70738-17-9

Upstream product

• 120-12-7 anthracene 
• 110-16-7 maleic acid 
• 6915-18-0 2-butenedioic acid 
• 111293-22-2 C₂₈H₃₀O₈ 
• 110-17-8 (2E)-but-2-enedioic acid 
• 23194-04-9 trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid dimethyl ester 

Downstream Products

• 41063-85-8 11R,12R-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen 
• 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 
• 5445-55-6 (R,R)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene 
• 93368-50-4 C₃₂H₂₈N₂O₂ 
• 83742-19-2 C₂₂H₂₂O₄ 
• 23194-04-9 trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid dimethyl ester 
• 23194-04-9 cis-9,10-dihydro-9,10-ethano-anthracene-dicarboxylic acid-(11.12)-dimethyl ester 

Relevant academic research and scientific papers

Synthesis of novel aza-heterocyclic derivatives from diester and diacid chlorides having the dibenzobarrelene skeleton

When attempting to synthesize the symmetric aza-heterocyclic-substituted dibenzobarrelene derivatives from the 2-aminobenzimidazole (or 2-aminoimidazoline) with diacid chlorides and diester in the presence of various organic bases, different products were isolated in high yield. NMR spectroscopic analysis proved these products to be dibenzobarrelene-substituted fused benzimidazodiazepine, imidazolinediazepine, and dicarboxamides derivatives. Cyclic or noncyclic dicarboxamides with the dibenzobarrelene skeleton have been synthesized for the first time using these methods.

Simple and highly efficient chiral dopant molecules possessing both rod- and arch-like units

A simple chiral dopant molecule (R)-1 with both rod- and arch-like units was prepared, and extremely large helical twisting powers (+123 to +228 μm-1) in nematic liquid crystal phases were achieved. We have demonstrated that the introduction of an arch-like unit in addition to rod-like units is highly effective in controlling the helical molecular alignment. As an application of the dopant, induction of blue phases by addition of a small amount of it was achieved. This journal is the Partner Organisations 2014.

Importance of C*-H based modes and large amplitude motion effects in vibrational circular dichroism spectra: The case of the chiral adduct of dimethyl fumarate and anthracene

The role played by the C-H based modes (C* being the chiral carbon atom) and the large amplitude motions in the vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra is investigated. The example of an adduct of dimethyl fumarate and anthracene, i.e., dimethyl-(+)-(11R,12R)-9,10- dihydro-9,10-ethanoanthracene-11,12-dicarboxylate, and two deuterated isotopomers thereof specially synthesized for this goal, are considered. By comparing the experimental and DFT calculated spectra of the undeuterated and deuterated species, we demonstrate that the C-H bending, rocking, and stretching modes in the VA and VCD spectra are clearly identified in well defined spectroscopic features. Further, significant information about the conformer distribution is gathered by analyzing the VA and VCD data of both the fingerprint and the C-H stretching regions, with particular attention paid to the band shape data. Effects related to the large amplitude motions of the two methoxy moieties have been simulated by performing linear transit (LT) calculations, which consists of varying systematically the relative positions of the two methoxy moieties and calculating VCD spectra for the partially optimized structures obtained in this way. The LT method allows one to improve the quality of calculated spectra, as compared to experimental results, especially in regard to relative intensities and bandwidths.

Asymmetric copper-catalyzed Diels-Alder reaction revisited: Control of the structure of bis(oxazoline) ligands

Synthesis of 1,4-bis(oxazoline) ligands bearing a bicyclo[2,2,2]backbone derived from 9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid was revisited. Starting from l- or d-amino alcohols and either (S,S) or (R,R)-dihydroethano trans-dicarboxylic acid, a complete series of ligands was evaluated in the copper-catalyzed Diels-Alder reaction. The most efficient ligands with a phenyl substituent on the oxazoline ring afforded enantiomeric excess up to 98%. This is different from previous results indicating that the best enantioselectivity involved a diastereomeric ligand with the meso-backbone.

Shape takes the lead: Templating organic 3D-frameworks around organometallic sandwich compounds

The novel organic-organometallic crystalline compounds [(η5- C5H5)2Co][(cis-deccaH)(cis-deccaH2)] (1), [(η5-C5H5)2Co][(cis- deccaH)(cis-deccaH2)]?H2O (2), [(η5- C5H5)2Co][trans-deccaH] (3), [(η5-C5H5)2Co][(trans-deccaH) (trans-deccaH2)] (4), [(η5-C5Me 5)2Co][cis-deccaH] (5), [(η5-C 5Me5)2Co][trans-deccaH]?4H2O (6), and [(η6-C6H6)2Cr][trans- deccaH] (7) have been prepared by direct reaction of neutral [(η5-C5H5)2Co], [(η5-C5Me5)2Co], and [(η6-C6H6)2Cr] with the organic compounds cis-9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride and trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (cis-decca and trans-deccaH2, respectively). The organic building blocks have been chosen because of their three-stem star-like shape and the difference in hydrogen-bonding capacity. It is shown that the formation of a honeycomb-type anionic arrangement around the organometallic cations does not require the assistance of strong hydrogen-bonding interactions. Depending on the stoichiometric ratio and on the presence of water molecules, rectangular and layered crystal packings are also obtained.

Synthesis and effects on chloroquine susceptibility in Plasmodium falciparum of a series of new dihydroanthracene derivatives

To suggest a mechanism of action for drugs capable to reverse the chloroquine resistance, a new set of 9,10-dihydro-9,10-ethano and ethenoanthracene derivatives was synthesized and compounds were tested with the aim to assess their effect on chloroquine s

PMR Spectral Studies of Diels-Alder Adducts: Anthracene-Crotonic Acid, Anthracene-Fumaric Acid and β-Naphthol-Fumaric Acid

A series of amides (III-XI and XVII) and esters (XII-XV) of the Diels-Alder adducts, anthracene-crotonic acid (I), anthracene-fumaric acid (II) and β-naphthol-fumaric acid (XVI) have been prepared and their PMR spectra recorded.The PMR data indicate that N,N-dimethylamide and N-methylanilide derivatives of the adducts have restricted rotation about the N-CO and C-CO bonds.A trans-stereochemistry have been assigned to H-11 and H-12 in compounds I-XV and to H-2 and H-3 in compound XVI.

Selective Clathrate Formation with the New Host Systems cis- and trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic Acid: Inclusion Properties and X-Ray Structure of an Encapsulated Acetic Acid Dimer

2+4 Cycloaddition of fumaric or maleic acid to anthracene produces the novel host molecules (1) and (2) respectively, which readily form inclusion compounds with a variety of solvents, among which acetic acid, as demonstrated by its crystal structure, gives true clathrate formation with encapsulated dimeric guest units.