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Chemical Compound Review: 

acetylenediide     acetylide

Synonyms:
 
 
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Disease relevance of acetylide

 

High impact information on acetylide

  • Silapropargyl/silaallenyl and silylene acetylide complexes of [Cp(CO)2W]+. Theoretical study of their interesting bonding nature and formation reaction [2].
  • Unlike [(eta5-C5Me4H)2ZrH]2(mu2,eta2,eta2-N2H2), the acetylide and alkyl zirconocene diazenido complexes are thermally robust, resisting alpha-migration and N2 cleavage up to temperatures of 115 degrees C. Dinitrogen functionalization with [(eta5-C5Me4H)2Zr]2(mu2,eta2,eta2-N2) was also accomplished by addition of proton donors [3].
  • The structure of the acetylide butenyne complex, trans-[Fe(dmpe)(2)(C[triple bond]CC(6)H(4)OCH(3))(eta(1)-C(C(6)H(5))=CH(C[triple bond]CC(6)H(4)OCH(3)))] (9a) was determined by single-crystal X-ray diffraction [4].
  • The key steps are the ring opening of epoxide 5 with acetylide 8 for the construction of the C12-C13 cis double bond and a practical hydrolytic kinetic resolution (HKR) developed by Jacobsen group for the introduction the chiral center at C3 [5].
  • Lithium acetylide addition followed by glycosylation with 3-(trimethylsilyl)propargyl alcohol converted the ribonolactone to silylated diynes [6].
 

Biological context of acetylide

  • The key steps include a stereoselective acetylide addition and the Ag+-mediated cyclization of an alpha-allenic alcohol to construct the trans-2,5-dihydrofuran [7].
  • The approach involves the use of three very efficient Evans oxazolidinone-mediated syn-aldol condensations, a high-yielding coupling between lithium acetylide ethylenediamine complex and a tosylate followed by methylation, and selective reduction to establish the C12-C13 (E) double bond [8].
 

Associations of acetylide with other chemical compounds

  • Lithium acetylide addition followed by oxidation/reduction and protective group manipulation provided the reveromycin B spiroketal core 8 which was converted into the reveromycin A (1) derivative 6 in order to confirm the stereochemistry of the spiroketal segment [9].
  • This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf [10].
  • A novel chemosensor, a cyclometalated platinum(II) bipyridyl acetylide complex containing a monoazacrown moiety in the acetylide ligand, which can signal Mg(2+) specifically and display large changes both in color and in luminescence intensity upon complexation with Mg(2+), is described [11].
  • A solid-state metathesis (exchange) reaction between hexachloroethane (C(2)Cl(6)) and lithium acetylide (Li(2)C(2)) with 5% cobalt dichloride (CoCl(2)) added as an initiator produces up to 7% carbon nanotubes, as observed via transmission electron microscopy [12].
  • The corresponding relationship between 'true' GFR (C1) and approximate GFR (i.e. based only on the second exponential--C2) was C1 = -0.58 + 1.012C2 -0.0011 C2(2) ml.min-1 For any level of renal function, the error in GFR/ECF volume, expressed as lambda 2, is less than the error in GFR expressed as C2 [13].
 

Gene context of acetylide

  • The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide [14].
  • The C10/C15 1,6-diol motif was installed using Carreira's asymmetric acetylide addition methodology [15].
  • These PB ligands have been used to prepare a series of complexes of the type [Re(PB)(CO)(3)Cl], [Pt(PB)(CCR)(2)](where -CCR is an acetylide ligand) and [Ru(bpy)(2)(PB)][PF(6)](2)(bpy = 2,2'-bipyridine) [16].
  • The key step of the preparation involved a diastereoselective addition of a lithium acetylide to an optically active alkynyl ketone under Cram chelation control [17].
 

Analytical, diagnostic and therapeutic context of acetylide

  • A novel luminescent acetylenediide-bridged tetranuclear copper(I) complex [Cu4(mu-Ph2Ppypz)4(mu 4-eta 1,eta 2-C identical to C)]-(ClO4)2 [Ph2Ppypz = 2-(diphenylphosphino-6-pyrazol-1-yl)pyridine] has been synthesized and structurally characterized by X-ray crystallography [18].

