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Chemical Compound Review:

KB-16127 bicyclo[2.2.2]oct-2-ene

Synonyms: AKOS006273027, FT-0693091, AC1L2236, BB 0262307, 931-64-6, ...

Nelsen, S.F. et al., Nishinaga, T. et al., Wakamiya, A. et al., Endo, Y. et al.

Endo, Yoshimi, Ohta, Suzuki, Ohta,

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High impact information on Bicyclo[2.2.2]octene

The remarkably stable SbF(6)(-) salts of the radical cations of bithiophene 1(2T) and terthiophene 1(3T), completely surrounded by bicyclo[2.2.2]octene (BCO) units, were obtained by one-electron oxidation of the neutral precursors with NO(+)SbF(6)(-), and their solid-state structures were determined by X-ray crystallography [1].
Candidate estrogen receptor (ER) ligands with two phenolic residues on a three-dimensional hydrophobic core structure (carborane, bicyclo[2.2.2]octene, or adamantane) were synthesized and biologically evaluated [2].
Novel oligothiophenes surrounded by bicyclo[2.2.2]octene (abbreviated as BCO) frameworks ranging from dimer to hexamer, 1(nT) (n = 2, 3, 4, 6), were prepared, and their structures and electronic properties were investigated [3].

Gene context of Bicyclo[2.2.2]octene

The bicyclo[2.2.2]oct-2-ene radical cation (1(.+)) exhibits matrix ESR spectra that have two very different types of gamma-exo hydrogens (those hydrogens formally in a W-plan with the alkene pi bond), a(2H) about 16.9 G and a(2H) about 1.9 G, instead of the four equivalent hydrogens as would be the case in an untwisted C(2v) structure [4].

References

Crystal structures and spectroscopic characterization of radical cations and dications of oligothiophenes stabilized by annelation with bicyclo[2.2.2]octene units: sterically segregated cationic oligothiophenes. Nishinaga, T., Wakamiya, A., Yamazaki, D., Komatsu, K. J. Am. Chem. Soc. (2004) [Pubmed]
Potent estrogen receptor ligands based on bisphenols with a globular hydrophobic core. Endo, Y., Yoshimi, T., Ohta, K., Suzuki, T., Ohta, S. J. Med. Chem. (2005) [Pubmed]
Synthesis and properties of novel oligothiophenes surrounded by bicyclo[2.2.2]octene frameworks. Wakamiya, A., Yamazaki, D., Nishinaga, T., Kitagawa, T., Komatsu, K. J. Org. Chem. (2003) [Pubmed]
Ionized bicyclo[2.2.2]oct-2-ene: a twisted olefinic radical cation showing vibronic coupling. Nelsen, S.F., Reinhardt, L.A., Tran, H.Q., Clark, T., Chen, G.F., Pappas, R.S., Williams, F. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]

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