162427-79-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(2-FLUOROPHENYL)ETHANOL is used as a building block for the synthesis of orally active lysophosphatidic acid receptor-1 (LPA1) antagonists. These LPA1 antagonists are important in the development of medications targeting various diseases and conditions, as they can modulate the biological effects of lysophosphatidic acid, a signaling molecule involved in cell proliferation, survival, and migration.
The application of (R)-1-(2-FLUOROPHENYL)ETHANOL in the synthesis of LPA1 antagonists is significant because it allows for the development of more effective and targeted treatments for conditions such as cancer, fibrosis, and cardiovascular diseases. By incorporating (R)-1-(2-FLUOROPHENYL)ETHANOL into the structure of LPA1 antagonists, researchers can potentially improve the pharmacokinetic properties, bioavailability, and overall efficacy of these therapeutic agents.

InChI:InChI=1/C8H9FO/c1-6(10)7-4-2-3-5-8(7)9/h2-6,10H,1H3/t6-/m1/s1

Upstream product

• 445-27-2 2'-Fluoroacetophenone 
• 394-46-7 2-fluorostyrene 
• 445-26-1 1-(2-fluorophenyl)ethanol 
• 75-24-1 trimethylaluminum 
• 446-52-6 2-Fluorobenzaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 75-16-1 methylmagnesium bromide 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 67-63-0 isopropyl alcohol 
• 1796-63-0 1-<2-Fluorphenyl>-ethyl-acetat 
• 179242-97-8 ((1-(2-fluorophenyl)vinyl)oxy)trimethylsilane 
• 446-49-1 1-ethyl-2-fluorobenzene 

Downstream Products

• 1396007-08-1 (R)-1-{4'-[5-((1-(2-fluorophenyl)ethoxy)carbonylamino)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid 
• 1265631-08-0 [3-(4-bromo-phenyl)-5-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester 
• 1265629-90-0 (4'-{4-[(R)-1-(2-fluoro-phenyl)-ethoxycarbonylamino]-5-methyl-isoxazol-3-yl}-biphenyl-4-yl)-acetic acid 
• 1228690-15-0 [5-(4-bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Iron(II) Complexes Containing Chiral Unsymmetrical PNP′ Pincer Ligands: Synthesis and Application in Asymmetric Hydrogenations

Four new chiral PNP′ pincer ligands with a scaffold consisting of a planar chiral ferrocene and a centro chiral aliphatic unit were synthesized and characterized. Treatment of anhydrous FeBr2(THF)2 with 1 equiv of the unsymmetrical chiral PNP′ pincer ligands afforded complexes of the general formula [Fe(PNP′)Br2]. In the solid state these complexes adopt a tetrahedral geometry with the PNP′ ligands coordinated in a ?°2P,N-fashion, as shown by X-ray crystallography. These complexes react with CO in the presence of NaBH4 to yield hydride complexes of the type [Fe(PNP′)(H)(Br)(CO)], which were isolated and tested as catalysts in the asymmetric hydrogenation of ketones. Enantioselectivities of up to 81% ee were obtained.

Short-Mesochannel SBA-15-Supported Chiral 9-Amino Epicinchonine for Asymmetric Transfer Hydrogenation of Aromatic Ketones

A short-mesochannel SBA-15 material functionalized with propylthiol groups was prepared by co-condensation and applied to the immobilization of chiral 9-amino epicinchonine. After complexing with [Ir(cod)Cl]2 (cod=1,5-cyclooctadiene), these mesoporous materials were evaluated as catalysts for the asymmetric transfer hydrogenation of aromatic ketones. Higher enantioselectivities and comparable, or even higher, catalytic activities were achieved compared with the free catalyst. Both the short mesochannel and co-condensation approach for short-mesochannel SBA-15 materials functionalized with propylthiol groups, [SSBA-SH(x)] materials were demonstrated to contribute to the excellent catalytic performance. In addition, the catalyst SSBA-AEC(5)/Ir (AEC=9-amino epicinchonine), with low 3-mercaptopropyltrimethoxysilane (MPTMS) content, showed the best catalytic performance; a high enantiomeric excess of 84 % (homogeneous ee=60 %) along with a conversion of 97 % was achieved within 1 h for asymmetric transfer hydrogenation of acetophenone. Moreover, these immobilized catalysts showed high stability during the reaction and could be recovered for reuse.

