264224-65-9

Basic information

• Product Name: 2-Butanone, 4-hydroxy-4-(4-nitrophenyl)-, (4R)-
• CAS NO: 264224-65-9
• Molecular Formula: C10H11NO4
• Molecular Weight: 209.202
• Mol File: 264224-65-9.mol
• Article Data: 184

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 4-hydroxy-4-(4-nitrophenyl)-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 4-hydroxy-4-(4-nitrophenyl)-, (4R)-(264224-65-9)
• EPA Substance Registry System: 2-Butanone, 4-hydroxy-4-(4-nitrophenyl)-, (4R)-(264224-65-9)

Safety Data

• Hazardous Substances Data: 264224-65-9(Hazardous Substances Data)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 67-64-1 acetone 
• 88958-64-9 1-(4-nitrophenyl)-1-hydroxy-3-butanone 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 147-85-3 L-proline 
• 71444-29-6 (2RS)-2-[(RS)-hydroxy-(4-nitrophenyl)methyl]cyclohexanone 
• 71444-30-9 (2SR)-2-[(SR)-hydroxy-(4-nitrophenyl)methyl]cyclohexanone 
• 619-73-8 4-nitrobenzyl chloride 
• 108-22-5 Isopropenyl acetate 
• 141-97-9 ethyl acetoacetate 
• 78-93-3 butanone 
• 75-07-0 acetaldehyde 

Downstream Products

• 1048378-02-4 C₁₈H₁₉N₃O₃ 
• 1204698-94-1 (1R,3S)-1-(4-nitrophenyl)-1,3-butanediol 
• 1356828-04-0 (1S,3S)-1-(4-nitrophenyl)-1,3-butanediol 
• 1356828-01-7 (1R,3R)-1-(4-nitrophenyl)-1,3-butanediol 
• 1356828-06-2 (1S,3R)-1-(4-nitrophenyl)-1,3-butanediol 

Relevant articles and documents

Highly diastereo- and enantioselective direct aldol reactions of cycloketones with aldehydes catalyzed by a trans-4-tert-butyldimethylsiloxy-l-proline amide

An organocatalyst derived from trans-4-hydroxy-l-proline and (1S,2S)-1,2-diphenyl-2-aminoethanol catalyzes the direct aldol reactions of cycloketones with a wide scope of aldehydes in high yields and with excellent diastereoselectivities of up to >99:1 an

Microwave-assisted asymmetric organocatalysis. A probe for nonthermal microwave effects and the concept of simultaneous cooling

(Chemical Equation Presented) A series of five known asymmetric organocatalytic reactions was re-evaluated at elevated temperatures applying both microwave dielectric heating and conventional thermal heating in order to probe the existence of specific or nonthermal microwave effects. All transformations were conducted in a dedicated reactor setup that allowed accurate internal reaction temperature measurements using fiber-optic probes. In addition, the concept of simultaneous external cooling while irradiating with microwave power was also applied in all of the studied cases. This method allows a higher level of microwave power to be administered to the reaction mixture and, therefore, enhances any potential microwave effects while continuously removing heat. For all of the five studied (S)-proline-catalyzed asymmetric Mannich- and aldol-type reactions, the observed rate enhancements were a consequence of the increased temperatures attained by microwave dielectric heating and were not related to the presence of the microwave field. In all cases, in contrast to previous literature reports, the results obtained either with microwave irradiation or with microwave irradiation with simultaneous cooling could be reproduced by conventional heating at the same reaction temperature and time in an oil bath. No evidence for specific or nonthermal microwave effects was obtained.

(S)-Histidine-based dipeptides as organic catalysts for direct asymmetric aldol reactions

The structure/activity relationships for some (S)-histidine-based dipeptide catalysts in direct aldol reactions have been examined. The reactivities and stereoselectivities are shown to be dependent upon the intramolecular cooperation of side-chain functi

Proline-derived N-sulfonylcarboxamides: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions

Proline catalysis of the asymmetric direct aldol reaction involves both the secondary amine function and the carboxyl group of the amino acid. N-Sulfonylcarboxamides are known to be of similar acidity as carboxylic acids, and three N-arylsulfonyl derivati

Broadening the aldolase catalytic antibody repertoire by combining reactive immunization and transition state theory: New enantio- and diastereoselectivities

Nine efficient aldolase antibodies were generated by using hapten 1. This hapten unites reactive immunization and the transition state analogue approach in a single molecule. Characterization of two of these antibodies reveals that they are highly proficient (up to 1000-fold better than any other antibody catalyst) and enantioselective catalysts for aldol and retro- aldol reactions and exhibit enantio-and diastereoselectivities opposite to that of antibody 38C2.

Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides

Peptides with prolyl N-termini, attached to a PEG-polystyrene (TG) synthesis resin, have been tested as heterogeneous catalysts for the aldol reaction between acetone and p-nitrobenzaldehyde. Proline directly attached to TG showed good activity but poor e

Discovery of new peptide-based catalysts for the direct asymmetric aldol reaction

A series of oligo-peptide based catalysts were prepared using Fmoc solid-phase peptide synthesis. It was found that peptides with N-terminal proline residues catalyzed an aldol reaction yielding enantiomeric enriched product. Peptide H-Pro-Glu-Leu-Phe-OH

New N-terminal prolyl-dipeptide derivatives as organocatalysts for direct asymmetric aldol reaction

A series of new N-terminal prolyl-dipeptide derivatives have been synthesized and evaluated as organocatalysts for the direct asymmetric aldol reaction of acetone with electron-deficient aromatic aldehydes. At room temperature, the presence of 10 mol % of

1(R),2(R)-Bis[(S)-prolinamido]cyclohexane/[bmim][BF4] ionic liquid as an efficient catalytic system for direct asymmetric aldol reactions

A direct asymmetric aldol reaction between unmodified ketones and aldehydes was achieved for the first time using the 1(R),2(R)-bis[(S)-prolinamido]cyclohexane/[bmim][BF4] ionic liquid catalytic system.

Bronsted acids as additives for the direct asymmetric aldol reaction catalyzed by L-prolinethioamides. Direct evidence for enamine-iminium catalysis

(Chemical Equation Presented) The use of protonated L-prolinethioamide instead of the free base derivative 1 as the organocatalyst for the direct aldol addition has a profound and appreciable effect on both the yield and the stereochemical course of the reaction. 4-Nitrobenzaldehyde (2) reacts with acetone in the presence of the protonated catalyst 1·TFA, affording aldol product 3 with a yield up to 99% and an ee up to 98%. The catalyst loading can be lowered to 2.5 mol %. More than 20 different acids were investigated as an additive, and its role as cocatalyst has been discussed. Furthermore, reactions of L-prolinethioamide salts with acetone have been monitored using ESI-MS and 1H NMR techniques, giving insight into the mechanism of the direct aldol reaction. The presumed formation of the iminium salt 10 has been unambiguously confirmed.

NOBIN-prolinamide organocatalyzed enantioselective direct aldol reaction: Remarkable activity in apolar medium

Amides easily obtained from enantiopure (R)- and (S)-NOBIN and L-proline have been shown to promote the enantioselective direct aldol reaction under low catalytic loadings (5 mol%), in apolar hexane as the solvent and using only a slightly higher molar ex

Proline-catalyzed asymmetric direct aldol reaction assisted by D-camphorsulfonic acid in aqueous media

Asymmetric aldol reactions of aromatic aldehydes with various ketones catalyzed by L-proline with D-camphorsulfonic acid as co-catalyst have been developed in aqueous media. High reactivity and modest to excellent enantioselectivity has been achieved. Geo

Synthesis of proline derivatives of bile acids and their evaluation as organocatalysts in the asymmetric direct aldol reaction

A new family of bile acid derived organocatalysts was obtained by linking l- or d-proline to amino derivatives of cholic and deoxycholic acids, which were used to promote the asymmetric direct aldol reaction between acetone and 4-nitrobenzaldehyde. Both t

Chiral ionic liquid containing L-proline unit as a highly efficient and recyclable asymmetric organocatalyst for Aldol reaction

A functionalized chiral ionic liquid (CIL) containing L-proline unit exhibits as a highly efficient and recyclable asymmetric organocatalyst for aldol condensation of aldehydes and ketones in [Bmim][BF4] at room temperature, which afford the co

Benzoimidazole-pyrrolidine (BIP), a highly reactive chiral organocatalyst for aldol process

A new chiral benzoimidazole-pyrrolidine ligand (BIP) was shown to catalyze an aldol process in the presence of an equimolar amount of a Br?nsted acid, leading to the aldol adduct in high yield and enantioselectivity. Remarkably, the aldol reaction was sti

Mining Sequence Space for Asymmetric Aminocatalysis: N-Terminal Prolyl-Peptides Efficiently Catalyze Enantioselective Aldol and Michael Reactions

N-Terminal prolyl-peptides efficiently catalyze asymmetric aldol and Michael reactions between acetone and p-nitrobenzaldehyde or β-nitrostyrene, respectively.

Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions

In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1–4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S

Pro-phe derivatives as organocatalysts in asymmetric aldol reaction

The aldol reaction which is the most important one among the C-C bond forming reactions, is widely used by synthetic organic chemists to obtain β-hydroxycarbonyl compounds which are important starting components for biologically active compounds in optica

Combination of a Metal-N-Heterocyclic-Carbene Catalyst and a Chiral Aminocatalyst within a Covalent Organic Framework: A Powerful Cooperative Approach for Relay Asymmetric Catalysis

Incorporation of metal catalysis and organocatalysis has emerged as a promising way for developing new and valuable organic reactions. This catalytic strategy would potentially enable unprecedented transformations not possible by the existing metal cataly