References

  1. Versatile photosensitization system for 1O2-mediated oxidation of alkenes based on nafion-supported platinum(II) terpyridyl acetylide complex. Zhang, D., Wu, L.Z., Yang, Q.Z., Li, X.H., Zhang, L.P., Tung, C.H. Org. Lett. (2003) [Pubmed]
  2. Silapropargyl/silaallenyl and silylene acetylide complexes of [Cp(CO)2W]+. Theoretical study of their interesting bonding nature and formation reaction. Ray, M., Nakao, Y., Sato, H., Sakaba, H., Sakaki, S. J. Am. Chem. Soc. (2006) [Pubmed]
  3. Dinitrogen functionalization with terminal alkynes, amines, and hydrazines promoted by [(eta5-C5Me4H)2Zr]2(mu2,eta2,eta2-N2): observation of side-on and end-on diazenido complexes in the reduction of N2 to hydrazine. Bernskoetter, W.H., Pool, J.A., Lobkovsky, E., Chirik, P.J. J. Am. Chem. Soc. (2005) [Pubmed]
  4. Acetylide-bridged organometallic oligomers via the photochemical metathesis of methyl-iron(II) complexes. Field, L.D., Turnbull, A.J., Turner, P. J. Am. Chem. Soc. (2002) [Pubmed]
  5. Total synthesis of epothilone a through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C. Liu, Z.Y., Chen, Z.C., Yu, C.Z., Wang, R.F., Zhang, R.Z., Huang, C.S., Yan, Z., Cao, D.R., Sun, J.B., Li, G. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  6. Synthesis of spirocyclic C-arylribosides via cyclotrimerization. Yamamoto, Y., Hashimoto, T., Hattori, K., Kikuchi, M., Nishiyama, H. Org. Lett. (2006) [Pubmed]
  7. A short total synthesis of (+)-furanomycin. VanBrunt, M.P., Standaert, R.F. Org. Lett. (2000) [Pubmed]
  8. Total synthesis of (-)-pironetin. Dias, L.C., De Oliveira, L.G., De Sousa, M.A. Org. Lett. (2003) [Pubmed]
  9. Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B. Cuzzupe, A.N., Hutton, C.A., Lilly, M.J., Mann, R.K., McRae, K.J., Zammit, S.C., Rizzacasa, M.A. J. Org. Chem. (2001) [Pubmed]
  10. Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin. Suzuki, K., Nakata, T. Org. Lett. (2002) [Pubmed]
  11. A luminescent chemosensor with specific response for Mg2+. Yang, Q.Z., Wu, L.Z., Zhang, H., Chen, B., Wu, Z.X., Zhang, L.P., Tung, C.H. Inorganic chemistry. (2004) [Pubmed]
  12. Enhanced solid-state metathesis routes to carbon nanotubes. Mack, J.J., Tari, S., Kaner, R.B. Inorganic chemistry. (2006) [Pubmed]
  13. Expressing glomerular filtration rate in terms of extracellular fluid volume. Peters, A.M. Nephrol. Dial. Transplant. (1992) [Pubmed]
  14. Sulfonyl-stabilized oxiranyllithium-based approach to polycyclic ethers. Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin. Mori, Y., Nogami, K., Hayashi, H., Noyori, R. J. Org. Chem. (2003) [Pubmed]
  15. Total synthesis of pyranicin. Strand, D., Rein, T. Org. Lett. (2005) [Pubmed]
  16. Complexes of substituted derivatives of 2-(2-pyridyl)benzimidazole with Re(I), Ru(II) and Pt(II): structures, redox and luminescence properties. Shavaleev, N.M., Bell, Z.R., Easun, T.L., Rutkaite, R., Swanson, L., Ward, M.D. Dalton transactions (Cambridge, England : 2003) (2004) [Pubmed]
  17. First asymmetric synthesis of a differentially silyl-protected tris(alkynyl)methyl methyl ether. Convertino, V., Manini, P., Schweizer, W.B., Diederich, F. Org. Biomol. Chem. (2006) [Pubmed]
  18. A novel luminescent copper(I) complex containing an acetylenediide-bridged, butterfly-shaped tetranuclear core. Song, H.B., Wang, Q.M., Zhang, Z.Z., Mak, T.C. Chem. Commun. (Camb.) (2001) [Pubmed]
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