6583-74-0

Basic information

• Product Name: Cyclopent[a]indene-2,8-dione,1,3-diphenyl-
• CAS NO: 6583-74-0
• Molecular Weight: 334.374
• Mol File: 6583-74-0.mol

Chemical Properties

• CAS DataBase Reference: Cyclopent[a]indene-2,8-dione,1,3-diphenyl- (CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopent[a]indene-2,8-dione,1,3-diphenyl- (6583-74-0)
• EPA Substance Registry System: Cyclopent[a]indene-2,8-dione,1,3-diphenyl- (6583-74-0)

Safety Data

• Hazardous Substances Data: 6583-74-0(Hazardous Substances Data)

Upstream product

• 485-47-2 indan-1,2,3-trione hydrate 
• 102-04-5 1,3-Diphenylpropanone 
• 17446-04-7 8-Hydroxy-2-oxo-1.3-diphenyl-8-(1.3-diphenyl-acetonyl)-2.8-dihydro-cyclopent(a)-inden 
• 98239-57-7 1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1a,3-diphenyl-1,1a-dihydro-1-aza-cyclopropa[1,5]cyclopenta[1,2-a]indene-2,4-dione 

Downstream Products

• 98239-57-7 1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1a,3-diphenyl-1,1a-dihydro-1-aza-cyclopropa[1,5]cyclopenta[1,2-a]indene-2,4-dione 
• 43074-35-7 9-oxo-1,4-bis(phenyl)fluorene 
• 6583-78-4 1,3,4-triphenylfluoren-9-one 
• 20990-47-0 3-Acetyl-1.4-methano-1.2.3.4-tetrahydro-fluorendion-(9.10) 
• 20933-49-7 2-Cyan-1.4-diphenyl-2.3-dihydro-fluorenon-⁽⁹⁾ 
• 6583-77-3 1,2,4-Triphenyl-fluorenon 
• 6583-73-9 1,2,3,4-tetraphenylfluorenone 
• 6583-75-1 1,4-Diphenyl-fluorenon-2,3-dicarbonsaeure-dimethylester 
• 20933-47-5 3-Methyl-1.4-diphenyl-fluorenon-⁽⁹⁾ 
• 21184-62-3 1.4-Diphenyl-fluorenon-⁽⁹⁾-dicarbonsaeure-(2.3)-diaethylester 
• 17446-10-5 2-Hydroxy-8-oxo-2-butyl-1,3-diphenyl-2,8-dihydro-cyclopentinden 
• 10273-55-9 1.4-Bis-1.2.4-triphenyl-fluorenonyl-⁽³⁾-benzol 
• 6662-93-7 1,2,4-Triphenyl-3-phenylethinyl-fluorenon 
• 17446-09-2 2-Hydroxy-8-oxo-1,3-diphenyl-2-benzyl-2,8-dihydro-cyclopentinden 

Relevant articles and documents

Diels-alder reaction of isobenzofurans/cyclopentadienones with tetrathiafulvalene: Preparation of naphthalene, fluoranthene, and fluorenone derivatives

Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.

The unexpected product of Diels-Alder reaction between “indanocyclon” and maleimide

A heterocyclic compound commonly known as “indanocyclon” undergoes an unexpected Diels-Alder addition with maleimide. The resulting product has been isolated and characterized in order to get an information about its structure and possible mechanism of th

Synthesis of fluorene- and spirobifluorene-fused thiophenes

A novel synthetic route to fluorene- and spirobifluorene-fused thiophenes is explored by starting with ninhydrin. The Diels-Alder cycloaddition was employed to construct the key intermediate, 2,3-bis(hydroxymethyl)-1,4-diphenyl- fluorenone, which was furt

A detailed investigation of the reaction of 5,9-diphenylbenz[a]azulene with dialkyl acetylenedicarboxylates leading to dialkyl 8,12- diphenylbenzo[a]heptalene-6,7-dicarboxylates

The synthesis of 5,9-diphenylbenz[azulene (1) from 1,3- diphenylcyclopent[a]indene-2,8-dione (4) and cyclopropene has been re- investigated. The reduction of the decarbonylated cycloadduct 5 with LiAlH4/AlCl3 in Et2O leads not only to the expected 7,10- dihydrobenz[a]azulene 6, but also to small amounts of the cyclopropa[b]fluorenes exo-7 and endo-7 (cf. Scheme 2), the structures of which have been determined by X-ray crystal-structure analysis (cf. Fig. 1). The reaction of 1 with dialkyl acetylenedicarboxylates (ADR) in MeCN at 100°in the presence of 2 mol-% of catalysts such as [RuH2(PPh3)4] results mainly in the formation of the expected 8,12-diphenylbenzo[a]heptalene-6,7- dicarboxylates 3. A thorough investigation of the reaction mixture of 1 and dimethyl acetylenedicarboxylate (ADM) revealed the presence of a number of intermediates and side products (Scheme 5). Most important was the isolation and identification of the cyclobutene intermediate 9a (cf. Fig. 4), which is formed by a zwitterionic rearrangement of the primary adduct 2a of 1 and ADM and represents the direct precursor of the heptalene-diester 3a. Compounds of type 9a have so far only been postulated as necessary intermediates in the thermal reaction of azulenes and ADR to give corresponding heptalenedicarboxylates. Compound 9a is photochemically unstable and undergoes rearrangement even under the influence of normal laboratory light into a mixture of trans-10a and cis-10a (Scheme 8). Both diastercoisomers are also found in the original reaction mixture of 1 and ADM, but not when the reaction is performed under exclusion of light. On heating in MeCN at 100°, or better in DMFa1 150°, trans-10a and cis-10a undergo rearrangement to the fluoranthene-1,2-dicarboxylate 11a (Scheme 9), which is also present in the original reaction mixture of 1 and ADM. The catalysts do not accelerate the reaction of 1 and ADR, bul they lead to better yields of the benzo[a]heptalene-6,7-dicarboxylates 3, especially in the reaction of 1 with diisopropyl acetylenedicarboxylate (ADiP) (cf Tables 1 and 2).

Addition of Phthalimidonitrene to Tetrasubstituted Cyclopentadienones

The aziridines (3, 7, 10) obtained by the cycloaddition of phthalimidonitrene (1) to indanocyclone (2), phencyclone (6) and acecylone (9) undergo cycloreversion when treated with hydrazine hydrate, through the intermediacy of N-aminoaziridines.Aziridine (3) when treated with p-TsOH gives (5).Thermolysis of the aziridines (3) and (10) furnishes the rearranged products.