The enantioselective reduction of 2′-fluoroacetophenone utilizing a simplified CBS-reduction procedure

We have developed a practical, non-enzymatic, catalytic process for the enantioselective reduction of 2′-fluoroacetophenone. A number of catalysts were screened for the oxazaborolidine-type reduction of this ketone to obtain an optimized system. We have s

Novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone

The invention discloses a novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone. The preparation method of a chiral alcohol compound shown as formula IV comprises the following step of: reacting a ketone compound shown as formula V with hydrogen under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound to obtain the chiral alcohol compound shown as the formula IV; the preparation method of a chiral tetralone compound shown as formula VI comprises the following step of: under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound, reacting an alpha, beta-unsaturated ketone compound shown as formula VII with hydrogen to obtain the chiral tetralone compound shown as the formula VI. The method has the advantages of easy synthesis of raw materials, mild reaction conditions, simple operation, high stereoselectivity and the like, the ee value of the product is up to 92%, and the yield is up to 99%.

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.

Imine containing C2-Symmetric chiral half sandwich η6-p-cymene-Ru(II)- phosphinite complexes: Investigation of their catalytic activity in the asymmetric transfer hydrogenation of ketones

New chiral C2-symmetric bis(phosphinite) ligands containing imine group were synthesized from 1-({[(1R,2R)-2-{[(2-hydroxynaphthalen-1-yl)methylidene] amino}cyclohexyl]- imino}methyl)- naphthalen-2-ol and two equivalents of Ph2PCl, (i-Pr)2PCl or (Cy)2PCl, in high yields. Binuclear C2-symmetric half sandwich η6-p-cymene-Ru(II) complexes of the chiral phosphinite ligands were synthesized by treating of [Ru(η6-p-cymene)(μ-Cl)Cl]2 with the phosphinites in 1:1 M ratio in CH2Cl2. Their catalytic activities in asymmetric transfer hydrogenation (ATH) were investigated for the reaction of acetophenone derivatives with isopropyl alcohol. The corresponding optically active secondary alcohols were obtained in excellent levels of conversion (96–99%) and moderate enantioselectivity (up to 60% ee). Among three complexes investigated, complex 4 was the most efficient one.

Redox-driven deracemization of secondary alcohols by sequential ether/O2-mediated oxidation and Ru-catalyzed asymmetric reduction

The deracemization of benzylic alcohols has been achieved using a redox-driven one-pot two-step process. The racemic alcohols were oxidized by bis(methoxypropyl) ether and oxygen to give the ketone intermediates, followed by an asymmetric transfer hydrogenation with a chiral ruthenium catalyst. This compatible oxidation/reduction process gave the enantiomerically enriched alcohols with up to 95% ee values.

C1-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model

A family of ferrocene-based chiral PNP ligands is reported. These tridentate ligands were successfully applied in Mn-catalyzed asymmetric hydrogenation of ketones, giving high enantioselectivities (92%～99% ee for aryl alkyl ketones) as well as high efficiencies (TON up to 2000). In addition, dialkyl ketones could also be hydrogenated smoothly. Manganese intermediates that might be involved in the catalytic cycle were analyzed. DFT calculation was carried out to help understand the chiral induction model. The Mn/PNP catalyst could discriminate two groups with different steric properties by deformation of the phosphine moiety in the flexible 5-membered ring.

Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System

Bioreductions catalyzed by alcohol dehydrogenases (ADHs) play an important role in the synthesis of chiral alcohols. However, the synthesis of ethyl (S)-4-chloro-3-hydroxybutyrate [(S)-CHBE], an important drug intermediate, has significant challenges concerning high substrate or product inhibition toward ADHs, which complicates its production. Herein, we evaluated a novel ADH, SmADH31, obtained from the Stenotrophomonas maltophilia genome, which can tolerate extremely high concentrations (6 M) of both substrate and product. The coexpression of SmADH31 and glucose dehydrogenase from Bacillus subtilis in Escherichia coli meant that as much as 660 g L-1 (4.0 M) ethyl 4-chloroacetoacetate was completely converted into (S)-CHBE in a monophasic aqueous system with a >99.9% ee value and a high space-time yield (2664 g L-1 d-1). Molecular dynamics simulation shed light on the high activity and stereoselectivity of SmADH31. Moreover, five other optically pure chiral alcohols were synthesized at high concentrations (100-462 g L-1) as a result of the broad substrate spectrum of SmADH31. All these compounds act as important drug intermediates, demonstrating the industrial potential of SmADH31-mediated bioreductions.

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.