3034-05-7

Basic information

• Product Name: 6-chloro-2-phenylchroman-4-one
• Synonyms: 6-chloro-2-phenylchroman-4-one
• CAS NO: 3034-05-7
• Molecular Formula: C₁₅H₁₁ClO₂
• Molecular Weight: 258.69964
• Mol File: 3034-05-7.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 427.5°C at 760 mmHg
• Flash Point: 181°C
• Appearance: /
• Density: 1.293g/cm³
• Vapor Pressure: 1.63E-07mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 6-chloro-2-phenylchroman-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-2-phenylchroman-4-one(3034-05-7)
• EPA Substance Registry System: 6-chloro-2-phenylchroman-4-one(3034-05-7)

Safety Data

• Hazardous Substances Data: 3034-05-7(Hazardous Substances Data)

Usage

Structure

Chroman-4-one with a chlorine atom at the 6th position and a phenyl group at the 2nd position

Classification

Derivative of chroman-4-one; belongs to the class of organic compounds known as benzopyrans

Applications

Used in pharmaceuticals and agrochemicals

Biological Activity

Exhibits potential biological activity, making it valuable in drug discovery and development

Scaffold for Synthesis

Its structural features make it a valuable scaffold for designing and synthesizing new compounds with potential therapeutic properties.

InChI:InChI=1/C15H11ClO2/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-8,15H,9H2

Upstream product

• 1218-24-2 3-phenyl-1-(2'-hydroxy-5'-chlorophenyl)-2-propen-1-one 
• 97723-88-1 6-Chloro-2-phenyl-chroman-4-ol 
• 131942-08-0 1-(3-Bromo-1-phenyl-prop-2-ynyloxy)-4-chloro-benzene 
• 92433-58-4 6-chloro-2-phenylchroman-4-one oxime 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 100-52-7 benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 1218-24-2 5'-chloro-2'-hydroxychalcone 
• 487-26-3 Flavanone 
• 121434-38-6 phenyliodonium bis(phenylsulfonyl)-methylide 
• 1101612-97-8 C₂₀H₁₉ClO₄ 
• 3262-89-3 triphenylboroxine 
• 33533-99-2 6-chloro-4H-chromen-4-one 

Downstream Products

• 10420-73-2 6-chloroflavone 
• 42972-67-8 6-chloro-3-phenyl-4H-chromen-4-one 
• 1218-24-2 5'-chloro-2'-hydroxychalcone 
• 206256-69-1 6-chloro-3-(4-chlorobenzylidene)flavanone 
• 373357-14-3 4,6-dichloro-2-phenyl-2H-3-chromene carbaldehyde 

Relevant articles and documents

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.