Cyclophane

Summary

In organic chemistry, a cyclophane is a hydrocarbon consisting of an aromatic unit (typically a benzene ring) and a chain that forms a bridge between two non-adjacent positions of the aromatic ring. More complex derivatives with multiple aromatic units and bridges forming cagelike structures are also known. Cyclophanes are well-studied examples of strained organic compounds. [n]-Cyclophanes Structures Paracyclophanes adopt the boat conformation normally observed in cyclohexanes. Smaller value of n lead to greater distortions. X-ray crystallography on '[6]paracyclophane' shows that the aromatic bridgehead carbon atom makes an angle of 20.5° with the plane. The benzyl carbons deviate by another 20.2°. The carbon-to-carbon bond length alternation has increased from 0 for benzene to 39 pm. Despite their distorted structures, cyclophanes retain their aromaticity, as determined by UV-vis spectroscopy. Reactivity With regards to their react

Official source

https://en.wikipedia.org/wiki/Cyclophane

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Synthesis of Fijiolide A via an Atropselective Paracyclophane Formation

Nicolai Cramer, Christoph Heinz

Fijiolide A is a secondary metabolite isolated from a marine-derived actinomycete and displays inhibitory activity against TNF-α-induced activation of NFκB, an important transcription factor and a potential target for the treatment of different cancers and inflammation related diseases. Fijiolide A is a glycosylated complex paracyclophane, which is structurally closely related to the Bergman-aromatization product of enediyne C-1027. We report an enantioselective synthesis offijiolide A demonstrating the power of fully intermolecular ruthenium-catalyzed [2 + 2 + 2] cyclotrimerizations with three different alkynes to assemble the heavily substituted central arene core. The characteristic strained [2.6]-paracyclophane structure is accessed by a templated atropselective macroetherification reaction.

American Chemical Society2015

Total Synthesis of Fijiolide A

Nicolai Cramer, Christoph Heinz

Fijiolide A is a secondary metabolite isolated from a marine-derived actinomycete of the genus Nocardiopsis. It was found to significantly reduce the TNF-alpha induced activity of the transcription factor NF kappa B, which is considered a promising target for the treatment of cancer and inflammation-related diseases. We disclose an enantioselective synthesis of fijiolide A enabled by a fully intermolecular, yet regioselective cyclotrimerization of three unsymmetrical alkynes to construct its tetra-substituted arene core. An atropselective macroetherification enables the assembly of the strained [2.6]paracyclophane motif. A late-stage glycosylation of the macrocyclic aglycone at its tertiary alcohol position allowed for the first total synthesis of fijiolide A.

Schweizerische Chemische Gesellschaft2016

From central to planar chirality, the first example of atropenantioselective cycloetherification

Jieping Zhu

Using chiral quaternary ammonium hydroxide as base, cycloetherification of a linear achiral diarylheptanoid compd., by way of an intramol. SNAr reaction, provides corresponding enantiomerically enriched cyclophane in good to excellent yield. [on SciFinder (R)]

2003