485318-53-4Relevant articles and documents
Base-Promoted Rearrangement of 1,5-Dibromopentacyclo2,5.03,9.04,8>decane-6,10-dione: Easy Entry of a Novel Cage System, 10-Oxa-9-oxopentacyclo2,4.03,6.05,8>decane
Nigo, Tomohiro,Hasegawa, Takeshi,Kuwatani, Yoshiyuki,Ueda, Ikuo
, p. 2068 - 2072 (1993)
The Diels-Alder dimerization of 2-bromo-2,4-cyclopentadienone ethylene acetal (2) gave endo-2,7-dibromodicyclopentadiene-1,8-dione 1,8-bis(ethylene acetal) (3) as a minor product in a 4.5percent yield. Ultraviolet irradiation of 5 led to dimerization product 7. Deacetalization was accomplished by treating with concentrated sulfuric acid to give 1,5-dibromopentacyclo2,5.03,9.04,8>decane-6,10-dione (9). Compound 9 was converted into a new cage system, 10-oxa-9-oxopentacyclo2,4.03,6.05,8>decane, in a high yield by treating with 5percent aqueous potassium hydroxide at 80 deg C.
Decagram Synthesis of Dimethyl 1,4-Cubanedicarboxylate Using Continuous-Flow Photochemistry
Collin, Diego E.,Jackman, Edward H.,Jouandon, Nicolas,Sun, Wei,Light, Mark E.,Harrowven, David C.,Linclau, Bruno
, p. 1307 - 1314 (2020/11/19)
The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. A straightforward approach is reported for the scale-up of a [2+2] photocycloaddition step using convenient home-made flow photoreactors to access dimethyl 1,4-cubanedicarboxylate on decagram-scale in 33-40% yield over 8 steps. The process is demonstrated on 3.4 g·h -1input with 30 minutes residence time, enabling to reduce the process time and to avoid the use of batch photoreactors. Completion of the characterisation of the photocycloadduct and its hydrates is reported.
Cubane Arrives on the Cucurbituril Scene
Jelínková, Kristyna,Surmová, Heda,Matelová, Alena,Rouchal, Michal,Prucková, Zdeňka,Dastychová, Lenka,Ne?as, Marek,Vícha, Robert
supporting information, p. 2698 - 2701 (2017/05/24)
Cubane, an intriguing chemical curiosity first studied in the early 1960s, has become a valuable structural motif and has recently been involved in the structures of a great number of prospective compounds. The first dicationic supramolecular guest 5 is prepared and derived from a 1,4-disubstituted cubane moiety, and its binding behavior toward cucurbit[n]urils (CBn) and cyclodextrins (CD) is studied. The bisimidazolium salt 5 forms 1:1 inclusion complexes with CB7, CB8, and β-CD with the respective association constants (6.7 ± 0.5) × 1011 M-1, (1.5 ± 0.2) × 109 M-1, and 2 M-1 in water. The solid-state structures of the 5@CB7 and 5@CB8 complexes are also reported.
Structure-activity relationships of N-substituted 4-(trifluoromethoxy) benzamidines with affinity for GluN2B-containing NMDA receptors
Beinat, Corinne,Banister, Samuel D.,Hoban, Jane,Tsanaktsidis, John,Metaxas, Athanasios,Windhorst, Albert D.,Kassiou, Michael
, p. 828 - 830 (2014/02/14)
GluN2B subtype-selective NMDA antagonists represent promising therapeutic targets for the symptomatic treatment of multiple CNS pathologies. A series of N-benzyl substituted benzamidines were synthesised and the benzyl ring was further replaced with various polycyclic moieties. Compounds were evaluated for activity at GluN2B containing NMDA receptors where analogues 9, 12, 16 and 18 were the most potent of the series, replacement of the benzyl ring with polycycles resulted in a complete loss of activity.
Pilot-Scale Production of Dimethyl 1,4-Cubanedicarboxylate
Falkiner, Michael J.,Littler, Stuart W.,McRae, Kenneth J.,Savage, G. Paul,Tsanaktsidis, John
, p. 1503 - 1509 (2014/01/06)
A scalable process for the preparation of high purity dimethyl 1,4-cubanedicarboxylate (3) is reported. The work described herein builds on previous synthetic work from this and other laboratories, to provide a reliable process that can be used to prepare multigram quantities of 3 in a partially telescoped, 8 step process, with minimal purification of intermediates.
Synthesis of a novel chiral cubane-based Schiff base ligand and its application in asymmetric nitro-aldol (Henry) reactions
Ingalsbe, Michelle L.,St. Denis, Jeffrey D.,Gleason, James L.,Savage, G. Paul,Priefer, Ronny
experimental part, p. 98 - 102 (2010/05/18)
The first reported cubane-based chiral Schiff base ligand has been successfully synthesized. This ligand has been evaluated on the nitro-aldol (Henry) reaction. The reactions were performed in the presence of four different copper salts, using eight different solvents, and five different temperatures. The highest enantioselectivity obtained for this novel ligand was ～39% ee.
Thermochemical properties of iodinated cubane derivatives
Griffiths, Justin R.,Tsanaktsidis, John,Savage, G. Paul,Priefer, Ronny
experimental part, p. 15 - 20 (2010/04/25)
Since the initial synthesis of cubane, numerous derivatives have been made with a diverse range of physical, chemical, and biological properties. Some iodinated cubane derivatives have been reported to be thermolytically unstable and/or rearrange in situ. An iodinated cubane-containing, norbornene-based polymer showed rapid thermo-decomposition during TGA studies. Bis-(4-iodocubylmethyl)-dialkoxy disulfide undergoes fragmentation more easily than its non-iodinated counterpart. The synthesis and thermal behaviour of a library of iodinated cubane compounds are herein reported. Most of the iodinated cubane derivatives showed melting/decomposition with no exotherm upon cooling. 4-Iodo-1-vinylcubane was observed to rearrange to 4-vinyl-trans-β-iodostyrene and its cyclooctatetraene intermediate during DSC analysis. TGA studies on 1-iodo-4-(hydroxymethyl)-cubane suggest that this particular iodinated cubane scaffold is mostly prone to rapid thermo-decomposition.
Dimethyl cubane-1,4-dicarboxylate: A practical laboratory scale synthesis
Bliese, Marianne,Tsanaktsidis, John
, p. 189 - 192 (2007/10/03)
Complete experimental details for the preparation of dimethyl cubane-1,4-dicarboxylate (1) in multigram quantities, from cyclopentanone (2), in an overall yield of c. 23% are presented.
