Bicyclo[1.1.1]pentane is an organic compound, the simplest member of the bicyclic bridged compounds family. It is a hydrocarbon with formula C5H8. The molecular structure consists of three rings of four carbon atoms each.
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| Preferred IUPAC name
Bicyclo[1.1.1]pentane | |||
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C5H8 | |||
| Molar mass | 68.119 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bicyclo[1.1.1]pentane is a highly strained molecule.
Usage
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Kenneth Wiberg and Frederick Walker used bicyclo[1.1.1]pentane to make [1.1.1]propellane.[1]
The bicyclo[1.1.1]pentane structure has been used as an unusual bioisostere for a phenyl ring.[2]
See also
editReferences
edit- ^ Wiberg, Kenneth B.; Walker, Frederick H. (1982). "[1.1.1]Propellane". J. Am. Chem. Soc. 104 (19): 5239–5240. doi:10.1021/ja00383a046.
- ^ Stepan, Antonia F.; Subramanyam, Chakrapani; Efremov, Ivan V.; Dutra, Jason K.; O’Sullivan, Theresa J.; DiRico, Kenneth J.; McDonald, W. Scott; Won, Annie; Dorff, Peter H. (2012-04-12). "Application of the Bicyclo[1.1.1]pentane Motif as a Nonclassical Phenyl Ring Bioisostere in the Design of a Potent and Orally Active γ-Secretase Inhibitor". Journal of Medicinal Chemistry. 55 (7): 3414–3424. doi:10.1021/jm300094u. ISSN 0022-2623. PMID 22420884.