13491-13-9

Usage

Uses

Used in Flavor and Fragrance Industry:
(R)-2-Phenyl-3-methylbutanoic acid is used as a flavoring agent for its unique olfactory properties, adding depth and complexity to the taste profiles of food and beverages. Its ability to impart a slightly sweet aroma makes it a sought-after ingredient in the creation of various consumable products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (R)-2-Phenyl-3-methylbutanoic acid is utilized in the manufacturing process of drugs. Its chiral nature allows for the development of enantiomer-specific medications, which can have different therapeutic effects and reduce potential side effects associated with racemic mixtures.
Used in Chemical Synthesis:
(R)-2-Phenyl-3-methylbutanoic acid serves as a key intermediate in the synthesis of various organic compounds. Its reactivity and structural features make it a versatile building block for the production of specialty chemicals and other complex molecules.
Used in Research and Development:
Due to its chiral properties, (R)-2-Phenyl-3-methylbutanoic acid is an important compound in scientific research, particularly in the study of stereochemistry, asymmetric synthesis, and the development of new methodologies for enantioselective reactions.

InChI:InChI=1/C11H14O2/c1-8(2)10(11(12)13)9-6-4-3-5-7-9/h3-8,10H,1-2H3,(H,12,13)/t10-/m1/s1

Upstream product

• 72615-27-1 2-phenyl-3-methylbutyric acid methyl ester 
• 134837-57-3 (S)-1-{[Dimethyl-((E)-(R)-4-methyl-3-phenyl-pent-1-enyl)-silanyl]-methyl}-2-methoxymethyl-pyrrolidine 
• 4412-08-2 3-methyl-2-phenylbut-2-enoic acid 
• 103-82-2 phenylacetic acid 
• 75-26-3 isopropyl bromide 
• 103979-23-3 3-phenyl-4-methylpent-1-ene 
• 3508-94-9 3-methyl-2-phenylbutyric acid 
• 124931-81-3 (R_a)-phenylacetic acid 2'-hydroxy[1,1']binaphthalenyl-2-ester 
• 300-57-2 allylbenzene 
• 134837-45-9 chloromethyl(cinnamyl)dimethylsilane 
• 134837-46-0 cinnamyldimethyl-<(S)-2-methoxymethylpyrrolidinylmethyl>silane 

Downstream Products

• 23406-60-2 (2R)-3-methyl-2-phenylbutan-1-ol 
• 13490-79-4 (R)-(-)-3-methyl-2-phenylbutyramide 
• 23406-61-3 (-)-(R)-1-Chlor-2-phenyl-3-methyl-butan 
• 934838-72-9 N-benzyloxy-4-(3-methyl-2-phenyl-butyrylamino)-benzamide 
• 22573-54-2 (R)-3-phenyl-4-methylpentanoic acid 
• 1337959-57-5 C₁₂H₁₃NOS₂ 

Relevant academic research and scientific papers

Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol

We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.

HDAC3-SELECTIVE INHIBITORS

Disclosed herein are selective HDAC inhibitors. In some embodiments, the compounds are selective HDAC3 inhibitors. The compounds are useful to treat a variety of conditions, including cancers, i.e., breast cancer, cachexia, and liver steatosis.

Targeting breast cancer stem cells by novel HDAC3-selective inhibitors

Although histone deacetylase (HDAC) inhibitors have been known to suppress the cancer stem cell (CSC) population in multiple types of cancer cells, it remains unclear which HDAC isoforms and corresponding mechanisms contribute to this anti-CSC activity. Pursuant to our previous finding that HDAC8 regulates CSCs in triple-negative breast cancer (TNBC) cells by targeting Notch1 stability, we investigated related pathways and found HDAC3 to be mechanistically linked to CSC homeostasis by increasing β-catenin expression through the Akt/GSK3β pathway. Accordingly, we used a pan-HDAC inhibitor, AR-42 (1), as a scaffold to develop HDAC3-selective inhibitors, obtaining the proof-of-concept with 18 and 28. These two derivatives exhibited high potency and isoform selectivity in HDAC3 inhibition. Equally important, they showed in vitro and/or in vivo efficacy in suppressing the CSC subpopulation of TNBC cells via the downregulation of β-catenin.

Iridium-catalyzed enantioselective hydrogenation of α,β- unsaturated carboxylic acids with tetrasubstituted olefins

A highly efficient asymmetric hydrogenation of α,β-unsaturated carboxylic acids with tetrasubstituted olefin catalyzed by chiral spiro iridium complexes has been developed for the preparation of chiral α-substituted carboxylic acids in excellent enantioselectivities (up to 99% ee).

Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones

The parallel resolution of racemic pentafluorophenyl 2-aryl/ phenylpropanoates and butanoates using an equimolar combination of quasi-enantiomeric Evans oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-ones in good yield. This methodology was used to resolve a series of structurally related 2-aryl/phenylpropanoic and butanoic acids.

Enantiopure tert-butyl(phenyl)phosphine oxide. Chirality-recognition ability and mechanism

When enantiopure tert-butyl(phenyl)phosphine oxide 1 was used as a resolving agent, it showed an acceptable to good chirality-recognition ability for several kinds of racemic carboxylic acids 2. A study on a chirality-recognition mechanism based on X-ray crystallographic analyses of the diastereomeric complexes of 2 with 1 revealed that the complex crystals consisted of helical columns and that 1 was not responsible for the formation of the helical column and occupied a void between the columns; although 1 interacted with 2 via a hydrogen bond to primarily form a pair with 2, the complex crystals were mainly stabilized by the accumulation of weak interactions, such as CH/π, π/π and CH...O interactions, between 1/1, 1/2 and 2/2.

Introduction of single mutation changes arylmalonate decarboxylase to racemase

The introduction of only one mutation based on the estimated reaction mechanism endowed arylmalonate decarboxylase with a racemase activity, which catalyses racemisation of α-arylpropionates. The Royal Society of Chemistry 2006.

Rational design of CH/π interaction sites in a basic resolving agent

A novel synthetic basic resolving agent, cis-1-aminobenz[f]indan-2-ol (ABI), was rationally designed by introducing effective CH/π interaction sites to cis-1-aminoindan-2-ol (AI), whose chiral recognition ability has been reported from our laboratory. ABI was applicable to a wide variety of racemic arylalkanoic acids and showed moderate to excellent chiral recognition ability, which was obviously higher than that of AI. The fundamental and important role of CH/π interactions, such as tunable CH(sp2)/π and CH(sp 3)/π interactions, in the chiral recognition by ABI was revealed by X-ray crystallographic study.

Modular chiral ligands: The profiling of the Mandyphos and Taniaphos ligand families

A set of 11 ferrocenyl based diphosphine ligands (eight Mandyphos and three Taniaphos) was tested in more than 150 experiments using 20 test reactions. For the assessment of new ligands, a two-pronged strategy was developed consisting of a basic and an extended profiling. The basic profiling showed that the choice of the substituents at the P atoms has a significant effect on the catalyst performance. In the extended profiling it was confirmed that the Mandyphos ligands, in particular M4 with two bis(3,5-dimethyl-4-methoxyphenyl)phosphino groups, and the Taniaphos ligands, especially the all-phenyl derivative T1, showed good to outstanding performances in the hydrogenation of selected α- and β-enamides, acrylic acid derivatives, itaconates, β-ketoesters and 1,3-diketones yielding the corresponding products with up to 99% ee and at substrate/catalyst ratios up to 25,000.

The crystallographic structure of a Lewis acid-assisted chiral Bronsted acid as an enantioselective protonation reagent for silyl enol ethers

It is difficult to control the enantioselectivity in the protonation of silyl enol ethers with simple chiral Bronsted acids, mainly due to bond flexibility between the proton and its chiral counterion, the orientational flexibility of the proton, and the fact that the proton sources available are limited to acidic compounds such as chiral carboxylic acids. To overcome these difficulties, we have developed a Lewis acid-assisted chiral Bronsted acid (LBA) system. The coordination of Lewis acids with Bronsted acids restricts the orientation of protons and increases their acidity. Optically active binaphthol (BINOL) derivative·SnCl4 complexes are very effective as enantioselective protonation reagents for silyl enol ethers. However, their exact structures have not yet been determined. We describe here optically active 1,2-diarylethane-1,2-diol derivative·SnCl4 as a new type of LBA for the enantioselective protonation as well as its crystallographic structure. A variety of optically active 1,2-diarylethane-1,2-diols could be readily prepared by asymmetric syn-dihydroxylation. This is a great advantage over BINOL for the flexible design of a new LBA. The most significant finding is that we were able to specify the conformational direction of the H-O bond of LBA, which has some asymmetric inductivity, by X-ray diffraction analysis. The stereochemical course in the enantioselective protonation of silyl enol ethers using LBA would be controlled by a linear OH/π interaction with an initial step. The absolute stereopreference in enantioselective reactions using BINOL·SnCl4 can also be explained in terms of this uniformly mechanistic interpretation. Copyright