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Usage

Uses

Used in Pharmaceutical Industry:
10,11-DIHYDRO-5 H-DIBENZO[A,D]CYCLOHEPTENE is used as the base structure for the development of various tricyclic antidepressants. These antidepressants are designed to modulate the levels of neurotransmitters in the brain, such as serotonin and norepinephrine, to alleviate symptoms of depression and anxiety.
Additionally, studies suggest that Dibenzosuberane and its analogues may possess anti-viral properties, making them potential candidates for the development of new antiviral drugs to combat various viral infections.

InChI:InChI=1/C15H14/c1-3-7-14-11-15-8-4-2-6-13(15)10-9-12(14)5-1/h1-8H,9-11H2

Upstream product

• 24620-79-9 C₁₉H₂₀N₂O*ClHO₄ 
• 835-78-9 [2-(2-phenylethyl)phenyl]methanol 
• 6141-55-5 5-diazo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene 
• 256-81-5 suberene 
• 32832-96-5 2-phenethylbenzaldehyde 
• 15323-21-4 10,10’,11,11’-tetrahydro-5H,5’H-5,5’-bidibenzo[a,d][7]annulene 
• 66686-42-8 3,9-Di-t-butyl-7,12-dihydro-5H-dibenzothiocin-6,6-dioxid 
• 1021-91-6 N-[tricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,3,5,7,9,12,14-heptaen-2-ylidene]hydroxylamine 
• 137445-37-5 2-(4-tert-butylphenethyl)-5-tert-butylbenzaldehyde 
• 22927-07-7 1,2-bis(4-tert-butylphenyl)ethane 
• 194418-07-0 2-(2-phenylethyl)benzaldehyde tosylhydrazone 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 138771-02-5 1,2-bis(3-formyl-4-phenyl)ethane 
• 59485-34-6 1,2-bis(2-bromophenyl)ethane 

Downstream Products

• 954374-34-6 2-(10,11-dihydro-5H-benzo[a,d]cyclohepten-5-yl)-1,3-diphenylpropane-1,3-dione 
• 6047-29-6 5,6,11,12-tetrahydrodibenz[b,f]azocin-6-one 
• 1259394-39-2 (S)-N-[((R)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-10-ylamino)(4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide 
• 1402593-21-8 2-(2-(nonylamino)phenethyl)benzaldehyde 
• 1198215-05-2 2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-phenylethan-1-one 
• 1210-35-1 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one 
• 2222-33-5 dibenzosuberenon 

Relevant academic research and scientific papers

Carbonyl and olefin hydrosilylation mediated by an air-stable phosphorus(iii) dication under mild conditions

The readily-accessible, air-stable Lewis acid [(terpy)PPh][B(C6F5)4]21 is shown to mediate the hydrosilylation of aldehydes, ketones, and olefins. The utility and mechanism of these hydrosilylations are considered.

Activation of Molecular Hydrogen by Arylcarbenes

The hydrogenation reactions of diphenylcarbene 1, fluorenylidene 2, and dibenzocycloheptadienylidene 3 were investigated in solid H2 and D2 matrices and in H2- and D2-doped argon matrices at cryogenic temperatures. The reactivity of the carbenes towards H2 increases in the order 12, 2 and 3 react fast under the same conditions via quantum chemical tunneling. In D2 both 1 and 3 are stable, whereas 2 slowly reacts. The different reactivity of the three carbenes is rationalized in terms of differing carbene stabilization energies.

Transformation of Trifluorotoluenes Triggered by Titanium(IV) Chloride-Catalyzed Hydrodefluorination using Hydrosilanes

The titanium tetrachloride-catalyzed hydrodefluorination reaction of trifluorotoluene derivatives was developed using triethylsilane as the reducing agent. The reaction produced various toluene derivatives with high chemoselectivities by means of readily accessible reagents. This hydrodefluorination process was extended to the intramolecular Friedel-Crafts benzylation reaction, furnishing polycyclic aromatics of various ring sizes in good yields.

Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes

A series of ketones and aldehydes are reduced in toluene under H2 in the presence of 5 mol % B(C6F5)3 and either cyclodextrin or molecular sieves affording a facile metal-free protocol for reduction to alcohols. Similar treatment of aryl ketones resulted in metal-free deoxygenation yielding aromatic hydrocarbons.

Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

Iodine was demonstrated to be an efficient catalyst for disproportionation of aryl-substituted ethers under solvent-free reaction conditions. Variously substituted 1,1,1′,1′-tetraaryldimethyl ethers were transformed into the corresponding diarylketone and diarylmethane derivatives. I 2-catalyzed transformation of 4-methoxyphenyl substituted ethers yielded mono- and dialkylated Friedel-Crafts products as well. Treatment of trityl alkyl and trityl benzyl ethers with a catalytic amount of iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic studies it was established that a substantial portion of the C-H bond scission took place in the rate-determining step, while the carbonyl oxygen atom originated from the starting ether, and not from the air. The transformation took place under air and under argon, and HI was not a functioning catalyst.

Flow-vacuum pyrolysis of dibenzocycloheptane derivatives on zeolites catalysts. IV

The pyrolysis of 10,11-dihydro-5H-dibenzo[a,d]cicloheptadien-5-ol (4) and of 5H-dibenzo[a,d]cycloheptatrien-5-ol (5) in flowvacuum conditions (advanced vacuum, inert atmosphere) on zeolites at 300°C is presented. The reaction products were identified by GC/MS using authentic samples and a reaction mechanisms involving cationic species as intermediates were proposed. A comparison with the pyrolysis of the same compounds performed in FVP conditions on quartz is presented.

High catalytic efficiency of nanostructured molybdenum trioxide in the benzylation of arenes and an investigation of the reaction mechanism

The synthesis and characterization of nanostructured MoO3 with a thickness of about 30 nm and a width of about 450 nm are reported. The composition formula of the MP (precipitation method) precursor was estimated to be [(NH4)2O]0.169·MoO 3· (H2O)0.239. The calcination of the precursor in air afforded nanostructured pellets of the α-MoO3 phase. The nano-structured MoO3 catalyst exhibited high efficiency in catalyzing the benzylation of various arenes with substituted benzyl alcohols, which were strikingly different to common bulk MoO3. Most reactions offered >99% conversion and >99% selectivity to monoalkylated compounds. MoO3 is a typical acid catalyst. However, the benzylation reaction over nanostructured MoO3 does not belong to the acid-catalyzed type or defect site-catalyzed type, since the catalyst has no acidity and defect site on surface. Characterization with thermal, spectroscopic, and electronic techniques reveal that the catalyst contains fully oxygen-coordinated MoO 6 octahedrons on the surface but partially reduced species (Mo 5+) within the bulk phase. The terminal oxygen atoms of Mo=O bonds on the (010) basal plane resemble oxygen anion radicals and act as active sites for the adsorption and activation of benzyl alcohols by electrophilic attack. Such sites are indispensable for catalytic reactions since the blocking of these sites by electron acceptors, such as tetracyanoethylene (TCNE), can greatly decrease catalytic activity. This work represents a successful example of combining a heterogeneous catalysis study with nanomaterial synthesis.

New method for the reduction of benzophenones with Raney Ni-Al alloy in water

Raney Ni-Al alloy in a dilute alkaline aqueous solution has been shown to be a powerful reducing agent, which is highly effective in the reduction of benzophenones to the corresponding hydrocarbon derivatives, in the absence of any organic solvents. Copyright Taylor & Francis Group, LLC.

Nanostructured molybdenum oxides and their catalytic performance in the alkylation of arenes

We report for the first time that nanostructured MoO3 is an excellent catalyst for the alkylation of a wide range of arenes with substituted benzyl alcohols as alkylating agents. The Royal Society of Chemistry.

BF3·2CF3CH2OH (BF 3·2TFE), an efficient superacidic catalyst for some organic synthetic transformations

BF3 · 2CF3CH2OH complex was found to be a very effective superacidic catalyst comparable in acid strength to at least that of 100% anhydrous sulfuric acid for various acid-catalyzed organic transformations such as isomerizations, rearrangements, ionic hydrogenation of various ketones, and aromatics with triethylsilane and nitration of aromatics with metal nitrate. Studies of the pivalaldehyde-methyl isopropyl ketone rearrangement and the benzopinacol to phenanthrene transformation suggest that the complex has an acidity comparable to that of 100% anhydrous sulfuric acid. The structure and properties of the 1:2 boron trifluoride-trifluoroethanol complex have been further studied using NMR (1H, 13C, 19F, 11B) and DFT calculations at the B3LYP/6- 311++G**//B3LYP/6-31G* level.