2344-70-9

Usage

Uses

1. Used in Chemical Synthesis:
4-Phenyl-2-butanol is used as a reagent for the direct alkylation of amines with primary and secondary alcohols through biocatalytic hydrogen borrowing. This application takes advantage of its chemical properties to facilitate specific reactions in the synthesis of various compounds.
2. Used in Personal Care Industry:
4-Phenyl-2-butanol is used as a component in the preparation of personal care compositions, particularly those that comprise malodor reduction compositions. Its aromatic, floral-fruity odor makes it a suitable ingredient for creating pleasant scents in personal care products.
3. Used in Polymer Production:
When 4-Phenyl-2-butanol reacts with sulfuric acid, it yields polymers. This property can be utilized in the polymer industry to create new materials with specific properties, such as enhanced strength or flexibility, depending on the desired application.

Preparation

The optically inactive product can be prepared by hydrogenation of benzylidene acetone in alcohol solution; under pressure in the presence of platinum oxide, palladium oxide or ferrous sulfate; by reduction with magnesium in methanol.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 6461, 1989 DOI: 10.1016/S0040-4039(01)88994-2

InChI:InChI=1/C10H14O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9,11H,7-8H2,1H3/t9-/m1/s1

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 917-64-6 methyl magnesium iodide 
• 75-16-1 methylmagnesium bromide 
• 2550-26-7 4-Phenyl-2-butanone 
• 3277-89-2 phenethylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 17488-65-2 (+)-1t-Phenyl-buten-⁽¹⁾-ol-⁽³⁾ 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 1896-62-4 (E)-benzalacetone 
• 2167-39-7 (+/-)-2-methyloxetane 
• 75-56-9 methyloxirane 
• 6921-34-2 benzylmagnesium chloride 
• 67-63-0 isopropyl alcohol 
• 1689-71-0 cis-1,2-diphenyloxirane 

Downstream Products

• 96735-17-0 formic acid-(1-methyl-3-phenyl-propyl ester) 
• 10415-88-0 4-phenylbut-2-yl acetate 
• 91244-87-0 Chlormethyl-<4-phenyl-butyl-(2)>-ether 
• 143097-80-7 2-bromo-4-phenylbutane 
• 126745-47-9 N,4-dimethyl-N-(4-phenylbutan-2-yl)benzenesulfonamide 
• 126745-48-0 N-(3-phenyl-1-methyl-propyl)-N'-(ethoxycarbonyl)hydrazinecarboxylic acid ethyl ester 
• 150501-74-9 <3-(Triisopropylsiloxy)butyl>benzene 
• 75178-13-1 4-phenylbutan-2-yl hexanoate 
• 85733-06-8 1-methyl-3-phenylpropyl 2-methylpropionate 
• 130260-31-0 (E)-3-Phenyl-acrylic acid 1-methyl-3-phenyl-propyl ester 
• 126745-55-9 C₂₂H₂₉NO₄S 
• 101196-33-2 1-(1-Methyl-3-phenyl-propoxy)-1,3-dihydro-benzo[c]thiophene 2,2-dioxide 
• 86748-50-7 4-Phenyl-2-butyl O-Acetylmandelate 
• 101001-90-5 <2,2'-bipyridin>-6(1H)-one 

Relevant academic research and scientific papers

Zwitterionic amidinates as effective ligands for platinum nanoparticle hydrogenation catalysts

