Chemistry:1-Ethynylcyclohexanol

From HandWiki
Short description: Chemical compound
1-Ethynylcyclohexanol
1-Ethynylcyclohexanol.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC8H12O
Molar mass124.183 g·mol−1
3D model (JSmol)
Melting point30–33 °C (86–91 °F)

1-Ethynylcyclohexanol (ECX) is an alkynyl alcohol derivative which is both a synthetic precursor to, and an active metabolite of the tranquilizer ethinamate, and has similar sedative, anticonvulsant and muscle relaxant effects. It has been sold as a designer drug, first being identified in the UK in March 2012.[1][2][3][4]

Preparation

Synthesis of 1-ethynylcyclohexanol from cyclohexanone.

1-Ethynylcyclohexanol can be prepared from cyclohexanone by the reacting it with sodium acetylide in liquid ammonia, followed by an acidic work-up.[5]

See also

References

  1. "Action of sodium acetylide on cyclic ketones. I. Synthesis of 1-ethynylcyclohexanol.". Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) 9: 1299–1302. 1936. ISSN 0044-4618. 
  2. "An efficient and quick laboratory scale method for the ethynylation of some aliphatic and cycloaliphatic carbonyl compounds.". Synthetic Communications 18 (2): 131–4. February 1988. doi:10.1080/00397918808077336. 
  3. "Acetylene derivatives. CLX. Condensation of aldehydes and ketones with acetylene under pressure. New method of synthesis of acetylenic alcohols.". Zhurnal Obshchei Khimii 23: 1900–1904. 1953. ISSN 0044-460X. 
  4. "Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)". Lisbon: EMCDDA. May 2013. https://www.emcdda.europa.eu/system/files/publications/734/EMCDDA-Europol_2012_Annual_Report_final_439477.pdf. 
  5. "1-ETHYNYLCYCLOHEXANOL". Organic Syntheses 29: 47. 1949. doi:10.15227/orgsyn.029.0047. http://orgsyn.org/demo.aspx?prep=CV3P0416.