72656-47-4

Usage

Uses

Used in Pharmaceutical Production:
(+)-ETHYL (R)-3-HYDROXY-3-PHENYLPROPIONATE is used as a chiral building block for the synthesis of chiral drugs and pharmaceutical intermediates. Its unique stereochemistry allows for the creation of biologically active compounds that are essential in the development of new medications.
Used in Organic Synthesis:
In the field of organic synthesis, (+)-ETHYL (R)-3-HYDROXY-3-PHENYLPROPIONATE serves as a key component in the assembly of complex organic molecules. Its reactivity and chirality make it a valuable asset in the synthesis of a wide range of organic compounds.
Used in Flavor and Fragrance Industry:
(+)-ETHYL (R)-3-HYDROXY-3-PHENYLPROPIONATE is utilized as a key ingredient in the production of aromas and perfumes. Its distinctive scent profile contributes to the creation of unique fragrances and flavorings in various consumer products.

InChI:InChI=1/C11H14O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7,10,12H,2,8H2,1H3/t10-/m1/s1

Upstream product

• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 100-52-7 benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 1117-96-0 Diazoethan 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 623-48-3 ethyl iodoacetae 
• 64-17-5 ethanol 
• 93617-86-8 (4S)-(+)-3-bromoacetyl-4-(1-methylethyl)-2-oxazolidinone 
• 14371-10-9 (E)-3-phenylpropenal 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 3480-87-3 3-hydroxy-3-phenylpropanoic acid 
• 1663-61-2 triethoxymethylbenzene 
• 889130-06-7 (R)-3-(dimethylphenylsilyl)-3-phenylpropanoic acid ethyl ester 
• 17938-20-4 dimethylphenyl(phenylmethyl)silane 

Downstream Products

• 24506-17-0 ethyl (R)-3-hydroxy-3-phenylbutanoate 
• 77085-24-6 (S)-3-chloro-3-phenyl-propionic acid ethyl ester 
• 100036-03-1 (S)-3-bromo-3-phenyl-propionic acid ethyl ester 
• 6414-71-7 (R)-3-ethoxy-3-phenyl-propionic acid ethyl ester 
• 37504-79-3 (R)-ethyl 3-acetoxy-3-phenylpropanoate 
• 58692-70-9 methyl (R)-3-hydroxy-3-phenylpropanoate 
• 100929-22-4 (1'S,3S)-3-Hydroxy-3-phenyl-N-(1-phenylethyl)propionamid 
• 100929-21-3 (1'S,3R)-3-Hydroxy-3-phenyl-N-(1-phenylethyl)propionamid 
• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 103548-16-9 (R)-3-phenyl-1,3-dihydroxypropane 
• 131294-12-7 ethyl [(3R)-(tert-butyldimethylsilyloxy)-3-phenyl]propionate 
• 552302-57-5 ethyl (2S)-4-(benzyloxy)-2-[(R)-hydroxy(phenyl)methyl]-3-(nitromethyl)butanoate 
• 33401-74-0 ethyl (3R)-3-hydroxy-3-phenylpropionate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Relevant academic research and scientific papers

Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof

The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.

Chiral ferrocene-indole diphosphine ligand as well as preparation method and application thereof

The invention relates to a chiral ferrocene-indole diphosphine ligand as well as a preparation method and application thereof. The specific preparation method comprises the following steps: dissolving an indole compound and a chiral ferrocene phosphine ac

Enantioselective Reformatsky Reaction of Ketones Catalyzed by Chiral Indolinylmethanol

A reliable and practical Reformatsky reaction of ethyl iodide acetate with ketones for the synthesis of chiral β-hydroxyl carbonyl compounds in good yields and excellent enantioselectivities is presented. A readily available dihydroindole derivative was u

Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof

The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase: Sm ADH2 via an environmentally friendly TBCR system

Alcohol dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asymmetric synthesis of chiral alcohols; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the by-product, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technology. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, v/v) concentration. Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the by-product acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcohols are synthesised at a high substrate loading (>150 g L-1) without adding external coenzymes. Among these, about 780 g L-1 (6 M) ethyl acetoacetate is completely converted into ethyl (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L-1 d-1 space-time yield. Molecular dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcohols on an industrial scale.

