1200-88-0Relevant academic research and scientific papers
Thallium in Organic Synthesis. 56. A Novel Oxidative Intramolecular Cyclization/Rearrangement of 5-Norbornene-trans-2,3-dicarboxylic Acid with Thallium(III) Trifluoracetate (TTFA)
Taylor, Edward C.,Jagdmann, G.Erik,McKillop, Alexander
, p. 3373 - 3375 (1980)
Treatment of 5-norbornene-trans-2,3-dicarboxylic acid (5) with thallium(III) trifluoracetate (TTFA) and BF3*Et2O results in oxidative intramolecular cyclization, accompanied by rearrangement, to give the previously unknown 5,7-dihydroxy-2,3-norbornanedicarboxylic acid di-γ-lactone (9).
Synthesis of (1S*,2S*,3S*,4S*,5S*,6S*,7S*,8S*)-1,2,7,8-Tetrachlorotricyclo3,8>octane-4,5-dicarboxylic Acid. Novel Entry into the C2-Bissecocubane System
Baker, Colin J.,Fray, Gordon I.,Geen, Graham R.,Ryan, Keith
, p. 793 - 796 (1994)
Photocaging of the known Diels-Alder dimer of 2,3-dichlorocyclopentadienone, compound 1, followed by alkali-induced double ring-cleavage of the resulting caged diketone rac-2 or its dihydrate rac-3, led to the title tetrachloro dicarboxylic acid rac-5, thus affording a novel entry into the inherently chiral tricyclo3,8>octane (C2-bissecocubane) system.Electrolysis of the disodium salt of rac-5- gave the tetrachloro alkene rac-14, from which other derivatives were obtained by standard methods.
Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons
?apan, Irfan,Servi, Süleyman
, p. 131 - 142 (2018)
Novel imidazoline derivatives were synthesized from the norbornene and dibenzobarrelene skeletons which were obtained by the Diels-Alder reactions of anthracene and cyclopentadiene with the different dienophiles, such as fumaronitrile and fumaric acid. Synthesis of the C-2 substituted imidazolines was performed with high yields from various dinitriles and diacyl dichlorides.
Resolution of (±)-Bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic Acid: Crystal Structure of Its Cinchoninium Salt
Jiménez, Lissette,González, Teresa,Brice?o, Alexander,Agrifoglio, Giuseppe,Pastrán, Jesús,Dorta, Romano
, p. 203 - 207 (2016/05/02)
Abstract: Single crystals of (+)-cinchoninium (+)-bicyclo[2.2.1]hept-5-ene-trans-2-carboxyl-3-carboxylate (S,S)-2 were obtained upon resolution of racemic (±)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid rac-1 with (+)-cinchonine. An X ray diffraction analysis established the most important secondary interactions between the ions that are deemed responsible for the diastereomeric separation process. From (S,S)-2 enantiomerically pure (+)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid (S,S)-1 was isolated in 72 % yield. Graphical Abstract: An X-ray diffraction analysis of (+)-cinchoninium (+)-bicyclo[2.2.1]hept-5-ene-trans-2-carboxyl-3-carboxylate (S,S)-2 established the most important secondary interactions between the ions that are deemed responsible for the diastereomeric separation process.[Figure not available: see fulltext.]
Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents
Hickey, Shane M.,Ashton, Trent D.,Khosa, Simren K.,Robson, Ryan N.,White, Jonathan M.,Li, Jian,Nation, Roger L.,Yu, Heidi Y.,Elliott, Alysha G.,Butler, Mark S.,Huang, Johnny X.,Cooper, Matthew A.,Pfeffer, Frederick M.
supporting information, p. 6225 - 6241 (2015/06/08)
A series of structurally amphiphilic biscationic norbornanes have been synthesised as rigidified, low molecular weight peptidomimetics of cationic antimicrobial peptides. A variety of charged hydrophilic functionalities were attached to the norbornane scaffold including aminium, guanidinium, imidazolium and pyridinium moieties. Additionally, a range of hydrophobic groups of differing sizes were incorporated through an acetal linkage. The compounds were evaluated for antibacterial activity against both Gram-negative and Gram-positive bacteria. Activity was observed across the series; the most potent of which exhibited an MIC's ≤ 1 μg mL-1 against Streptococcus pneumoniae, Enterococcus faecalis and several strains of Staphylococcus aureus, including multi-resistant methicillin resistant (mMRSA), glycopeptide-intermediate (GISA) and vancomycin-intermediate (VISA) S. aureus.