Ligand control of metal nanoparticles (MNPs) is rapidly gaining importance as ligands can stabilize the MNPs and regulate their catalytic properties. Herein we report the first example of Pt NPs ligated by imidazolium-amidinate ligands that bind strongly through the amidinate anion to the platinum surface atoms. The binding was established by15N NMR spectroscopy, a precedent for nitrogen ligands on MNPs, and XPS. Both monodentate and bidentate coordination modes were found. DFT showed a high bonding energy of up to -48 kcal mol-1 for bidentate bonding to two adjacent metal atoms, which decreased to -28 ± 4 kcal mol-1 for monodentate bonding in the absence of impediments by other ligands. While the surface is densely covered with ligands, both IR and13C MAS NMR spectra proved the adsorption of CO on the surface and thus the availability of sites for catalysis. A particle size dependent Knight shift was observed in the13C MAS NMR spectra for the atoms that coordinate to the surface, but for small particles, ～1.2 nm, it almost vanished, as theory for MNPs predicts; this had not been experimentally verified before. The Pt NPs were found to be catalysts for the hydrogenation of ketones and a notable ligand effect was observed in the hydrogenation of electron-poor carbonyl groups. The catalytic activity is influenced by remote electron donor/acceptor groups introduced in the aryl-N-substituents of the amidinates; p-anisyl groups on the ligand gave catalysts several times faster the ligand containing p-chlorophenyl groups.

Heterogeneous selective hydrogenation of trans-4-phenyl-3-butene-2-one to allylic alcohol over modified Ir/SiO2 catalyst

The heterogeneous selective hydrogenation of trans-4-phenyl-3-butene-2-one to allylic alcohol, catalyzed by Ir/SiO2 stabilized with phosphines and modified by cinchona alkaloids, was described herein. Under the optimized conditions, the chemoselectivity to α,β-unsaturated alcohol was more than 99% with enantioselectivity up to 46%.

HYDROGEN TRANSFER REACTIONS FROM ALCOHOLS TO α,β-UNSATURATED KETONES: Cl, A VERY ACTIVE CATALYST PRECURSOR

A high catalytic activity, with turnover up to 900 cycles/min, is displayed by Cl in hydrogen transfer reactions from propan-2-ol to α,β-unsaturated ketones in a weakly alkaline medium.

First example of selective hydrogenation of unconstrained α,β-unsaturated ketone to α,β-unsaturated alcohol by molecular hydrogen

Unprecedent hydrogenation of unhindered α,β-unsaturated ketones to unsaturated alcohols by molecular H2 on gold supported on Fe2O3 catalysts.

Electrocatalytic Oxidative Hydrofunctionalization Reactions of Alkenes via Co(II/III/IV) Cycle

Here we disclose a general Co(II/III/IV) electrocatalytic platform for alkene functionalization. Driven by electricity, a set of the oxidative hydrofunctionalization reactions via hydrogen atom transfer were demonstrated without the need for stochiometric chemical oxidants. The scope of the reactions encompasses hydroalkoxylation, hydroacyloxylation, hydroarylation, semipinacol rearrangement, and deallylation. Mechanistic studies and stereochemical evidence support an ECEC process involving an electrochemically generated organocobalt(IV) intermediate. This work presents an example of reactivity space expansion in electrocatalysis in the VB12-system by going beyond the common oxidation states of Co(I/II/III).

Discovery and Redesign of a Family VIII Carboxylesterase with High (S)-Selectivity toward Chiral sec-Alcohols

Highly enantioselective lipase has been widely utilized in the preparation of versatile enantiopure chiral sec-alcohols through kinetic or dynamic kinetic resolution. Lipase is intrinsically (R)-selective, and it is difficult to obtain (S)-selective lipase. Recent crystal structures of a family VIII carboxylesterase have revealed that the spatial array of its catalytic triad is the mirror image of that of lipase but with a catalytic triad that is distinct from lipase. We, therefore, hypothesized that the family VIII carboxylesterase may exhibit (S)-enantioselectivity toward sec-alcohols similar to (S)-selective serine protease, whose catalytic triad is also spatially arrayed as its mirror image. In this study, a homologous enzyme (carboxylesterase from Proteobacteria bacterium SG_bin9, PBE) of a known family VIII carboxylesterase (pdb code: 4IVK) was prepared, which showed not only moderate (S)-selectivity toward sec-alcohols such as 3-butyn-2-ol and 1-phenylethyl alcohol but also (R)-selectivity toward particular sec-alcohols among the substrates explored. Furthermore, the (S)-selectivity of PBE has been significantly improved by rational redesign based on molecular modeling. Molecular modeling identified a binding pocket composed of Ser381, Ala383, and Arg408 for the methyl substituent of (R)-1-phenylethyl acetate and suggested that larger residues may increase the enantioselectivity by interfering with the binding of the slow-reacting enantiomer. As predicted, substituting Ser381with larger residues (Phe, Tyr, and Trp) significantly improved the (S)-selectivity of PBE toward all sec-alcohols explored, even the substrates toward which the wild-type PBE exhibits (R)-selectivity. For instance, the enantioselectivity toward 3-butyn-2-ol and 1-phenylethyl alcohol was improved from E = 5.5 and 36.1 to E = 2001 and 882, respectively, by single mutagenesis (S381F).

