Bicyclo(1.1.1)pentane

Last updated
The correct title of this article is Bicyclo[1.1.1]pentane. The substitution of any brackets is due to technical restrictions.
bicyclo[1.1.1]pentane
Bicyclo-1.1.1-pentane.svg
Bicyclo-1.1.1-pentane-based-on-UGIQIK-3D-bs-17.png
Names
Preferred IUPAC name
Bicyclo[1.1.1]pentane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C5H8/c1-4-2-5(1)3-4/h4-5H,1-3H2
    Key: MKCBRYIXFFGIKN-UHFFFAOYSA-N
  • C1C2CC1C2
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).

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.

Contents

Bicyclo[1.1.1]pentane is a highly strained molecule.

Usage

[1.1.1]Propellane 1.1.1-propellane.svg
[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

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; 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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