402741-05-3

Basic information

• Product Name: 2-Butanone, 3-hydroxy-4-[(4-methoxyphenyl)amino]-4-phenyl-, (3S,4R)-
• CAS NO: 402741-05-3
• Molecular Formula: C17H19NO3
• Molecular Weight: 285.343
• Mol File: 402741-05-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 3-hydroxy-4-[(4-methoxyphenyl)amino]-4-phenyl-, (3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 3-hydroxy-4-[(4-methoxyphenyl)amino]-4-phenyl-, (3S,4R)-(402741-05-3)
• EPA Substance Registry System: 2-Butanone, 3-hydroxy-4-[(4-methoxyphenyl)amino]-4-phenyl-, (3S,4R)-(402741-05-3)

Safety Data

• Hazardous Substances Data: 402741-05-3(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 116-09-6 hydroxy-2-propanone 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 

Downstream Products

• 402741-11-1 (4R,5S)-5-acetoxy-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butylester 
• 402741-09-7 (4R,5S)-5-acetyl-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 67341-01-9 (R)-N-(tert-butoxycarbonyl)phenylglycinol 
• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 
• 402741-08-6 (4R,5S)-5-acetyl-3-(4-methoxyphenyl)-4-phenyloxazolidin-2-one 

Relevant articles and documents

Proline catalyzed two-component, three-component and self-asymmetric Mannich reactions promoted by ultrasonic conditions

The proline catalyzed two-component and three-component asymmetric Mannich reaction with hydroxyacetone and self-Mannich reaction with propanal were performed successfully under ultrasonic conditions in 1 h to afford Mannich products in 90-98% isolated yi

Solid-Phase Synthesis of β-Amino Ketones Via DNA-Compatible Organocatalytic Mannich Reactions

One-bead-one-compound (OBOC) libraries constructed by solid-phase split-and-pool synthesis are a valuable source of protein ligands. Most OBOC libraries are comprised of oligoamides, particularly peptides, peptoids, and peptoid-inspired molecules. Further diversification of the chemical space covered by OBOC libraries is desirable. Toward this end, we report here the efficient proline-catalyzed asymmetric Mannich reaction between immobilized aldehydes and soluble ketones and anilines. The reaction conditions do not compromise the amplification of DNA by the PCR. Thus, this chemistry will likely be useful for the construction of novel DNA-encoded libraries by solid-phase synthesis.

Efficient catalysts for asymmetric Mannich reactions

Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields a

Effects of dendritic interface on enantioselective catalysis by polymer-bound prolines

Dendritic effects have been observed in the past for a number of metal-based catalysts, but only rarely for organocatalysts, and particularly chiral organocatalysts. In the current study, l-proline was immobilized as an ester or amide on polyether dendritic spacers attached to polystyrene. The ester-including catalysts showed a remarkable positive dendritic effect on yield, but even more so on enantioselectivity, in the aldol reaction of acetone with aromatic aldehydes. The positive dendritic effect of the aforementioned catalytic systems on the yield, diastereo- and enantioselectivity of a three-component Mannich reaction was of an even greater magnitude. A series of experiments marked the possibility of catalysis by homogenous l-proline, detached from the resin during the reaction, highly unlikely. Model comparative studies with catalysts equipped with linear or only partially dendritic spacers emphasized the superiority of the fully dendritic spacer architecture.

2-pyrrolidinecarboxylic acid ionic liquid as a highly efficient organocatalyst for the asymmetric one-pot Mannich reaction

A. novel one-pot: three-component asymmetric Mannich reaction using [EMIm][PrO] (1) as a catalyst has been developed. By employing this new reaction system, a variety of optically active ss-amino carbonyl compounds were synthesized in up to 99% yield with up to >99 dr and >99% ee. The reaction conditions have been optimized and the mechanism for the asymmetric induction is discussed.

Organocatalytic, asymmetric, one-pot, three-component Mannich reaction of hydroxyacetone

The direct three-component asymmetric Mannich reactions of hydroxyacetone with anilines and aromatic aldehydes in the presence of (2S,5S)-5- (methoxycarbonyl)pyrrolidine-2-carboxylic acid afforded syn-1,2-amino alcohols in good-to-excellent yields (55～91%

A novel design of roof-shaped anthracene-fused chiral prolines as organocatalysts for asymmetric Mannich reactions

A new class of artificial anthracene-fused chiral proline catalysts has been synthesized from the Diels-Alder adduct of anthracene and maleic anhydride via lithiation/carboxylation of 6 as a key step. Chiral resolution of racemic amino acids was carried o

The scope of the direct proline-catalyzed asymmetric addition of ketones to imines

A full account of catalytic direct asymmetric Mannich-type reactions is presented describing the scope of amino acid-catalyzed additions of unmodified ketones to a large variety of imines. These reactions are performed under very mild, operationally simpl

The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols

We have developed proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines. Several of the studied reactions provide β-amino carbonyl compounds (Mannich products) in excellent enantio-, diastereo-, regio-, an