Cyclopropanol Explained

Cyclopropanol is an organic compound with the chemical formula C₃H₆O. It contains a cyclopropyl group with a hydroxyl 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 to rearrangement, undergoing structural isomerization to form propanal.^{[1] [2]} This property is useful synthetically: cyclopropanol can be used as a synthon for the homoenolate of propanal. The chemical is also useful as a reagent to introduce a cyclopropyl group into ester, sulfate, and amine linkages. The resulting cyclopropyl-containing compounds have been used in investigations of potential antiviral drugs^[3] and of modulators of protein trafficking.^[4]

Notes and References

1. The Reaction of Epichlorohydrin with the Grignard Reagent . Magrane, J. K. . Cottle, D. L. . J. Am. Chem. Soc. . 64 . 1942 . 3 . 484–487 . 10.1021/ja01255a004 .
2. The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol . Stahl, G. W. . Cottle, D. L. . J. Am. Chem. Soc. . 65 . 9 . 1943 . 1782–1783 . 10.1021/ja01249a507 .
3. Antiviral compounds . Cottell, J. J.; Link, J. O. Schroeder, S. D.; Taylor, J.; Tse, W.; Vivian, R. W.; Yang, Z.-Y. . WO . 2009005677 . application . 2009-01-08 .
4. Modulators of protein trafficking . Bulawa, C. E.; Devit, M.; Elbaum, D. . WO . 2009062118 . application . 2009-05-14 .