1134-71-0

Basic information

• Product Name: ethyl (3S)-3-phenylbutanoate
• Synonyms: ethyl (3S)-3-phenylbutanoate
• CAS NO: 1134-71-0
• Molecular Weight: 192.258
• Mol File: 1134-71-0.mol
• Article Data: 157

Chemical Properties

• CAS DataBase Reference: ethyl (3S)-3-phenylbutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (3S)-3-phenylbutanoate(1134-71-0)
• EPA Substance Registry System: ethyl (3S)-3-phenylbutanoate(1134-71-0)

Safety Data

• Hazardous Substances Data: 1134-71-0(Hazardous Substances Data)

Upstream product

• 1504-72-9 ethyl 3-phenylbut-2-enoate 
• 14618-12-3 diethyl (1-phenylethyl)malonate 
• 19040-53-0 Trimethylphenyllead 
• 623-70-1 ethyl (E)-crotonate 
• 945-93-7 ethyl (Z)-3-phenylbut-2-enoate 
• 86537-63-5 Ethyl 2-Phenyl-2-propenyl carbonate 
• 64-17-5 ethanol 
• 1196-67-4 (E)-β-methylcinnamaldehyde 
• 591-50-4 iodobenzene 
• 1473421-66-7 (R)-ethyl 3-bromobutanoate 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 126434-58-0 (-)-(R)-Ethyl 3-(mesyloxy)butanoate 
• 71-43-2 benzene 
• 2996-92-1 phenyl trimethylsiloxane 

Downstream Products

• 6072-57-7 3-methylindanone 
• 4593-90-2 3-phenylbutyric acid 
• 142612-03-1 rel-(2S,3R)-ethyl 2-deuterio-3-phenylbutanoate 
• 142612-03-1 rel-(2R,3R)-ethyl 2-deuterio-3-phenylbutanoate 
• 2722-36-3 3-phenyl-1-butanol 
• 34335-30-3 3-(4-carboxy-phenyl)-butyric acid 
• 4179-16-2 (+/-)-3-<4-Methoxycarbonyl-phenyl>-buttersaeure-methylester 
• 1134-71-0 ethyl (3R)-3-phenylbutanoate 
• 772-14-5 (R)-3-phenylbutyric acid 
• 4593-90-2 (S)-2-phenylbutanoic acid 
• 53983-15-6 ethyl-5-amino-4-phenyl-isoxazole-3-carboxylate 
• 28811-80-5 ethyl 3-cyclohexylbutanoate 
• 1327773-68-1 4-methyl-N-(3-phenylbutyl)benzenesulfonamide 
• 91552-73-7 2-Amino-2-methyl-4-phenyl-pentan 

Relevant articles and documents

Immobilization of Optically Active Rhodium-Diphosphine Complexes on Porous Silica via Hydrogen Bonding

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Rhodium-catalyzed conjugated addition of aryllead reagents to α,β-unsaturated carbonyl compounds in air and water

In the presence of a rhodium catalyst, α,β-unsaturated esters and ketones (1a-f) react with phenyltrimethyllead 2 in aqueous media and under an air atmosphere to give the corresponding conjugated addition products (3a-e) in high yields.

Alteration of enzyme activity and enantioselectivity by biomimetic encapsulation in silica particles

Direct encapsulation of esterase or lipase fused with the silica-precipitating R5 peptide from Cylindrotheca fusiformis in silica particles afforded high yields of active entrapped protein. The hydrolytic activity of both enzymes against p-nitrophenyl butyrate was similarly affected by encapsulation and the enantioselectivity of the esterase was both improved and inverted. The Royal Society of Chemistry 2012.

Chiral (iminophosphoranyl)ferrocenes: Highly efficient ligands for rhodium- and iridium-catalyzed enantioselective hydrogenation of unfunctionalized olefins

A series of chiral (iminophosphoranyl)ferrocenes (1-3) are highly efficient ligands for Rh- and Ir-catalyzed hydrogenation of a number of unfunctionalized olefins; almost perfect enantiomeric excesses (up to 99% ee) have been achieved under mild reaction conditions. The Royal Society of Chemistry 2006.

