127707-68-0

Basic information

• Product Name: (4R)-4-hydroxy-4-phenylbutan-2-one
• CAS NO: 127707-68-0
• Molecular Weight: 164.204
• Mol File: 127707-68-0.mol
• Article Data: 304

Chemical Properties

• CAS DataBase Reference: (4R)-4-hydroxy-4-phenylbutan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-hydroxy-4-phenylbutan-2-one(127707-68-0)
• EPA Substance Registry System: (4R)-4-hydroxy-4-phenylbutan-2-one(127707-68-0)

Safety Data

• Hazardous Substances Data: 127707-68-0(Hazardous Substances Data)

Upstream product

• 1896-62-4 (E)-benzalacetone 
• 1743-36-8 1-phenylbut-3-yn-1-ol 
• 100-52-7 benzaldehyde 
• 67-64-1 acetone 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 57519-88-7 1,1-dichloro-1-phenyl-2,2,2-trimethyldisilane 
• 116-11-0 2-Methoxypropene 
• 108-05-4 vinyl acetate 
• 75815-80-4 (1S)-N-(1-methylethylidene)-1-phenylethylamine 
• 86734-65-8 3-(Dimethyl-hydrazono)-1-phenyl-2-(toluene-4-sulfinyl)-butan-1-ol 
• 213337-22-5 1-(hydrodimethylsilyloxy)-1-phenyl-3-butyne 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 1833-53-0 2-(Trimethylsilyloxy)propene 

Downstream Products

• 5381-93-1 (4S)-4-hydroxy-4-phenylbutan-2-one 
• 5381-93-1 (4R)-4-hydroxy-4-phenylbutan-2-one 
• 118918-39-1 (+)-(4R)-4-acetyloxy-4-phenyl-2-butanone 
• 1896-62-4 (E)-benzalacetone 
• 103729-86-8 (+/-)-1-phenylbutane-1,3-diol 
• 118100-60-0 syn-(1R,3R)-1-phenylbutane-1,3-diol 
• 68263-59-2 N-benzylnonaneamide 
• 100-46-9 benzylamine 
• 112420-27-6 anti-(1S,3R)-1-phenylbutane-1,3-diol 
• 90026-44-1 anti-(1R,3S)-1-phenylbutane-1,3-diol 
• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 90026-47-4 syn-(1S,3S)-1-phenylbutane-1,3-diol 
• 89358-10-1 3-methyl-1-phenylhex-5-ene-1,3-diol 

Relevant articles and documents

Selective reduction of α,β-epoxyketones to β-hydroxyketones using silyllithium reagents

2,3-Epoxy-1-phenyl-1-propanone was reduced to 3-hydroxy-1-phenyl-1-propanone using dimethylphenyl-, methyldiphenyl- or triphenylsilyllithium in THF at -40 °C. The methyldiphenylsilyllithium reagent was superior, providing the product in 70% yield. The rea

Enantioselective Aldol Condensations Catalyzed by Poly(ethylene glycol)-Supported Proline

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Efficient and chemoselective reduction of carbonyl compounds with supported gold catalysts under transfer hydrogenation conditions

A new heterogeneous catalytic transfer hydrogenation (CTH) system, consisting of a non-flammable supported Au catalyst along with 2-propanol as the hydrogen donor, was proven to be effective for chemoselective reduction of a wide range of aromatic ketones and aldehydes to the corresponding alcohols. The Royal Society of Chemistry.

Effect of additives on the proline-catalyzed ketone-aldehyde aldol reactions

The effect of bases, acids, and water as additives in proline-catalyzed ketone-aldehyde aldol reactions has been studied. While the reaction appears to be relatively tolerant to small amounts of tertiary amine bases or weak acids, it stops completely with strong acids. The use of water as an additive had a highly beneficial effect on reactions that were conducted with a stoichiometric ratio of ketone to aldehyde, especially with cyclic ketones. This allows the efficient use of more precious ketones such as 4-thianone as donors in the direct enantioselective aldol and facilitates purification.

