Bicyclo(1.1.1)pentane
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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| IUPAC name
bicyclo[1.1.1]pentane | |
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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
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]
gollark: Some very alty thing?
gollark: I think I need about a gazillion more reds.
gollark: GWs are probably sliiiiiightly less common.
gollark: Probably.
gollark: There would be less strain if it only checked for the dragons once the first time you use it and then added the others when you got them.
See also
References
- 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.
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