705-73-7

Usage

Uses

Used in Flavor and Fragrance Industry:
DL-1-phenylpentan-2-ol is used as a flavoring agent for its mild, green, sweet odor and earthy undernote, adding unique and pleasant aromas to various products in the flavor and fragrance industry.
Used in Pharmaceutical Industry:
DL-1-phenylpentan-2-ol is used as an impurity in the synthesis of Prolintane (P756100), a compound with potential pharmaceutical applications. Its presence in the synthesis process may contribute to the overall effectiveness or characteristics of the final product.
Used in Cheese Production:
DL-1-phenylpentan-2-ol is found in Gruyere de Comte cheese, where it contributes to the unique taste and aroma profile of this specific cheese variety. Its presence in the cheese may enhance the sensory experience for consumers.

Preparation

From phenyl acetaldehyde and propyl magnesium bromide; also by hydrogenation of propyl benzyl ketone.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 2175, 1980 DOI: 10.1016/S0040-4039(00)78990-8

InChI:InChI=1/C11H16O/c1-2-6-11(12)9-10-7-4-3-5-8-10/h3-5,7-8,11-12H,2,6,9H2,1H3

Upstream product

• 6683-92-7 1-phenylpentan-2-one 
• 1589-82-8 phenylmagnesium bromide 
• 123-72-8 butyraldehyde 
• 6921-34-2 benzylmagnesium chloride 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 2397-68-4 sodium tetraethylaluminate 
• 770-09-2 benzyltrimethylsilane 
• 62673-31-8 benzyl(bromo)zinc 
• 108-88-3 toluene 
• 71-36-3 butan-1-ol 
• 927-77-5 n-propylmagnesium bromide 
• 101-41-7 benzeneacetic acid methyl ester 
• 97-93-8 triethylaluminum 
• 100-44-7 benzyl chloride 

Downstream Products

• 6683-92-7 1-phenylpentan-2-one 
• 188432-44-2 O-1-benzylbutyl S-methyl dithiocarbonate 
• 63951-01-9 RS-(+/-)-1-phenyl-2-aminopentane 
• 100368-82-9 2-Formamino-1-phenyl-pentan 
• 92925-72-9 2-Phenyl-hex-1-en-3-one 
• 91787-11-0 1-benzylbutyl tosylate 

Relevant academic research and scientific papers

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into α-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.

Polynucleotides encoding enantioselective carboxylesterases and methods of making same

The present invention relates to a polynucleotide encoding an enzyme having carboxylesterase [E.C.3.1.1.1] activity.

Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions

The versatility of Kluyveromyces marxianus CBS 6556 growing cells in the enantioselective reduction of ketone functionalities to the corresponding alcohols was exploited. In particular, methyl ketones were reduced to (S)-alcohols with ees of up to 96%. Longer chain alkyl ketones afforded, under the same experimental condition, (R)-alcohols with an ee of up to 84%. Interestingly, carbon-carbon double and the triple bonds can also be reduced in the presence of Kluyveromyces marxianus CBS 6556 yeast. A cyclic ketone, such as 2-tetralone, was also quantitatively reduced to its corresponding (S)-alcohol with ee = 76%.

A case of pictet-spengler revisited: Application to the synthesis of dihydroisocoumarins

The reaction of Pictet-Spengler was revisited, and its modified conditions were applied to develop a general methodology toward the synthesis of dihydroisocoumarins containing a no-electron rich aromatic ring.

Recombinant porcine liver esterases, their use and a method for the production thereof

The invention relates to biotechnologically expressible, enzymically active recombinant porcine liver esterases, to a biotechnological method for the preparation thereof and to the use thereof in organic synthesis. The monomeric subunits of recombinant porcine liver esterase are truncated at their C-terminal end, compared with naturally occurring porcine liver esterase subunits. Moreover, it has proved to be an additional advantage to truncate the N-terminal end as well.

Highly efficient alkylation of epoxides with R3Al/H2O systems based on the double activation of epoxy oxygens

Alkylation of epoxides can be effected with trialkylaluminum/water system, which is much superior to the parent trialkylaluminum. Bidentate bis(dialkyl)aluminoxanes and their hypothetical analogues seem to be active species for the double activation of epoxy substrates. Such double-activation ability is emphasized using several synthetic examples in comparison with the corresponding monodentate derivatives. The double coordination complex formation of bidentate (Me2Al)2O is characterized with THF by 1H and 13C NMR spectroscopy.

General Approach to Highly Functionalized Benzylic Organometallics of Zinc and Copper

A general synthesis of highly functionalized benzylic zinc organometallics is described.The corresponding copper derivatives, formed by a transmetalation with CuCN*2LiCl, react in high yields with allylic halides, enones, acyl chlorides, and aldehydes.