120523-16-2

Basic information

• Product Name: (R)-4-CHROMANOL
• Synonyms: (R)-4-CHROMANOL;SPECS 131/40242452
• CAS NO: 120523-16-2
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Mol File: 120523-16-2.mol

Chemical Properties

• Melting Point: 68-70 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 266.6±29.0 °C(Predicted)
• Appearance: /
• Density: 1.208±0.06 g/cm3(Predicted)
• PKA: 14.12±0.20(Predicted)
• CAS DataBase Reference: (R)-4-CHROMANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-CHROMANOL(120523-16-2)
• EPA Substance Registry System: (R)-4-CHROMANOL(120523-16-2)

Safety Data

• Hazardous Substances Data: 120523-16-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-4-CHROMANOL is used as a precursor in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows for the development of new medications with potential therapeutic benefits.
Used in Organic Chemical Reactions:
In the field of organic chemistry, (R)-4-CHROMANOL serves as a valuable starting material for a range of chemical reactions. Its versatility as a reactant enables the creation of diverse chemical compounds with different applications.
Used in Antioxidant Applications:
(R)-4-CHROMANOL is used as an antioxidant in the food and cosmetic industries to prevent oxidative damage and extend the shelf life of products. Its antioxidant properties help protect cells from free radicals, which can cause cellular damage and contribute to aging and various diseases.
Used in Anti-Inflammatory Applications:
Due to its potential anti-inflammatory properties, (R)-4-CHROMANOL is being explored for use in the development of anti-inflammatory drugs. These drugs could be used to treat conditions such as arthritis, asthma, and other inflammatory disorders.
Used in Cardiovascular Health:
(R)-4-CHROMANOL is used as a component in the development of drugs aimed at promoting cardiovascular health. Its potential benefits in this area include reducing the risk of heart disease and improving overall heart function.

Upstream product

• 493-08-3 chromane 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 254-04-6 2H-chromene 
• 6538-94-9 3,4-epoxy-chroman 
• 1481-93-2 4-hydroxychroman 
• 766-77-8 Dimethylphenylsilane 
• 491-38-3 1-benzopyran-4(4H)-one 
• 180469-87-8 (-)-(3R,4S)-Epoxychromane 
• 574014-07-6 (-)-(4S)-[4-2H]-chromane 
• 574014-11-2 (+)-(4R)-[4-2H]-chromane 
• 574014-06-5 (+/-)-[4-2H]-chromane 
• 180469-85-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3S,4S)-3-bromo-chroman-4-yl ester 
• 108-05-4 vinyl acetate 
• 76-86-8 Triphenylsilyl chloride 

Downstream Products

• 1346229-02-4 (S)-benzyl chroman-4-ylcarbamate 
• 1346228-94-1 (S)-4-(benzyloxy)chroman 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 1481-93-2 4-hydroxychroman 
• 1313511-63-5 (R)-(chroman-4-yloxy)triphenylsilane 
• 676134-13-7 tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6-neopentyl-3,4-dihydro-2H-chromen-4-yl]amino}propylcarbamate 
• 1448783-65-0 C₂₆H₃₂F₂N₂O₄ 
• 676134-45-5 N-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6-isopropoxy-3,4-dihydro-2H-chromen-4-yl]amino}propyl)acetamide 
• 1448783-64-9 C₂₆H₃₂F₄N₂O₃ 
• 1448783-63-8 C₂₆H₃₁F₂N₃O₃ 
• 1448783-62-7 C₂₄H₂₈F₄N₂O₃ 
• 1448783-61-6 C₂₅H₃₁F₃N₂O₃ 
• 777056-99-2 C₂₂H₂₈F₂N₂O₃ 

Relevant articles and documents

The hydrogenation/transfer hydrogenation network: Asymmetric hydrogenation of ketones with chiral η6-arene/N-tosylethylenediamine- ruthenium(II) catalysts

Chiral η6-arene/N-tosylethylenediamine-Ru(II) complexes, known as excellent catalysts for asymmetric transfer hydrogenation of aromatic ketones in basic 2-propanol, can be used for asymmetric hydrogenation using H2 gas. Active catalysts are generated from RuCl[(S,S)-TsNCH(C6H5)CH(C6H5)NH2](η6-p-cymene) in methanol, but not 2-propanol, or by combination of Ru[(S,S)-TsNCH(C6H5)CH(C6H5)NH](η6-p-cymene) and CF3SO3H or other non-nucleophilic acids. This method allows, for the first time, asymmetric hydrogenation of simple ketones under acidic conditions. Hydrogenation of base-sensitive 4-chromanone and its derivatives with the S,S catalyst proceeds in methanol with a substrate-to-catalyst molar ratio of 1000-3000 (10 atm) to 7000 (100 atm), giving (S)-4-chromanols with 97% ee quantitatively. The reaction can be achieved even on a 2.4 kg scale. The mechanistic rationale for the catalytic efficiency is presented. Copyright

Rh(II)-Cp-TsDPEN catalyzed aqueous asymmetric transfer hydrogenation of chromenones into saturated alcohol: C=C and C=O reduction in one step

As an efficient catalyst for asymmetric transfer hydrogenation reaction (ATH reaction) of α,β-unsaturated ketones, Rh-Cp-TsDPEN (Cp = 1,2,3,4,5-pentamethylcyclopenta-1,3-diene, TsDPEN = N-(p-toluenesulfonyl)-1,2- diphenyl- ethylenediamine) shows high chemoselectivity on C=O and C=C reduction. In our method, both C=O and C=C bonds in a variety of chromenone derivatives were reduced efficiently in aqueous media, resulting in at least 98% ee and up to 99% yields in a convenient way without further purification. The product was a useful intermediate for deriving chiral chroman-4-amine, which was reported as an effective agent against hypotension and inflammatory pain by inhibiting human bradykinin B1 receptor.

