92496-65-6

Usage

Definition

ChEBI: A monohydroxyflavanone in which the hydroxy group is located at position 3'.

Upstream product

• 121245-86-1 (2E)-1-(2-hydroxyphenyl)-3-(3-hydroxyphenyl)-2-propen-1-one 
• 100-83-4 meta-hydroxybenzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 121245-86-1 1-(2-hydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 87199-18-6 3-hydroxyphenylboronic acid 
• 108-95-2 phenol 
• 3055-86-5 3-phenoxypropionitrile 
• 491-38-3 1-benzopyran-4(4H)-one 
• 591-20-8 3-Bromophenol 
• 13709-05-2 3-methoxymethoxybenzaldehyde 
• 75848-97-4 2',3-dihydroxy-αβ-dihydrochalcone 

Downstream Products

• 6563-37-7 3',4'-dihydroxyflavanone 
• 1386980-99-9 3-(4-oxochroman-2-yl)phenyl phenylcarbamate 
• 70460-18-3 3'-hydroxyflavone 

Relevant academic research and scientific papers

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

A cationic cyclodextrin clicked bilayer chiral stationary phase for versatile chiral separation in HPLC

A cationic cyclodextrin (CD) clicked bilayer chiral stationary phase (CSP) was developed via click chemistry for chiral separations in multimode high-performance chromatography (HPLC). The versatility of this new CSP was evaluated using 17 model racemic pairs including aromatic alcohols, flavonoids and isoxazoline enantiomers in both reversed-phase (RP) and normal-phase (NP) HPLC. The CD functionality-enhanced chiral selectivity was elucidated in different elution modes. Higher chiral resolutions were shown in the RP-elution mode due to the inclusion complexation in comparison to the NP-elution mode. The highest chiral resolution of 4.40 was achieved for 4ClPh-OPr, with 12 racemic pairs baseline separated in RP-HPLC. The addition of organic modifiers in mobile phases plays an important role in optimizing the enantioselectivities of the cationic CD bilayer CSP in NP-HPLC.

Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

The mixed chloro- and methyl- functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl)phenylcarbamate and per(2-chloro-5-methyl)phenylcarbamate β-CD clicked CSPs (i.e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.

Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis

Utilizing photoredox/nickel dual catalysis, diverse flavanones have been synthesized by coupling novel 2-trifluoroboratochromanone building blocks with aryl and heteroaryl bromide partners. The newly reported trifluoroboratochromanones can be easily accessed from the corresponding chromones on multigram scale. This represents a general route for accessing natural and unnatural flavanones that were previously formed through a synthetically more restrictive ring closure route from chalcone precursors.

Efficient HPLC enantiomer separation using a pillared homochiral metal-organic framework as a novel chiral stationary phase

HPLC enantioseparation of racemates using novel pillared homochiral metal-organic framework-silica composite as chiral stationary phase has been successfully demonstrated.

Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions

[Figure not available: see fulltext.] A nanosilica-supported dual acidic ionic liquid on the basis of 1-methyl-3-(4-sulfobutyl)imidazolium hydrogen sulfate was synthesized and used as an efficient, green, non-corrosive, non-toxic, heterogeneous, and reusable catalyst for the synthesis of some new and known substituted flavanones. The synthesis was done by the condensation of 2'-hydroxyacetophenone with different aldehydes and the subsequent cyclization of the resulting 2'-hydroxychalcone in the presence of the catalyst. High yields of the products, short reaction times, and solvent-free conditions characterize this new method.

Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for one-pot synthesis of 2-aryl-chromene-4-ones (flavanones)

Silica ferric hydrogensulphate is an efficient heterogeneous catalyst for cyclisation of 2-hydroxychalcones to their corresponding flavanones (chromanone). This intramolecular oxa-Michael reaction was carried out in high yields in the presence of electron donating and electron withdrawing groups in the chalcone structure. Also, we found that aniline can act as an organic co-catalyst in direct synthesis of flavanones from 2-hydroxyacethophenone and aldehydes in the presence of Fe(HSO4)3/SiO2. Flavanones were prepared in high yields in a new catalytic system with similar substituted effect in the indirect cyclisation method. The catalyst in all the above reactions is reusable without significant decreases in its activity after four times of recycling.

Synthesis of flavanones using methane sulphonic acid as a greencatalystand comparision under different conditions

Flavonoids are an important class of natural products with wide range activities. Flavonoids includes flavone, flavanone, flavane & flavanol. The synthetic route invovles synthesis of chalcone followed by ring closing to give flavanone. So many catalysts were mentioned in past literature. But most efficient catalyst is methane sulphonic acid.It is easy to handle,less reaction time &easily available. Flavanones were synthesized from chalcone using methane sulphonic acid under thermal condition, microw wave and ultrasound condition.Flavanones are syntheisized in very less time compared to other conditions.

Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents

This study was designed to synthesize and evaluate flavanone derivatives with phenylcarbamate moiety as potent acetylcholinesterase (AChE) inhibitors and anti-amnestic agents for management of AD. The synthesis of carbamate-substituted flavanone derivativ