26307-17-5

Basic information

• Product Name: 2,5-Dimethyl-3,4-diphenylcyclopentadienone
• Synonyms: 2,5-Dimethyl-3,4-diphenylcyclopentadienone
• CAS NO: 26307-17-5
• Molecular Formula: C₁₉H₁₆O
• Molecular Weight: 260.33
• Mol File: 26307-17-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 423.8°C at 760 mmHg
• Flash Point: 186.3°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 2.17E-07mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 2,5-Dimethyl-3,4-diphenylcyclopentadienone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethyl-3,4-diphenylcyclopentadienone(26307-17-5)
• EPA Substance Registry System: 2,5-Dimethyl-3,4-diphenylcyclopentadienone(26307-17-5)

Safety Data

• Hazardous Substances Data: 26307-17-5(Hazardous Substances Data)

Usage

Physical state

Yellow crystalline solid

Classification

Aryl ketone

Uses

Organic synthesis building block, pharmaceutical and agrochemical industries, academic research

Molecular structure

Contains two methyl groups and two phenyl rings attached to a cyclopentadienone core

Properties

Imparts specific reactivity and stability useful for various chemical reactions and applications.

InChI:InChI=1/C19H16O/c1-13-17(15-9-5-3-6-10-15)18(14(2)19(13)20)16-11-7-4-8-12-16/h3-12H,1-2H3

Upstream product

• 96-22-0 pentan-3-one 
• 134-81-6 benzil 
• 5423-06-3 4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-enone 
• 75609-03-9 1,2-diphenyl-3,5-dimethyl-6,7-dibenzyloxycarbonyl-4-oxo-6,7-diazabicyclo<3.2.0>hept-2-ene 
• 75609-08-4 1,2-diphenyl-3,5-dimethyl-6-benzyloxycarbonyl-4-oxo-6,7-diazabicyclo<3.2.0>hept-2-ene 
• 75609-04-0 1,2-diphenyl-3,5-dimethyl-4-oxo-6,7-diazabicyclo<3.2.0>hept-2-ene 
• 35228-93-4 (3aR,4S,7R,7aR)-2,4,7,7a-Tetramethyl-3,3a,5,6-tetraphenyl-3a,4,7,7a-tetrahydro-4,7-methano-indene-1,8-dione 

Downstream Products

• 68326-92-1 6,9-dimethyl-2,7,8-triphenyl-(5ac,9ac)-5a,6,9,9a-tetrahydro-6r,9c-methano-benzo[f][1,3]oxazepin-10-one 
• 56983-31-4 7,8a-dimethyl-3,5a,6-triphenyl-(5at,8at)-1,5,5a,8a-tetrahydro-1r,5c-etheno-cyclopenta[e][1,3]oxazepin-8-one 
• 83298-56-0 (1S,2S,7R,8R)-1,8-Dimethyl-9,10-diphenyl-3,6-dithia-tricyclo[6.2.1.0^2,7]undeca-4,9-dien-11-one 
• 79981-09-2 (1R,4S,4aS,10aR)-1,4-Dimethyl-2,3-diphenyl-1,4,4a,5,6,7,8,9,10,10a-decahydro-1,4-methano-benzocycloocten-11-one 
• 63904-18-7 (1R,4S,4aR,10aS)-1,4-Dimethyl-2,3-diphenyl-1,4,4a,5,6,7,8,9,10,10a-decahydro-1,4-methano-benzocycloocten-11-one 
• 110949-75-2 endo-anti-1,9-dimethyl-10,11-diphenyl-5-oxatetracyclo<7,2,1,0^2,8,0^4,6>dodec-10-ene-3,7,12-trione 
• 51755-49-8 cis-1-acetyl-3,6,7a-trimethyl-4a,5-diphenyl-7-oxo-1,4a,7,7a-tetrahydrocyclopent<1,3,4>-oxadiazine 
• 75609-11-9 2,3-Diacetyl-1,4-dimethyl-5,6-diphenyl-2,3-diaza-bicyclo[2.2.1]hept-5-en-7-one 
• 75918-98-8 6,7-diphenyl-1,2,2,4,4,5-hexamethylbicyclo<3.2.1>oct-6-ene-3,8-dione 
• 99217-10-4 (1R,4S,4aS,9aR)-1,4-Dimethyl-2,3-diphenyl-4,4a,5,6,7,8,9,9a-octahydro-1H-1,4-methano-benzocyclohepten-10-one 
• 99266-83-8 (1R,4S,4aR,9aS)-1,4-Dimethyl-2,3-diphenyl-4,4a,5,6,7,8,9,9a-octahydro-1H-1,4-methano-benzocyclohepten-10-one 

Relevant articles and documents

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

Facile multistep synthesis of isotruxene and isotruxenone

(Chemical Equation Presented) Three multistep approaches toward facile syntheses of isotruxene (1) and isotruxenone (3) are reported. The ortho-para conjugated backbone in the precursor 4 was constructed by either Co-catalyzed [2 + 2 + 2] cyclotrimerization or the [4 + 2] Diels-Alder reactions. The regioselectivity of the triple intramolecular Friedel-Crafts acylation of 4 plays the key role in determining the overall yield. Compared to the previous one-step method, the current approaches are more efficient in terms of product yield (27-36% vs 4-18%) and purification (i.e., free of column chromatography).

Synthesis of Some New Polynuclear Compounds by Cycloaddition Reaction

A large number of 7,9-disubstituted derivatives (I) of cyclopentacenaphthylene-8(H)-one and 2,5-disubstituted derivatives (II) of 3,4-diphenylcyclopentadienone have been synthesized by condensing acenaphthaquinone and benzil separately with suitable 1,3-disubstituted propan-2-ones.The 3-(o- and p-methoxytolyl)cyclopentadienones (IX) have been synthesized by Friedel-Crafts reaction of appropriate methyl cresyl ethers and phenacyl chloride.These dienones have been subjected to Diels-Alder reaction with acenaphthylene and a new acetylenic dienophile (V) (whose synthesis is also described in this paper) to yield a large number of polynuclear aromatic compounds having fluoranthene and p-quaterphenyl nuclei, which have been finally characterised by elemental analyses, IR and PMR spectral data.