59512-47-9

Basic information

• Product Name: threo-4-hydroxy-3-methyl-4-(4-nitrophenyl)butan-2-one
• CAS NO: 59512-47-9
• Molecular Weight: 223.229
• Mol File: 59512-47-9.mol

Chemical Properties

• CAS DataBase Reference: threo-4-hydroxy-3-methyl-4-(4-nitrophenyl)butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: threo-4-hydroxy-3-methyl-4-(4-nitrophenyl)butan-2-one(59512-47-9)
• EPA Substance Registry System: threo-4-hydroxy-3-methyl-4-(4-nitrophenyl)butan-2-one(59512-47-9)

Safety Data

• Hazardous Substances Data: 59512-47-9(Hazardous Substances Data)

Upstream product

• 516-05-2 methyl-propanedioic acid 
• 55591-35-0 1,1'-(4-nitro-phenylmethanediyl)-bis-piperidine 
• 2382-59-4 2-methyl-3-oxobutanoic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 78-93-3 butanone 
• 814-75-5 3-bromo-butanone 

Relevant articles and documents

Asymmetric aldol reaction catalyzed by modularly designed organocatalysts

The self-assembly of the precatalyst modules, which are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for cata

Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones

Direct asymmetric aldol reaction catalyzed by C2-Symmetrical chiral primary amine organocatalysts

Three novel C2-symmetrical chiral primary amines were synthesized from chiral BINOL and diamines. Then their catalytic activities in the asymmetric aldol reactions were evaluated, and the result indicated that 1c was the optimal organocatalyst.

Acyclic amino acids catalyzed direct asymmetric aldol reactions in aqueous media assisted by 2,4-dinitrophenol

The catalytic capabilities of acyclic amino acids for the direct asymmetric aldol reactions assisted by 2,4-dinitrophenol in aqueous media were investigated. Several acyclic amino acids catalyzed asymmetric aldol reactions with excellent stereoselectivity, and afforded the corresponding β-hydroxy ketones in high yields and up to 99% ee. Our result suggested that the L-isoleucine was the most effective one. Springer Science+Business Media, LLC 2010.

Chiral amine-polyoxometalate hybrids as recoverable asymmetric enamine catalysts under neat and aqueous conditions

Solid acid-chiral amine hybrids have been synthesized and explored as recyclable and reusable enamine-type asymmetric catalysts. Simple chiral amine-polyoxometalate (CA-POM) hybrids were identified as the optimal catalysts to promote a range of enamine-ba

Water versus solvent-free conditions for the enantioselective inter- and intramolecular aldol reaction employing l-prolinamides and l-prolinethioamides as organocatalysts

Organocatalysts 1, derived from L-proline and (1S,2R)-cis-l-aminoindan-2-ol or (R)-l-aminoin-dane, are evaluated as promoters in the direct asymmetric aldol reaction between ketones and aromatic aldehydes in the presence of water and under solvent-free reaction conditions. L-Prolinethioamides 1c and 1d exhibited higher enantioselectivity than the corresponding prolinamides 1a and 1b in the model aldol reaction between cyclohexanone and 4-nitro-benzaldehyde in the presence of 4-nitrobenzoic acid as cocatalyst. In particular, L-prolinethioamide 1d (5 mol%), derived from L-proline and (R)-1-amino-indane, is shown as the most efficient organocatalyst studied promoting the direct aldol reaction of cyclo-alkyl, alkyl, and a-functionalized ketones with aromatic aldehydes in the presence of water and under solvent-free reaction conditions employing only 2 equivalents of nucleophile. Generally, anft-aldol products are obtained in high yields and excellent diastereo- and enantioselectivities (up to > 98/2 until syn, up to 98% ee). Solvent-free conditions give slightly higher dr and ee than using water as solvent. In addition, organocatalyst Id can be easily recovered by extractive work-up and reused. Prolinethio-amide Id (5 mol%) in combination with 4-NO2C6H4CO2H (5 mol%) is also a very effective or-ganocatalytic system for the asymmetric solvent-free intramolecular Haj os-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to other reported catalysts in organic solvents.

Direct aldol reactions catalyzed by intramolecularly folded prolinamide dendrons: Dendrimer effects on stereoselectivity

Dendritic effects on both the enantioselectivity and diastereoselectivity of the direct aldol reaction were observed for pyridine-2,6-dicarboxamide dendrons terminated with l-prolinamides.

Rational combination of two privileged chiral backbones: Highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones

(Figure Presented) A new class of organocatalysts has been designed by rational combination of proline with cinchona alkaloids. The chiral amine 3a, prepared from L-proline and cinchonidine, has been found to be an efficient catalyst for the direct aldol reactions of acetone or 2-butanone with a wide range of aldehydes (up to 98% ee). The cinchonidine backbone is essential to the reaction efficiency and enantioselectivity.

A novel DNA-catalyzed aldol reaction

A novel DNA-catalyzed aldol reaction in water has been developed. This approach will be helpful in learning the role of DNA as a catalyst in the early stage during the development of life on earth. Georg Thieme Verlag Stuttgart.