61828-55-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(2-Phenylethyl)chroman-4-one is used as a potential therapeutic agent for the development of new drugs due to its antioxidant and anti-inflammatory properties. These properties make it a promising candidate for the treatment of various diseases where oxidative stress and inflammation play a significant role.
Used in Nutraceutical Industry:
(S)-2-(2-Phenylethyl)chroman-4-one can be used as an additive in the nutraceutical industry to enhance the antioxidant and anti-inflammatory properties of dietary supplements and functional foods. Its natural occurrence in some plants and fruits may also contribute to the development of novel, plant-based health products.
Used in Cosmetic Industry:
The antioxidant and anti-inflammatory properties of (S)-2-(2-Phenylethyl)chroman-4-one may also find applications in the cosmetic industry, where it could be used to develop skincare products aimed at reducing inflammation and promoting skin health.
Used in Research and Development:
(S)-2-(2-Phenylethyl)chroman-4-one serves as a valuable compound for research and development in the fields of chemistry, biology, and pharmacology. Its unique structure and properties make it an interesting subject for further investigation into its potential uses and effects on human health and disease.

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 3277-89-2 phenethylmagnesium bromide 
• 491-38-3 1-benzopyran-4(4H)-one 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 90-02-8 salicylaldehyde 
• 104-55-2 3-phenyl-propenal 
• 936182-86-4 tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate 
• 61828-47-5 2-phenethylchroman-4-ol 
• 115085-81-9 4-<(tert-Butyldimethysilyl)oxy>-1-benzpyrylium trifluoromethanesulfonate 
• 536-74-3 phenylacetylene 
• 61828-53-3 2-phenethyl-4H-chromen-4-one 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 60068-17-9 trimethyl<2-<1-<(trimethylsilyl)oxy>ethenyl>phenoxy>silane 

Relevant academic research and scientific papers

Catalytic asymmetric conjugate addition of Grignard reagents to chromones

A highly regio- and enantioselective copper catalysed direct conjugate addition of Grignard reagents to chromones has been developed taking advantage of the reduced reactivity of the resulting magnesium enolates. This methodology tolerates a broad scope of alkyl Grignards including secondary alkyl magnesium reagents as well as functionalised chromones.

SYNTHESIS OF SMALL MOLECULES INSPIRED BY PHOMOXANTHONE A

Methods, compositions, and kits are provided for synthesizing bioactive chromane, the method including: constructing a tertiary ether stereocenter enantioselectively by catalyzed alkynylation of a substituted chromenone to obtain a chromanone; reducing alkyne and ketone in the chromanone to obtain a chroman; and converting ester to methyl group thereby obtaining chromane.

Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions

The stereocontrolled construction of biologically relevant chromanones and tetrahydroxanthones has been achieved through the addition of alkynes to benzopyrylium trilfates under the influence of copper bis(oxazoline) catalysis. Excellent levels of enantiocontrol (63–98 % ee) are achieved in the addition of a variety of alkynes to an array of chromenones with a hydrogen in the 2-position. Promising levels of enantiocontrol (54–67 % ee) are achieved in the alkynylation of chromenones with esters in the 2-position, generating tertiary ether stereocenters resembling those frequently found in naturally occurring metabolites.

A Facile Enantioselective Alkynylation of Chromones

The first catalytic enantioselective alkynylation of chromones is reported. In this process, chromones are silylated to form silyloxybenzopyrylium ions that lead to silyl enol ethers after Cu-catalyzed alkyne addition using StackPhos as a ligand. The outcome of the reaction is impacted by distal ligand substituents with differing electronic character and it was found that successful reactions could be achieved with different ligand congeners by using different solvents. This sequence enables access to different products by protonation or further functionalization, thus increasing complexity in a divergent manner. The transformation is high yielding over a broad scope to provide a variety of useful chromanones in high enantioselectivity.

Synthesis of chiral chromanols: Via a RuPHOX-Ru catalyzed asymmetric hydrogenation of chromones

Chiral chromanols and their derivatives have been synthesized via a RuPHOX-Ru catalyzed asymmetric hydrogenation of chromones in high yields, >20:1 drs and with up to 99.9% ee. Control experiments show that the reaction undergoes two sequential asymmetric hydrogenation steps of the CC and CO double bonds. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 1000 S/C), and the resulting products can be transformed to several biologically active compounds.

Rhodium-Catalyzed Annulations of 1,3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein

A rhodium-catalyzed 2-ethylacrolein-promoted protocol enables the annulation reactions of 1,3-dienes with either salicylaldehydes or 2-hydroxybenzyl alcohols leading to 2-alkylchroman-4-ones with high regioselectivity. This research highlights the use of 2-ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4-hydroacylation pathway to access unsaturated linear ketones with subsequent oxo-Michael addition. (Figure presented.).

Metal-free oxidative decarbonylative alkylation of chromones using aliphatic aldehydes

A decarbonylative alkylation of chromones via radical conjugate addition under metal-free conditions was developed using aliphatic aldehydes as alkylating reagents. A series of 2-tertiary, secondary, and even primary alkylated chromanones were obtained in moderate to excellent yields.

A highly enantioselective access to chiral chromanones and thiochromanones: Via copper-catalyzed asymmetric conjugated reduction of chromones and thiochromones

The chromanone scaffold is a privileged structure in heterocyclic chemistry and drug discovery. A highly efficient copper-catalyzed asymmetric conjugated reduction of chromones is developed to give chiral chromanones with good yields (80-99%) and excellent ee values (94->99% ee). Particularly noteworthy is that chiral thiochromanones are also constructed using this method in 74-87% yields with 96-97% ee. The established asymmetric synthesis paves the way for their further pharmaceutical studies.

Ruthenium-NHC-catalyzed asymmetric hydrogenation of flavones and chromones: General access to enantiomerically enriched flavanones, flavanols, chromanones, and chromanols

Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O-heterocycles - flavanones, chromanones, flavanols, and chromanols - by means of an enantioselective Ru/NHC-catalyzed hydrogenation process (see scheme; NHC=N-heterocyclic carbene, PCC=pyridinium chlorochromate). Copyright

An efficient procedure for the preparation of natural products bearing the 2-(2-phenylethyl)chromone skeleton

Several 2-(2-phenylethyl)chromones have been shown to possess neuroprotective activity. However, limited synthetic methods have been disclosed to construct the 2-(2-phenylethyl)chromone skeleton. Herein, we report a straightforward 3-step preparation of f