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Chemical Compound Review:

Tolane 2-phenylethynylbenzene

Synonyms: Tolan, Diphenylethyne, CHEMBL223309, NSC-5185, ACMC-1AYRV, ...

Tiede, D.M. et al., Evrard, D. et al., Schaub, T. et al., Spain, J.C. et al., Nagano, Y. et al., et al.

Spain, Nishino, Witholt, Tan, Duetz, Tiede, Zhang, Chen, Yu, Lindsey,

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Disease relevance of DIPHENYLACETYLENE

Acinetobacter sp. strain F4 catalyzed the overall conversion of diphenylacetylene to a yellow metabolite, which was identified as a putative meta ring fission product (2-hydroxy-8-phenyl-6-oxoocta-2,4-dien-7-ynoic acid [RFP]) [1].

High impact information on DIPHENYLACETYLENE

Structures of modular supramolecular architectures consisting of a hexameric, diphenylethyne-linked porphyrin macrocyclic array and the corresponding host-guest complex formed by inclusion of a tripyridyl guest molecule were characterized in solution using high-angle X-ray scattering [2].
The a(g) vibrational modes of the C(triple bond)C stretching and of the phenyl ring motion were observed in the fluorescence spectra of diphenylacetylene and 1,4-diphenylbutadiyne [3].
The reactions of 1 with ethylene and CO under atmospheric pressure or with equimolar amounts of diphenylacetylene lead to the compounds [Ni(iPr(2)Im)(2)(eta(2)-C(2)H(4))] (2), [Ni(iPr(2)Im)(2)(eta(2)-C(2)Ph(2))] (3), and [Ni(iPr(2)Im)(2)(CO)(2)] (4) in good yields [4].
Bacterial monooxygenase enzymes catalyze a regiospecific single-step hydroxylation of diphenylacetylene to yield meta- and para-hydroxydiphenylacetylene [5].
The catalytic properties of the title cluster toward the homogeneous hydrogenation of phenylacetylene, diphenylethyne and phenyl-1-propyne have been investigated as a function of temperature, pressure, solvents, substrate and cluster concentrations, and counterions [6].

References

Production of 6-phenylacetylene picolinic acid from diphenylacetylene by a toluene-degrading Acinetobacter strain. Spain, J.C., Nishino, S.F., Witholt, B., Tan, L.S., Duetz, W.A. Appl. Environ. Microbiol. (2003) [Pubmed]
Structural characterization of modular supramolecular architectures in solution. Tiede, D.M., Zhang, R., Chen, L.X., Yu, L., Lindsey, J.S. J. Am. Chem. Soc. (2004) [Pubmed]
Symmetry switching of the fluorescent excited state in alpha,omega-diphenylpolyynes. Nagano, Y., Ikoma, T., Akiyama, K., Tero-Kubota, S. J. Am. Chem. Soc. (2003) [Pubmed]
Efficient C-F and C-C activation by a novel N-heterocyclic carbene-nickel(0) complex. Schaub, T., Radius, U. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
Biosynthesis of hydroxydiphenylacetylene by regiospecific monooxygenation. Luckarift, H.R., Johnson, G.R., Spain, J.C. Chem. Commun. (Camb.) (2004) [Pubmed]
The Pd(4)(dppm)(4)(H)(2)(2+) cluster: a precatalyst for the homogeneous hydrogenation of alkynes. Evrard, D., Groison, K., Mugnier, Y., Harvey, P.D. Inorganic chemistry. (2004) [Pubmed]

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