103515-22-6

Basic information

• Product Name: dibenzobarallene
• Synonyms: dibenzobarallene
• CAS NO: 103515-22-6
• Molecular Weight: 276.291
• Mol File: 103515-22-6.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: dibenzobarallene(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzobarallene(103515-22-6)
• EPA Substance Registry System: dibenzobarallene(103515-22-6)

Safety Data

• Hazardous Substances Data: 103515-22-6(Hazardous Substances Data)

Upstream product

• 108-31-6 maleic anhydride 
• 120-12-7 anthracene 
• 1442690-41-6 propargylcyanoacrylate anthracene adduct 
• 1442690-35-8 4-nitrobenzyl cyanoacrylate anthracene adduct 
• 119858-92-3 cyanoacrylate benzyl ester-anthracene adduct 

Downstream Products

• 125344-89-0 C₂₇H₁₈N₂O₂ 
• 137094-03-2 C₂₆H₁₉NO₄ 
• 137092-91-2 C₂₆H₁₉NO₄ 
• 137093-29-9 C₂₆H₁₉NO₄ 
• 137093-57-3 C₂₆H₂₁NO₂ 
• 137094-02-1 C₂₆H₁₉NO₄ 
• 137093-39-1 5-(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido) isophthalic acid 
• 137093-46-0 C₂₄H₁₇NO₃ 
• 59252-52-7 N-(2'-methoxyphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide 
• 137093-47-1 N-(p-Methoxyphenyl)-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid 
• 137093-20-0 C₂₅H₁₇NO₄ 
• 137093-32-4 C₂₅H₁₇NO₄ 
• 137092-88-7 C₂₅H₁₇NO₄ 
• 137093-49-3 N-(p-Nitrophenyl)-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid 

Relevant articles and documents

Stereospecificity and concertedness of Retro-Diels-Alder fragmentation in some diester systems upon chemical ionization

Retro-Diels-Alder (RDA) fragmentation of cis- and trans-2,3-diethoxycarbonyl-5,6,7,8-dibenzobicyclo[2.2.2] octanes under isobutane and methane chemical ionization conditions is highly stereospecific, giving rise to protonated diethyl maleate and fumarate, respectively. This behaviour indicates a single-step concerted mechanism, analogous to the ground-state RDA process that occurs in neutral molecules in the condensed phase. The analogous dissociation is partially stereospecific in stereoisomeric endo-, exo- and trans-2,3-diethoxycarbonylbicyclo [2.2.1]heptanes and non-stereospecific in endo-, exo- and trans-2,3-diethoxycarbonyl-5,6-benzobicyclo [2.2.2]octanes, indicating the involvement of a stepwise mechanism in the latter two systems. The different behaviour of the above systems is explained in terms of the energy of the RDA fragmentation. The differentiation and quantitative estimates of protonated diethyl maleate and fumarate were obtained from collision-induced dissociation measurements.

Discovery of novel small molecule inhibitors of S100P with in vitro anti-metastatic effects on pancreatic cancer cells

S100P, a calcium-binding protein, is known to advance tumor progression and metastasis in pancreatic and several other cancers. Herein is described the in silico identification of a putative binding pocket of S100P to identify, synthesize and evaluate novel small molecules with the potential to selectively bind S100P and inhibit its activation of cell survival and metastatic pathways. The virtual screening of a drug-like database against the S100P model led to the identification of over 100 clusters of diverse scaffolds. A representative test set identified a number of structurally unrelated hits that inhibit S100P-RAGE interaction, measured by ELISA, and reduce in vitro cell invasion selectively in S100P-expressing pancreatic cancer cells at 10 μM. This study establishes a proof of concept in the potential for rational design of small molecule S100P inhibitors for drug candidate development.

Reactions of polycyclic arene systems stabilized and activated by cyclopentadienylruthenium cations

