42177-25-3

Usage

Uses

Used in Chemical Synthesis:
(R)-(+)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL is used as a coupling reagent for the synthesis of ferrocene aminophosphoxazoline ligands. Its specific stereochemistry and chemical properties make it a valuable component in the creation of these complex organic molecules, which have potential applications in various fields, including pharmaceuticals, materials science, and catalysis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL may be utilized as a key intermediate in the development of novel drugs, particularly those targeting specific biological receptors or enzymes. Its unique structure and reactivity can be exploited to create new molecules with improved efficacy, selectivity, and pharmacokinetic properties.
Used in Materials Science:
(R)-(+)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL can also be employed in the field of materials science, where it may be used to develop new materials with specific optical, electronic, or mechanical properties. Its incorporation into polymers or other molecular structures could lead to the creation of advanced materials for various applications, such as sensors, displays, or energy storage devices.
Used in Catalyst Development:
In the development of catalysts, (R)-(+)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL may serve as a crucial component in the design of new catalysts for various chemical reactions. Its chiral nature and reactivity can be harnessed to create catalysts with enhanced selectivity and activity, leading to more efficient and environmentally friendly chemical processes.

InChI:InChI=1/C12H12O/c1-9(13)11-8-4-6-10-5-2-3-7-12(10)11/h2-9,13H,1H3/t9-/m1/s1

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 1127-76-0 1-ethylnapthelene 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 57573-90-7 acetic acid 1-(1-naphthyl)ethyl ester 
• 108-05-4 vinyl acetate 
• 214260-95-4 (3R,1'R,2''RS)-3-methyl-5-(2-tetrahydropyranyloxy)pentanoic acid (1'-α-naphthyl)ethyl ester 
• 75-24-1 trimethylaluminum 
• 66-77-3 1-naphthaldehyde 
• 826-74-4 1-vinylnaphthalene 
• 108-24-7 acetic anhydride 
• 24425-00-1 diisopropyl pyrocarbonate 
• 22651-87-2 cyclohexanecarboxylic acid anhydride 
• 16837-38-0 nicotinic anhydride 
• 54519-07-2 vinyl ester of 3-phenylpropionic acid 

Downstream Products

• 57605-95-5 1-(1-naphthyl)ethanol 
• 876307-40-3 (R)-1-(naphthalen-1-yl)ethyl benzoate 

Relevant academic research and scientific papers

PQXdpap: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols

Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and 1,1,2-trichloroethane enabled the preparation of either compound of a pair of enantiomerically pure alcohols (>99% ee) from a single catalyst.

Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst is essential to ensure two distinct pathways for the forward and reverse reactions. These reactions convert a large number of racemic aryl alkyl alcohols into their enantiomerically enriched forms in good yields and enantioselectivities.

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.

Axial chirality in biaryl N,N-dialkylaminopyridine derivatives bearing an internal carboxy group

Axial chirality in N,N-dimethylaminopyridines as well as N,N-dipropylaminopyridines bearing an internal carboxy group were evaluated based on their racemization barriers and circular dichroism spectra. The half-life of racemization of N,N-dipropylaminopyridine derivative 2 was estimated to be 19.7 days at 20°C. Its enantiomers isolated as optically active forms showed positive-negative and negative-positive Cotton effects for (+)-2 and (?)-2, respectively, from 310 to 210 nm. Furthermore, (?)-2 was applied as a chiral nucleophilic catalyst and exhibited asymmetric induction in acylative kinetic resolution of 1-(1-naphthyl)ethane-1-ol.

New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms

Recently, we reported the development of new chiral stationary phases (CSPs) for liquid chromatography (LC) based on chiral derivatives of xanthones (CDXs). Based on the most promising CDX selectors, 12 new CSPs were successfully prepared starting from suitable functionalized small molecules including xanthone and benzophenone derivatives. The chiral selectors comprising one, two, three, or four chiral moieties were covalently bonded to a chromatographic support and further packed into LC stainless-steel columns (150?×?2.1?mm I.D.). The enantioselective performance of the new CSPs was evaluated by LC using different classes of chiral compounds. Specificity for enantioseparation of some CDXs was observed in the evaluation of the new CSPs. Besides, assessment of chiral recognition mechanisms was performed by computational studies using molecular docking approach, which are in accordance with the chromatographic parameters. X-Ray analysis was used to establish a chiral selector 3D structure.

Asymmetric Catalytic Meerwein-Ponndorf-Verley Reduction of Ketones with Aluminum(III)-VANOL Catalysts

We report herein an efficient aluminum-catalyzed asymmetric MPV reduction of ketones with broad substrate scope and excellent yields and enantiomeric inductions. A variety of aromatic (both electron-poor and electron-rich) and aliphatic ketones were converted to chiral alcohols in good yields with high enantioselectivities (26 examples, 70-98percent yield and 82-99percent ee). This method operates under mild conditions (-10 °C) and low catalyst loading (1-5 mol percent). Furthermore, this process is catalyzed by the earth-abundant main-group element aluminum and employs 2-propanol as the hydride source.

RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.

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.

An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones

We report the design of a new iron catalyst for the asymmetric transfer hydrogenation of ketones. This type of iron catalyst combines the structural characteristics of the Noyori hydrogenation catalyst (an axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl fragment and the metal-ligand bifunctional motif) and an ene(amido) group that can activate the iron center. After activation by 8 equivalents of potassiumtert-butoxide, (SA,RP,SS)-7aand (SA,RP,SS)-7bare active but nonenantioselective catalysts for the transfer hydrogenation of acetophenone and α,β-unsaturated aldehydes at room temperature in isopropanol. A maximum turnover number of 14480 was observed for (SA,RP,SS)-7ain the reduction of acetophenone. The right combination of the stereochemistry of the axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl group and the carbon-centered chiral amine-imine moiety in (SA,RP,RR)-7b′afforded an enantioselective catalyst for the preparation of chiral alcohols with moderate to good yields and a broad functional group tolerance.

Preparation method of R-1-(naphthalene-1-yl) ethanol

The invention relates to a preparation method of R-1-(naphthalene-1-yl) ethanol. The preparation method comprises the following step: carrying out asymmetric hydrogenation reaction on 1-naphthyl ethylketone under the catalysis of a catalyst; and the catalyst has structural characteristics as shown in the following formula (I). The R-1-(naphthalene-1-yl) ethanol product prepared through the preparation method is higher in chiral purity; meanwhile, the high conversion rate is guaranteed, the reaction can be carried out under the lower pressure condition, large-scale production and application are facilitated, the adopted catalyst can be recycled, heavy metal pollution is avoided, and the cost is reduced.