Coumarin, 3-benzoyl-4-phenyl-

Base Information

• Chemical Name: Coumarin, 3-benzoyl-4-phenyl-
• CAS No.: 19725-29-2
• Molecular Formula: C22H14O3
• Molecular Weight: 326.351
• DSSTox Substance ID: DTXSID401277567
• Nikkaji Number: J46.719G
• Wikidata: Q63392831
• Mol file: 19725-29-2.mol

Synonyms:Coumarin, 3-benzoyl-4-phenyl-;3-benzoyl-4-phenylchromen-2-one;3-Benzoyl-4-phenylcoumarin;19725-29-2;DTXSID401277567;3-Benzoyl-4-phenyl-2H-chromen-2-one #;3-Benzoyl-4-phenyl-2H-1-benzopyran-2-one;Q63392831

Chemical Property of Coumarin, 3-benzoyl-4-phenyl-

Chemical Property:

• Melting Point: 100 - 101 °C
• PSA: 47.28000
• LogP: 4.69100
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 326.094294304
• Heavy Atom Count: 25
• Complexity: 550

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C(=O)OC3=CC=CC=C32)C(=O)C4=CC=CC=C4

Technology Process of Coumarin, 3-benzoyl-4-phenyl-

There total 12 articles about Coumarin, 3-benzoyl-4-phenyl- 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: 81.0%

phenyl 3-phenylprop-2-ynoate (100954-03-8) + benzoyl chloride (98-88-4) → 3-benzoyl-4-phenyl-2H-chromen-2-one (19725-29-2)

Guidance literature:

With 2,6-dimethylpyridine; fac-tris[2-phenylpyridinato-C²,N]iridium(III); In acetonitrile; at 100 ℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation; Schlenk technique;

DOI:10.1016/j.tetlet.2018.04.033

Reference yield: 81.0%

phenyl 3-phenylprop-2-ynoate (100954-03-8) + C17H12F3NO3 → 3-benzoyl-4-phenyl-2H-chromen-2-one (19725-29-2)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); triethylamine; In acetonitrile; at 80 ℃; for 20h; Schlenk technique; Irradiation; Inert atmosphere; Green chemistry;

DOI:10.1039/d1ob01568k

Reference yield: 77.0%

phenyl 3-phenylprop-2-ynoate (100954-03-8) + benzaldehyde (100-52-7) → 3-benzoyl-4-phenyl-2H-chromen-2-one (19725-29-2)

Guidance literature:

With dipotassium peroxodisulfate; tetrabutylammomium bromide; In 1,2-dichloro-ethane; at 90 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/jo502220b

upstream raw materials:

bromobenzene

2-Hydroxybenzophenone

ethyl 3-oxo-3-phenylpropionate

2-(hydroxy(phenyl)methyl)phenol

Refernces

• 1、 Yang, Shuai,Tan, Hui,Ji, Wangqin,Zhang, Xiangbiao,Li, Pinhua,Wang, Lei. "Visible Light-Induced Decarboxylative Acylarylation of Phenyl Propiolates with α-Oxocarboxylic Acids to Coumarins Catalyzed by Hypervalent Iodine Reagents under Transition Metal-Free Conditions". . p. 443 - 453. Retrieved 2017.
• 2、 Liu, Yu,Wang, Qiao-Lin,Zhou, Cong-Shan,Xiong, Bi-Quan,Zhang, Pan-Liang,Kang, Shuang-Jian,Yang, Chang-An,Tang, Ke-Wen. "Visible-light-mediated cascade difunctionalization/cyclization of alkynoates with acyl chlorides for synthesis of 3-acylcoumarins". . p. 2038 - 2041. Retrieved 2018.
• 3、 Wang, Qiumei,Yang, Chao,Jiang, Chao. "Visible-light-promoted radical acylation/cyclization of alkynoates with aldehydes for the synthesis of 3-acylcoumarins". supporting information. p. 8196 - 8204. Retrieved 2018/11/23.