Atropselective Dibrominations of a 1,1′-Disubstituted 2,2′-Biindolyl with Diverging Point-to-Axial Asymmetric Inductions. Deriving 2,2′-Biindolyl-3,3′-diphosphane Ligands for Asymmetric Catalysis

On the 1H NMR timescale, 2,2′-biindolyls with (R)-configured (1-alkoxyprop)-2-yl, (1-hydroxyprop)-2-yl, or (1-siloxyprop)-2-yl substituents at C-1 and C-1′ are atropisomerically stable at 30 °C. A 2,2′-biindolyl (R,R)-17 a of that kind and achiral (!) brominating reagents gave the atropisomerically stable 3,3′-dibromobiindolyls (M)- and/or (P)-18 a at best atropselectively—because of point-to-axial asymmetric inductions—and atropdivergently, exhibiting up to 95 % (M)- and as much (P)-atropselectivity. This route to atropisomerically pure biaryls is novel and should extend to other substrates and/or different functionalizations. The dibromobiindolyls (M)- and (P)-18 a furnished the biindolyldiphosphanes (M)- and (P)-14 without atropisomerization. These syntheses did not require the resolution of a racemic mixture, which distinguishes them from virtually all biaryldiphosphane syntheses known to date. (M)- and (P)-14 acted as ligands in catalytic asymmetric allylations and hydrogenations. Remarkably, the β-ketoester rac-25 c was hydrogenated trans-selectively with 98 % ee; this included a dynamic kinetic resolution.

Molecular Insights into the Ligand-Reactant Interactions of Pt Nanoparticles Functionalized with α-Amino Acids as Asymmetric Catalysts for β-Keto Esters

The asymmetric hydrogenation of ?-keto esters over α-amino acid-functionalized Pt nanoparticles was explored in order to expand our understanding of ligand-reactant interactions underlying the chiral induction. A comprehensive investigation aimed at the quantification of the nonlinear effects demonstrated that for most of the ligands and reactants enantiodifferentiation is determined by 1 : 1 ligand-reactant interaction. However, attachment of phenyl substituents to the ligands or reactants likely involves the formation of more intricate intermediate complexes. We have shown that the asymmetric bias is sensitive to even small changes in the geometry of the ligand. Additionally, we have found that alkali metal cations, which balance the negative charge of the ligand's carboxyl group and originate from the metal hydroxide used for ligand functionalization, play a key role in the process of chiral induction. As the nature of the cation can be varied by simply changing the metal hydroxide used during functionalization, this finding opens an additional possibility to control the stereoselectivity by tuning the ligand-reactant interaction.

Method for preparing chiral beta-hydroxycarboxylate compound

The invention provides a method for preparing a chiral beta-hydroxycarboxylate compound, comprising the following steps: dissolving [Ir(COD)Cl]2, a ligand and an alkaline additive in a solvent, stirring at room temperature, carrying out in-situ synthesis of a catalyst, dissolving a substrate beta-hydroxycarboxylate compound in a solvent, adding the prepared catalyst, and introducing hydrogen to carry out an asymmetric catalytic hydrogenation reaction on the substrate beta-hydroxycarboxylate compound. The reaction conditions are as follows: pressure is 10-100 atmospheres, the reaction temperature is 0-200 DEG C, and the reaction time is 12-48 hours. The reaction activity and selectivity are high, and the hydrogenation reaction conditions are mild. The method is suitable for various beta-hydroxycarboxylate compounds; the substrate application range is wide; and the reaction process causes little environmental pollution.

Asymmetric Transfer Hydrogenation in Thermomorphic Microemulsions Based on Ionic Liquids

A thermomorphic ionic-liquid-based microemulsion system was successfully applied for the Ru-catalyzed asymmetric transfer hydrogenation of ketones. On the basis of the temperature-dependent multiphase behavior of the targeted microemulsion, simple product separation as well as catalyst recycling could be realized. The use of water-soluble ligands improved the immobilization of the catalyst in the microemulsion phase and significantly decreased the catalyst leaching into the organic layer upon extraction of the product. Eventually, the optimized microemulsion system could be applied to a wide range of aromatic ketones that were reduced with good isolated yields (up to 98%) and enantioselectivities (up to 97%), while aliphatic ketones were less successful.

On the basis of the phenethylamine skeleton chiral P, N, N ligand compound and its manufacturing method and application (by machine translation)

The present invention provides a chiral P based on the skeleton of the phenethylamine, N, N ligand compound and its manufacturing method and application, surfactant-ethylamine skeleton chiral P, N, N ligand compound of preparation method is as follows: under the protection of nitrogen, the chiral phenylethylamine - [...] compound with 2 - chloromethyl oxazole oxazoline compounds soluble in the reaction solvent, adding alkali, reflux reaction, filtering, desolvation, column chromatography to obtain the required chiral P, N, N ligand compound. In particular to the β - ketoacid ester compound in asymmetric catalytic hydrogenation reaction. The invention of the phenethylamine skeleton chiral P, N, β - keto ester N ligand can be applied to the asymmetric catalytic hydrogenation reaction, can be high yield and high enantio-selectively for the preparation of chiral β - hydroxy ester. (by machine translation)