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Chemical Compound Review

Phenylethyne     ethynylbenzene

Synonyms: Ethynylbenzene, PubChem15340, CHEMBL234833, NSC-4957, ACMC-1ASVJ, ...
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Disease relevance of ethynylbenzene


High impact information on ethynylbenzene

  • The pincer-ligated species (PCP)Ir (PCP = kappa3-C6H3-2,6-(CH2PtBu2)2) is found to promote dimerization of phenylacetylene to give the enyne complex (PCP)Ir(trans-1,4-phenyl-but-3-ene-1-yne) [3].
  • Platinum participation in the hydrogenation of phenylacetylene by Ru5(CO)15(C)[Pt(PBu(t)3)] [4].
  • (6)Li, (13)C, and (19)F NMR spectroscopies show that deprotonation of quinazolinones and phenylacetylene in THF/pentane solutions with lithium hexamethyldisilazide affords a mixture of lithium quinazolinide/PhCCLi mixed dimer and mixed tetramer along with PhCCLi dimer [5].
  • This contribution explores the relation between molecular second hyperpolarizabilities (gamma) and molecular architecture in phenylacetylene dendrimers using the semiempirical molecular orbital method, that is, INDO/S method [6].
  • In contrast, the gamma(s)() value of D25 is found to be about 6 times as small as that of the para-substituted phenylacetylene oligomer (L25) composed of 24 units of phenylacetylenes [6].

Chemical compound and disease context of ethynylbenzene


Biological context of ethynylbenzene


Associations of ethynylbenzene with other chemical compounds


Gene context of ethynylbenzene

  • However, the copolymers with the phenylacetylene bearing a tert-butyldimethylsiloxy group with intermediate bulkiness at the para position showed no ICD change with temperature [10].
  • The enantioselective cycloaddition of CHT and phenylacetylene with BINOL phosphoramidite ligand 4 afforded the cycloadduct 3a (R = Ph) in 91% yield and 74% ee [11].
  • The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions [12].

Analytical, diagnostic and therapeutic context of ethynylbenzene


  1. Differential inhibition in vivo of ammonia monooxygenase, soluble methane monooxygenase and membrane-associated methane monoxygenase by phenylacetylene. Lontoh, S., DiSpirito, A.A., Krema, C.L., Whittaker, M.R., Hooper, A.B., Semrau, J.D. Environ. Microbiol. (2000) [Pubmed]
  2. Phenylacetylene reversibly inhibits the phenol hydroxylase of Pseudomonas sp. CF600 at high concentrations but is oxidized at lower concentrations. Kagle, J., Hay, A.G. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  3. Dimerization of alkynes promoted by a pincer-ligated iridium complex. C-C reductive elimination inhibited by steric crowding. Ghosh, R., Zhang, X., Achord, P., Emge, T.J., Krogh-Jespersen, K., Goldman, A.S. J. Am. Chem. Soc. (2007) [Pubmed]
  4. Platinum participation in the hydrogenation of phenylacetylene by Ru5(CO)15(C)[Pt(PBu(t)3)]. Adams, R.D., Captain, B., Zhu, L. J. Am. Chem. Soc. (2004) [Pubmed]
  5. Structural and rate studies of the 1,2-additions of lithium phenylacetylide to lithiated quinazolinones: influence of mixed aggregates on the reaction mechanism. Briggs, T.F., Winemiller, M.D., Collum, D.B., Parsons, R.L., Davulcu, A.H., Harris, G.D., Fortunak, J.M., Confalone, P.N. J. Am. Chem. Soc. (2004) [Pubmed]
  6. Theoretical study on second hyperpolarizabilities of phenylacetylene dendrimer: toward an understanding of structure-property relation in NLO responses of fractal antenna dendrimers. Nakano, M., Fujita, H., Takahata, M., Yamaguchi, K. J. Am. Chem. Soc. (2002) [Pubmed]
  7. Mechanism of acylation of lithium phenylacetylide with a Weinreb amide. Qu, B., Collum, D.B. J. Org. Chem. (2006) [Pubmed]
  8. Molecular structure and benzene ring deformation of three ethynylbenzenes from gas-phase electron diffraction and quantum chemical calculations. Campanelli, A.R., Arcadi, A., Domenicano, A., Ramondo, F., Hargittai, I. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  9. Length dependent folding kinetics of phenylacetylene oligomers: structural characterization of a kinetic trap. Elmer, S.P., Pande, V.S. The Journal of chemical physics. (2005) [Pubmed]
  10. Temperature dependence of helical structures of poly(phenylacetylene) derivatives bearing an optically active substituent. Morino, K., Maeda, K., Okamoto, Y., Yashima, E., Sato, T. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  11. First cobalt(I)-catalyzed [6 + 2] cycloadditions of cycloheptatriene with alkynes. Achard, M., Tenaglia, A., Buono, G. Org. Lett. (2005) [Pubmed]
  12. Narrow-rim functionalization of calix[4]arenes via Sonogashira coupling reactions. Al-Saraierh, H., Miller, D.O., Georghiou, P.E. J. Org. Chem. (2005) [Pubmed]
  13. pH-selective synthesis and structures of alkynyl, acyl, and ketonyl intermediates in anti-Markovnikov and Markovnikov hydrations of a terminal alkyne with a water-soluble iridium aqua complex in water. Ogo, S., Uehara, K., Abura, T., Watanabe, Y., Fukuzumi, S. J. Am. Chem. Soc. (2004) [Pubmed]
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