29393-19-9

Usage

Uses

Used in Fragrance and Flavor Industry:
(2R)-1-phenylbutan-2-ol is used as a key component in the production of fragrances and flavors due to its pleasant odor. Its distinctive scent makes it a valuable addition to a wide range of products, enhancing their appeal to consumers.
Used as a Solvent:
(2R)-1-phenylbutan-2-ol is also utilized as a solvent in various chemical processes. Its ability to dissolve other substances makes it a versatile and useful tool in the laboratory and in industrial applications.
Used as an Intermediate in Organic Synthesis:
(2R)-1-phenylbutan-2-ol serves as an intermediate in the synthesis of other organic compounds. Its unique structure allows it to be a building block for creating more complex molecules, which can be used in a variety of industries.
Used in Pharmaceutical Applications:
(2R)-1-phenylbutan-2-ol has been studied for its potential pharmaceutical applications, including its use as an anti-inflammatory and anti-nociceptive agent. Its ability to reduce inflammation and alleviate pain makes it a promising candidate for the development of new medications.
Overall, (2R)-1-phenylbutan-2-ol's unique chemical structure and properties make it a valuable compound with a wide range of industrial and scientific applications.

Upstream product

• 33603-06-4 (+)-1-amino-2-phenylbutane 
• 1007-32-5 benzyl ethyl ketone 
• 100-39-0 benzyl bromide 
• 123-38-6 propionaldehyde 
• 75-16-1 methylmagnesium bromide 
• 701-70-2 1-phenyl-2-butanol 
• 86527-08-4 (R,S)-1-phenyl-2-butyl acetate 
• 2386-64-3 ethylmagnesium chloride 
• 222016-68-4 (R,R)-p-Chlorophenyl-1-chloro-2-phenylethyl sulfoxide 
• 158703-50-5 (2S,3R)-4-phenyl-2,3-epoxybutane 
• 108-22-5 Isopropenyl acetate 
• 6052-66-0 1-phenyl-3-buten-2-ol 
• 1163305-45-0 (2R,S(R))-3-iodo-1-[2-(p-tolylsulfinyl)phenyl]but-3-en-2-ol 
• 557-20-0 diethylzinc 

Downstream Products

• 81012-82-0 (2-bromobutyl)benzene 
• 1271984-17-8 C₁₁H₁₄O₂ 
• 701-70-2 (S)-1-phenylbutan-2-ol 
• 701-70-2 1-phenyl-2-butanol 
• 1007-32-5 benzyl ethyl ketone 
• 30543-89-6 (R)-1-Benzyl-propylamine 
• 851317-57-2 3-(1-cyclohexylmethyl-propoxycarbonylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Ligand-Enabled β-Methylene C(sp3)?H Arylation of Masked Aliphatic Alcohols

Despite recent advances, reactivity and site-selectivity remain significant obstacles for the practical application of C(sp3)?H bond functionalization methods. Here, we describe a system that combines a salicylic-aldehyde-derived L,X-type directing group with an electron-deficient 2-pyridone ligand to enable the β-methylene C(sp3)?H arylation of aliphatic alcohols, which has not been possible previously. Notably, this protocol is compatible with heterocycles embedded in both alcohol substrates and aryl coupling partners. A site- and stereo-specific annulation of dihydrocholesterol and the synthesis of a key intermediate of englitazone illustrate the practicality of this method.

Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus

We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.

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.

Chiral thiazolidines in the enantioselective ethylation of aldehydes: An experimental and computational study

A library of new chiral thiazolidines was prepared starting from L-cysteine and D-penicillamine in a simple, one-step procedure. 2-Arylthiazolidines were obtained, as diastereoisomeric mixtures, with good yields and in short reaction times, through a new and greener procedure, using microwave irradiation. Their use as chiral ligands in the enantioselective ethylation of aromatic aldehydes was studied and optimized, originating good to excellent conversions and ee up to 94% in 6 h. A series of heteroaromatic and aliphatic substrates were also enantioselectively ethylated with success, with ee up to 77%. The distinct opposite chirality in L-cysteine and D-penicillamine makes the use of these ligands an interesting approach for obtaining both the (S) and (R) enantiomers of the chiral alcohols, compounds with potential applications in the area of fine chemistry. NMR studies were carried out using a diastereoisomeric mixture of thiazolidines, allowing the identification of the most stable structure. Computational studies confirmed this result and also gave important insight into the species involved in the catalytic cycle of the enantioselective alkylation.