One vinylidene group of [(CpRu)(η6-dibenzo-p-quinodimethane)]+PF 6- (1) (Cp = η5-cyclopentadienyl), in which highly reactive dibenzo-p-quinodimethane is stabilized by coordination to ruthenium, underwent Diels-Alder cycloaddition from the exo face with 2,3-dimethyl-1,3-butadiene to give a novel spiro derivative of dibenzo-p-quinodimethane (2). X-ray analysis of 2 (C27H27F6PRu) confirmed its structure and showed it to crystallize in the monoclinic space group P21/n with a = 16.079(5) A?, b = 11.682(3) A?, c = 13.508(4) A?, β = 91.03(3)°, and Z = 4. The Cp* (Cp* = η5-pentamethylcyclopentadienyl) analogue of 1 did not react with 2,3-dimethyl-1,3-butadiene. The η6-localization effect of cyclopentadienylruthenium cations can also be used to activate polycyclic aromatic hydrocarbons toward Diels-Alder and catalytic hydrogenation reactions. [(Cp*Ru)(η6-anthracene)]+TfO- (3) underwent quantitative Diels-Alder reaction from the exo face with maleic anhydride under mild conditions (83°C) to give [trans-(endo-Cp*Ru)(η 6-9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride)]+TfO- (4) selectively. Reaction of anthracene under identical conditions gave only 19% conversion. Reaction of maleic anhydride with [CpRu(η6-naphthalene)]+PF6- (6) was not successful. However, hydrogenation of 6 in methanol (1 atm, 24°C, 6 h) took place smoothly in the presence of a heterogeneous Pd/C catalyst to give [CpRu(η6-1,2,3,4-tetrahydronaphthalene)]+PF 6- (7) in high yield. The Cp* analogue of 6 gave similar results. Noncomplexed naphthalene remained largely unreacted under identical conditions (61% remaining), and a substantial proportion remained (32%) after 24 h. The Cp*Ru and CpRu groups in 4 and 7 can be removed by photolysis in acetonitrile to cleanly give 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride (5) and 1,2,3,4-tetrahydronaphthalene (8), respectively, as well as generating Cp- and Cp*-ruthenium tris(acetonitrile) salts, which can be used to make more complexed arene.

Experimental survey of the kinetics of acene Diels-Alder reactions

The rate profiles for pseudo-first-order reactions between tetracene and selected dienophiles. The reactivity ranged roughly two orders of magnitude, from the slowest reacting dienophile (2,3-dichloromaleic anhydride, light blue) to the fastest dienophile (N-methylmaleimide, orange). Other utilized dienophiles included, in order of reactivity, maleic anhydride (navy), tetrafluoro-1,4-benzoquinone (purple), and p-benzoquinone (green).

Lipase catalyzed desymmetrization of roof shape cis-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene

Biocatalyzed desymmetrization of roof shape meso cis-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene has been achieved. The absolute configuration of the product is established by single crystal X-ray analysis of its diastereomer prepared with R-chloropropionic acid. Single crystal analysis of the chiral roof shape monoacetate shows a P-helical motif due to the extended intramolecular hydrogen bonding while the racemic sample exhibits intermolecular double hydrogen bonding holding two molecules together as a dimmer.

Stereo-specific synthesis of hydroanthracene-dicarboximides

Compound 3, N-((1S)-1-cyclohexylethyl)-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)- dicarboximide-1,2,3,4-octahydro, was obtained by ruthenium-assisted hydrogenation of the hydroanthracene-dicarboximide 2 under mild conditions (3 bar H2 and room temperature). In contrast to other related compounds, dicarboximides 2 and 3 were stereo-selectively obtained, confirmed by both solid state (X-ray diffraction) and solution (NMR). This selectivity denoted a hindered rotation around the N-CH axis together with the aromatic hydrogen bond acceptor behaviour of the hydroanthracene skeleton towards a methylene of the cyclohexyl group of the imide moiety. In addition, the nature of the metallic species involved in the hydrogenation process was also investigated.

Polycyclic Maleimide-based Scaffold as New Privileged Structure for Navigating the Cannabinoid System Opportunities

The discovery of the relevant role played by a dysregulation of the endogenous cannabinoid system in several pathological conditions has prompted an extensive research in this field. In this Letter, a series of cannabinoid receptor ligands bearing a previously unexplored polycyclic scaffold was designed and synthesized, in order to evaluate the potential of a new easily affordable privileged structure. The new compounds showed an appreciable affinity and a significant selectivity for the CB2 receptor and are endowed with an intriguing noncompetitive antagonist behavior. Due to the ability of the polycyclic structure to be easily modified in different ways, these compounds could represent convenient chemical tools to be exploited in order to better understand the endocannabinoid system impact on physiopathological conditions.

Electrostatically Driven CO-πAromatic Interactions

A series of N-arylimide molecular balances were developed to study and measure carbonyl-aromatic (CO-π) interactions. Carbonyl oxygens were observed to form repulsive interactions with unsubstituted arenes and attractive interactions with electron-deficient arenes with multiple electron-withdrawing groups. The repulsive and attractive CO-πaromatic interactions were well-correlated to electrostatic parameters, which allowed accurate predictions of the interaction energies based on the electrostatic potentials of the carbonyl and arene surfaces. Due to the pronounced electrostatic polarization of the C=O bond, the CO-πaromatic interaction was stronger than the previously studied oxygen-πand halogen-πaromatic interactions.