to control the regioselectivity of vinylogous anions upon condensation with aldehydes is described.Addition occurred preferentially at the γ position with substituted crotonates and 2-ethylidene-1,3-dithiane (6).Experiments dem

REGIOSELECTIVE CONTROL OF ALLYL ANIONS WITH CADMIUM CHLORIDE: α vs. γ CONDENSATION WITH ALDEHYDES

A general method for directing the condensation of allyl anions such as 2 with aldehydes preferentially to the γ position of the unsaturated nucleophile is described.The procedure employs cadmium chloride to control the regioselectivity and will facilitat

A General Synthesis of 5,6-Dihydro-α-pyrones

Crotonate esters substituted at C-3 by alkyl, alkoxy, or dialkylamino groups are deprotonated and the resulting dienolates added to aldehydes and ketones.Kinetic reaction is at C-2 of the ester, leading to the isolation of 2-alkyl-3-hydroxy esters such as 3 and 4 if the reaction mixture is quenched at -70 deg C.However, retroaldolization occurs readily.If the initial reaction mixtures are allowed to warm to 15 deg C before workup, the isolated products are 5,6-dihydro-α-pyrones (such as 5), accompanied in some cases by the (E)-4-substituted crotonate (such as 6).The method has been applied to the synthesis of a series of retinoid lactones (5f,18,21a-c) which are of interest as potential antineoplastic agents.