Bicyclo(1.1.1)pentane

Short description: Chemical compound

bicyclo[1.1.1]pentane  |  |

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Names
Preferred IUPAC name

Bicyclo[1.1.1]pentane

Identifiers

CAS Number

* 311-75-1

3D model (JSmol)

* Interactive image

ChemSpider |

* 119929

PubChem CID

* 136153

InChI

* InChI=1S/C5H8/c1-4-2-5(1)3-4/h4-5H,1-3H2

Key: MKCBRYIXFFGIKN-UHFFFAOYSA-N

SMILES

* C1C2CC1C2

Properties

Chemical formula

| 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).

Infobox references

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.

Bicyclo[1.1.1]pentane is a highly strained molecule.

## Usage

[1.1.1]Propellane

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

* Housane

## References

1. ↑ Wiberg, Kenneth B.; Walker, Frederick H. (1982). "[1.1.1]Propellane". J. Am. Chem. Soc. 104 (19): 5239–5240. doi:10.1021/ja00383a046.
2. ↑ Stepan, Antonia F.; Subramanyam, Chakrapani; Efremov, Ivan V.; Dutra, Jason K.; O’Sullivan, Theresa J.; DiRico, Kenneth J.; McDonald, W. Scott; Won, Annie et al. (2012-04-12). "Application of the Bicyclo[1.1.1pentane 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. https://figshare.com/articles/Application_of_the_Bicyclo_1_1_1_pentane_Motif_as_a_Nonclassical_Phenyl_Ring_Bioisostere_in_the_Design_of_a_Potent_and_Orally_Active_Secretase_Inhibitor/2531245.

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*[CID]: Compound ID