81576-55-8

Usage

Uses

Used in Flavor and Fragrance Industry:
(S)-(+)-methyl 2-(4-isobutylphenyl)propionate is used as a flavoring agent for its sweet, fruity odor, contributing to the creation of various fruit flavors and perfumes. Its ability to mimic natural fruit scents makes it a desirable component in the development of artificial flavors and fragrances.
Used in Pharmaceutical Applications:
(S)-(+)-methyl 2-(4-isobutylphenyl)propionate is used as a potential therapeutic agent for its anti-inflammatory and analgesic properties. As an enantiomer of ibuprofen, a well-known NSAID, it has been investigated for its potential to provide similar benefits in managing pain and reducing inflammation. (S)-(+)-methyl 2-(4-isobutylphenyl)propionate's chiral nature adds to its intrigue and potential for targeted drug development.

Upstream product

• 186581-53-3 diazomethane 
• 58609-73-7 2-(4-isobutylphenyl)propanenitrile 
• 67-56-1 methanol 
• 51146-57-7 (R)-ibuprofene 
• 113544-36-8 (S)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 51146-56-6 (S)-ibuprofen 
• 106499-33-6 (R)-1-(4-Isobutyl-phenyl)-1,1-dimethoxy-propan-2-ol 
• 133868-69-6 (S)-(-)-2-(4-isobutylphenyl)propionitrile 
• 298197-67-8 1,1-bis(trimethylsilyloxy)-2-(4-isobutylphenyl)propene 
• 100743-63-3 (S)-1,1-dimethoxy-1-(4-isbutylphenyl)-2-propanol 
• 119408-05-8 2-(4-isobutylphenyl)prop-1-en-1-one 
• 134018-89-6 (R,S)-ibuprofen vinyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 51146-56-6 (S)-ibuprofen 
• 110773-62-1 S-2-(p-isobutylphenyl)propionaldehyde 
• 1403251-50-2 (S)-methyl 2-(2-(N-(1,3-dioxoisoindolin-2-yl)acetamido)-4-isobutylphenyl)propanoate 
• 1403251-49-9 (S)-methyl 2-(3-(N-(1,3-dioxoisoindolin-2-yl)acetamido)-4-isobutylphenyl)propanoate 
• 92761-68-7 (S)-2-(4-isobutylphenyl)-N-((R)-1-phenylethyl)acetamide 
• 92761-69-8 (R)-N-benzyl-2-(4-isobutylphenyl)propanamide 
• 114937-04-1 (4R)-2-<(1S)-1-(4-(2-Methylpropyl)phenyl)ethyl>thiazolidine-4-carboxylic Acid 
• 114937-30-3 (2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol 

Relevant academic research and scientific papers

Stereospecific 1,2-aryl migration in 2-hydroxy alkyl aryl acetals with PPh3/CC14. Synthesis of optically active ibuprofen and naproxen

Treatment of 2-hydroxy acetals (R)-(-)-1 and (R)-(-)-3 with PPh3 and CC14 resulted in a stereospecific 1,2-aryl migration leading to the asymmetric synthesis of (R)-(-)-2 and (R)-(-)-4 respectively.

Catalytic Intermolecular C(sp3)-H Amination: Selective Functionalization of Tertiary C-H Bonds vs Activated Benzylic C-H Bonds

A catalytic intermolecular amination of nonactivated tertiary C(sp3)-H bonds (BDE of 96 kcal·mol-1) is reported for substrates displaying an activated benzylic site (BDE of 85 kcal·mol-1). The tertiary C(sp3)-H bond is selectively functionalized to afford α,α,α-Trisubstituted amides in high yields. This unusual site-selectivity results from the synergistic combination of Rh2(S-Tfpttl)4, a rhodium(II) complex with a well-defined catalytic pocket, with tert-butylphenol sulfamate (TBPhsNH2), which leads to a discriminating rhodium-bound nitrene species under mild oxidative conditions. This catalytic system is very robust, and the reaction was performed on a 50 mmol scale with only 0.01 mol % of catalyst. The TBPhs group can be removed under mild conditions to afford the corresponding NH-free amines.

Rh-Catalyzed cascade C-H activation/C-C cleavage/cyclization of carboxylic acids with cyclopropanols

Merging both C-H and C-C activation in a tandem process is a marked challenge. A novel Rh(iii)-catalyzed C-H activation/ring opening C-C cleavage/cyclization of carboxylic acids with cyclopropanols was developed for the synthesis of 3-substituted phthalides andα,β-butenolides. This reaction displays excellent functional group tolerance with respect to both carboxylic acids and cyclopropanols and features relatively mild conditions. Remarkably, the utility of this method was highlighted by the rapid construction of bioactive compounds bearing a 3-substituted phthalide frameworkvialate-stage functionalization.

