5445-55-6

Usage

Uses

Used in Chemical Synthesis:
TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL is used as a key intermediate in the synthesis of dibenzo[b,f]oxepin scaffolds. This application is particularly relevant in the field of organic chemistry, where the compound serves as a building block for the creation of more complex and functionalized molecules.
In the Synthesis of Dibenzo[b,f]oxepin Scaffolds:
TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL is used as a starting material for the Ullmann-type etheration reaction. This reaction involves the formation of an ether linkage between the hydroxyl groups of the compound and another aromatic or heteroaromatic molecule. The resulting dibenzo[b,f]oxepin scaffolds are valuable in various applications, such as pharmaceuticals, agrochemicals, and materials science, due to their diverse chemical properties and potential for further functionalization.

InChI:InChI=1/C18H18O2/c19-9-15-16(10-20)18-12-6-2-1-5-11(12)17(15)13-7-3-4-8-14(13)18/h1-8,15-20H,9-10H2/t15-,16-,17?,18?/m1/s1

Upstream product

• 23194-04-9 trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid dimethyl ester 
• 120-12-7 anthracene 
• 33216-00-1 (11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid 
• 78392-59-3 di-<(1S)-endo>-(-)-borneyl fumarate 
• 593279-33-5 di(+)-isomenthyl fumarate 
• 593279-35-7 di(+)-fenchyl fumarate 
• 593279-34-6 di(-)-isopulegyl fumarate 
• 108-05-4 vinyl acetate 
• 5445-55-6 trans-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethano-anthracene 
• 108-21-4 Isopropyl acetate 
• 123-86-4 acetic acid butyl ester 
• 141-78-6 ethyl acetate 
• 36326-57-5 racemic-9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid 
• 23194-05-0 (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid 

Downstream Products

• 5445-55-6 (S,S)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene 
• 88929-24-2 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen 
• 41063-85-8 11R,12R-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen 
• 106750-89-4 trans-11,12-dichloromethyl-9,10-dihydro-9,10-ethanoanthracene 
• 88873-78-3 11R,12R-Bis-(p-toluensulfonyloxymethyl)-9,10-ethano-perhydro-anthracen 
• 88873-79-4 11R,12R-Bis-(diphenylphosphinomethyl)-9,10-ethano-perhydro-anthracen 

Relevant academic research and scientific papers

Synthesis and antiproliferative action of a novel series of maprotiline analogues

The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymp

Roof shape amines: Synthesis and application as NMR chiral solvating agents for discrimination of α-functionalized acids We wish to dedicate this paper to Professor Sukh Dev on the occasion of his 90th birthday

A series of new chiral roof shape amines have been prepared from anthracene involving simple chemical steps and enzymatic resolution of isomers. The amines were screened as chiral solvating agents for the discrimination of enantiomers of several α-functionalized acids by the 1H NMR analysis. The system can also be used to accurately measure enantiomeric excess of mandelic acid by 1H NMR analysis. The roof shape CSAs were capable of detecting the shift in the signals for the standard four nuclei of 1H, 13C, 19F and 31P of various optically active acids.

Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels-Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels-Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers.

Lipase catalyzed resolution of trans-11,12-bis(hydroxymethyl)-9,10-dihydro- 9,10-ethanoanthracene: Facile access to both enantiomers and the synthesis of their amino derivatives

The lipase mediated resolution of roof shaped trans-11,12- bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene using vinyl acetate as an acetylating reagent is achieved. This method gives easy access to both enantiomers of the molecule in very high enantiomeric purity. The chiral diol is converted to diamino and aminoalcohol derivatives by simple chemical transformations.

Asymmetric cycloaddition routes to both enantiomers of trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid

Fumarates prepared from a series of optically active alcohols were used as dienophiles in Lewis acid catalyzed asymmetric cycloadditions to anthracene. The reactions gave high yields and d.e.'s of the diester cycloaddition products and acid hydrolysis could be performed under conditions yielding only about 10% racemization. The reactions form a valuable synthetic pathway to both enantiomers of the bicyclic dicarboxylic acid, since di-(-)-menthyl fumarate yielded the (-)-(S,S)-enantiomer and di-(+)-iso-menthyl fumarate the (+)-(R,R)-enantiomer of the acid. The other fumarates, obtained from (-)-borneol, (+)-fenchol and (-)-isopulegol, likewise gave the (-)-(S,S)-enantiomer of the acid. The absolute stereochemistry of the products was confirmed via a single crystal X-ray crystallographic structure determination of the brucine salt of the (-)-(S,S)-enantiomer.

Selectivity for the methoxycarbonylation of ethylene versus CO-ethylene copolymerization with catalysts based on C4-bridged bidentate phosphines and phospholes

The C4-bridged phospholes 11,12-bis(2,3,4,5-tetramethylphospholylmethyl)-9,10-dihydro-9,10-ethano- anthracene (cis, 4a; trans, 4b) and diphosphines 11,12-bis(diphenylphosphinomethyl)-9,10-dihydro-9,10-ethano-anthracene (cis, 5a; trans, 5b) and their corresponding palladium complexes [(P-P)PdCl2] (6a-d) have been prepared and characterized. Single-crystal X-ray analyses of 6a-d have been undertaken and they reveal that 4a and b and 5a and b coordinate in a bidentate manner forming seven-membered chelate rings with natural bite angles between 98.62 and 100.30°. The palladium-catalyzed carbonylation of ethylene has been studied using 4a and b and 5a and b. Catalyst mixtures generated from 4a and b, palladium acetate and methanesulfonic acid are selective for the copolymerization of ethylene with carbon monoxide, generating low molecular weight polymers. Surprisingly, the activity of catalyst systems based on cis-(4a) is markedly higher than that based on its trans-isomer, 4b. The marked influence of the nature of the four-carbon tether is highlighted by comparative catalyst testing with [{1,4-bis(2,3,4,5-tetramethylphospholyl)butane}Pd(OAc)2], which rapidly decomposes under the conditions used for copolymerization. In contrast, under identical conditions catalyst mixtures formed from 5a and b show a marked dependence of the selectivity on the stereochemistry of the ethano-anthracene tether, the former generating a low molecular weight copolymer while the latter generate mainly methyl propanoate. Interestingly, polyketone generated from catalysts based on bisphosphole 4a has a markedly higher average molecular weight than that formed using its diphenylphosphino counterpart, 5a.

Synthesis of novel conjugated polymers containing alternating hexa-1,3,5-triene and bi-p-phenylene or ter-p-phenylene segments

Novel conjugated polymers containing alternating hexa-1,3,5-triene and bi- or ter-p-phenylene segments are synthesised using a precursor polymer approach.