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Cyclopropanol

From Wikipedia, the free encyclopedia
Cyclopropanol
Names
Preferred IUPAC name
Cyclopropanol
Other names
Cyclopropyl alcohol, Hydroxycyclopropane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.217.724Edit this at Wikidata
  • InChI=1S/C3H6O/c4-3-1-2-3/h3-4H,1-2H2 checkY
    Key: YOXHCYXIAVIFCZ-UHFFFAOYSA-N checkY
  • OC1CC1
Properties
C3H6O
Molar mass58.080 g·mol−1
Density0.917 g/mL[1]
Boiling point101 to 102 °C (214 to 216 °F; 374 to 375 K)[2]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Cyclopropanol is an organic compound with the chemical formula C3H6O. It contains acyclopropyl group with ahydroxyl group attached to it. The compound is highly unstable due to the three-membered ring, and is susceptible to reactions that open the ring. It is highly prone torearrangement, undergoingstructural isomerization to formpropanal.[3][4] This property is useful synthetically: cyclopropanol can be used as asynthon for the homoenolate of propanal. The chemical is also useful as a reagent to introduce a cyclopropyl group intoester,sulfate, andamine linkages. The resulting cyclopropyl-containing compounds have been used in investigations of potentialantiviral drugs[5] and of modulators ofprotein trafficking.[6]

References

[edit]
  1. ^Roberts, J. D.; Chambers, V. C. (1951). "Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine".J. Am. Chem. Soc.73 (7):3176–3179.doi:10.1021/ja01151a053.
  2. ^Jongejan, J. A.; Duine, J. A. (1987). "Enzymatic hydrolysis of cyclopropyl acetate. A facile method for medium- and large-scale preparations of cyclopropanol".Tetrahedron Lett.28 (24):2767–2768.doi:10.1016/S0040-4039(00)96204-X.
  3. ^Magrane, J. K.; Cottle, D. L. (1942). "The Reaction of Epichlorohydrin with the Grignard Reagent".J. Am. Chem. Soc.64 (3):484–487.doi:10.1021/ja01255a004.
  4. ^Stahl, G. W.; Cottle, D. L. (1943). "The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol".J. Am. Chem. Soc.65 (9):1782–1783.doi:10.1021/ja01249a507.
  5. ^WO application 2009005677, Cottell, J. J.; Link, J. O. Schroeder, S. D.; Taylor, J.; Tse, W.; Vivian, R. W.; Yang, Z.-Y., "Antiviral compounds", published 2009-01-08 
  6. ^WO application 2009062118, Bulawa, C. E.; Devit, M.; Elbaum, D., "Modulators of protein trafficking", published 2009-05-14 
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