145624-57-3

Basic information

• Product Name: 4H-Pyran-4-one, 2,3-dihydro-2-(2-phenylethyl)-, (2S)-
• CAS NO: 145624-57-3
• Molecular Formula: C13H14O2
• Molecular Weight: 202.253
• Mol File: 145624-57-3.mol

Chemical Properties

• CAS DataBase Reference: 4H-Pyran-4-one, 2,3-dihydro-2-(2-phenylethyl)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-4-one, 2,3-dihydro-2-(2-phenylethyl)-, (2S)-(145624-57-3)
• EPA Substance Registry System: 4H-Pyran-4-one, 2,3-dihydro-2-(2-phenylethyl)-, (2S)-(145624-57-3)

Safety Data

• Hazardous Substances Data: 145624-57-3(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 71735-01-8 (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene 
• 54125-02-9 danishefsky's diene 
• 194233-66-4 (1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-N,N-dimethyl-1,3-butadien-1-amine 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 
• 439286-12-1 (S)-5-Hydroxy-7-phenyl-1-[(E)-piperidin-1-ylimino]-heptan-3-one 
• 214853-90-4 (S)-4-(2-phenylethyl)oxetane-2-one 

Relevant articles and documents

A Family of Chiral Ferrocenyl Diols: Modular Synthesis, Solid-State Characterization, and Application in Asymmetric Organocatalysis

Readily available chiral diol scaffolds are useful as sources of chirality for asymmetric synthesis, however, few such scaffolds are readily available in enantiopure form. Reported herein is a cheap and modular synthesis of a novel family of chiral ferroc

Evaluation of catalyst acidity and substrate electronic effects in a hydrogen bond-catalyzed enantioselective reaction

A modular catalyst structure was applied to evaluate the effects of catalyst acidity in a hydrogen bond-catalyzed hetero Diels-Alder reaction. Linear free energy relationships between catalyst acidity and both rate and enantioselectivity were observed, wh

Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3- butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of

Asymmetric hetero Diels-Alder reaction catalyzed by chromium complexes of heterogeneously hybridized salen/salan ligands

Various heterogeneously or homogeneously hybridized salen/salan ligands were synthesized, and study of hetero Diels-Alder reactions using their chromium complexes as catalysts revealed that a well-designed heterogeneously hybridized ligand serves as a chi

BINOlate-magnesium catalysts for enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes

An efficient catalytic enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes using the magnesium binaphthoxide system has been developed, affording a variety of 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and with

Methods of performing cycloadditions, reaction mixtures, and methods of performing asymmetric catalytic reactions

Methods of performing cycloadditions are described that include (a) combining a first reactant and a second reactant in a hydrogen bonding solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form a cycloadduc

Storable, powdered chiral zirconium complex for asymmetric aldol and hetero Diels-Alder reactions

A storable, powdered chiral zirconium catalyst for asymmetric aldol and hetero Diels-Alder reactions has been developed. The catalyst has the same activity as that prepared in situ even after being stored for 3 months. Moreover, this chiral Zr catalyst wo

Axially chiral biaryl diols catalyze highly enantioselective hetero-diels-alder reactions through hydrogen bonding

Axially chiral 1,1′-biaryl-2,2′-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels-Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful

A new dirhodium(II) carboxamidate complex as a chiral Lewis acid catalyst for enantioselective hetero-Diels-Alder reactions

Excellent enantioselectivities (up to 99% ee) and turnover numbers (up to 48000) were attained in the hetero-Diels-Alder reaction of a diverse range of aldehydes and activated dienes catalyzed by [Rh2(S-bptpi) 4] (see scheme).

Assembled Dendritic Titanium Catalysts for Enantioselective Hetero-Diels-Alder Reaction of Aldehydes with Danishefsky's Diene

A new type of dendritic 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN)-derived Schiff-base ligands have been synthesized and applied to the titanium-catalyzed hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes. These reactions afforded the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in quantitative yields and with excellent enantioselectivities (up to 97.2% ee). The disposition of the dendritic wedges and the dendron size in the ligands were found to have significant impact on the enantioselectivity of the reaction. The recovered dendritic catalyst could be reused without further addition of the Ti source or a carboxylic acid additive for at least three cycles, retaining similar activity and enantioselectivity. The high stability of this type of assembled dendritic titanium catalyst may be attributed to the stabilization effect of large-sized dendron units in the catalyst molecule. The other important phenomenon observed with this catalyst system is that a higher degree of asymmetric amplification has been achieved by attachment of the dendron unit to the chiral ligand, which represents a new advantage of dendrimer catalysts for asymmetric reactions using chiral ligands of lower optical purity.