3312-38-7

Basic information

• Product Name: 1H-Inden-1-one, 2-(4-methoxyphenyl)-3-phenyl-
• CAS NO: 3312-38-7
• Molecular Formula: C22H16O2
• Molecular Weight: 312.368
• Mol File: 3312-38-7.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1H-Inden-1-one, 2-(4-methoxyphenyl)-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Inden-1-one, 2-(4-methoxyphenyl)-3-phenyl-(3312-38-7)
• EPA Substance Registry System: 1H-Inden-1-one, 2-(4-methoxyphenyl)-3-phenyl-(3312-38-7)

Safety Data

• Hazardous Substances Data: 3312-38-7(Hazardous Substances Data)

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 85-44-9 phthalic anhydride 
• 94796-78-8 3-bromo-2-(4-methoxyphenyl)-1H-inden-1-one 
• 98-80-6 phenylboronic acid 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 7380-78-1 4-(phenylethynyl)anisole 
• 374538-03-1 2-methoxycarbonylphenylboronic acid 
• 696-62-8 para-iodoanisole 
• 766-97-2 4-n-methylphenylacetylene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 24785-38-4 1-methoxy-4-[2-(4-methylphenyl)ethynyl]benzene 
• 13939-06-5 molybdenum hexacarbonyl 
• 816423-11-7 (1-(4-methoxyphenyl)prop-2-yne-1,1-diyl)dibenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 13304-40-0 2-(4-hydroxyphenyl)-3-phenyl-1-indenone 
• 52033-66-6 2-(4-methoxyphenyl)-3-phenyl-1H-indene 

Relevant articles and documents

Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)6 as a CO Surrogate

Transition-metal-catalyzed carbonylation of alkynes has emerged as a powerful engine for the synthesis of indenone compounds. Herein, we reported the development of an effective Pd-catalyzed ligand-free carbonylation of o-bromoaryl iodides with alkynes to afford indenone compounds. A broad range of functional groups on o-bromoaryl iodides and alkynes were tolerated in this protocol, giving carbonylation products. Furthermore, considering the factors of safety and operability, Mo(CO)6 was introduced into the reaction as a carbonyl source. Mechanistic investigations suggested that the reaction proceeded through sequential oxidative addition, alkyne insertion, carbonyl insertion, and reductive elimination steps to produce the observed carbonylation indenone products. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized to form synthetic useful derivatives via an environmentally friendly way.

Synthesis of Indenones via Palladium-Catalyzed Ligand-Free Carbonylation

A palladium-catalyzed ligand-free carbonylation reaction has been developed for the synthesis of indenones. Under CO atmosphere, this cascade reaction proceeded smoothly to provide the desired indenones in moderate to excellent yields with good functional-group compatibility. The mechanistic investigations suggested the in situ formation of palladium nanoparticles and this transformation was driven by a controlled reaction sequence of alkyne insertion followed by carbonylation and annulation to form the indenone framework. (Figure presented.).

Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes

Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones in good yields. Excellent regioselectivities were observed, when silyl aryl alkynes were used. The intermediate 3-silyl-2-aryl-substituted indenones were converted to 2,3-diaryl indenones by a three-step protocol involving C-Si bromination and Suzuki-Miyaura coupling reaction.