Chiral bis(N-tosylamino)phosphine- and TADDOL-phosphite-oxazolines as ligands in asymmetric catalysis

A series of P,N-ligands containing a chiral oxazoline ring and a chiral bis(N-tosylamino)phosphine group derived from a 1,2-diamine or a chiral cyclic phosphite group derived from TADDOL has been prepared. These compounds proved to be efficient ligands for enantiocontrol of palladium-catalyzed allylic alkylations and iridium-catalyzed hydrogenations of olefins.

Enantioselective hydrogenation of olefins with planar chiral iridium ferrocenyloxazolinylphosphine complexes

Chiral iridium Fc-PHOX complexes were readily prepared from Fc-PHOX, [Ir(cod)Cl]2 and NaBArF (or NaPF6) in high yields. They were applied as catalysts in the enantioselective hydrogenation of olefins to afford the corresponding produ

Rhodium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carbonyl Compounds via Thiourea Hydrogen Bonding

The strategy of secondary interaction enables enantioselectivity for homogeneous hydrogenation. By introducing hydrogen bonding of substrates with thiourea from the ligand, α,β-unsaturated carbonyl compounds, such as amides and esters, are hydrogenated wi

Iridium-Catalyzed Enantioselective Hydrogenation of Olefins

Cationic iridium complexes with chiral P,N-ligands and tetrakis[3,5- (trifluoromethyl)phenyl]borate (BArF) as the counterion are efficient homogeneous catalysts for the enantioselective hydrogenation of olefins. The complexes are readily prepared, air-sta

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USP7 as a deubiquitinase plays important roles in regulating the stability of some oncoproteins including MDM2 and DNMT1, and thus represents a potential anticancer target. Through comparative analysis of USP7 co-crystal structures in complex with the rep

Enantioselective hydrogenation of olefins with axial chiral iridium QUINAP complex

(S)-QUINAP reacted with [Ir(cod)Cl]2 to form a new chelating iridium complex in 77.4% yield. The iridium complex was proved to be a highly efficient catalyst for the enantioselective hydrogenation of olefins. 33.4-95.1% ee were obtained for the hydrogenation of unfunctionalized olefins and 90.8-96.1% ee were obtained for functionalized olefins.

Chemical, pharmacological, and in vitro metabolic stability studies on enantiomerically pure RC-33 compounds: Promising neuroprotective agents acting as σ1 receptor agonists

Our recent research efforts identified racemic RC-33 as a potent and metabolically stable σ1 receptor agonist. Herein we describe the isolation of pure RC-33 enantiomers by chiral chromatography, assignment of their absolute configuration, and

Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine - Copper catalyst [14]

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Monohydride-Dichloro Rhodium(III) Complexes with Chiral Diphosphine Ligands as Catalysts for Asymmetric Hydrogenation of Olefinic Substrates

We report full details of the synthesis and characterization of monohydride-dichloro rhodium(III) complexes bearing chiral diphosphine ligands, such as (S)-BINAP, (S)-DM-SEGPHOS, and (S)-DTBM-SEGPHOS, producing cationic triply chloride bridged dinuclear rhodium(III) complexes (1 a: (S)-BINAP; 1 b: (S)-DM-SEGPHOS) and a neutral mononuclear monohydride-dichloro rhodium(III) complex (1 c: (S)-DTBM-SEGPHOS) in high yield and high purity. Their solid state structure and solution behavior were determined by crystallographic studies as well as full spectral data, including DOSY NMR spectroscopy. Among these three complexes, 1 c has a rigid pocket surrounded by two chloride atoms bound to the rhodium atom together with one tBu group of (S)-DTBM-SEGPHOS for fitting to simple olefins without any coordinating functional groups. Complex 1 c exhibited superior catalytic activity and enantioselectivity for asymmetric hydrogenation of exo-olefins and olefinic substrates. The catalytic activity of 1 c was compared with that of well-demonstrated dihydride species derived in situ from rhodium(I) precursors such as [Rh(cod)Cl]2 and [Rh(cod)2]+[BF4]? upon mixing with (S)-DTBM-SEGPHOS under dihydrogen.

