4383-18-0

Usage

Uses

Used in Fragrance Industry:
2-Phenyl-2-pentanol is used as a fragrance ingredient for its floral, rose-like scent, contributing to the production of perfumes, soaps, and other fragrance products.
Used in Food and Beverage Industry:
In the food and beverage sector, 2-Phenyl-2-pentanol serves as a flavoring agent, enhancing the taste and aroma of various products.
Used in Pharmaceutical Industry:
2-Phenyl-2-pentanol finds applications in the pharmaceutical field, although the specific uses are not detailed in the provided materials.
Used as a Solvent in Chemical Processes:
2-PHENYL-2-PENTANOL also functions as a solvent in various chemical processes, facilitating reactions and aiding in the production of different chemicals and materials.

InChI:InChI=1/C11H16O/c1-3-9-11(2,12)10-7-5-4-6-8-10/h4-8,12H,3,9H2,1-2H3/t11-/m0/s1

Upstream product

• 4111-09-5 2-Hydroxy-2-methyl-pentanenitrile 
• 107-87-9 2-Pentanone 
• 106-94-5 propyl bromide 
• 98-86-2 acetophenone 
• 917-64-6 methyl magnesium iodide 
• 495-40-9 propiophenone 
• 97-93-8 triethylaluminum 
• 98-83-9 isopropenylbenzene 
• 3262-89-3 triphenylboroxine 
• 4743-74-2 2-phenylpent-4-en-2-ol 
• 29443-43-4 propionaldehyde hydrazone 
• 10557-57-0 propylmagnesium iodide 
• 591-51-5 phenyllithium 
• 611-74-5 N,N-dimethylbenzamide 

Downstream Products

• 5676-32-4 α-n-propylstyrene 
• 53172-85-3 (Z)-2-phenyl-2-pentene 
• 70303-28-5 (E)-pent-2-en-2-ylbenzene 
• 104388-16-1 (1-Methyl-1-propyl-heptyl)-benzene 
• 104388-17-2 (1,2-Dimethyl-1-propyl-butyl)-benzene 
• 98-86-2 acetophenone 
• 52992-91-3 (S)-2-phenyl-2-pentanol 
• 52992-90-2 (R)-2-phenyl-2-pentanol 
• 139470-88-5 (+/-)-2-phenylpent-2-yl hydroperoxide 
• 90832-28-3 meso-4,5-Dimethyl-4,5-diphenyloctan 
• 2719-52-0 2-phenylpentane 
• 104388-11-6 (1-Methyl-1-methylselanyl-butyl)-benzene 
• 90599-77-2 (1-methyl-1-chlorobutyl)benzene 
• 53172-84-2 (E/Z)-2-phenylpent-2-ene 

Relevant academic research and scientific papers

Hydrogenation reaction method

The invention relates to a hydrogenation reaction method, and belongs to the technical field of organic synthesis. The hydrogenation reaction method provided by the invention comprises the following steps: carrying out a hydrogen transfer reaction on a hydrogen acceptor compound, pinacol borane and a catalyst in a solvent in the presence of proton hydrogen, so that the hydrogen acceptor compound is subjected to a hydrogenation reaction; the catalyst is one or more than two of a palladium catalyst, an iridium catalyst and a rhodium catalyst; the hydrogen acceptor compound comprises one or morethan two functional groups of carbon-carbon double bonds, carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogentriple bonds and epoxy. The method is mild in reaction condition, easy to operate, high in yield, short in reaction time, wide in substrate application range, suitable for carbon-carbon double bonds,carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogen triple bonds and epoxy functional groups, good in selectivity and high in reaction specificity.

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds

Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.

On the effect of backbone modifications in 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole

We report on the effect of small side-chain modifications to the structure of 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole (1b) on its reactivity, as expressed by the initial rate v0 in a model reaction, and show how the latter can be successfully correlated to an easily determined physical parameter p, a 13C NMR chemical shift. The relationship v0～ p is already present in the simplest starting material devoid of the hypervalent bond and the iodine core and, therefore, presents an interesting approach towards the future scaffold-optimization of this class of reagents. The reactivity of hypervalent-iodine-based trifluoromethylating agents, as expressed by the initial rate v0 in a model reaction, correlates to an easily determined physical parameter p, a 13C NMR chemical shift.

Introducing deep eutectic solvents to polar organometallic chemistry: Chemoselective addition of organolithium and grignard reagents to ketones in air

Despite their enormous synthetic relevance, the use of polar organolithium and Grignard reagents is greatly limited by their requirements of low temperatures in order to control their reactivity as well as the need of dry organic solvents and inert atmosphere protocols to avoid their fast decomposition. Breaking new ground on the applications of these commodity organometallics in synthesis under more environmentally friendly conditions, this work introduces deep eutetic solvents (DESs) as a green alternative media to carry out chemoselective additions of ketones in air at room temperature. Comparing their reactivities in DES with those observed in pure water suggest that a kinetic activation of the alkylating reagents is taking place, favoring nucleophilic addition over the competitive hydrolysis, which can be rationalized through formation of halide-rich magnesiate or lithiate species. Turning lithium green: A new protocol for the selective addition of Grignard and organolithium reagents to ketones in green, biorenewable, and deep eutectic solvents (DESs) is reported. The protocol establishes a bridge between main-group organometallic compounds and green solvents (ChCl=choline chloride; see picture). The DESs are superior reaction media for highly polar organometallic compounds.

Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones

Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.

Kinetic resolution of hydroperoxides with enantiopure phosphines: Preparation of enantioenriched tertiary hydroperoxides

An efficient reductive kinetic resolution strategy capable of accessing optically active tertiary hydroperoxides is reported. Readily accessible tertiary hydroperoxides are resolved with commercially available (R)- or (S)-xylyl-PHANEPHOS with selectivity factors as large as 37. The resulting bis(phosphine oxide) can be recycled in high yields. The isolated mono(phosphine oxide) intermediate resolved hydroperoxides with the same selectivity as the parent bisphosphine. Copyright

An effect of application of chiral aluminium alkoxides and amides as adducts to zirconium catalyzed carbo- and cycloalumination of olefins

This paper is dedicated to a study of properties of the following novel optically active organoaluminium compounds (OACs): (1S,2S)-l,7,7-trimethyl-2-[(dialkylalumina)oxy]-bicyclo[2.2.1]heptanes and (1S)-N-(dialkylalumina)-6,7-dimethoxy-1-methyl-1,2,3,4 -tetrahydroisoquinolines. The synthesis of the chiral OACs was carried out in the reaction of either natural camphor or salsolidine with both AlEt3 and i-Bu2AlH. The main goal of the research was to investigate the stereodifferentiating activity of the chiral OACs in the olefin carbo- and cycloalumination reactions, catalyzed by Cp2ZrCl2.

Samarium(II) triflate as a new reagent for the grignard-type carbonyl addition reaction

On treatment of a THF solution of Sm(OTf)3 with 1 equiv of an organolithium or organomagnesium reagent at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)2] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of 2-phenylethyl iodide in the presence of HMPA. The Sm(OTf)2 reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)2 gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)2 reagent.

Preparation of Samarium(II) Triflate and It Mediated Grignard-type Reaction. In Situ Formation and Reaction of New Organosamarium Reagents

Samarium(II) triflate was readily prepared by reaction of samarium(III) triflate with sec-butyllithium at room temperature in THF.Its reducing ability was examined by pinacol coupling of carbonyl compounds.Sm(OTf)2 mediated Grignard-type reaction in THF-HMPA effectively; alkylation and allylation of ketones or aldehydes by simple alkyl, allyl, and benzyl halides proceeded via organosamarium intermediates.