Application of robust ketoreductase from Hansenula polymorpha for the reduction of carbonyl compounds

Enzyme-catalysed asymmetric reduction of ketones is an attractive tool for the production of chiral building blocks or precursors for the synthesis of bioactive compounds. Expression of robust ketoreductase (KRED) from Hansenula polymorpha was upscaled and applied for the asymmetric reduction of 31 prochiral carbonyl compounds (aliphatic and aromatic ketones, diketones and β-keto esters) to the corresponding optically pure hydroxy compounds. Biotransformations were performed with the purified recombinant KRED together with NADP+ recycling glucose dehydrogenase (GDH, Bacillus megaterium), both overexpressed in Escherichia coli BL21(DE3). Maximum activity of KRED for biotransformation of ethyl-2-methylacetoacetate achieved by the high cell density cultivation was 2499.7 ± 234 U g–1DCW and 8.47 ± 0.40 U·mg–1E, respectively. The KRED from Hansenula polymorpha is a very versatile enzyme with broad substrate specificity and high activity towards carbonyl substrates with various structural features. Among the 36 carbonyl substrates screened in this study, the KRED showed activity with 31, with high enantioselectivity in most cases. With several ketones, the Hansenula polymorpha KRED catalysed preferentially the formation of the (R)-secondary alcohols, which is highly valued.

Novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone

The invention discloses a novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone. The preparation method of a chiral alcohol compound shown as formula IV comprises the following step of: reacting a ketone compound shown as formula V with hydrogen under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound to obtain the chiral alcohol compound shown as the formula IV; the preparation method of a chiral tetralone compound shown as formula VI comprises the following step of: under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound, reacting an alpha, beta-unsaturated ketone compound shown as formula VII with hydrogen to obtain the chiral tetralone compound shown as the formula VI. The method has the advantages of easy synthesis of raw materials, mild reaction conditions, simple operation, high stereoselectivity and the like, the ee value of the product is up to 92%, and the yield is up to 99%.

Cobalt-Catalyzed Radical Hydroamination of Alkenes with N-Fluorobenzenesulfonimides

An efficient and general radical hydroamination of alkenes using Co(salen) as catalyst, N-fluorobenzenesulfonimide (NFSI) and its analogues as both nitrogen source and oxidant was successfully disclosed. A variety of alkenes, including aliphatic alkenes, styrenes, α, β-unsaturated esters, amides, acids, as well as enones, were all compatible to provide desired amination products. Mechanistic experiments suggest that the reaction underwent a metal-hydride-mediated hydrogen atom transfer (HAT) with alkene, followed by a pivotal catalyst controlled SN2-like pathway between in situ generated organocobalt(IV) species and nitrogen-based nucleophiles. Moreover, by virtue of modified chiral cobalt(II)-salen catalyst, an unprecedented asymmetric version was also achieved with good to excellent level of enantiocontrol. This novel asymmetric radical C?N bond construction opens a new door for the challenging asymmetric radical hydrofunctionalization.

Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI

Grignard-type additions were readily achieved under the mediation of CuI (10 mol%) and samarium (2 equiv.) by employing various organohalides,e.g.benzyl, aryl, heterocyclic and aliphatic halides (Cl, Br or I), and diverse carbonyl compounds (e.g.carbonic esters, carboxylic esters, acid anhydrides, acyl chlorides, ketones, aldehydes, propylene epoxides and formamides) to afford alcohols, ketones and aldehydes, respectively, with high efficiency and chemoselectivity, in which the organosamarium intermediate might be involved.