Flavanone

Base Information

• Chemical Name: Flavanone
• CAS No.: 487-26-3
• Deprecated CAS: 24271-98-5
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: 29329900
• European Community (EC) Number: 207-654-8
• NSC Number: 50393
• UNII: WX22P730FB
• DSSTox Substance ID: DTXSID9022318
• Nikkaji Number: J11.632G
• Wikidata: Q27077305
• NCI Thesaurus Code: C68459
• Pharos Ligand ID: DA7BC2RPL6TP
• Metabolomics Workbench ID: 129984
• ChEMBL ID: CHEMBL274318
• Mol file: 487-26-3.mol

Synonyms:(+-)-flavanone;flavanone;flavanone, (+-)-isomer;flavanone, (R)-isomer;flavanone, (S)-isomer;flavanone, 2-(14)C-labeled

Chemical Property of Flavanone

Chemical Property:

• Appearance/Colour: Very slightly yellow powder
• Vapor Pressure: 3.6E-06mmHg at 25°C
• Melting Point: 76-78 °C(lit.)
• Refractive Index: 1.603
• Boiling Point: 386.2 °C at 760 mmHg
• Flash Point: 181.9 °C
• PSA: 26.30000
• Density: 1.192 g/cm³
• LogP: 3.39310
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

98% ^*data from raw suppliers

Flavanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC=CC=C2C1=O)C3=CC=CC=C3
• General Description: Flavanone is a key intermediate in stereospecific ring contraction reactions mediated by hypervalent iodine oxidants like iodobenzene diacetate (PIDA) in the presence of sulfuric acid and trimethyl orthoformate (TMOF). The transformation proceeds via a hypervalent iodine intermediate and aryl migration, yielding highly stereoselective products such as trans-methyl 2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, with the reaction's outcome dictated by the configuration of the C-2 center in flavanone.

Technology Process of Flavanone

There total 297 articles about Flavanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

(R)-3-Hydroxy-1-(2-hydroxy-phenyl)-3-phenyl-propan-1-one (351458-84-9) → (E)-2'-hydroxy-chalcone (888-12-0) + (2S)-flavanone (487-26-3,17002-31-2,24271-98-5,27439-12-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(01)00567-6

Reference yield: 79.0%

2'-hydroxy-3-phenylpropiophenone (3516-95-8) → FLAVONE (525-82-6,66585-04-4) + Flavanone (487-26-3) + 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1214-47-7)

Guidance literature:

2'-hydroxy-3-phenylpropiophenone; With palladium(II) trifluoroacetate; copper diacetate; In dimethyl sulfoxide; at 100 ℃; for 15h; Inert atmosphere;

With hydrogenchloride; In water; dimethyl sulfoxide; ethyl acetate; at 100 ℃; for 24h; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/d1ra01672e

Reference yield: 72.0%

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1214-47-7) → FLAVONE (525-82-6,66585-04-4) + Flavanone (487-26-3)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; cesium acetate; In dimethyl sulfoxide; at 120 ℃; Solvent;

DOI:10.1021/acs.orglett.7b03325

upstream raw materials:

(2S,4S)-(+)-cis-4-hydroxyflavan

sulfuric acid

(S)-3,4-dihydro-2-phenyl-2H-1-benzopyran

(R)-3-Hydroxy-1-(2-hydroxy-phenyl)-3-phenyl-propan-1-one

Downstream raw materials:

FLAVONE

3-hydroxyflavone

(2S,3S)-methyl 2-phenyl-2,3-dihydrobenzofuran-3-carboxylate

(2R,3R)-3-hydroxyflavanone

Refernces

New insight into the mechanism of hypervalent iodine oxidation of flavanones

10.1016/S0040-4020(02)00360-5

The research aims to investigate the mechanism of a stereospecific ring contraction of flavanones to form 2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates using iodobenzene diacetate (PIDA) in the presence of sulfuric acid in trimethyl orthoformate (TMOF). The study's conclusions are based on evidence from NMR, CD, and chiral HPLC, which support a mechanism involving the formation of a hypervalent iodine intermediate followed by an aryl migration. The research demonstrates that the transformation is highly stereoselective and controlled by the configuration of the C-2 center, leading to the major product trans-methyl 2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylate (4a). Key chemicals used in the process include PIDA, sulfuric acid, TMOF, and various flavanones.