2-acetyl-3H-benzo[f]chromen-3-one

Base Information

• Chemical Name: 2-acetyl-3H-benzo[f]chromen-3-one
• CAS No.: 727-80-0
• Molecular Formula: C15H10O3
• Molecular Weight: 238.243
• Hs Code.: 2914399090
• European Community (EC) Number: 632-339-0
• DSSTox Substance ID: DTXSID00353684
• Nikkaji Number: J1.217.775E
• Wikidata: Q82131399
• ChEMBL ID: CHEMBL1501880
• Mol file: 727-80-0.mol

Synonyms:2-acetyl-3H-benzo(f)chromen-3-one;2AHBC

Chemical Property of 2-acetyl-3H-benzo[f]chromen-3-one

Chemical Property:

• PSA: 47.28000
• LogP: 3.14880
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 238.062994177
• Heavy Atom Count: 18
• Complexity: 410

Purity/Quality:

95% ^*data from raw suppliers

2-Acetyl-3H-benzo[f]chromen-3-one ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=CC3=CC=CC=C32)OC1=O
• Uses: 2-Acetyl-3H-benzo[f]chromen-3-one is an intermediate in the synthesis of benzo[f]coumarin derivatives with antitumor activity.

Technology Process of 2-acetyl-3H-benzo[f]chromen-3-one

There total 9 articles about 2-acetyl-3H-benzo[f]chromen-3-one 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: 99.0%

O-Merrifield resin-bound 4-(2-acetoacetylethyl)phenol + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 3-acetylbenzo[f]coumarin (727-80-0)

Guidance literature:

With piperidine; In ethanol; for 2.5h; Heating;

DOI:10.1055/s-2005-872142

Reference yield: 97.0%

ethyl acetoacetate (141-97-9) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 3-acetylbenzo[f]coumarin (727-80-0)

Guidance literature:

With piperidine; In ethanol; at 80 ℃; for 0.025h; Microwave irradiation; Green chemistry;

DOI:10.1016/j.tet.2019.02.034

Reference yield: 79.0%

1-<(4'-nitrophenylimino)methyl>-2-naphthol (134835-13-5) → 3-acetylbenzo[f]coumarin (727-80-0)

Guidance literature:

With piperidine; In ethanol; for 0.5h; Heating;

upstream raw materials:

ethyl acetoacetate

2-hydroxynaphthalene-1-carbaldehyde

(2-acetyl-3-oxo-2,3-dihydro-1H-benzo[f]chromen-1-yl)-phosphonic acid dimethyl ester

trisdimethylamino 2-acetyl (3H)naphtho[2,1-b](1H-3-oxo-pyran-1-yl)phosphorane

Downstream raw materials:

1-(5,6-benzocoumarin-3-yl)-3-phenylpropene-1-one

C₃₀H₂₂N₄O₃

N-(4-Methoxy-phenyl)-N-[5-(3-oxo-3H-benzo[f]chromen-2-yl)-6H-[1,3,4]thiadiazin-2-yl]-acetamide

N-[5-(3-Oxo-3H-benzo[f]chromen-2-yl)-6H-[1,3,4]thiadiazin-2-yl]-N-p-tolyl-acetamide

Refernces

• 1、 Abid, Souhir,Allouche, Noureddine,Ammar, Houcine,Bazureau, Jean-Pierre,Bouzanna, Walid,Feriani, Anouar,Ghazouani, Lakhdar,Hajji, Raouf,Khdhiri, Emna,Mnafgui, Kais. "(E)-N’-(1-(3-oxo-3H-benzo[f]chromen-2-yl)ethylidene)benzohydrazide protecting rat heart tissues from isoproterenol toxicity: Evidence from in vitro and in vivo tests". . . Retrieved 2020.
• 2、 Abdul-Rida, N. A.,Adnan, Sh.,Jaber, Q. A. H.. "Boosting 3H-Benzo[f]chromen-3-one Chalcone with Anti-inflammatory Drugs: Synthesis, Characterization, and Evaluation of Cytotoxicity and Antimicrobial Activity". . p. 1622 - 1627. Retrieved 2020.
• 3、 Chan, Yi-Huan,Sasidharan, Sreenivasan,Shanmugapriya,Yeap, Guan-Yeow. "Novel reaction-based chemosensor for Al3+ detection using hybrid framework of chalcone-coumarin in aqueous phase and its anticancer activity". . . Retrieved 2021/11/30.
• 4、 Deepa, Appadurai,Lavanya, Raja,Lee, Shyi-Long,Mathivanan, Venkatesan,Padmini, Vediappen,Ramamoorthy, Jaganathan,Sathya, Vijayakumar,Srinivasadesikan, Venkatesan. "A chemodosimeter for selective fluorogenic and chromogenic detection of phenylenediamine isomers". . . Retrieved 2022/01/19.