A simple method for resolution of endo-/exo-monoesters of trans-norborn-5-ene-2,3-dicarboxylic acids into their enantiomers
Kovalenko, Vitaly N.,Kozyrkov, Yurii Yu.
, p. 151 - 155 (2015/03/04)
Separation of optical isomers obtainable from trans-norborn-5-ene-2,3-dicarboxylic acid methyl and tert-butyl monoesters was performed by crystallization of the respective salts prepared with (R)- and (S)-1-phenylethylamine. Starting from racemic endo-monomethyl ester of trans-norborn-5-ene-2,3-dicarboxylic acid, prepared by partial hydrolysis of the cyclopentadiene-dimethyl fumarate adduct, the corresponding (2R, 3R)-endo-monoester was isolated in 97% enantiomeric excess (ee) yield after seven repeated crystallizations from tetrachloromethane. Starting from exo-mono-tert-butyl ester of the same acid, prepared by alcoholysis of the cyclopentadiene-maleic anhydride adduct followed by isomerization, (2R, 3R)-exo-monoester was isolated in >98% ee yield after four repeated crystallizations from ethanol. Crystallization of the acids from the mother liquor yielded products with inverse stereochemical configuration.
High-Load, ROMP-Generated Oligomeric Bis-acid Chlorides: Design of Soluble and Insoluble Nucleophile Scavengers
Moore, Joel D.,Byrne, Robert J.,Vedantham, Punitha,Flynn, Daniel L.,Hanson, Paul R.
, p. 4241 - 4244 (2007/10/03)
(Equation presented) An efficient strategy for scavenging a host of nucleophiles utilizing an oligomeric bis-acid chloride (OBAC), generated from the ROM polymerization of trans-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl dichloride, is described. The reactivity and high load of the OBAC reagent is exploited in the scavenging of amines, alcohols, and thiols that are present in excess following a common benzoylation event. Following the scavenging event, these oligomers can be precipitated with EtOAc and filtered (SiO2), leaving benzoylated nucleophiles in excellent yield and purity.
Optical Resolution of trans-Bicycloheptane-2,3-diamine: Chiral Recognition in the Crystal of its Complex with (2R,3R)-O,O'-Dibenzoyltartaric Acid
Hatano, Keiichiro,Takeda, Tadahiro,Saito, Reiko
, p. 579 - 584 (2007/10/02)
The synthesis of trans-bicycloheptane-2,3-diamine (6c), its optical resolution via formation of its complex with (2R,3R)-O,O'-dibenzoyltartaric acid (-BTA), and the crystal structure determination of this complex by X-ray diffraction techniques are reported.The absolute configuration of 6c in the complex has been determined to be (S,S)-6c from the endowed chirality of -BTA, thus optical resolution of 6c is achieved.Crystal data for the (S,S)-6c*(-BTA) complex is reported: C25H28N2O8*2H2O, M = 520.54, monoclinic P21, a = 9.150(1), b = 8.581(1), c = 17.036(1) Angstroem, β = 103,30(1) deg, V = 1301(2) Angstroem3, Z = 2, R = 0.037.The crystal of the molecular complex is found to have a multilamellar structure partitioned by thin hydrogen bonded sheets containing complex ammonium-carboxylate-water hydrogen bonds.Attached on both sides of the sheet, monolayer templates with benzoyl groups of -BTA and bicycloheptane fragments of 6c stack with the next templates to form hydrophobic bilayers.In the monolayer template, a cavity is formed surrounded by two pairs of two benzoyl groups distinguished from each other by their orientations toward the hydrogen bond sheet.The cavity provides a final site for the chiral recognition of 6c.The (S,S)-enantiomer of 6c is probably distinguished from the (R,R)-enantiomer by the favourable orientation of bicycloheptane skeleton in the cavity.
A stereoselective biocatalytic Diels-Alder reaction
Rao,Srinivasan,Bhanumathi
, p. 5959 - 5960 (2007/10/02)
Baker's yeast catalyzes the stereoselective Diels-Alder reaction of cyclopentadiene 1 with dienophiles 2, 4 and 6. A predominant formation of exo isomer is observed in some cases.