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Catalytic asymmetric conjugate reduction of β,β-disubstituted α,β-unsaturated sulfones

(Chemical Equation Presented) Access to a chiral sulfone: Asymmetric conjugate reduction of β,β-disubstituted α,β-unsaturated 2-pyridylsulfones with silanes under CuI/binap catalysis provides chiral sulfones with excellent chemical yields and e

Studies on the Enantiomers of RC-33 as Neuroprotective Agents: Isolation, Configurational Assignment, and Preliminary Biological Profile

In this study we addressed the role of chirality in the biological activity of RC-33, recently studied by us in its racemic form. An asymmetric synthesis procedure was the first experiment, leading to the desired enantioenriched RC-33 but with an enantiom

Indene Derived Phosphorus-Thioether Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

A family of phosphite/phosphinite-thioether ligands have been tested in the Ir-catalyzed asymmetric hydrogenation of a range of olefins (50 substrates in total). The presented ligands are synthesized in three steps from cheap indene and they are air-stable solids. Their modular architecture has been crucial to maximize the catalytic performance for each type of substrate. Improving most Ir-catalysts reported so far, this ligand family presents a broader substrate scope, covering different substitution patterns with different functional groups, ranging from unfunctionalized olefins, through olefins with poorly coordinative groups, to olefins with coordinative functional groups. α,β-Unsaturated acyclic and cyclic esters, ketones and amides werehydrogenated in enantioselectivities ranging from 83 to 99% ee. Enantioselectivities ranging from 91 to 98% ee were also achieved for challenging substrates such as unfunctionalized 1,1′-disubstituted olefins, functionalized tri- and 1,1′-disubstituted vinyl phosphonates, and β-cyclic enamides. The catalytic performance of the Ir-ligand assemblies was maintained when the environmentally benign 1,2-propylene carbonate was used as solvent. (Figure presented.).

New application possibilities of Reformatzky reagent for synthesis of substituted acetic acid ethyl ester

When generated in dichloromethane, the Reformatzky reagent from ethyl bromoacetate can react with diphenylchloromethane, 1-bromoadamantane and 1-phenylethyl chlorides to form the corresponding α-substituted ethyl acetates in excellent to good yields. The mechanism of these Reformatzky reactions is interpreted in terms of a carbocation as intermediate which originates from the interaction of the alkyl halide with the organozinc bromide.

Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol

We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.

Synthesis and Asymmetric Alkene Hydrogenation Activity of C2-Symmetric Enantioenriched Pyridine Dicarbene Iron Dialkyl Complexes

Enantioenriched N-alkyl-imidazole-substituted pyridine dicarbene iron dialkyl complexes have been synthesized and characterized by 1H NMR and zero-field 57Fe M?ssbauer spectroscopies as well as single-crystal X-ray diffraction. In benzene-d6, reversible coordination of N2 was observed establishing an equilibrium between a five-coordinate, S = 1 iron dialkyl derivative and the corresponding six-coordinate, diamagnetic dinitrogen complex. A modest enantioselectivity of 45% enantiomeric excess (ee) was observed for the catalytic asymmetric hydrogenation of 1-isopropyl-1-phenyl ethylene at 4 atm of H2 using 10 mol % of an enantioenriched iron dialkyl precatalyst, (ACNC)Fe(CH2SiMe3)2 ((ACNC) = bis(alkylimidazol-2-ylidene)pyridine). Decreasing the H2 pressure to 1 atm increased the ee to 70%. Incubation experiments established that the reaction of the iron dialkyl precatalysts with H2 initiates a background reaction leading to the generation of a less selective catalyst; suppressing this pathway is crucial for obtaining high enantioselectivity. The attempted hydrogenation of methyl-2-acetamidoacrylate identified a deactivation pathway where N-H bond activation generated an iron alkyl κ2-amidate alkyl. For productive catalytic reactions, deuterium labeling studies are consistent with a pathway for hydrogenation involving fast, reversible [2,1]-alkene insertion and a slow, enantiodetermining [1,2]-insertion. Monitoring the catalytic alkene hydrogenation reaction by NMR spectroscopy supports a homogeneous active catalyst that also undergoes C-H activation of the ACNC ligand backbone as a competing reaction.