In vitro biocatalytic pathway design: Orthogonal network for the quantitative and stereospecific amination of alcohols

The direct and efficient conversion of alcohols into amines is a pivotal transformation in chemistry. Here, we present an artificial, oxidation-reduction, biocatalytic network that employs five enzymes (alcohol dehydrogenase, NADP-oxidase, catalase, amine dehydrogenase and formate dehydrogenase) in two concurrent and orthogonal cycles. The NADP-dependent oxidative cycle converts a diverse range of aromatic and aliphatic alcohol substrates to the carbonyl compound intermediates, whereas the NAD-dependent reductive aminating cycle generates the related amine products with >99% enantiomeric excess (R) and up to >99% conversion. The elevated conversions stem from the favorable thermodynamic equilibrium (K′eq = 1.88 × 1042 and 1.48 × 1041 for the amination of primary and secondary alcohols, respectively). This biocatalytic network possesses elevated atom efficiency, since the reaction buffer (ammonium formate) is both the aminating agent and the source of reducing equivalents. Additionally, only dioxygen is needed, whereas water and carbonate are the by-products. For the oxidative step, we have employed three variants of the NADP-dependent alcohol dehydrogenase from Thermoanaerobacter ethanolicus and we have elucidated the origin of the stereoselective properties of these variants with the aid of in silico computational models.

A Chiral Metal-Organic Material that Enables Enantiomeric Identification and Purification

We show that CMOM-3S, a previously unreported porous crystalline metal-organic material that exhibits intrinsic homochirality, serves as a general-purpose chiral crystalline sponge (CCS) and a chiral stationary phase (CSP) for gas chromatography (GC). The properties of CMOM-3S are enabled by nano-sized channels connected to adaptable molecular recognition sites that mimic enzyme-binding sites. Further, CMOM-3S is composed of inexpensive components, facile to prepare, and requires only trace amounts of analyte. When coupled with the thermal and hydrolytic stability of CMOM-3S, these features mean that a coated fused silica capillary column in which CMOM-3S serves as a CSP is both more versatile and more robust than three benchmark commercial columns. That the enantiomer with the longer GC retention time is consistently captured in CCS experiments enables CMOM-3S to serve as a powerful tool to enable both chiral purification and enantiomer identification.

IRON(II) CATALYSTS CONTAINING TRIDENTATE PNP LIGANDS, THEIR SYNTHESIS, AND USE THEREOF

The application describes catalytic materials for hydrogenation or asymmetric hydrogenation. In particular, the application describes iron(ll) complexes containing tridentate diphosphine PNP ligands useful for catalytic hydrogenation.

D-Penicillamine and L-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

D-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous L-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes, resulting in very good, albeit slightly lower selectivities, up to 89%. The combined use of these two types of thiazolidines constitutes a very interesting strategy for synthesizing both (S) and (R) enantiomers of chiral secondary alcohols, thus leading the way to a myriad of useful optically active products with opposite absolute configurations.

Development of Axially Chiral Cyclo-Biaryldiol Ligands with Adjustable Dihedral Angles

A new type of axially chiral cyclo-[1,1′-biphenyl]-2,2′-diol (CYCNOL) ligands with adjustable dihedral angles have been developed by varying the bridge chain length. Eight-, nine- and ten-membered cyclo-ligands were prepared and evaluated by using two representative examples: enantioselective additions of diethylzinc to aldehydes and organometallic reagents to enones. The results revealed that the fine regulation of dihedral angles through variation of the bridge chain length was effective in the asymmetric synthesis.

Dual enzymatic dynamic kinetic resolution by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase and Candida antarctica lipase B

The immobilization of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (TeSADH) using sol-gel method enables its use to racemize enantiopure alcohols in organic media. Here, we report the racemization of enantiopure phenyl-ring-containing secondary alcohols using xerogel-immobilized W110A TeSADH in hexane rather than the aqueous medium required by the enzyme. We further showed that this racemization approach in organic solvent was compatible with Candida antarctica lipase B (CALB)-catalyzed kinetic resolution. This compatibility, therefore, allowed a dual enzymatic dynamic kinetic resolution of racemic alcohols using CALB-catalyzed kinetic resolution and W110A TeSADH-catalyzed racemization of phenyl-ring-containing alcohols.