31796-72-2

Basic information

• Product Name: (S)-(+)-α-phenyl-2-pyridylmethanol
• Synonyms: (S)-(+)-α-phenyl-2-pyridylmethanol
• CAS NO: 31796-72-2
• Molecular Weight: 185.225
• Mol File: 31796-72-2.mol

Chemical Properties

• CAS DataBase Reference: (S)-(+)-α-phenyl-2-pyridylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-α-phenyl-2-pyridylmethanol(31796-72-2)
• EPA Substance Registry System: (S)-(+)-α-phenyl-2-pyridylmethanol(31796-72-2)

Safety Data

• Hazardous Substances Data: 31796-72-2(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 100-52-7 benzaldehyde 
• 1121-60-4 pyridine-2-carbaldehyde 
• 17624-36-1 2-pyridyllithium 
• 504-29-0 2-aminopyridine 
• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 626-05-1 2,6-Dibromopyridine 
• 98-98-6 2-Picolinic acid 
• 101-82-6 2-Benzylpyridine 
• 108-00-9 N,N-dimethylethylenediamine 
• 33240-34-5 cyclopentylmagnesium bromide 
• 21970-13-8 (pyridin-2-yl)magnesium bromide 
• 130318-72-8 methyldiphenyltelluronium tetraphenylborate 
• 109-04-6 2-bromo-pyridine 

Downstream Products

• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 40473-17-4 2‐(chloro(phenyl)methyl)pyridine 
• 5583-33-5 (R)-(-)-α-phenyl-2-pyridylmethanol 
• 101-82-6 2-Benzylpyridine 
• 90672-61-0 1-methyl-4-(phenyl-[2]pyridyl-methyl)-piperazine 
• 4372-44-5 methyl-(phenyl-pyridin-2-yl-methyl)-amine 
• 69378-19-4 (phenyl-pyridin-2-yl-methyl)-pyridin-2-yl-amine 
• 148669-37-8 4-(phenyl-pyridin-2-ylmethoxy)-1-[3-(2-nitrophenoxy)propyl]piperidine 
• 107060-28-6 {Ni(OH)2(C₁₂H₁₁NO)3} 
• 106955-11-7 {Ni(OH)2(C₁₂H₁₁NO)2} 
• 106197-23-3 {Cu(OCH(C₅H₄N)C₆H₅)2} 

Relevant articles and documents

New efficient conditions for the reduction with NADH models

New conditions were used for the efficient reduction of various nitroalkenes and two prochiral ketones by using NADH mimics. The present procedure is very useful since it does not involve magnesium perchlorate which is replaced by magnesium bromide in THF. High conversions were observed. The new conditions were checked in asymmetric reductions.

Electronic Effect-Guided Rational Design of Candida antarctica Lipase B for Kinetic Resolution Towards Diarylmethanols

Herein, we developed an electronic effect-guided rational design strategy to enhance the enantioselectivity of Candida antarctica lipase B (CALB) mutants towards bulky pyridyl(phenyl)methanols. Compared to W104A mutant previously reported with reversed S-stereoselectivity toward sec-alcohols, three mutants (W104C, W104S and W104T) displayed significant improvement of S-enantioselectivity in the kinetic resolution (KR) of various phenyl pyridyl methyl acetates due to the increased electronic effects between pyridyl and polar residues. The electronic effects were also observed when mutating other residues surrounding the stereospecificity pocket of CALB, such as T42A, S47A, A281S or A281C, and can be used to manipulate the stereoselectivity. A series of bulky pyridyl(phenyl) methanols, including S-(4-chlorophenyl)(pyridin-2-yl) methanol (S-CPMA), the intermediate of bepotastine, were obtained in good yields and ee values. (Figure presented.).

Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -

Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.

Nitrous oxide as a diazo transfer reagent: The synthesis of triazolopyridines

Nitrous oxide is a potential diazo transfer reagent, but its applications in organic chemistry are scarce. Here, we show that triazolopyridines and triazoloquinolines are formed in the reactions of metallated 2-alkylpyridines or 2-alkylquinolines with N2O. The reactions can be performed under mild conditions and give synthetically interesting triazoles in moderate to good yields.

Palladium-Catalyzed Direct Arylation of 2-Pyridylmethyl Silanes with Aryl Bromides

The first palladium-catalyzed direct arylation of 2-pyridylmethyl silanes with aryl bromides to generate a diverse array of aryl(2-pyridyl)-methyl silane derivatives has been developed. This protocol facilitates access to various kinds of heterocycle-containing silanes in good to excellent yields (40 examples, 66-97% yield) with good functional group tolerance. The scalability of this transformation is demonstrated.

Tunable System for Electrochemical Reduction of Ketones and Phthalimides

Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.

Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions

Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.

Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2

Abstract: Chiral heterocyclic secondary alcohols have received much attention due to their widespread use in pharmaceutical intermediates. In this study, Lactobacillus kefiri P2 biocatalysts isolated from traditional dairy products, were used to catalyze the asymmetric reduction of prochiral ketones to chiral secondary alcohols. Secondary chiral carbinols were obtained by asymmetric bioreduction of different prochiral substrates with results up to > 99% enantiomeric excess (ee). (R)-1-(benzofuran-2-yl)ethanol 5a, which can be used in the synthesis of pharmaceuticals such as bufuralols potent nonselective β-blockers antagonists, Amiodarone (cardiac anti-arrhythmic), and Benziodarone (coronary vasodilator), was produced in gram-scale, high yield and enantiomerically pure form using L. kefiri P2 biocatalysts. The gram-scale production was carried out, and 9.70?g of (R)-5a in enantiomerically pure form was obtained in 96% yield. Also, production of (R)-5a in terms of yield and gram scale through catalytic asymmetric reduction using the biocatalyst was the highest report so far. This is a cost-effective, clean and eco-friendly process for the preparation of chiral secondary alcohols compared to chemical processes. From an environmental and economic perspective, this biocatalytic method has great application potential, making it a green and sustainable way of synthesis. Graphical Abstract: [Figure not available: see fulltext.]

Green synthesis method of polyaryl substituted methanol

The invention relates to a green synthesis method of polyaryl substituted methanol, in particular to a method for efficiently synthesizing polyaryl substituted methanol in a polar aprotic solvent under the condition of an oxidizing agent by taking polyaryl substituted methane as a raw material and alkali as an additive. The method provided by the invention is green and environment-friendly, avoids using expensive metal catalysts, and has the advantages of low cost, few reaction steps, short time, high yield and the like.

Production of enantiopure chiral aryl heteroaryl carbinols using whole‐cell Lactobacillus paracasei biotransformation

Aryl and heteroaryl chiral carbinols are useful precursors in the synthesis of drugs. Lactobacillus paracasei BD87E6, which is obtained from a cereal based fermented beverage, was investigated as whole cell biocatalyst for the bioreduction of different ketones (including aromatic, hetero-aromatic and fused bicyclic ketone) into chiral carbinols, which can be used as a pharmaceutical intermediate. The study shows that bioreduction of aryl, heteroaryl and fused bicyclic ketone (1–5) to their corresponding chiral carbinols (1a–5a) in excellent enantioselectivity (>99%) with high yields. This study gave the first example for an enantiopure production of (S)-6-chlorochroman-4-ol (3a), which has many antioxidant activity, by a biological method. For asymmetric bioreduction of other prochiral ketones, these results open way to use of L. paracasei BD87E6 as biocatalysts. Also, the present process shows a hopeful and alternative green synthesis for the production of enantiopure carbinols in a mild, inexpensive and environmentally friendly process.