Synthesis of Alkenylboronic Esters: An Alternative Route to Trisubstituted Homoallylic Alcohols

New alkenylboronic esters were synthesised from halo-substituted alkenylboronic esters through cross-coupling reactions. Upon Johnson rearrangement, enantiomerically pure allylboronates bearing a stereogenic centre in the position α to the boron moiety were obtained in moderate yield (53 %; 29 % over six steps from the protected propargylic alcohols). The products of these reactions were separable by medium-pressure liquid chromatography, and could be used in highly stereoselective allylation reactions to synthesise enantiomerically enriched homoallylic alcohols containing a 1,1,2-trisubstituted (Z)-configured double bond.

Chiral spiroborate esters catalyzed highly enantioselective direct aldol reaction

Asymmetric catalysis of chiral spiroborate esters with an O3BN framework toward the direct aldol reaction of acetone and aromatic aldehydes was examined, and a new, efficient chiral catalyst was discovered. In the presence of the novel catalyst

Proline-catalysed asymmetric aldol reaction in the room temperature ionic liquid [bmim]PF6

Proline-catalysed asymmetric direct aldol reaction of different aromatic aldehydes with acetone and several other ketones in the room temperature ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate achieved good yields of aldolisation products

A multifunctional proline-based organic catalyst for enantioselective aldol reactions

The synthesis of multifunctional organic catalysts, easily obtained by the condensation of (S)-proline with 1,1′-binaphthyl-2,2′-diamine is reported. These C2 as well as C1 symmetric prolinamides were shown to be able to promote the

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Highly enantioselective direct Aldol reaction catalyzed by organic molecules

We have demonstrated that a new class of L-proline-based organic compounds catalyzed the direct aldol reaction between aldehydes and acetone to provide β-hydroxy ketones in good yields. The reaction is efficient, and 5-10 mol % of the catalyst and excelle

Ionic liquid-supported proline as catalyst in direct asymmetric aldol reaction

Ionic-liquid-supported proline derivative was synthesized starting from L-proline and was used to catalyze direct asymmetric aldol reaction of acetone with aldehydes. The yield and optical purity of the condensation products, the corresponding β-hydroxy carbonyl compounds were comparable with those obtained under homogeneous conditions. Moreover, the catalyst can be reused for at least four times.

Expanding the utility of one-pot multistep reaction networks through compartmentation and recovery of the catalyst

Controlled catalysis: The combination of magnetically and gravimetrically recoverable catalysts such as the nanoparticle-bound base (see picture; blue) and the resin-bound acid (green), respectively, allow the application of non-complementary catalysts to multistep, one-pot reaction cascades (e.g. A→B→C). The catalysts are recovered after reaction and reused in subsequent, unrelated reactions. (Figure Presented)

Zr(OtBu)4-catalysed synthesis of acetone aldol adducts and domino aldol-Tishchenko reactions with diacetone alcohol as enol equivalent

Zr(OtBu)4 was found to be a potent catalyst for the synthesis of acetone aldol adducts with diacetone alcohol as enol equivalent and for domino aldol-Tishchenko reaction giving rise to 1,3-anti-diol monoesters with excellent diastereoselectivity.

Directed methallylations as a synthetic route to 1,3-polyols

The directed methallylation of β-hydroxyaldehydes and ketones with methallylboronic acid is examined. The reaction proceeds with good to excellent selectivity with ketones.

Bisprolinediamides with the binaphthyl backbone as organocatalysts for the direct asymmetric aldol reaction

A series of L-prolineamides derived from various aromatic diamines including 1,1′-binaphthyl-2,2′-diamine, were prepared in good yields. They were evaluated as catalysts for the direct asymmetric aldol reaction. The presence of the binaphthyl and proline

An amphiphilic and photoswitchable organocatalyst for the aldol reaction based on a product-imprinted polymer

A series of amphiphilic molecularly imprinted polymers (MIP1, MIP2, MIP3, MIP4, MIP5, and MIP6) containing hydrophobic photoresponsive sites and hydrophilic catalytically active sites were fabricated using bifunctional monomers. These polymers were characterized by scanning electron microscopy, N2 adsorption–desorption analysis, Fourier Transform infrared spectroscopy, thermal gravimetric analysis, and ultraviolet–visible spectroscopy. The catalytic activity of the amphiphilic molecularly imprinted polymer was investigated towards the aldol reaction between p-nitroaldehyde and acetone (a molecular enlargement reaction) in a mixed solvent of DMSO and water at room temperature. The polymer catalyst MIP3 performs best, and displayed good conversions with low catalyst loading (5 mol% of L-hydroxyproline with respect to the aldehyde) and photoswitching properties (photo-regulated conversion difference of 20%). Compared with the corresponding non-imprinted polymer, a higher binding capacity, higher conversion, and better photoswitching properties were obtained when the molecularly imprinted polymer was used as the catalyst, illustrating the importance of the specific cavities in the molecularly imprinted polymer.