Synthetic method of chiral 2-aryl propionate

The invention belongs to the technical field of chemical synthesis, and relates to a synthetic method of chiral 2-aryl propionate, in particular to enantioselective synthesis of 2-aryl propionate. Thesynthetic method comprises the following steps: adding a copper salt, a chiral phosphine ligand, a silicon-hydrogen compound (in terms of SiH), ROH and 2-aryl acrylate in a certain ratio into a reaction bottle, carrying out a reaction in a reaction solvent at -50 to 40 DEG C for 0.25-6 h, and successively performing hydrolyzing, liquid separating, extracting, washing, drying and column chromatography after the reaction is finished, thereby obtaining the target compound 2-aryl propionate. Compared with the prior art, the method has the advantages that the 2-aryl acrylate is reduced by adopting a Cu catalytic system, a catalyst, namely a Cu compound is low in price, and the limitation of hydrogen high-pressure reduction and a noble metal catalyst is broken through. Chiral 2-aryl propionic acid can be obtained through a simple hydrolysis reaction of 2-aryl propionate, and a part of the compounds of 2-aryl propionate are effective components of current commercially-available drugs suchas ibuprofen and naproxen.

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)

Efficient resolution of profen ethyl ester racemates by engineered Yarrowia lipolytica Lip2p lipase

Enzyme-catalyzed enantiomer discrimination is still a great challenge for the development of industrial pharmaceutical processes. For the resolution of ibuprofen, naproxen and ketoprofen racemates, three major anti-inflammatory drugs, only lipases from Candida rugosa present a high selectivity if solvent and surfactant use is discarded. However, their catalytic activities are too low. In the present work, we demonstrate that the lipase Lip2p from the yeast Yarrowia lipolytica has a higher catalytic activity than C. rugosa lipases to hydrolyze the ethyl esters of ibuprofen, naproxen and ketoprofen, but its selectivity is not sufficient [E?=?52 (S); 11 (S) and 1.5 (R) respectively]. The enantioselectivity was further improved by site-directed mutagenesis, targeted at the substrate binding site and guided by molecular modelling studies. By investigating the binding modes of the (R)- and (S)-enantiomers in the active site, two amino acid residues located in the hydrophobic substrate binding site of the lipase, namely residues 232 and 235, were identified as crucial for enantiomer discrimination and enzyme activity. The (S) enantioselectivity of Lip2p towards ethyl ibuprofen esters was rendered infinite (E???300) by replacing V232 by an A or C residue. Substitution of V235 by C, M, S, or T amino acids led to a great increase in the (S)-enantioselectivity (E???300) towards naproxen ethyl ester. Finally, the variant V232F enabled the efficient kinetic resolution of ethyl ketoprofen ester enantiomers [(R)-enantiopreference; E???300]. In addition to the increase in selectivity, a remarkable increase in velocity by 2.6, 2.7 and 2.5?times, respectively, was found for ibuprofen, naproxen and ketoprofen ethyl esters.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Asymmetric cross-coupling of racemic α-bromo esters with aryl Grignard reagents catalyzed by cyclopropane-based bisoxazolines cobalt complexes

Four new cyclopropane-based bisoxazolines were synthesized and applied to cobalt-catalyzed cross-coupling reactions between racemic α-bromo esters and aryl Grignard reagents. The reaction afforded a series of chiral α-arylalkanoic esters with high yields and good enantioselectivities (up to 93% yield, 92:8 er). This research focuses on the cross-coupling between racemic α-bromopropanoate and p-isobutylphenyl Grignard reagent's which provides ibuprofen ester efficiently. Furthermore, ibuprofen ester 7e was transformed into (S)-ibuprofen (99:1 er) via hydrolysis and recrystallization.

Optimized hybrid nanospheres immobilizing Rhizomucor miehei lipase for chiral biotransformation

In this study, the immobilization of Rhizomucor miehei lipase into hybrid nanospheres containing a liposomal core was reported. Organic internal liposomal enzyme phase was protected by inorganic silica matrix, obtained with and without surfactant, that st

Catalytic methyl transfer from dimethylcarbonate to carboxylic acids

Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and green potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected phenols, and the mild reaction conditions enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism proceeding by direct methyl transfer from dimethylcarbonate to the substrate.