Enantioselective acylation of chroman-4-ols catalysed by lipase from Pseudomonas cepecia (Amano PS)

Lipase Amano PS catalysed acylation of (±)-chroman-4-ols using vinyl acetate as the acyl donor in n-hexane gave (R)-(+)-chroman-4-ol acetates and (S)-(-)-chroman-4-ols in high enantiomeric excess. The relationship between the position of the substituents in the chroman-4-ol to the ee and the spatial characteristics of the enzyme active site are proposed.

Enantioselective reduction of 4-chromanone and its derivatives by selected filamentous fungi

Biotransformation of 4-chromanone and its derivatives in the cultures of three biocatalysts: Didymosphaeria igniaria, Coryneum betulinum and Chaetomium sp. is presented. The biocatalysts were chosen due to their capability of enantiospecific reduction of low-molecular-weight ketones (acetophenone and its derivatives and α- and β-tetralone). The substrates were reduced to the respective S-alcohols with high enantiomeric excesses, according to the Prelog's rule. In the culture of Chaetomium sp. after longer biotransformation time an inversion of configuration of the formed alcohols was also observed. The highest yield of transformation was observed for 6-methyl-4-chromanone. In all the tested cultures, the higher was the molecular weight of a chromanone, the lower conversion percent was observed.

An improved method for chiral oxazaborolidine-catalyzed reduction of 4- chromanone analogs and MK-0499

Addition of isopropanol to the stoichiometric reduction of ketones 4 - 8 using oxazaborolidine-borane complex 3 or the oxazaborolidine-catalyzed reduction of 4-chromanone analogs (1, 7 - 9) enhances the enantioselectivity of the reduction.

γ-Sultam-cored N,N-ligands in the ruthenium(II)-catalyzed asymmetric transfer hydrogenation of aryl ketones

The synthesis of new enantiopure syn- and anti-3-(α-aminobenzyl)-benzo-γ-sultam ligands 6 and their application in the ruthenium(ii)-catalyzed asymmetric transfer hydrogenation (ATH) of ketones using formic acid/triethylamine is described. In particular, benzo-fused cyclic ketones afforded excellent enantioselectivities in reasonable time employing a low loading of the syn ligand-containing catalyst. A never-before-seen dynamic kinetic resolution (DKR) during reduction of a γ-keto carboxylic ester (S7) derivative of 1-indanone is realized leading as well to excellent induction.

Structural Effects on the Enantioselective Acetylation of 4-Hydroxychromans Catalyzed by Microbial Lipases

Kinetic resolutions of a series of racemic 4-hydroxychromans by the Candida cylindracea lipase catalysed acetylation are described.Correlation between structure (conformation) and enantioselectivity is discussed.

Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Asymmetric catalytic reactions are among the most convenient and environmentally benign methods to obtain optically pure compounds. The aim of this study was to develop a green system for the asymmetric transfer hydrogenation of ketones, applying chiral Ru catalyst in aqueous media and mechanochemical energy transmission. Using a ball mill we have optimized the milling parameters in the transfer hydrogenation of acetophenone followed by reduction of various substituted derivatives. The scope of the method was extended to carbo- and heterocyclic ketones. The scale-up of the developed system was successful, the optically enriched alcohols could be obtained in high yields. The developed mechanochemical system provides TOFs up to 168 h?1. Our present study is the first in which mechanochemically activated enantioselective transfer hydrogenations were carried out, thus, may be a useful guide for the practical synthesis of optically pure chiral secondary alcohols.

Practical access to (S)-heterocyclic aromatic acetates via CAL-B/Na2CO3-deacylation and Mitsunobu reaction protocol

Herein, we report the preparation of enantiomerically pure forms of 2,3-dihydrobenzofuran-3-ol (1), chroman-4-ol (2), thiochroman-4-ol (3), 1-(furan-2-yl) ethanol (5) and 1-(thiophen-2-yl) ethanol (6), through a kinetic resolution catalysed by Candida antarctica lipase B/Na2CO3 hydrolysis sequence in organic media. The (R)-furnished alcohols and the (S)-remained acetates are recovered enantiopures (ee?>99%, E???200, Conv = 50%). Those ideal enzymatic kinetic resolution (EKRs) are well incorporated to the Mitsunobu inversion protocol in a one pot procedure to give (S)-heterocyclic acetates (1a–3a) in good to high enantiomeric excess (88%–92% ee). Whilst, the (S)-heteroaromatic acetates (5a and 6a) are given with moderate enantiomeric excess (51%–62% ee). All the (S)-acetates are given in good isolated chemical yields (>80%) allowing to overcome the maximum of 50% yield which could be usually reached in a regular kinetic resolution processes.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.