Asymmetric aldol reactions using (4R-trans)-2-(1-methylethenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid, bis-ethyl ester, a chiral precursor of the acetone enolate

(4R-trans)-2-(1-Methylethenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid, bis-ethyl ester upon oxidation with trimethylamine oxide gives a chiral enol borate that condenses with aldehydes to give optically active 4-hydroxy-2-alkanones in 55-77percent yield and 41-65percent e.e.

Chiral diols: A new class of additives for direct aldol reaction catalyzed by L-proline

(Chemical Equation Presented) Nine C2 symmetric diols have been examined as additives in the L-proline-catalyzed direct aldol reaction with significant improvement in enantioselectivity, conversion efficiency, and yield. Loading of 1 mol % of (S)-BINOL leads to the desired products in up to 98% ee and 90% yield. A transition state is proposed.

Ionic-liquid-supported organocatalyst: Efficient and recyclable ionic-liquid-anchored proline for asymmetric aldol reaction

Ionic-liquid-anchored (2S,4R)-4-hydroxyproline 12 catalyzes direct asymmetric aldol reactions with comparable enantioselectivities in DMSO, and with superior enantioselectivities in neat acetone or 2-butanone, than (S)-proline (8) (up to 28% ee difference

Proline-catalyzed direct asymmetric aldol reactions [13]

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Organocatalyzed asymmetric reactions via microwave activation

Organocatalyzed asymmetric microwave-assisted reactions are described. Significant rate enhancements and a decrease of catalyst loading via microwave activation have been observed, while maintaining good to high yields and selectivities compared to litera

Primary amine catalyzed direct asymmetric aldol reaction assisted by water

L-Valine was found to be an active catalyst in the asymmetric direct aldol reaction. The aldol reaction of a variety of aromatic aldehydes with acetone was catalyzed by 20 mol % of l-valine at 35°C with the aldol products obtained in moderate to good yields (48-83%) and enantiomeric excesses (42-72%). The reaction was more efficient catalytically with best results observed in the presence of 1 mol equiv of water, with respect to the aldehyde, in either DMSO or DMF as solvent. The effect of water concentration on the reaction rate and enantioselectivity was also investigated. Thus, with increasing water concentration in DMSO there was decreasing enantioselectivity. However, the reaction in the presence of l-phenylalanine showed a lower level of reactivity and enantioselectivity to afford the aldol in 25% with 31% ee. In marked contrast, reaction with l-phenylglycine resulted in the negligible formation of the aldol (a new strategy in the design of new bioorganic catalysts for direct asymmetric aldol reactions.

Efficient aldol condensation in aqueous biphasic system under microfluidic conditions

A microfluidic system was applied to aldol reaction in aqueous biphasic medium. Advantageous aspects of microfluidic conditions, that is, efficient mixing, fast heat transfer, and residence time control led to the high-yielding reaction of acetone enolate with even α-proton-containing aldehydes in biphasic aqueous-acetone system, by minimizing the formation of self-condensation products.

High-pressure-promoted asymmetric aldol reactions of ketones with aldehydes catalyzed by L-proline

High-pressure conditions were applied to direct asymmetric aldol reactions between ketones and aldehydes with L-proline as a commercially available chiral amino acid catalyst.

Polymer-supported proline-decorated dendrons: Dendritic effect in asymmetric aldol reaction

The yield and enantioselectivity of an asymmetric aldol reaction, catalyzed by a proline derivative immobilized on polystyrene via dipolar cycloaddition, are remarkably improved by the dendronization of the support. The Royal Society of Chemistry.

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