Chalcone

Base Information

• Chemical Name: Chalcone
• CAS No.: 94-41-7
• Deprecated CAS: 1801869-81-7
• Molecular Formula: C15H12O
• Molecular Weight: 208.26
• Hs Code.: 29143900
• DSSTox Substance ID: DTXSID8022531
• Wikidata: Q97974701
• ChEMBL ID: CHEMBL4777263
• Mol file: 94-41-7.mol

Synonyms:1,3 Diphenyl 2 Propen 1 One;1,3-Diphenyl-2-Propen-1-One;Benzalacetophenone;Benzylideneacetophenone;Chalcone;Chalkone

Chemical Property of Chalcone

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 55-59 °C
• Refractive Index: 1.625
• Boiling Point: 346.61 °C at 760 mmHg
• Flash Point: 150.062 °C
• PSA: 17.07000
• Density: 1.097 g/cm³
• LogP: 3.58270
• Storage Temp.: Storage temperature: no restrictions.
• Solubility.: dioxane: soluble1g/10 mL, clear, colorless
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 208.088815002
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

≥98% ^*data from raw suppliers

Chalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)C2=CC=CC=C2
• Description: Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.
• Uses: 1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. Chalcone is used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. It also inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase.

Technology Process of Chalcone

There total 323 articles about Chalcone 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: 44.0%

acetophenone (98-86-2) + benzyl alcohol (100-51-6,185532-71-2) → 1-Phenylethanol (98-85-1,13323-81-4) + dihydrochalcone (1083-30-3) + benzalacetophenone (94-41-7)

Guidance literature:

With ceria; In para-xylene; at 150 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature; Time; chemoselective reaction; Mechanism; Kinetics;

DOI:10.1039/c5cy01607j

Reference yield: 44.0%

acetophenone (98-86-2) + benzyl alcohol (100-51-6,185532-71-2) → 1-Phenylethanol (98-85-1,13323-81-4) + benzalacetophenone (94-41-7)

Guidance literature:

With yttrium(III) oxide; In para-xylene; at 150 ℃; for 24h; under 760.051 Torr;

DOI:10.1039/c5cy01607j

Reference yield: 43.0%

1,3-diphenyl-2-propynone (7338-94-5) → (Z)-chalcone (94-41-7) + 1,3-diphenyl-propen-3-one (614-47-1)

Guidance literature:

With silver hexafluoroantimonate; chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); triphenylphosphine; tert-butyl alcohol; In acetonitrile; at 60 ℃; for 24h; diastereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0040-1707395

upstream raw materials:

1,3,5-triphenyl-1,5-pentanedione

cinnamonitrile

2-bromo-1,3-diphenyl-2-propen-1-one

ethanol

Downstream raw materials:

10-(3-oxo-1,3-diphenyl-propyl)-anthrone

1,3-diphenyl-3-piperidin-1-yl-propan-1-one

(2E)-1,1,2,4-tetraphenyl-1,3-butadiene

(3-oxo-1,3-diphenyl-propyl)-phenyl-phosphinic acid

Refernces

Lipophilic Bis(monoaza crown ether) Derivatives: Synthesis and Cation-Complexing Properties

10.1021/jo00375a041

This study investigates the selective reduction of chalcone (1) using anthracene hydride (AH-). The researchers found that AH- rapidly and in high yields formed the anionic Michael adduct (2) with chalcone, along with the known dimerization product (5). Prolonged reaction with excess AH- converted the Michael adduct (2) to the enolate (7) of anthracene (A) and saturated ketone (8). The study highlights that the partial structure ArCCCO is necessary for this disproportionate fragmentation, suggesting an intermediary role between the enone dianion (e.g., 2-) and the aromatic group stabilizing the second negative charge. The Michael adduct formed with xanthene (XH) did not fragment, suggesting that the presence of a removable hydrogen at the appropriate position is essential for the formation of the saturated carbonyl compound from its Michael adduct. The study concludes that reduction of the carbonyl functionality does not occur in any of the reactions, providing insights into the mechanism of selective reduction of the C=C bond of chalcone by anthracene hydride.

Enantiospecific synthesis of an indolizidine alkaloid, (+)-ipalbidine

10.1016/S0040-4039(03)00563-X

The study details the enantiospecific total synthesis of the indolizidine alkaloid (+)-ipalbidine, a nonaddictive analgesic with additional biological activities. The synthesis starts from (?)-pyroglutamic acid and involves several key steps. Initially, the alcohol derived from pyroglutamic acid methyl ester is converted to a tosylate, which is then reacted with a higher-order cuprate reagent to form an olefinic amide. This amide is condensed with a bromide, prepared from an ester through reduction and bromination steps, to yield a diene. The diene undergoes ozonolysis to form a diketone, which is then subjected to an intramolecular McMurry coupling reaction using low-valent titanium to construct the desired carbon-carbon double bond, yielding the core structure of ipalbidine. The final steps include reduction of the amide function and debenzylation to obtain the natural product. The study also explores an alternative synthetic path involving the elimination of a vic-diol function from a major byproduct of the McMurry coupling. The developed synthetic strategy is noted for its potential applicability to the synthesis of other biologically active alkaloids.