29412-62-2Relevant academic research and scientific papers
An efficient synthesis of pentacyclo2,5.03,8.04,7>octane-1,4-dicarboxylates
Eremenko, L. T.,Romanova, L. B.,Ivanova, M. E.,Ignat'eva, E. L.
, p. 770 - 771 (1993)
Dialkyl pentacyclo2,5.03,8.04,7>octane-1,4-dicarboxylates (where alkyl is methyl, iso-propyl, 2-fluoro-2,2-dinitroethyl, or 2,2,2-trinitroethyl) were prepared in high yields by O-alkylation of 1,4-cubanedicarboxylic acid with the corresponding monoalkyl sulfates. - Keywords: pentacyclo2,5.03,8.04,7>octane-1,4-dicarboxylic acid, esters; monoalkyl sulfates, O-alkylation.
Mechanistic Study of Base-Promoted Rearrangement of 1,5-Dibromopentacyclo2,5.03,9.04,8>decane-6,10-dione to 10-Oxa-9-oxopentacyclo2,4.03,6.05,8>decane-3-carboxylic Acid
Hasegawa, Takeshi,Nigo, Tomohiro,Kuwatani, Yoshiyuki,Ueda, Ikuo
, p. 2676 - 2681 (1993)
The conversion of 1,5-dibromopentacyclo2,5.03,904,8>decane-6,10-dione (1) to 10-oxa-9-oxopentacyclo2,4.03,6.05,8>decane-3-carboxylic acid (6) on treatment with 5percent aqueous potassium hydroxide was shown to proceed through 1, exo-7-dibromo-9-oxotetracyclo2,5.03,8>nonane-endo-4-carboxylic acid (2).Treatment of 1 with the base in heavy water gave rise to 2-d-6 deuterated at the 2-position, but 2 gave the protium analog 6 after the same treatment.These results are discussed in relation to reactions of similar compounds which have been previously described in the literature.
Cubane derivatives 1. Synthesis and molecular structures of the esters of 1,4-cubanedicarboxylic acid
Eremenko, L. T.,Romanova, L. B.,Ivanova, M. E.,Eremenko, I. L.,Nefedov, S. E.,Struchkov, Yu. T.
, p. 619 - 623 (1994)
An effective methods of esterification of 1,4-cubanedicarboxylic acid with alkylsulfuric acids is proposed.The derivatives of alkanols with substantially different pKa values are obtained in high yields.Molecular structures of the esters obtained are confirmed by various methods.The X-ray study showed a remarcable effect of the nature of an alkyl radical on the geometry of the cubane core. - Key words: 1,4-cubanedicarboxylic acid, esterification, alkylsulfuric acids, X-ray method.
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 (2013)
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.
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
, 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.
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.
Indirect monobromination of the cubane nucleus. The synthesis of dimethyl 2-bromocubane-1,4-dicarboxylate
Bliese, Marianne,Fanning, Lisa-Ann,Gable, Robert W.,Lowe, David A.,Tsanaktsidis, John
, p. 593 - 597 (2007/10/03)
The preparation of dimethyl 2-bromocubane-1,4-dicarboxylate (3) is described starting from the readily available (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7- methano-1H-indene-1,8-dione 8-ethylene ketal (4).
